Greek Islands Custom Trips

plan and book your tailor-made trip with a local travel specialist

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Experience the highlights and hidden gems of the Greek islands! Our local travel specialists will help you put together an amazing custom island-hopping trip that will show you an authentic slice of Greece's scenic beauty, culture, and history.

Want to explore the best that Greece has to offer? Get started by describing your ideal trip, and we'll connect you with a local specialist to plan out the details.

Greece Travel Insights

Al fresco dining at its finest
Map of Relaxed Athens, Santorini, Naxos & Mykonos - 8 Days
Relaxed Athens, Santorini, Naxos & Mykonos - 8 Days

Escape the troubles of the world with eight days in the Cyclades. You'll arrive in Athens, then head to the islands to explore famous Mykonos and Santorini as well as lesser-known but spectacular Naxos. Enjoy your Greek vacation filled with sun, sailing, and sampling, with cooking classes and traditional dinners accompanying your days of blissful idleness.

Turn a new corner
Map of Family Adventures in Athens and the Cyclades - 10 Days
Family Adventures in Athens and the Cyclades - 10 Days

Walk hand in hand through the brightly colored doors of the Cyclades with this 10-day family itinerary. After an Athenian mythology tour, you'll sail to the islands for a slew of activities, with farm dinners, bike rides, horseback tours, and a cruise through the caldera on wooden ship all on the agenda.

A rock formation frames the sea on Corfu, Greece
Ultimate Guide to Island Hopping in Greece

Cyclades, Saronic, Dodecanese, Sporades: to plan an island-hopping trip around Greece, you'll need some background on each of the island groups. Read on to learn what to expect, where to go, and how to start planning your adventure.

Ermoupoli waterfront on Syros
Map of Relaxing Secret Cyclades - 12 Days
Relaxing Secret Cyclades - 12 Days

Take 12 days to explore some of the lesser-known islands of the Cyclades. Start by sampling street food in Athens before venturing out to sea. You'll stop on Syros, Tinos, Naxos, and Ios, with enough stately homes, savory food tours, and sunny beaches to keep you in serenity long after your trip is over.

Tinos
Map of Active Cyclades: Tinos, Naxos & Ios - 10 Days
Active Cyclades: Tinos, Naxos & Ios - 10 Days

Explore some of the lesser-known islands of the Cyclades on this jam-packed adventure. Over a week and a half, you'll hike through the hills of Tinos, go scuba diving off Naxos, and paddle to secluded beaches on Ios. End your journey with a thrilling bike ride around historical and modern Athens.

Paleokastritsa bay on Corfu
Map of Discover Rhodes, Crete & Corfu - 14 Days
Discover Rhodes, Crete & Corfu - 14 Days

Odysseus's journey lasted 10 years as he tried to get home after the Trojan War. Your two-week journey will take a little less time, but hopefully feel equally legendary with this itinerary. After a mythology tour in Athens, you'll head to the island of Rhodes to explore its medieval old town. Proceed to Crete to wander the Palace of Knossos, once home to the labyrinth of the Minotaur, then sail to some of the very places Odysseus set foot from Corfu before you return to Athens.

How it works
Chat with specialist icon Step 1
Tell us what kind of trip you want
Complete our quick travel quiz
Chat icons Step 2
Chat with a local travel specialist
Work out the details together
Credit card icon Step 3
Securely book your trip
100% satisfaction guaranteed

Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Chris Gravas
active 3 hours ago

Chris Gravas

I design entire journeys that mitigate issues before they arise. I ensure the best possible orchestration of all services included. I provide human accountability in real time. My name is...

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Travel specialist Eirini Tzoka
active 1 hour ago

Eirini Tzoka

My name is Eirini, I am a travel specialist and I was born and raised in Athens. My family originated from Northwestern Greece, and it was this area's raw beauty and long-standing heritage that got...

