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 35 mins 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 4 hours 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 2 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 2 days 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

Our trip that we booked through KimKim with our agent Erika was one amazing day after another!
Greece | May 5 - May 15, 2026

Elaina
Elaina B.
Richmond, KY, USA | Reviewed on May 22, 2026
Our trip that we booked through KimKim with our agent Erika was better than we even dreamed it could be! From the very beginning we were amazed at how perfectly Erika had matched the tours to our distinct likes and wants. The food tour in Athens with Alternative Athens was so fascinating to be able to understand the story behind why this food and the way it is prepared is important and what to look for when buying these items. Sitting around the tables with others as conversations erupted and... Read more

Our trip that we booked through KimKim with our agent Erika was better than we even dreamed it could be! From the very beginning we were amazed at how perfectly Erika had matched the tours to our distinct likes and wants. The food tour in Athens with Alternative Athens was so fascinating to be able to understand the story behind why this food and the way it is prepared is important and what to look for when buying these items. Sitting around the tables with others as conversations erupted and enjoying the food was a highlight. Naxos was our favorite island and one we know we would choose to return to. The Adriana hotel was so convenient and beautiful with the ability to walk to everything within 10 minutes, and we loved eating our lovely breakfast outside every morning. The countryside walk with Naxos Cultural Tours was absolutely amazing and our guide Elizabeth was fantastic. Her knowledge and just overall kindness and joy about everything and everyone we encountered was intoxicating. The Gerofinikas Hotel on Sifnos though was the ultimate highlight of our trip. It was like walking into a dream world of luxury that we didn't know existed! Everything is geared around being outside and all your needs were met with such quiet kindness. The staff truly made you believe they existed only to make your trip magnificent. From delicious food eaten outside with the most stunning landscape, to handcrafted drinks from the bar to the on demand coffee shop we felt so pampered. We truly did not want to leave that magical place. The experience we will never forget though was the cooking class at Narlis Farms. Cooking with George in his farmhouse, walking his farm as he educated us on farming without water, and then eating the dishes we made around his large kitchen table will be what we will continue to daydream about for many years. Milos was full of beautiful beaches that continued to take your breath away, and the catamaran adventure would've been much more enjoyable if it hadn't been 65 and cloudy, but no one can control the weather! We loved our food and wine tour though with Micheal from Travel Me to Milos! We felt like we were hanging out with an old friend who truly wanted us to love his home and we could've stayed with him all day. All in all, the trip was way more than we had hoped to experience, and we truly didn't have one low point or regret. I've never been able to say that about an international trip, so we are extremely grateful to KimKim and have told all our friends about the great value of your travel agency. Thank you!

Hotel Reviews
Adriani Hotel
Naxos Town

We loved the ability to walk to anything we desired in town. Everything was within a 10 minute walk. The morning breakfast were such a highlight as well as the food was a wide range of delicious authentic Greek food and we always chose the option of eating outside on the covered patio amongst the beautiful flowers and weather. The owners were so helpful and we even rented a car through them that gave us the ability to travel all across the island. Our room was spacious and very comfortable with a large shared sundeck and view of the city. A great experience!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Gerofinikas Boutique Hotel
Sifnos

The Gerofinikas Hotel was like stepping into a magical land of luxury from the first moment we walked through the entrance in the hedge. We both seriously gasped! The extraordinary view that you receive from anywhere that you're outside in the resort is worth the stay alone, but the experience doesn't end there. They pamper you with a private small scale restaurant only available to guests that serves breakfast, lunch and dinner, where you can either eat inside or on the covered patio with that incredible view. A full service coffee bar and bar open all day where they will serve you by the pool or lounging area. Each room has a secluded patio with that once again incredible view where you can lounge away. The staff was so calming and kind and truly made you feel that they existed to make your stay the best it could possibly be. It is only a 10-15 min walk from two nearby towns with many restaurant offerings as well if you choose to go out. Our stay at the Gerofinikas Boutique Hotel will forever be the highlight or our trip to Greece, and I will go so far to say that you should go to Sifnos, if only to experience this hotel. We will never forget it.

Authenticity & Character
Location
Staff
Their kindness and desire to make your stay as wonderful as possible.
Cleanliness & Comfort
Activity Reviews
Private Food & Wine Discovery Drive
Private Food & Wine Discovery Drive
Milos

Taking this tour with Michael was like hanging out with an old friend from the moment we got in the car. He was so fun, knowledgeable and real about growing up on this island, the good and the bad. We had so many great conversations and his love and passion for Milos is so evident. We would've hung out with him all day!

Quality of Experience
Guides, Drivers and Staff
Transport
The car was a brand new Mercedes SUV, so it was definitely luxurious.
Traditional Cooking Class at Country Farm
Traditional Cooking Class at Country Farm
Sifnos

This experience was hands down the highlight of our trip. Getting to spend this time with George around his table, in his kitchen and as he walked us through his fields explaining how to grow produce without water will be an experience we will never forget. His knowledge and love for preserving these ancient ways enchanted us and helped us realize what life on this island was truly like and what is being lost. Plus when do you get to sit around a table with a celebrity chef getting to eat food that he lovingly prepared? It was like being invited over for a family dinner but with a loving education provided as well. This is definitely a not to be missed experience for foodies and nature lovers alike!

