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Sydney Hubbard

I’ve spent a lot of time traveling around Greece, from sailing between islands to exploring some of the quieter places that don’t always make the typical itineraries. That firsthand experience, along with lots of behind-the-scenes research, helps shape the trips I design.

I really enjoy the planning process and helping make a big trip feel manageable and exciting. I’d love to help you plan a Greece adventure that feels just right for you! 🇬🇷💙

How did you get involved in travel?

"I really fell in love with travel right after high school, when I challenged myself to visit one new country every year. I’m 15 countries in now and definitely not slowing down.

I’ve traveled solo, with friends, and spent years planning trips for the people around me. At this point, I’m the default travel planner in my group. What keeps me excited about travel is how much it gives back on both sides. I’ve seen how thoughtful, sustainable tourism can directly support local communities, and I’ve also felt how stepping into new cultures shifts your perspective in ways that stick with you.

For me, travel is really about connection, between people, cultures, and those small, meaningful moments that stay with you long after you’re home."

Please share a unique travel experience you will never forget.

"On my last trip to Greece, one of my favorite surprises was a day trip to Aegina, known as the pistachio capital of the country. We visited a small, family-run farm that’s been passed down for generations, and it was my first time seeing pistachios growing in real life. I had no idea how much hands-on work goes into cultivating them.

The family explained how Aegina’s soil and climate are what make these pistachios so special, and then came the fun part: tasting. Pistachio pesto, brittle, baklava… and the standout was the pistachio butter.

It’s now my top recommendation for a Greek souvenir (so delicious and easy to bring home!). If you love pistachios, Aegina is one of those underrated stops that’s absolutely worth it."

Top itineraries and travel advice
Family itineraries
Luxury itineraries
Road trip itineraries
Honeymoon itineraries

Recent trip reviews for Sydney

A three generations family trip to Greece...
Greece | May 30 - Jun 9, 2026

Mark
Mark P.
Dallas, TX | Reviewed on Jun 15, 2026
We loved working with Kim Kim. Sydney was excellent in creating an itinerary that fit three generations of interests including the mythology tour of the Acropolis, the food tour in Athens, the day trip to Delphi, and our farm visit/cooking class in Naxos which was our favorite. The experience so relaxed having every transportation connection pre-still planned, organized and payed for. Thanks Kim Kim. Read more

We loved working with Kim Kim. Sydney was excellent in creating an itinerary that fit three generations of interests including the mythology tour of the Acropolis, the food tour in Athens, the day trip to Delphi, and our farm visit/cooking class in Naxos which was our favorite. The experience so relaxed having every transportation connection pre-still planned, organized and payed for. Thanks Kim Kim.

Hotel Reviews
Argo Boutique Hotel
Naxos

This place felt cramped including the breakfast area, the bedrooms for four people, the pool, etc. The staff was generally kind and welcoming. We did have an issue with my mom being locked out of the main building when we were trying to check out at 5:30am for our 7:15am flight. No one was at the desk and we had to leave cash to pay for water we had purchased since no one was there. Otherwise the hotel was clean, it was in a good location and the staff was generally friendly and helpful.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Being available at the front desk for checkouts before the earliest departing boat or flight at the local airport.
Akrotiri Hotel
Paros

This was a lovely hotel. The four bedroom was a bit tight for four people but we made it work. There juts not enough room to unfold everyone’s carryon luggage. The pool, views and friendliness of staff were excellent.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
The four bedroom was small. It was hard to layout our carryon luggage in this room and have space to walk. We made it work but it took creative thinking. The rooms and spaces were always very clean. The breakfast were outstanding.
Sweet Home Hotel
Athens

Great location in Athens. The breakfast was fantastic. The rooms were very comfortable.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on Jun 17, 2026

Mark,
Thanks so much for your kind words! I love hearing that the trip was a great fit for all three generations + that the Naxos farm visit/cooking class was a family favorite! I’ve done that one myself and loved it too, so it’s always extra fun when travelers connect with it as much as I did. It was such a pleasure helping plan your family’s time in Greece! 🩵

Our Amazing Trip to Greece
Greece | May 23 - Jun 1, 2026

A
Aaron W.
Upland, CA | Reviewed on Jun 02, 2026
Sydney planned an amazing trip to Greece. She took thoughts on what we wanted to experience and turned it into a reality. From Athens to Milos to Santorini to Crete, we were able to experience all of Greece. The private tours, the private sunset cruise, and I can go on and on and on. Sydney is the best and KimKim too! Thank you for another well thought out and planned trip! Read more

Sydney planned an amazing trip to Greece. She took thoughts on what we wanted to experience and turned it into a reality. From Athens to Milos to Santorini to Crete, we were able to experience all of Greece. The private tours, the private sunset cruise, and I can go on and on and on.

