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, and Corfu - 14 Days
Discover Rhodes, Crete, and 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 in its medieval old town. Proceed to Crete to wander the Palace of Knossos, once home to 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 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 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 Marianna Loupou
active 54 mins ago

Marianna Loupou

I’m a travel specialist with a genuine love for creating one-of-a-kind experiences that feel just right for each traveler. My journey in the travel world has taken me through many exciting paths, ...

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Travel specialist Marianna Pianelli-Blatsouka
active 23 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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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

Wonderful planning and vacationing experience
Greece | Apr 11 - Apr 18, 2026

C
Caitlin C.
Ashburn, VA | Reviewed on Apr 22, 2026
Chris did a wonderful job planning our Greece vacation, as well as ensuring our trip was going as planned while we were enjoying it! We were in good hands and would recommend Chris for future trips! Read more

Chris did a wonderful job planning our Greece vacation, as well as ensuring our trip was going as planned while we were enjoying it! We were in good hands and would recommend Chris for future trips!

Hotel Reviews
Blue Dolphins Hotels & Villas
Firostefani, Santorini

The views the views the views!! The room was great with the master bed facing out to the beautiful views! The staff was very friendly and the breakfast brought to your room was phenomenal!

Authenticity & Character
The hotel was exactly the feel I was looking for!
Location
Walkable to town and food, right on the cliff with amazing views
Staff
Very helpful and friendly!
Cleanliness & Comfort
Princess of Naxos
Naxos

The staff were very friendly and accommodating - they wanted to make sure we had a good trip and offered great suggestions and help if needed.

Authenticity & Character
Location
15-20 min walk to town, but right on the beach
Staff
Very helpful and engaging! Offered great suggestions for what to do including renting cars, driver service and booking tours.
Cleanliness & Comfort
Achilleas Hotel
Athens

It was within walking distance to all of the Athens adventures, shopping and food that we wanted.

Authenticity & Character
Location
Walkable to all the things we wanted to do - food, tours and shopping
Staff
Cleanliness & Comfort
Activity Reviews
All Time Classic Santorini
All Time Classic Santorini
Santorini

I felt like we got to see so much on this tour!

Quality of Experience
Such a variety - different beaches, great views, amazing food adventure!
Food
Exceptional!!
Guides, Drivers and Staff
Both our driver and guide were just as wonderful on day 2!
Transport
Perfect
We Guide You In The Past
We Guide You In The Past
Santorini

This was so cool and I knew nothing about this prior to coming! Our guide knew lots of great details

Quality of Experience
Guides, Drivers and Staff
Both the driver and guide were great!!
Transport
Perfect for our family
Naxos Old Town, Castle & Portara Sunset Tour
Naxos Old Town, Castle & Portara Sunset Tour
Naxos

I loved this tour because there was so much more to the city than I would have realized on my own! It was great to learn the history of the town and see the different architecture and history.

Quality of Experience
Tour guide was great and very knowledgeable
Guides, Drivers and Staff
The guide was very friendly and knowledgeable
Transport
This was a walking tour and felt very doable even for my two kids - ages 6 &7
Naxos Villages Food Tour
Naxos Villages Food Tour
Naxos

I loved that this tour went inland to the small villages, we got to see so much more than the “tourist” perspective, as well as meet great people and try delicious food!

Quality of Experience
Felt very authentic from the locations we went to, the information we were provided, the people we met and the food we ate.
Food
So great to try so many delicious things! A great variety!
Guides, Drivers and Staff
Our driver and guide were both great!
Transport
The transport van was perfect
Mythology for Families
Mythology for Families
Athens

Our tour guide was wonderful - she was so engaging with the kids and brought different activities for them to do too!

Quality of Experience
The tour guide! She was knowledgeable and very kid / cat friendly!
Guides, Drivers and Staff
Best part was our guide
Local specialist: Chris Gravas
Chris
Chris Gravas
Local specialist in Las Vegas, NV, USA | Replied on Apr 22, 2026

Dear Caitlin,

Thank you very much for your kind words, recommendation and wonderful review! I really appreciate you taking the time to share your impressions and experiences from your trip. I will share your feedback with all related drivers, partners and guides, they will surely appreciate it.

Should you wish to plan a future trip to Greece and/or Italy, you know where to find me.

Until that time, all the best and safe travels!

Warm greetings,
Chris

Best Trip Ever!
Greece | Apr 4 - Apr 12, 2026

Alicia
Alicia O.
Seattle, WA | Reviewed on Apr 19, 2026
We had the perfect trip to Greece, great weather, no crowds and the trip was seamlessly planned. It was so amazing to have a driver pick us up from each drop off location. We had plenty of time in each location and loved all the excursions that were planned for us! Read more

We had the perfect trip to Greece, great weather, no crowds and the trip was seamlessly planned. It was so amazing to have a driver pick us up from each drop off location. We had plenty of time in each location and loved all the excursions that were planned for us!

Hotel Reviews
NLH Monastiraki
Athens

Very nice staff and great location to walk to everything in Athens!

Authenticity & Character
It was clean and nice!
Location
Great location, easy to walk to everything!
Staff
Very helpful and welcoming
Cleanliness & Comfort
small, but modern and clean!
Above Blue Suites
Santorini

The view was breathtaking, but it did lack in a few areas. The shower was darling, but we were never able to get the water to be anything but scalding or freezing. The hot tub on the deck, was cute, but only luke warm, and the pool was freezing. The pool chairs were comfortable, but old and beat up.

