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, 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.

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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
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Chat with a local travel specialist
Work out the details together
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Securely book your trip
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Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Angela (Aggeliki) Giannioti
active 2 hours ago

Angela (Aggeliki) Giannioti

Hi everyone! I am Angela (or as my Greek friends call me, Aggeliki). Let me introduce myself: I am a travel and adventure lover just like you! I work in the travel industry, for a quiet few years...

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Travel specialist Chris Gravas
active 2 hours ago

Chris Gravas

My name is Chris and I have a passion for authentic experiences, cultural awakenings, and nature explorations. As a partner of a local boutique travel agency, I take every chance to explore Greece...

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Travel specialist Chris Leontopoulos
active 13 mins ago

Chris Leontopoulos

Hello, my name is Chris I am Canadian by birth, but my family’s roots can be traced centuries back to two beautiful mountain villages in Greece. One in the shadow of Mount Olympus, and one very...

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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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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

We loved our trip to Greece!
Greece | Oct 7 - Oct 15, 2025

Kate
Kate R.
Stoneham, MA | Reviewed on Oct 16, 2025
We loved our trip to Greece and couldn’t have done it without Erica and Lea and their team! Everything went smoothly and we truly enjoyed participating in all the tours they suggested and planned. We felt like we had a more authentic experience, and especially enjoyed getting to know all the Greek guides and drivers who shared so many stories about their country. From the Foodie and e-bike tours in Naxos to the Alternative Athens neighborhood tour to the Santorini sunset catamaran ride, we... Read more

We loved our trip to Greece and couldn’t have done it without Erica and Lea and their team! Everything went smoothly and we truly enjoyed participating in all the tours they suggested and planned. We felt like we had a more authentic experience, and especially enjoyed getting to know all the Greek guides and drivers who shared so many stories about their country. From the Foodie and e-bike tours in Naxos to the Alternative Athens neighborhood tour to the Santorini sunset catamaran ride, we learned alot about Greece! Naxos is now our favorite island. 😍

Hotel Reviews
Kasimatis by La Perla
Santorini

Incredible place!!! Just gorgeous 💖

Authenticity & Character
A ton of character, a renovated wine cellar space perched on top of the calderon with stunning views of the sea!!🌊
Location
Loved the town of Imeriviglio!! Cute, had everything we needed and quiet.
Staff
Very professional and helpful. Hard workers!
Cleanliness & Comfort
Loved the bathroom and porch with the view the best.
Santana Beach Suites
Naxos

Beautiful view of the Aegean Sea and beach and lovely roofdeck with hot tub. Was a little farther away from Naxos Town than we expected but no worries we figured out the bus system for going back and forth to town for the tours. 😊

Authenticity & Character
Very spacious. A wedding was taking place there on our second day.
Location
Sometimes the bus schedule changed so it was a little tricky but not a big deal.
Staff
Very friendly and helpful.
Cleanliness & Comfort
Water drainage in room could have been a little better. Had to use extra towels.
NLH Monastiraki
Athens

A lovely and extremely comfortable place. We are especially grateful that we could stay another night in our same room after Delta postponed our flight home to Boston the next day. The rooftop view of the Acropolis at night was also stunning and the location perfect to getting to all the sites we wanted to see.

Authenticity & Character
We live small boutique and charming hotels.
Location
Right in the middle of everything!
Staff
All 3 front desk people.
Cleanliness & Comfort
The bed was super comfy with crisp clean sheets and cozy comforter.
Activity Review
Neighborhoods of Athens Discovery Walk
Neighborhoods of Athens Discovery Walk
Athens

Leo was awesome and we learned alot about Athens!