Sydney is the best and KimKim too!

Thank you for another well thought out and planned trip!

Hotel Reviews
Elia Ermou Athens Hotel
Athens
Santa Maria Luxury Suites & Spa
Milos, Cyclades
Ducato di Oia Boutique Hotel
Santorini

It was a bit on the older side - the room was not as nice as the other 2 hotels. But the service was impeccable.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Phaea Blue Palace
Agios Nikolaos

This was the highlight of our trip. The BEST hotel I have ever stayed in my entire life. I cannot say enough good things about this hotel.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Self-Guided Chasing the Santorini Sunset
Self-Guided Chasing the Santorini Sunset
Santorini
Acropolis Beat-the-Crowds Discovery Walk
Acropolis Beat-the-Crowds Discovery Walk
Athens
Self-guided Exploration of Plaka
Self-guided Exploration of Plaka
Milos
Private Day of Highlights
Private Day of Highlights
Milos

We really enjoyed the exclusivity of the day. Our guide was awesome. And we were able to see parts of Milos that we would have missed.

Quality of Experience
Guides, Drivers and Staff
Transport
Half Day Kleftiko Catamaran Adventure
Half Day Kleftiko Catamaran Adventure
Milos

One of the best Catamaran experiences we have had. Great captain and staff, food was amazing. We could have not asked for a better experience.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Sunset Caldera Cruise
Private Sunset Caldera Cruise
Santorini

WOW! The best!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Private Day Trip to Spinalonga Island
Private Day Trip to Spinalonga Island
Heraklion

We could have done this on our own. We were also supposed to have lunch included but we did not.

Quality of Experience
Guides, Drivers and Staff
Transport
Crete Wine & Culture Adventure: Private Tour of Peza Wineries, Olive Oil, and Traditional Pottery
Crete Wine & Culture Adventure: Private Tour of Peza Wineries, Olive Oil, and Traditional Pottery
Heraklion

WOW! Another highlight for us! The best experience! Spyros was amazing!

Quality of Experience
Food
Guides, Drivers and Staff
Spyros was the best guide, ever
Transport
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on Jun 03, 2026

Aaron,
I’m so glad you were able to experience such a beautiful mix of Athens, the islands, and Crete, and that the private experiences helped make the trip feel extra special. I'm excited to see where you and Cher go next! 🩵

Exceptional diverse trip to Greece
Greece | May 17 - May 27, 2026

Susan
Susan R.
Tinton Falls, NJ | Reviewed on May 28, 2026
Without exception, all of our guides were intelligent, knowledgeable, professional and fun. We felt like we started many of the guides as customers and ended our activities as friends! We engaged in a wide variety of activities from ebiking and hiking a gorge to fishing and a sunset cruise and all the drivers and guides were on time and excellent! Read more

Without exception, all of our guides were intelligent, knowledgeable, professional and fun.

We felt like we started many of the guides as customers and ended our activities as friends!

We engaged in a wide variety of activities from ebiking and hiking a gorge to fishing and a sunset cruise and all the drivers and guides were on time and excellent!

Hotel Reviews
Anteliz Suites
Fira

The service was exceptional and the location and views are magnificent! We had a room with a private infinity pool overlooking the caldera, it was stunning. The rooms and property were exceptionally clean and maintained. The breakfast overlooking the caldera is delicious and you have a full menu to choose from!

Authenticity & Character
Combination of location and staff
Location
Incredible views
Staff
Without exception every staff member was fabulous.
Cleanliness & Comfort
Crispy and white
GDM Megaron
Heraklion

Great location to the ferry and town center. Excellent views over the harbour. Quality breakfast buffet is a bonus. The rooftop bar and pool are a nice retreat after activities.

Authenticity & Character
Location
Right in the middle of it all
Staff
Very nice people working hard!
Cleanliness & Comfort
Very clean suite
Samaria Hotel
Chania Town

Samaria hotel is a boutique hotel with an exceptional location to everything Chania has to offer! The property is exceptionally clean and even smells wonderful. The pool is a hidden oasis. The breakfast buffet offers a wide variety to fuel up for your day!

Authenticity & Character
Location and service
Location
Right in the middle of the action!
Staff
Everyone is exceptionally attentive
Cleanliness & Comfort
Crispy white
Niche Hotel
Athens

We stayed one night at Niche Hotel. The property is an ideal location for all your acropolis type tours and offers an exceptional view of the acropolis from the rooftop bar and terrace! The rooms are exceptionally clean and the bed and pillows are really comfortable, and you can swap pillows for the type of sleeper you are! The breakfast buffet offers a wide variety of foods!