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Travel specialist Marianna Pianelli-Blatsouka
active 17 hours ago

Marianna Pianelli-Blatsouka

I’m Marianna, born between two cultures and now based in Athens. With Greek roots and an Italian sensibility, I design tailor-made journeys throughout Greece that blend refined comfort with...

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Travel specialist Penny Vasileiadi
active 13 hours ago

Penny Vasileiadi

I’m Penny, a Travel Specialist from Kalamata. I grew up among olive groves in the Peloponnese, and that close connection to local life still shapes the way I plan trips today. With a degree in...

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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

Emabarking On Our Greek Adventure!
Greece | Apr 19 - May 4, 2026

S
Suzanne T.
Ashburn, VA | Reviewed on May 12, 2026
We hit the ground with enthusiasm and excitement and were not disappointed. The accommodations were perfect for us with The Niche in Athens being our favorite. The reception and staff at all of our stays made us feel warmly welcomed and well supported. Hiking the Imbros Gorge on Crete was a stunning experience and we enjoyed eating, shopping and exploring the charming town of Chania. On to Santorini! We loved Hotel Keti and the staff. The many steps kept us in shape for our long walk... Read more

We hit the ground with enthusiasm and excitement and were not disappointed. The accommodations were perfect for us with The Niche in Athens being our favorite. The reception and staff at all of our stays made us feel warmly welcomed and well supported. Hiking the Imbros Gorge on Crete was a stunning experience and we enjoyed eating, shopping and exploring the charming town of Chania. On to Santorini! We loved Hotel Keti and the staff. The many steps kept us in shape for our long walk from Fira to Oia. It was a challenge but we would to it again! Santorini Sea Kayak provided us with a wonderful and entertaining day of paddling and spectacular views along the coast. Adonis and Nolan were the best guides ever! We were also treated to a homemade lunch.

Naxos was a treasure and a sweet change of pace. Although the winds were gusty and it was a bit chilly we stilled loved the island. One of our favorite tours was with Natural Cultural Tours. Our guide Christos was over the top fun, knowledgeable, and entertaining. Sadly we said goodbye the Greek Islands as we headed back to Athens and our long journey home. Thank you Kim Kim for giving us this opportunity!

Activity Review
Private Countryside Walk: Naxian Villages & Local Food
Private Countryside Walk: Naxian Villages & Local Food
Naxos
Local specialist: Erica Gerakos

Best Trip Ever!!
Greece | May 2 - May 11, 2026

L
Liz K.
Miami, FL | Reviewed on May 12, 2026
I can’t say enough about how incredible our trip to Greece was — and a huge part of that was thanks to Siena and the entire team at KimKim. From start to finish, everything felt seamless, thoughtful, and so well planned. Even the rainy weather during our Acropolis & Mythology Walk in Athens couldn’t dampen the experience. Our guide, Michael, was hilarious, engaging, and incredibly knowledgeable. Our Delphi day trip was equally memorable, and the lunch stop on the drive home — arranged by... Read more

I can’t say enough about how incredible our trip to Greece was — and a huge part of that was thanks to Siena and the entire team at KimKim. From start to finish, everything felt seamless, thoughtful, and so well planned.

Even the rainy weather during our Acropolis & Mythology Walk in Athens couldn’t dampen the experience. Our guide, Michael, was hilarious, engaging, and incredibly knowledgeable. Our Delphi day trip was equally memorable, and the lunch stop on the drive home — arranged by our driver Chris — ended up being one of the highlights of the entire trip.

In Chania, our History & Foodie Tour was absolutely delicious (and VERY filling), and our guide Aria was genuinely lovely. We were also lucky enough to have Nikos as our guide for both the Milia Mountain wine & olive oil tasting and the Balos Lagoon/Falassarna Beach tour — and he was truly exceptional. He had such a warm, welcoming energy that he made both excursions feel relaxed and personal. We also met wonderful people on each of our small group tours, which made the experience even more special.

Eva at the Alcanea Boutique Hotel was beyond kind and accommodating. The suite was beautiful, and the location honestly couldn't have been more perfect.