Quality of Experience
Leo was very well spoken and articulate. Spoke excellent English too!!
Guides, Drivers and Staff
Transport
Local specialist: Erica Gerakos
Photo taken by Kate R
Photo taken by Kate R
Read all Greece reviews

Janice told me I had fun and loved everything...
Greece | Sep 18 - Sep 29, 2025

Michael
Michael L.
Los Angeles, CA | Reviewed on Oct 16, 2025
Janice told me I had fun and loved everything ..... and I do not disagree with my wife. Coincidentally, I did love the trip although if she (Janice left out one or two tours ..... so I could rest that would have been nice to.). The islands and guides were memorable although those with thicker accents could have spoken slower and covered less. Overall I would highly recommend KIMKIM. Your responses to all questions were quick and thorough. Read more

Janice told me I had fun and loved everything ..... and I do not disagree with my wife. Coincidentally, I did love the trip although if she (Janice left out one or two tours ..... so I could rest that would have been nice to.). The islands and guides were memorable although those with thicker accents could have spoken slower and covered less. Overall I would highly recommend KIMKIM. Your responses to all questions were quick and thorough.

Hotel Reviews
Avra Hotel
Rafina, Attica

Super small ...... two separate beds pushed together ......

Authenticity & Character
Location
Staff
Desk staff not friendly ..... functional but not friendly
Cleanliness & Comfort
Nival Boutique Hotel
Sifnos

View wonderful. Location ok. To walk to "town" was on a very broken path that we got lost on the first time.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Phos Milos
Pollonia

Room very nice ...... location fine .......

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Elia Zampeliou Hotel
Chania

Location and view great.

Authenticity & Character
Location
Staff
One of the staff was not pleasant to deal with. Never smiled or friendly. The other people were fine
Cleanliness & Comfort
NLH Monastiraki
Athens

Breakfast and location great ...... room for us lazy Americans small.

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Private Delphi Day Trip
Private Delphi Day Trip
Athens
Quality of Experience
Guides, Drivers and Staff
Transport
Ancient Athens Acropolis & Mythology Walk
Ancient Athens Acropolis & Mythology Walk
Athens
Quality of Experience
Guides, Drivers and Staff
Transport
Self-Guided Local Markets Visit
Self-Guided Local Markets Visit
Athens
Quality of Experience
Local specialist: Siena Mueller
Read all Greece reviews

OMG… you guys are terrific! Everything was pl...
Greece | Oct 5 - Oct 13, 2025

Tom
Tom W.
Newark, NJ | Reviewed on Oct 14, 2025
OMG… you guys are terrific! Everything was planned out and all planned activities came off flawlessly. We had many times where pickups and drop offs occurred and everyone met us on time. Loved how Kimkim set up our tours that were all private. Maria in Athens was amazing. Very friendly and knowledgeable. Alexander showed us Mykonos in the four wheel jeep. Great guy! So friendly and showed us beautiful places that tourists don’t usually go. Then on Naxos, we helped prepare the Greek luncheon... Read more

OMG… you guys are terrific! Everything was planned out and all planned activities came off flawlessly. We had many times where pickups and drop offs occurred and everyone met us on time. Loved how Kimkim set up our tours that were all private. Maria in Athens was amazing. Very friendly and knowledgeable. Alexander showed us Mykonos in the four wheel jeep. Great guy! So friendly and showed us beautiful places that tourists don’t usually go. Then on Naxos, we helped prepare the Greek luncheon with Nikos and Constantina. We loved being with them and we found it so hard to leave! Then on to Santorini. Simply spectacular. The sunset cruise was truly a great way to end our trip. Also, a special thanks to the Kimkim team for surprising my wife with flowers and champagne on the boat for our 35th wedding anniversary. You had her crying for joy!
All of your accommodations were first class and located in the perfect locations. Loved how you planned the itinerary….Great job Kimkim . (We are also looking to book our 3rd Kimkim vacation to Morocco…. Hopefully sometime in 2026)

Regards,

Tom and Georgette Walsh

Hotel Reviews
Andronis Luxury Suites
Santorini

Simply amazing. The views will take your breath away,

Authenticity & Character
Staff goes out of their way to accommodate all of your needs. Their restaurant is spectacular with incredible sunset views.
Location
Perfectly located right on the cliff. Steps away from all the local shops,
Staff
Michelle went out of her way to insure we were totally comfortable.
Cleanliness & Comfort
Spotless room…. Hot tub overlooking the Agean Sea was incredible!
18 Grapes Hotel Naxos
Naxos

Great location!