Authenticity & Character
Right in the middle of Athens culture
Authenticity & Character
Right in the middle of Athens culture
Location
Can’t be better
Location
Can’t be better
Staff
Great people
Staff
Great people
Cleanliness & Comfort
Bed and pillows are great!
Cleanliness & Comfort
Bed and pillows are great!
Activity Review
South Coast E-Bike Adventure
South Coast E-Bike Adventure
Santorini

Ebiking is an exceptional way to see different areas of a city while exercising and not having the hassle of parking and traffic. Our tour was about 4 hrs and we explored many viewpoints and historical landmarks. Our guide Katarina was EXCELLENT! She was so friendly and welcoming and a top notch guide! She also took lots of candid photos of us and shared them at the end!

Quality of Experience
Combination of our guide and all the viewpoints
Guides, Drivers and Staff
KATARINA was great!
Transport
On time and reliable
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 30, 2026

Thank you, Susan! It's great to hear you had such an amazing experience with your guides. Having knowledgeable local guides really makes such a difference when traveling, so I love hearing this feedback 🩵

Overall, we had an amazing trip! Everyone was...
Greece | May 19 - May 27, 2026

R
Rana H.
Chicago, IL | Reviewed on May 28, 2026
Overall, we had an amazing trip! Everyone was very accommodating and friendly. The itinerary was easy to follow and detailed. We did run into some challenges with one of the driving companies in Mykonos, who left before we arrived from our ferry after it had been delayed. We reached an agreement with one of his colleagues but it did require a lot of pushing from our end. Our hotel in Santorini also had a power outage with no electricity or running water the night before our flight and we... Read more

Overall, we had an amazing trip! Everyone was very accommodating and friendly. The itinerary was easy to follow and detailed. We did run into some challenges with one of the driving companies in Mykonos, who left before we arrived from our ferry after it had been delayed. We reached an agreement with one of his colleagues but it did require a lot of pushing from our end. Our hotel in Santorini also had a power outage with no electricity or running water the night before our flight and we weren’t able to reach the hotel management and the alternative contact information they shared with us upon arrival, which was disappointing.

Hotel Reviews
Attalos Hotel
Athens
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Abasa Suites
Santorini

Very hard to get in contact with the hotel management; electricity and water cut off with no warning and no one was available in the office/picking up.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Anna Maria Mykonos Hotel
Mykonos
Authenticity & Character
Location
Closer to the central town
Staff
Cleanliness & Comfort
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on Jun 15, 2026

Rana - thank you for taking the time to leave a review. I’m really happy to hear you overall had such an amazing trip and found the itinerary easy to follow!

I’m really sorry to hear about the frustrating situations with the Mykonos transfer and the unexpected power outage in Santorini. Thank you for bringing these to our attention. We’ll be reaching out to both the transfer company and hotel directly to better understand what happened during your trip and help make sure future travelers don’t run into similar issues.

Thanks again for trusting myself and kimkim with your Greece trip 🩵

We were paired with Sydney as our Greece spec...
Greece | May 4 - May 14, 2026

B
Bill C.
Newark, NJ | Reviewed on May 20, 2026

We were paired with Sydney as our Greece specialist. It was the trip of a lifetime and I can’t stress how great Sydney was! EVERY place we stayed was in the perfect area. EVERY tour we went on was amazing! EVERY ride showed up right on time! We couldn’t have used a more knowledgeable and helpful planner. Perfect to a tee. Already thinking about what other country we will use KimKim for. Can’t wait!

Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 28, 2026

Thank you so much, Bill! I’m happy to hear you had such an awesome trip. It was a pleasure helping you plan everything, and I’m glad all the hotels, tours, and transfers worked out so smoothly for you guys. Can’t wait for kimkim to help with the next adventure whenever you’re ready! 🇬🇷💙

Spectacular Trip to Greece
Greece | May 5 - May 15, 2026

R
Regis C.
Atlanta, GA | Reviewed on May 19, 2026
Lana’s birthday trip to Greece was an unqualified success. You will recall that she alone coordinated with you for a variety of excursions and experiences. After the first draft was developed, she asked me for my thoughts; I do not recall suggesting any changes.
After arriving in Athens on Day 01, we rested briefly in the hotel and took pictures of the view out the window. It took us a day to confirm that we were seeing the Acropolis – but not the Parthenon because a building rose to...
Read more