One thing I especially appreciated was how supported we felt the entire time. Having contacts for every transfer and knowing KimKim was available if anything went wrong made traveling abroad feel easy and stress-free.

I would HIGHLY recommend KimKim to anyone planning a trip. We made memories we’ll never forget — and I know we’ll absolutely use them again in the future.

Hotel Reviews
Niche Hotel
Athens

The team at the Niche Hotel had a sweet welcome for us when we arrived - with rose petals all over our room and making a heart with the word "love" spelled out on our bed. It was such a sweet way to start our engagement trip.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
A for Athens
Athens

O.M.G. I asked Siena at KimKim for the best suite she could find for the final night of our engagement trip to Greece and she ABSOLUTELY delivered!! We stayed in a suite with the view of the Acropolis, that also had a balcony and overlooked the bustling city of Athens. Since we were only staying one night, we bought pizza and a bottle of wine and just took in everything right from our amazing room. Couldn't have asked for anything better.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Alcanea Boutique Hotel
Chania Town

Eva was absolutely the kindest and most accommodating host you could ask for. And the location at the city center of Chania was amazing!! Wouldn't wanted to have stayed anywhere else.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on May 13, 2026

Liz, it was such a pleasure designing this trip with you!! I was able to share my favorite hotels, guides, and locations, and it makes me so happy to hear you loved them all as much as I do! I love that so many of the people along the way helped make the experience feel personal and welcoming. Your final night overlooking the Acropolis with pizza and wine sounds like a magical experience, and I’m so grateful we could be a small part of those memories! I hope to plan your honeymoon trip in the future! 💛✨

An unforgettable honeymoon
Greece | May 3 - May 9, 2026

Trinity
Trinity G.
Newark, NJ | Reviewed on May 11, 2026
From the first driver who picked us up at the airport, to the hotel workers, taxi drivers, and tour guides, everyone was extremely friendly and helpful. We had the most wonderful experience and felt like royalty everywhere we went, that’s how good the service was! Our trip planner, Eirini, listened to our wishes and advised us on the best times to visit as well as suggested places worth seeing during the time we were not taking tours. I have never had a better vacation and will absolutely... Read more

From the first driver who picked us up at the airport, to the hotel workers, taxi drivers, and tour guides, everyone was extremely friendly and helpful. We had the most wonderful experience and felt like royalty everywhere we went, that’s how good the service was! Our trip planner, Eirini, listened to our wishes and advised us on the best times to visit as well as suggested places worth seeing during the time we were not taking tours. I have never had a better vacation and will absolutely use KimKim in the future!

Hotel Reviews
18 Micon Street
Athens
Authenticity & Character
Authenticity & Character
Location
On a small side street so can be hard to find but seemed to be a safe area and we had no issues
Location
On a small side street so can be hard to find but seemed to be a safe area and we had no issues
Staff
Very helpful and thoughtful! We had to leave earlier than breakfast time and the staff left out a bag full of breakfast for us to take! Very sweet (the food was also great)
Staff
Very helpful and thoughtful! We had to leave earlier than breakfast time and the staff left out a bag full of breakfast for us to take! Very sweet (the food was also great)
Cleanliness & Comfort
Cleanliness & Comfort
Honeymoon Petra Villas
Santorini

The views are to die for but beware there are many stairs!! Can’t have cliff side views without putting some work in. Food was good at the restaurant but you can get better in town

Authenticity & Character
Location
Close to many restaurants, walking distance to Fira. A drive from Oia. Hard to find your room sometimes as it is somewhat of a maze
Staff
Staff was always going above and beyond to make sure you have a great time!
Cleanliness & Comfort
Avgoustos Suites
Naxos

The bedrooms are to DIE for, from the double rainhead shower to the high tech blinds and the personal hot tub. We didn’t want to leave!! Quiet area and lots of privacy

