Greek Islands Custom Trips

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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.

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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 39 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 50 mins 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 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...

read more...
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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

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
Read all Greece reviews

Wonderful trip to Greece!
Greece | May 9 - May 18, 2026

J
Jeff S.
Atlanta, GA | Reviewed on May 20, 2026
All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets... Read more

All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets involved in the trip it was amazing that everything worked exactly as planned. The Kim Kim app with the itinerary, contact names and phone, tickets etc along with the chat feature was tremendously useful. The hotels were great, the drivers were prompt and courteous, the guides were knowledgeable and very easy/flexible to work with. I can’t say enough good things — probably the best trip that we’ve ever taken and Kim Kim was a key contributor. Will definitely use them in the future.

Local specialist: Siena Mueller
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Athens/Paros/Santorini, Greece
Greece | May 9 - May 17, 2026

Kathleen
Kathleen C.
Ashburn, VA | Reviewed on May 20, 2026
From the very first interaction I had with KimKim, I was very pleased. The right questions were asked to create the perfect plan to explore Greece. Every detail discussed about the trip played out flawlessly each day. The travel team was also very responsive before and during the trip (we had to change one of our excursions) and it was cared for and our itinerary was updated in less than an hour! This was a trip of a lifetime and I am so grateful that KimKim made my dream a reality. Read more

From the very first interaction I had with KimKim, I was very pleased. The right questions were asked to create the perfect plan to explore Greece. Every detail discussed about the trip played out flawlessly each day. The travel team was also very responsive before and during the trip (we had to change one of our excursions) and it was cared for and our itinerary was updated in less than an hour! This was a trip of a lifetime and I am so grateful that KimKim made my dream a reality.

Activity Reviews
Morning Caldera Catamaran Cruise
Morning Caldera Catamaran Cruise
Santorini
Quality of Experience
Food
Guides, Drivers and Staff
Transport
Traditional Vineyards & Wine Tasting Experience
Traditional Vineyards & Wine Tasting Experience
Santorini
Quality of Experience
Guides, Drivers and Staff
Transport
From Olive Groves to Vineyards: A Culinary Journey Through the Peloponnese
From Olive Groves to Vineyards: A Culinary Journey Through the Peloponnese
Athens
Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Siena Mueller
Read all Greece reviews
See more trip reviews by kimkim travelers

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.