Lana’s birthday trip to Greece was an unqualified success. You will recall that she alone coordinated with you for a variety of excursions and experiences. After the first draft was developed, she asked me for my thoughts; I do not recall suggesting any changes.
After arriving in Athens on Day 01, we rested briefly in the hotel and took pictures of the view out the window. It took us a day to confirm that we were seeing the Acropolis – but not the Parthenon because a building rose to perfectly block its view. That was rectified by going to the hotel rooftop at sunset on Day 02.
Our first excursion was with Katrine as our guide for a neighborhood food tour. While I am not a chef, and do not enjoy cooking, the details Katrine provided at each of the stops along the tour were quite informative. It was simply a superb start to our visit to Greece. If our tour ended with that tour, the trip to Greece would have been a clear success. Wonderful.
Our Day 02 with Michael was exemplary. While I had no particular interest in Greek mythology, he made the morning quite educational. It was only after another mythology tour on Mykonos with a delightful Elizabeth that I learned mythology provides a guidepost for navigating life, death, and a host of other challenges in life.
Day 03 began with different Elizabeth picking us up at the hotel in a snazzy Mercedes to begin a thoroughly enjoyable day at Hyra – and no cruise ships. When the church that she wanted us to visit was closed, we had a wonderful discussion on the ability to improvise without needing to be annoyed at the circumstance. Our engagement with the mules was fun – strangely, they did not appear to be stubborn! Our horse ride began on a low note - I was tethered to Lana’s horse whose bridle was being led by the guide – while two young Irish lasses were free to handle the reins of their beasts. On the return leg I was allowed full control and my ride was a perfect success – I even motioned the guide away when he attempted to regain control because the horse was nibbling at leaves on an overhanging tree. At the end of that day, I wished that Elizabeth could be our guide again – anywhere; she was incredibly engaging.
Day 04 at Mykonos was fun – the taxi driver humorously warned us that we would get lost in town. I’d not say we got lost, but the way back to the hotel was not perfectly direct. As we approached the hotel from our initial wandering, we stopped and watched the rehearsal of a community dance group in an amphitheater across from the hotel.
The start of Day 05 was an absolute success with Dimitri leading us on a hike from the family vineyard to the coast and back. It was more than exercise – it was pure entertainment and full of informative details about life outside town, careers, family, churches, religion, etc.
The second part of Day 05 was a bit of disappointment. The guide, Sylvia, made sure that we were photographed at all her favorite locations. That is not our style, but we accommodated her. Except for the windmills, we had already walked to the stops she led us too. Unlike the engaging, educational food tour by Katrine in Athens, Sylvia’s food tour was ultimately underwhelming. In fact, the meal that we had was the second worst of my life – and to be honest, I do not recall my worst meal. I nibbled at the gyros to be polite. At the conclusion of her tour, Sylvia insisted on guiding us to a pathway leading straight back to our hotel, before going in the direction of her car. When she was out of sight, we turned around and went back into town to wander. While hydrating back at our hotel, we spoke at length with another, engaging guest and then walked crossed the roadway to the amphitheater for the production version of the community dance group. While there were no subtitles (!) or translations available, it was enthralling!
Day 06 was fundamentally a rest day since Lana was not particularly enthused about a hike up Mt. Zeus. I was more than enthused, but that was not relevant, I’ll hike for three weeks come August.
The Day 07 bike tour on Naxos began with a hiccup. We generally are at meeting points ten minutes early and are present when the driver or guide arrives. That was not the case this day, so Lana coordinated with the hotel clerk to arrange a very short ride to the bike shop where we met Manos. We quickly made up for lost time and were soon on e-bikes headed for the hills. What an absolute gem of an excursion. The experience matched that of the Athens food tour with Katrina and Elizabeth’s tour of Hydra in terms of quality, content, and immersion into Greek culture. Time at the goat farm was simply priceless. Fabulous beyond words. The evening mythology tour, while somewhat repetitive, proved to be very enjoyable. I don’t recall ever listening to English being spoken with a foreign accent with such perfect enunciation and pronunciation -- and with captivating inflection. Elizabeth packaged an interesting evening and graciously melded the expertise of a very knowledgeable young member of our group.
Day 08 proved to be long and tiring. On the ferry dock we enjoyed conversing with our driver who also had driven us to the hotel on our first day at Naxos. While standing in the queue we had a good time with several fellow travelers. Since we had a reasonably late breakfast at the hotel, we were not hungry at (U.S.) lunchtime so we ate light snacks on the ferry. Another Dimitri met us at the hotel, and he was as energetic as any guide could be. Picking up on his energy, we told him that the performance bar had been set high by our previous guides. To give him full credit, he tried; but at a key point in the tour, he had to leave us to enter Akrotiri alone because he was not allowed to guide its tour. After he dropped us at the gate to Akrotiri, we had to navigate the site independently – no pamphlet was provided. I admit I did not research the site as I most certainly should have. Since we entered the site without a clue about its basics, I found a QR code that linked to an English website still in development. I also found a PDF I could download, but that was impractical on the iPhone. Halfway through the site I found audio snippets via QR, but the associated diagrams were tough to interpret and many of the objects discussed were not onsite – they were in museums. The breadth of the excavation was stunning – and I learned later that night that it might take another 100 years to finish excavation. After rejoining Dimitri outside Akrotiri, he gave us two options: visit another castle or nearby Red Beach. We chose the latter in hopes that it would bring the day to an early end. It did not and the lack of a lunch break began to take a toll on our energy and moods. After leaving the interesting beach he drove us slowly to another photo-op site and then slowly back to the hotel as if to end the tour closer to the contracted time. One last point about the tour – it was in a rattletrap vehicle that left me unable to understand much of Dimitri’s constant stream of data and eventually led me to tune him out. OK, to be fair to him, I wear hearing aids to restore consonants that over wise would be lost in the ethers. If the consonants were in fact restored during the ride, they were overwritten by the rattling. Lana and I ended the day with a short walk to a restaurant that tested my resolve to keep the hearing aids powered on. We did not get a seat with a wonderful view of the caldera, instead we were ushered to a table set partway into a serving isle. I asked to be moved inside where I then discovered I could not hear Lana over the din created by waiters, bar tenders, music, and acoustics. We asked to be moved again – and were offered a street side, outdoor seat on a very chilly night. All of that movement was of our making, and I apologized to the manager for being so picky at which point he entertained us with stories of really picky customers – a group in which he said we did not fit! We thoroughly enjoyed our meal and his gracious hospitality.
The single scheduled event on Day 09 is always one of Lana’s favorite events – a regional cooking class. The class was perfectly enjoyable; great hands-on participation. Oddly, the lunch and wine tasting afterwards was ostensibly redundant – the food was the same, but double in portion size -- and the wine was similar in the pairing. The only noticeable difference between the two sessions was the dessert. Regardless of the redundancy, the meals had exceptional Greek flavors.
The weather reports for Day 10 promised an overcast day with chilly temperatures matched by high winds which led me to research the possibility of cancellation – not a chance. We spent part of the morning stepping down the 588 steps leading to dockside. There I purchased a trophy (Greek) hat on the assumption that we would successfully ascend the staircase. We did so without the aid of mules and celebrated with ice cream cones. Following quick rehydration, we walked quickly north so we could walk out to the Rock. And then we stuffed warm clothes into a backpack and were driven to the port for our catamaran sunset cruise. The weather was not as forecast – we only needed sweaters. It was as glorious as every other day in Greece – a perfect conclusion to our very, very successful visits to Athens, Hydra, Mykonos, Naxos and Santorini.
Thank you, Sydney, for helping make Lana’s birthday travel a marvelous success.

Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 20, 2026

Regis,
I loved reading through your daily reflections (I can picture it all through your storytelling!). I’m so glad Lana’s birthday trip was a success and that so many experiences were highlights for you both. It was a pleasure helping bring this trip to life! 🩵
Sydney

Where do I begin? From the very start of the ...
Greece | May 5 - May 15, 2026

Lana
Lana C.
Jacksonville, FL | Reviewed on May 18, 2026
Where do I begin? From the very start of the planning process to the ten wonderful days we spent in Greece, Sydney was incredible. She took the information we shared about what we wanted to see and do and turned it into a spectacular vacation. Every detail was thoughtfully arranged, making it easy for us to enjoy each day—whether we were meeting a guide or wandering through the towns on our own. What stood out most was how personalized everything felt. Sydney truly listened to what we... Read more

Where do I begin? From the very start of the planning process to the ten wonderful days we spent in Greece, Sydney was incredible. She took the information we shared about what we wanted to see and do and turned it into a spectacular vacation. Every detail was thoughtfully arranged, making it easy for us to enjoy each day—whether we were meeting a guide or wandering through the towns on our own.

What stood out most was how personalized everything felt. Sydney truly listened to what we wanted and created an itinerary that perfectly matched our interests. From the activities to the pacing of the trip, it was clear that every choice had been made with care.

Each day unfolded seamlessly, with the perfect balance of guided experiences and free time to explore independently. We never felt rushed, yet we were able to see and do so much. Sydney’s organization and attention to detail made the trip completely stress-free, allowing us to simply enjoy every moment.

We began with a fabulous Evening Neighborhood Food Walk with Katerina of Greek Travel Tellers. This was our introduction to Athens and to Greece, and Katerina warmly welcomed us to her city. We sampled food and drinks from five different establishments while learning about the history, culture, and everyday life of Athens. It was the perfect way to begin our trip and immediately made us feel connected to the city.

Another standout experience was our day on Hydra with our guide, Elizabeth of Alternative Athens. Her knowledge of the island, combined with her warm personality and easygoing demeanor, made it feel as though we were wandering the town with an old friend. By the end of our time together, we wished we could meet her again the next morning for coffee.