Authenticity & Character
The food in gorgonna tavern below (as well as the breakfasts they serve in the hotel) changed my life!!! Literally, I’m trying to recreate the recipes at home
Authenticity & Character
The food in gorgonna tavern below (as well as the breakfasts they serve in the hotel) changed my life!!! Literally, I’m trying to recreate the recipes at home
Location
Wish it were closer to the port (you have to rent a car if you want to be in town) however the quietness and calmness of the area was refreshing
Location
Wish it were closer to the port (you have to rent a car if you want to be in town) however the quietness and calmness of the area was refreshing
Staff
The owner welcomed us before our room was ready with wine and a local charcuterie and sat and talked with us, telling us about the local things to do and what Naxos is known for. We have never had better service at a hotel!!!
Staff
The owner welcomed us before our room was ready with wine and a local charcuterie and sat and talked with us, telling us about the local things to do and what Naxos is known for. We have never had better service at a hotel!!!
Cleanliness & Comfort
Everything was clean from the first day we got there to the last day we left. Housekeeping was great!
Cleanliness & Comfort
Activity Reviews
Sea kayaking experience
Sea kayaking experience
Santorini

Our tour guides, jiannis and Nolan, were extremely friendly and fun to be around. They had as much fun working as we did being on the tour!

Quality of Experience
Guides, Drivers and Staff
Transport
Santorini wine tour
Santorini wine tour
Santorini

We did not know that we had a private tour until the day of, which made our day! Having your own private driver and tour guide makes you feel somehow famous

Quality of Experience
Guides, Drivers and Staff
Transport
Catamaran day cruise
Catamaran day cruise
Naxos

Very difficult to have perfect weather for something like this, possibly something you want to wait for the week of to book. We were both freezing and got sunburned at the same time

Quality of Experience
Nothing to do with the staff, they were amazing. The weather was just freezing due to the breeze which made the experience difficult to fully enjoy
Food
The food was all freshly prepared from scratch right on the boat!! Authentic and tasty
Guides, Drivers and Staff
Transport
Villages of Naxos food tour
Villages of Naxos food tour
Naxos

If you have any doubts, stop and just book it!!! We will be talking about this tour for years to come!!

Quality of Experience
Food
Life changing. We made sure to get good olive oil and honey before returning home!
Guides, Drivers and Staff
Transport
Local specialist: Eirini Tzoka
Eirini
Eirini Tzoka
Local specialist in Athens | Replied on May 12, 2026
Thank you so much for your incredibly kind words, Trinity!
It means so much to hear that your honeymoon was such a special experience from beginning to end and that you felt warmly welcomed and well cared for by everyone along the way. I’m especially happy that I could help create an itinerary that matched your wishes and made your time in Greece even more memorable.
Thank you again for trusting us with your vacation. It was truly a pleasure planning this journey for you, and I'm always here...
Read more

Thank you so much for your incredibly kind words, Trinity!
It means so much to hear that your honeymoon was such a special experience from beginning to end and that you felt warmly welcomed and well cared for by everyone along the way. I’m especially happy that I could help create an itinerary that matched your wishes and made your time in Greece even more memorable.
Thank you again for trusting us with your vacation. It was truly a pleasure planning this journey for you, and I'm always here to help you create another unforgettable trip in the future!
Wishing you both a lifetime filled with love, laughter and happiness,
Eirini

Why travelers love kimkim

Custom trips for independent travelers who are too busy to plan
Customize your trip with the help of a local travel specialist

Kimkim has handpicked the world’s top local travel specialists so you will have peace of mind and an unforgettable trip that meets your exact requirements.

Authentic travel experiences

Kimkim’s local specialists ensure that you will have the best experience based on up-to-date local insights. On top of that, the vast majority of your money will go straight to support and grow local economies.

Secure & easy booking

Once you are happy with the trip, you can easily book via kimkim’s secure payment platform.

Local support during your trip

You can always reach your local specialist with a quick message or call in case you hit a snag during your trip, or simply want some great local recommendations.