Quality of Experience
Food
FANTASTICALLY DELICIOUS!
Guides, Drivers and Staff
Transport
We were able to walk there in under 10 minutes from our hotel the Gerofinikas.
Private Countryside Walk: Naxian Villages & Local Food
Private Countryside Walk: Naxian Villages & Local Food
Naxos

We had the most amazing time with our wonderful guide Elizabeth who was so kind and truly joyful with everyone and animal we encountered. Her love and knowledge of Naxos completely shown through, and she led us on the most charming walking tour through several villages. When she learned of my love for Greek mythology, she immediately begin weaving her great knowledge of the local area with so many of the stories. This is something I will not forget! To be able to connect so many of this iconic stories with actual real places was amazing. The food, wine, liquor and people we became acquainted with through her were definitely a highlight of our trip to Greece. You don't want to miss this tour!

Quality of Experience
Food
It was all so fresh and absolutely delicious. Plus there was so much of it, that we couldn't finish half of what we were given!
Guides, Drivers and Staff
Elizabeth and our driver were wonderful hostsQ!
Transport
The car was very luxurious and seemed brand new.
Local specialist: Erica Gerakos

We had a fabulous trip to Greece. I had dream...
Greece | May 9 - May 18, 2026

J
Joanie S.
Atlanta, GA | Reviewed on May 21, 2026
We had a fabulous trip to Greece. I had dreamed of traveling there since I learned about Greek History in 6th grade. I had high expectations and I was not at all disappointed. First of all, our transport drivers were on time throughout the trip, and they were professional and personable. Our hotels were all comfortable and in locations where we could walk to restaurants, etc. We were especially impressed with ALL of the staff at the Melidron in Naxos. From the front desk to the young bar... Read more

We had a fabulous trip to Greece. I had dreamed of traveling there since I learned about Greek History in 6th grade. I had high expectations and I was not at all disappointed. First of all, our transport drivers were on time throughout the trip, and they were professional and personable. Our hotels were all comfortable and in locations where we could walk to restaurants, etc. We were especially impressed with ALL of the staff at the Melidron in Naxos. From the front desk to the young bar tender, to the women who prepared the homemade breakfast to the drivers, they were always there to help with suggestions and advice, they seemed as sad to see us leave as we were to say goodbye to them. We initially wondered if it would have been a better choice to stay in/near Naxos Town, since we ended up there at some point during each day, and didn't spend time on the beach except to walk by for pretty views a couple of times. But later we decided it was nice to stay in a more peaceful area that we got to know a bit better. The Santorini hotel view was spectacular, Wow!

We enjoyed all of our tours. A few of our guides were so impressive: Evita(I think that was her name) who led us through the Acropolis was outstanding, both with her knowledge of history and adapting our walking route for those who were having a bit of trouble with physically walking for long periods. Elizabeth in Naxos was fantastic, and George in Santorini was a very good guide as well. Our driver to Delphi, Nancy, was not a licensed guide, but we learned so much from her on the trip. She had lots of knowledge about Greece to share with us. We wanted to do a day trip outside of Athens and followed Siena's advice to go to Delphi. I don't think any of us knew anything about that place so I can't say we were excited, but it turns out we all really enjoyed learning about the history. Our guide there, Theo, was very knowledgeable and shared so much information about that city. I will mention that later we all commented that he was not so easy to understand, we all felt like we had to focus very intently to understand what he was saying. He seemed to talk very quickly and did not annunciate as clearly as our other guides. But we all really loved that day, including driving through two really cute towns up there, and the restaurant for lunch. I would love to go back there one day and explore the towns. We were a bit skeptical about how the marble carving experience in Naxos would be, it turns out that we all enjoyed a very different activity very much. We were also worried we would be very cold on the catamaran trip, after the weather report showed cool temps with lots of wind, but overall, it was sunny and quite comfortable until the sun went down.

The whole kimkim team was incredible. Siena listened to our needs and planned and a wonderful trip, willing to change things as needed. There were a few times we had questions while we were away, when we knew it was the middle of the night in the US. Each time somebody got back to us within minutes. It was truly amazing how quickly we would get a reply, even in the middle of the night on a weekend. We truly cannot hesitate to recommend kimkim to anyone, they make traveling so comfortable and easy. We would be happy to come back to any of these places again but there is also so much more of Greece to see. Can't wait to plan our next trip, the next one for us will be Croatia and Montenegro, about a year from now.

Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on May 21, 2026

Joanie, I absolutely loved working with you! Thank you for sharing all the photos throughout your trip. I felt like I was there with you all! I'm so happy our team delivered on your expectations, and you loved our vetted guides, hotels, and drivers. The Melidron Hotel & staff are especially lovely, I fully agree! I hope we get to work together again, but in the meantime, enjoy all of these Greece memories! 🇬🇷🕊️✨

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

B
Bill C.
Newark, NJ | Reviewed on May 21, 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

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.