We also thoroughly enjoyed our hike with Dimitrius of Yummy Pedals on the island of Mykonos. We walked along donkey trails and countryside footpaths, stopping at a small church in the middle of a field. Dimitrius explained that these churches, scattered outside of town, are family churches used for special celebrations and occasions. We continued to a peaceful beach, where we cooled our feet in the water while enjoying homemade lemonade and a local pastry specialty.

On Naxos, we took a bike ride with Manos of Aurelia e-Assist Bikes through the island’s rural countryside. Along the way, we visited an archaeological site, learned about agricultural traditions, toured a farm producing cheese using traditional methods, and stopped at an olive mill museum to taste local olive oils and olives. Afterwards, we enjoyed a light farm-to-table lunch featuring cheeses made on the farm, fresh produce, and local wine before returning to Naxos Town.

After a short rest, we joined a group for the Mythology Sunset Walk and Wines of Naxos, led by Elizabeth of Naxos Cultural Tours. Elizabeth described herself as a “mythology junkie,” and by the end of the tour, she had nearly made us mythology enthusiasts as well. She brought stories of gods such as Odysseus and Poseidon to life as we wandered through the streets of Naxos Town, ending in the medieval castle district, once home to the acropolis. We then enjoyed a wine tasting in honor of Dionysus, the god of wine, before concluding at the Portara—the gate of the Temple of Apollo—where we watched a picture-perfect sunset.

Our time on Santorini included a hike down the famous Karavolades Stairs—all 588 of them—which connect the Old Port of Fira to the clifftop town above. We made it down much faster than we made it back up and rewarded ourselves with gelato to celebrate the climb. We also hiked to Skaros Rock, a dramatic promontory on the Aegean side of the island that was once the site of a castle and later served as a gathering place for the Christian community until an earthquake in the 19th century destroyed the structure.

One of my favorite things to do while traveling is take a cooking class, and our class on Santorini did not disappoint. We visited a local winery, where we learned about the indigenous grape varieties that thrive in the volcanic soil and sampled several island wines. Our cooking class was led by Chef Chris of Artemis Karamolegos Winery, who guided us through the hands-on preparation of traditional dishes. I can’t wait to recreate them for friends at home.

Our final outing of the trip was a sunset catamaran cruise. We stopped at Mesa Pigadia and Red Beach for swimming and snorkeling and enjoyed a delicious Greek barbecue while watching a breathtaking sunset. It was the perfect ending to an unforgettable journey.

While we did much more than what I have shared here, these were the activities we enjoyed the most.

Greece was truly unforgettable, and Sydney played a huge role in making it such a special experience. I would highly recommend her to anyone looking for a beautifully planned and memorable vacation.

Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 20, 2026

Lana,
Thank you for such a thoughtful review. One of my favorite parts of this job is creating trips that feel highly customized to each traveler, so hearing which moments stood out to you both means the world! It sounds like you and Regis truly embraced Greece in the best way. Thank you for letting me be even just a small part of it 💙
Sydney

Amazing Vacation!
Greece | May 4 - May 14, 2026

K
Kristina C.
Ashburn, VA | Reviewed on May 18, 2026
Our trip to Greece was a once in a lifetime vacation and Sydney did an AMAZING job planning it. We loved that all of our transportation was done for us and we only had to meet our guides or drivers at the hotel. We all had different favorite things that we liked, but some of the ones we enjoyed the most were the food tour, the cooking class, the history of the Acropolois/Parthenon and the boat tour around Zakynthos. All of our tour guides were very knowledgeable and easy to talk to. I would... Read more

Our trip to Greece was a once in a lifetime vacation and Sydney did an AMAZING job planning it. We loved that all of our transportation was done for us and we only had to meet our guides or drivers at the hotel. We all had different favorite things that we liked, but some of the ones we enjoyed the most were the food tour, the cooking class, the history of the Acropolois/Parthenon and the boat tour around Zakynthos. All of our tour guides were very knowledgeable and easy to talk to. I would 100% use KimKim for other vacations in the future!

Hotel Reviews
Capolavoro Suites
Zante
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Leto Nuevo Hotel
Nafplio
Authenticity & Character
Location
Staff
Cleanliness & Comfort
The Foundry Suites
Athens

We loved the roof top garden area where we could see the Acropolis at night!

Authenticity & Character
Location
It was near everything and we could walk to the different markets.
Staff
Cleanliness & Comfort
Activity Reviews
Self-Guided Beach Day
Self-Guided Beach Day
Zakynthos

This was the day that we split up for a bit. My daughter and husband went to the beaches, while I had coffee and read a book. It was a light, easy day where we could take it a little bit easy.

