Greek Islands Custom Trips

plan and book your tailor-made trip with a local travel specialist
How kimkim works  
Our local travel specialists have been recommended by

Travelers love kimkim

- ., traveled to in
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.

See more travel articles about Greece
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 Penny Vasileiadi
active 1 day 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...
Travel specialist Chris Gravas
active 45 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...

read more...
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...

read more...
Travel specialist Eirini Tzoka
active 3 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...

read more...
See all Greece travel agents

Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

We had a fantastic time. Diving for Sea Urch...
Greece | May 21 - May 30, 2026

Noelle
Noelle S.
Belmar, NJ, USA | Reviewed on Jun 03, 2026

We had a fantastic time. Diving for Sea Urchins was incredible and super tasty!

Local specialist: Erica Gerakos
Read all Greece reviews

Everything about the trip was outstanding
Greece | May 17 - May 26, 2026

K
Ken W.
Dallas, TX | Reviewed on Jun 02, 2026
Everything about the trip was outstanding from a planning, support, and vendor perspective. Angela was on top of every aspect throughout the trip with boarding passes, drivers, and lodging preparation. The app with the agenda was a tremendous help. Read more

Everything about the trip was outstanding from a planning, support, and vendor perspective. Angela was on top of every aspect throughout the trip with boarding passes, drivers, and lodging preparation. The app with the agenda was a tremendous help.

Hotel Reviews
Sole d'oro Luxury Suites
Santorini

Hot tubs on roof were amazing and used nightly! In our two bedroom suite, bathrooms were outside the rooms.

Authenticity & Character
Location
Walking distance from Oia town center.
Staff
Cleanliness & Comfort
Antony Suites
Naxos

The multi-levels within the room was a bit tricky. 3 steps between bed and bathroom and bed and shower.

Authenticity & Character
Location
Near town and beach
Staff
Cleanliness & Comfort
Eiriana Suites
Milos

Beautiful hotel, no extra frills, but perfect for our trip.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Sweet Home Hotel
Athens

Easy walk to key sites.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Athens Highlights Mythology Tour
Athens Highlights Mythology Tour
Greece

Size of the party was too big for the guide to adapt for needs of individuals. Left a member of our party behind when they went to the WC. They never caught back up with the tour.

Quality of Experience
Guides, Drivers and Staff
Explore the South Coastline of Santorini with kayaks - Sunset including dinner in a Taverna!
Explore the South Coastline of Santorini with kayaks - Sunset including dinner in a Taverna!
Santorini

Incredible tour. The guide was fun and elevated the trip to the capabilities of the guests.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Caldera Hike (Day or Sunset) with meal 2026
Caldera Hike (Day or Sunset) with meal 2026
Santorini

This and the kayak tour were the highlights of the trip. The guide was amazing and tremendous fun.

Quality of Experience
Guides, Drivers and Staff
Transport
Aegean Lush Bike tour
Aegean Lush Bike tour
Naxos

Beautiful scenery

Quality of Experience
Guides, Drivers and Staff
Naxos Town Food Tour - afternoon with dinner
Naxos Town Food Tour - afternoon with dinner
Naxos

Guide was the highlight of this activity. Scenery was great, food good, walk fun.

Quality of Experience
Guides, Drivers and Staff
The guide's stories and experience were much of the fun.
Full Day Sailing Tour Around Milos (Catamaran from Adamas)
Full Day Sailing Tour Around Milos (Catamaran from Adamas)
Greece

Great staff that tried real hard. Very rough seas made the trip very tough for half our party.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Local specialist: Angela (Angeliki) Giannioti
Angela (Angeliki)
Angela (Angeliki) Giannioti
Local specialist in Greece | Replied on Jun 03, 2026
Thank you so much, Ken. It was truly a pleasure helping you and your family plan this journey through Athens, Milos, Naxos, and Santorini. I'm delighted to hear that the trip came together so smoothly and that the itinerary app, accommodations, activities, and local teams helped create such a memorable experience. Knowing that the kayak adventure and caldera hike became highlights of the trip is especially wonderful to hear. I also appreciate your thoughtful feedback regarding the Athens... Read more

Thank you so much, Ken.

It was truly a pleasure helping you and your family plan this journey through Athens, Milos, Naxos, and Santorini.

I'm delighted to hear that the trip came together so smoothly and that the itinerary app, accommodations, activities, and local teams helped create such a memorable experience. Knowing that the kayak adventure and caldera hike became highlights of the trip is especially wonderful to hear.

I also appreciate your thoughtful feedback regarding the Athens tour experience. Feedback like this is incredibly valuable and helps us continue improving the journeys we create for future travelers.

Thank you again for your trust throughout the planning process. It was a pleasure working with you, and I hope we have the opportunity to welcome you back to Greece again one day.

Warm regards,

Angeliki
GA Trips

Read all Greece reviews

We had a week's trip to Greece and I had a pl...
Greece | May 24 - May 31, 2026

M
Madhu L.
Canada | Reviewed on Jun 02, 2026
We had a week's trip to Greece and I had a pleseant experience with Gustavo in planning my iterinery and taking all the requirments and wishlist into account. The overall trip was relaxing and well planned, except few hiccups on two days but that was more of a miscommunication than any delibrate fault. Kids loved the historic visits, cruise and the cats!! Read more

We had a week's trip to Greece and I had a pleseant experience with Gustavo in planning my iterinery and taking all the requirments and wishlist into account. The overall trip was relaxing and well planned, except few hiccups on two days but that was more of a miscommunication than any delibrate fault. Kids loved the historic visits, cruise and the cats!!

Hotel Reviews
Grand Ambassador Aegean Luxury
Santorini

Awesome property with all amenities like private pool, full fledged kitchen, laundry and room cleaning services. Locaton is beautiful. We were staying in a 2 bedroom suite, Rooms are build with good amaneties but cave like appearence. The only issue I had there were the slippery stairs as i fell down on one of those during my stay. Staff was notified and they are pretty open to the feedback, so hope they work on it as it is safety realted issue.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Stairs are little slippery even without water with the slippers on
Paros Comfy Suites
Naousa Paros

A comparitevely new hotel with minimum waste policy, so they provide thermos to the guests with drinking water dispensor at different places on the property. Beutiful loaction with private beach and pools with some rooms. The are still working towards their kitchen , so breakfast options are not enough, but everything is made on demand.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Athens Manor Houses
Athens

In the heart of the city, everything is at walkable distance. Room and Breakfast was as expected. But USP would be its location.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Local specialist: Gustavo Camperos
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.