Authenticity & Character
Loved the rooftop restaurant with a magnificent view of the sunset over the mountains
Location
Comfortable short walk through a quaint town to get to the beach,
Staff
So Friendly and accommodating
Cleanliness & Comfort
Beautiful clean room with great views… loved our private hot tub,
Asty Hotel & Spa Mykonos
Mykonos

Located just above the main town.

Authenticity & Character
Location
Steps away from walking to the main town
Staff
All staff members were extremely helpful
Cleanliness & Comfort
Loved the bed…. Super comfortable
xenodocheio Milos
Athens

Centrally located…. Very comfortable and clean

Authenticity & Character
Location
Centrally located
Staff
So very friendly and helpful
Cleanliness & Comfort
Wonderful restaurant on the first floor.
Activity Reviews
Private Sunset Caldera Cruise
Private Sunset Caldera Cruise
Santorini

A must thing to do on Santorini. Our crew took care of all of our needs and took us to beautiful locations. The tour included a delicious Greek barbecue. There was plenty of time to swim and snorkel.

Quality of Experience
Crew members Demetrias and George were great.
Food
Greek salad, grilled chicken, pasta and wine
Guides, Drivers and Staff
Knowledgeable and went of there way to make sure we were having a great time
Transport
Our own 35 foot Yacht! Doesn’t get any better than that
Private Naxian Family Farm Experience & Wood-Fire Cooking Lesson
Private Naxian Family Farm Experience & Wood-Fire Cooking Lesson
Naxos

Constantina started off by giving us a complete tour of the farm and what they grow. The view from the farm was amazing. We helped prepare a luncheon with all fresh food right from the farm. While waiting for the food to cook in an open oven, Constantine and Nikkos entertained us with the history of Naxos. It was a great way to hear about Greek cuisine while drinking home made Rose wine.

Quality of Experience
Knowledgeable and friendly people.
4WD Jeep Island Adventure
4WD Jeep Island Adventure
Mykonos

We had Alexander take us all over Mykonos island. He took us to areas of the island far away from where tourists usually go. Fantastic photo opportunities.

Quality of Experience
Jeep was very clean and the driver provided water for us
Guides, Drivers and Staff
Alexander was very friendly and knew a lot of history about Mykanos
Transport
Private Acropolis & Highlights Walk with Food Tastings
Private Acropolis & Highlights Walk with Food Tastings
Athens

Maria was our guide for six hours. Very friendly and knowledgeable about the history of Athens.

Quality of Experience
Personal guide
Guides, Drivers and Staff
Very knowledgeable
Local specialist: Siena Mueller
Photo taken by Tom W
Photo taken by Tom W
Photo taken by Tom W
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on Oct 15, 2025
Wow — what an amazing review, Tom! Reading this absolutely made my day. I’m so happy everything went off flawlessly and that you loved the mix of experiences across Athens, Mykonos, Naxos, and Santorini. It sounds like you connected with so many wonderful locals — Maria, Alexander, Nikos, and Constantina are all such special people, and I know they’ll be thrilled to hear your kind words. 💛 I’m especially touched that the anniversary surprise made Georgette so happy — that was such a joy for... Read more

Wow — what an amazing review, Tom! Reading this absolutely made my day. I’m so happy everything went off flawlessly and that you loved the mix of experiences across Athens, Mykonos, Naxos, and Santorini. It sounds like you connected with so many wonderful locals — Maria, Alexander, Nikos, and Constantina are all such special people, and I know they’ll be thrilled to hear your kind words. 💛

I’m especially touched that the anniversary surprise made Georgette so happy — that was such a joy for our team to help arrange! Thank you again for trusting me and the Kimkim team with your trip. Trip #3 to Morocco is going to be another unforgettable one!

Read all Greece reviews
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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.