Quality of Experience
Private Island Cruise: Best Beaches, Caves, Small Islands
Private Island Cruise: Best Beaches, Caves, Small Islands
Zakynthos

Our driver picked us up at the hotel and took us to our boat. The experience was amazing as we saw the bluest and clearest water we have ever seen. We were able to see sea turtles, shipwreck beach, blue caves and dolphins on the tour.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Private Island Visit to Hydra or Spetses
Private Island Visit to Hydra or Spetses
Nafplio

Again, our driver picked us up at the hotel and took us to our boat for our day trip to Hydra. Hydra had a few beaches and lots of places to eat and shop.

Quality of Experience
Guides, Drivers and Staff
Our sea taxi was great and the driver gave us her business card for a ride back. She only needed 30 minutes of notice to pick us up.
Transport
Kayak & Snorkel Adventure in the Sunken City of Epidaurus
Kayak & Snorkel Adventure in the Sunken City of Epidaurus
Nafplio

Our driver met us at our hotel and took us to the kayak/snorkeling. Our guides were very knowledgable and it was a highlight of our vacation.

Quality of Experience
Guides, Drivers and Staff
The staff were very knowledgeable about the history of the tour.
Transport
Our driver drove us from our hotel directly to the company to kayak/snorkel.
Private Cooking Class in Nafplio
Private Cooking Class in Nafplio
Nafplio

This was another highlight of our trip. Costas and Agathi did a great job teaching us to cook Greek food. They were very knowledgeable when it came to Greek food.

Quality of Experience
Guides, Drivers and Staff
Savor, led by Costas and Agathi, were awesome at what they do and the food was amazing!
Transport
Our driver met us at our hotel, which was great, since the drive was about 10 minutes from hotel.
City Walking Tour of Nafplio
City Walking Tour of Nafplio
Nafplio

Our guide met us at the hotel and then showed us the historical facts about Nafplio. It was a good experience!

Quality of Experience
Guides, Drivers and Staff
Transport
Self-Guided Walk to Palamidi Fortress
Self-Guided Walk to Palamidi Fortress
Nafplio

We climbed all of the stairs to see the Palamidi Fortress and it did not disappoint. The climb was a struggle at times and we had to take breaks, but overall it was a good experience.

Quality of Experience
Private Sunset Tour to Cape Sounion
Private Sunset Tour to Cape Sounion
Athens

We had a great time with Theo driving us to the Temple of Psoiden. He showed us things we might not have noticed on the drive there. And the sunset was pretty amazing!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Morning Food Walk
Morning Food Walk
Athens

Our guide, Claire, did an awesome job of showing us the local foods and coffee we should drink.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Acropolis & Acropolis Museum Experience
Private Acropolis & Acropolis Museum Experience
Athens

We met our guide at the Acropolis and she did a fabulous job of showing us the Acropolis/Parthenon and the museum. We never would have learned that much history if we had gone by ourselves.

Quality of Experience
Guides, Drivers and Staff
Transport
Self-Guided Local Markets Visit
Self-Guided Local Markets Visit
Athens

All of the locals markets were within walking distance of our hotel. It was great to sight see by ourselves.

Quality of Experience
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 20, 2026

Kristina,
I’m so happy to hear the trip felt seamless and that everyone found something they loved. From the food experiences to the history and time on the water, you guys experienced everything I love about Greece! Thank you for trusting me with such a special trip, and I’d love to help with your next adventure someday! 🩵
Sydney

Fabulous Greece trip!
Greece | Apr 29 - May 8, 2026

Patricia
Patricia V.
Chicago, IL | Reviewed on May 11, 2026
Our trip was awesome! All the people we interacted with Kimkim were exceptional. We had bad weather in Santorini and they were able to reschedule our Catamaran sunset cruise so we didn’t miss anything! The local tour guides were all great very knowledgeable and personable!
We loved every place we visited
The rooms were all great and located in the heart of things easy to get around. All breakfast that was included was great except our place in Santorini could have been improved it lacked in...
Read more

Our trip was awesome! All the people we interacted with Kimkim were exceptional. We had bad weather in Santorini and they were able to reschedule our Catamaran sunset cruise so we didn’t miss anything! The local tour guides were all great very knowledgeable and personable!
We loved every place we visited
The rooms were all great and located in the heart of things easy to get around. All breakfast that was included was great except our place in Santorini could have been improved it lacked in comparison to the other places.
We would recommend KimKim without hesitation and will use them for future trips
Sydney was very helpful and patient!