Authenticity & Character
The gorgeous views
Location
It was easy to walk to good restaurants and to great hikes!
Staff
The staff was so sweet, we really like Mena at the front desk, so welcoming and sweet!
Cleanliness & Comfort
Water temps, and better towels, deck furniture could be improved!
Santana Beach Suites
Naxos

The view was gorgeous and the staff was so nice! The breakfast was so delicious!

Authenticity & Character
Great views!
Location
Beautiful view, but you did have to take a rather expensive cab ride to town!
Staff
They were so helpful, when we were having trouble with the internet!
Cleanliness & Comfort
Nice and clean!
Athenian Riviera
Vouliagmeni

It was perfect for one night in Athens, clean and in a good area to walk to restaurants!

Authenticity & Character
It had a very nice breakfast buffet!
Location
It was easy to walk to nice restaurants!
Staff
They were very helpful!
Cleanliness & Comfort
The beds were comfy!
Activity Reviews
Acropolis Beat-the-Crowds Discovery Walk
Acropolis Beat-the-Crowds Discovery Walk
Athens

It was nice to have a guide to learn about all the history at the Acropolis! It was a tiny bit to understand where to meet, but not a huge problem as they were very responsive on What's app!

Quality of Experience
She was very nice and easy to understand!
Guides, Drivers and Staff
Her knowledge!
Transport
Sunset Caldera Catamaran Cruise
Sunset Caldera Catamaran Cruise
Santorini

It was fun to be on a boat and the food was very good! We had a fun time talking to other guests. You could tell that the guides do lots of boat trips a day and were a little systematic in all there interactions with us!

Quality of Experience
It was an awesome place to watch the sunset!
Food
Good food and plenty of it, for our teen boys!
Guides, Drivers and Staff
They were okay, not very personable!
Transport
It was a very nice bus, just a scary ride!
Private Island Villages & Akrotiri Day Trip
Private Island Villages & Akrotiri Day Trip
Santorini

We loved getting to see so many things on the island so quickly! Our guide was a local, so he was very knowledgeable about everything on the island!

Quality of Experience
The local guide
Guides, Drivers and Staff
He was passionate about his job!
Transport
Nice clean big van!
Self-Guided Hike From Fira to Oia
Self-Guided Hike From Fira to Oia
Santorini

Gorgeous!

Quality of Experience
Naxos Sea Cave Kayaking Adventure with Transfers
Naxos Sea Cave Kayaking Adventure with Transfers
Naxos

We had so much fun on this excursion! The guides were awesome and we had a great day!

Quality of Experience
The guides were awesome!
Guides, Drivers and Staff
Very nice, knowledgeable and welcoming!
Transport
Niktarous was so nice and fun to talk to on the ride over!
Self-Guided  Apeiranthos Trip
Self-Guided Apeiranthos Trip
Naxos
Quality of Experience
Self Guided Beach Time in Naxos
Self Guided Beach Time in Naxos
Naxos

We rented a car and drove all around the island we had a fun day exploring the island

Quality of Experience
It was nice to have a free day to just explore the island!
Private Culture Walk with Food Tastings & Tavern Meal
Private Culture Walk with Food Tastings & Tavern Meal
Naxos

Our guide was so knowledgeable and kind, we had fun learning about the history of Naxos and eating the traditional foods!

Quality of Experience
Our guide was so nice, personable and knowledgeable!
Food
We liked the local cheese, the Orange Cake, and the traditional dishes!
Guides, Drivers and Staff
She was used to dealing with kids!
Transport
Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on Apr 21, 2026

This feedback is so helpful, Alicia! I'm so glad you and your family had a blast exploring Greece and valued the trip we designed together. Thank you for sharing the details about Above Blue Suites. 🙌

They took extremely good care of us.
Greece | Mar 24 - Mar 28, 2026

Don
Don W.
San Jose, CA | Reviewed on Apr 18, 2026
Whenever working with a company for the first time, there's always a bit of nervousness. Siena and the team soon made those jitters fade away. We told her what we wanted to do, and after asking a few more questions to paint the full picture, she planned an amazing trip for us. All guides were excellent. The accommodations were excellent. Always picked up at the time promised (I can't tell you how many times we've waited at the airport for our prearranged ride, only to have noone show up).... Read more

Whenever working with a company for the first time, there's always a bit of nervousness. Siena and the team soon made those jitters fade away. We told her what we wanted to do, and after asking a few more questions to paint the full picture, she planned an amazing trip for us. All guides were excellent. The accommodations were excellent. Always picked up at the time promised (I can't tell you how many times we've waited at the airport for our prearranged ride, only to have noone show up). Anyway, Siena and her team were in constant contact with us and also had a final zoom meeting prior to our adventure, just to go over everything on last time. Our experience in Meteora was lovely, as was our first (and not last) experience with Kimkim. We are well traveled and I can wholeheartedly recommend this company and the wonderful experience they put together for us.

Hotel Review
Divani Hotel Meteora
Kalampaka

The hotel as extremely attentive to our needs. Nice pool and workout area, as well and wonderful breakfasts and a pleasant bar. Perfectly located with nice views of the monasteries.

Authenticity & Character
Location
Everything is within walking distance
Staff
Very attentive and helpful
Cleanliness & Comfort
Rooms our nice. We had a nonsmoking room, but could still smell remnants of smoke. Without even asking, they moved us as soon as we mentioned it. Problem solved.
Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on Apr 21, 2026

It was an honor supporting you and Vivian on this trip! I'm so happy you enjoyed your time in Meteora and that the guides, transfers, and hotel were on point. Hopefully you'll be ready for a return visit to Greece in the near future!

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.