Hotel Reviews
Elia Zampeliou Hotel
Chania

Great location awesome view of the bay everything was close

Authenticity & Character
In the middle of everything loved the balcony
Location
Walked everywhere beautiful balcony views
Staff
The breakfast staff was excellent
Cleanliness & Comfort
Clean and comfortable
Abasa Suites
Santorini

Room was very large bathroom was very spacious staff was nice and helpful

Authenticity & Character
Breakfast was not as good or plentiful as the other places
Location
It was quiet and removed from all the tourist
Staff
Cleanliness & Comfort
Argo Boutique Hotel
Naxos

It is walkable close to beach it was noisy but not sure you can control and it was a little small

Authenticity & Character
Location
Staff
More knowledgeable about surroundings
Cleanliness & Comfort
Sweet Home Hotel
Athens

Host were exceptional breakfast was great! Good location close to everything

Authenticity & Character
Homey comfortable and safe
Location
Close to everything
Staff
Pleasant always creates us when coming and going
Cleanliness & Comfort
Small but comfortable had a chair to sit nice balcony
Activity Reviews
White Mountains Excursion with Wine & Olive Oil Tastings
White Mountains Excursion with Wine & Olive Oil Tastings
Chania

Beautiful drive

Quality of Experience
Beautiful views
Food
Excellent food selection and more than enough to eat
Guides, Drivers and Staff
Very smart and informative
Transport
Self Guided Museums of Chania
Self Guided Museums of Chania
Chania
Quality of Experience
Private Guided Walk Through Old Town Chania
Private Guided Walk Through Old Town Chania
Chania

Goody was great

Quality of Experience
Guides, Drivers and Staff
Goody was great
Transport
Self-Guided Local Markets Visit
Self-Guided Local Markets Visit
Chania

Cute town

Quality of Experience
Self-Guided Santorini Shopping
Self-Guided Santorini Shopping
Santorini
Quality of Experience
Sunset Caldera Catamaran Cruise
Sunset Caldera Catamaran Cruise
Santorini

Could have been an hour shorter probably because it was cold

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Guided Fira to Oia Hike
Guided Fira to Oia Hike
Santorini

Amazing views hike was moderate

Quality of Experience
Guides, Drivers and Staff
Lily was very energetic
Transport
Self Guided Beach Time in Naxos
Self Guided Beach Time in Naxos
Naxos

The weather didn’t allow us to enjoy

Quality of Experience
Private Countryside Walk: Naxian Villages & Local Food
Private Countryside Walk: Naxian Villages & Local Food
Naxos

Great time with Christos food was excellent

Quality of Experience
Food
Guides, Drivers and Staff
Christos and kostos were both very friendly
Transport
Self-Guided Local Markets Visit
Self-Guided Local Markets Visit
Naxos
Quality of Experience
Evening Neighborhood Food Walk
Evening Neighborhood Food Walk
Athens

Nice assortment of food to try

Quality of Experience
Look
Guides, Drivers and Staff
Clea was fantastic and knowledgeable
Transport
Ancient Athens Acropolis & Mythology Walk
Ancient Athens Acropolis & Mythology Walk
Athens

Very informative and interesting great tour guide Sophia

Quality of Experience
Guides, Drivers and Staff
Transport
We stayed close and were able to walk
Self-Guided Local Markets Visit
Self-Guided Local Markets Visit
Athens

Loved walking around and exploring things

Quality of Experience
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 30, 2026

Tricia,
It was such a pleasure helping plan your Greece adventure. I’m so glad the weather hiccup in Santorini didn’t keep you from enjoying that sunset cruise, and that your guides, hotels, and experiences made the trip so memorable. Thank you again for trusting kimkim. We’d love to help you plan your next adventure! 💙
Sydney

We fell in love with Greece after we met Geor...
Greece | May 3 - May 10, 2026

Patty
Patty R.
Seattle, WA | Reviewed on May 11, 2026
We fell in love with Greece after we met George (Byzantine and Christian Museum in Athens), Vera (Ancient Corinth), Marina (Nafplio) and Natalie (Mycenae and Epidaurus). Their education, openness to our interests and questions and passion for the people and places of Greece were inspiring! And I am not mentioning the friendly and capable drivers and hoteliers, or the beautiful vistas and fun discoveries. Kimkim was so easy to work with and I felt supported all the way. Read more

We fell in love with Greece after we met George (Byzantine and Christian Museum in Athens), Vera (Ancient Corinth), Marina (Nafplio) and Natalie (Mycenae and Epidaurus). Their education, openness to our interests and questions and passion for the people and places of Greece were inspiring!

And I am not mentioning the friendly and capable drivers and hoteliers, or the beautiful vistas and fun discoveries. Kimkim was so easy to work with and I felt supported all the way.

Hotel Review
Sweet Home Hotel
Athens

Fabulous breakfast comfortable room and good location. Such nice people.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Local specialist: Sydney Hubbard
Sydney
Sydney Hubbard
Local specialist in kimkim HQ | Replied on May 19, 2026

Patty,

Thank you for your kind words! It was a ton of fun planning your Greece adventure together.

Local guides can make such a meaningful impression during travel, especially when they share a personal love for their country and it's culture. Thank you again for trusting us with your travels, and I hope we'll have a chance to plan more together soon!

Sydney