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 Penny Vasileiadi
active 10 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...

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Travel specialist Chris Gravas
active 9 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 Eirini Tzoka
active 9 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 5 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

Greece 2026
Greece | May 29 - Jun 9, 2026

S
Stacey W.
Ashburn, VA | Reviewed on Jun 11, 2026
Angela did an amazing job planning our trip! She paid attention to every detail, provided thoughtful recommendations, and kept everything organized from start to finish. Her communication was excellent, and she made the entire planning process stress-free. I highly recommend her! 😊 Read more

Angela did an amazing job planning our trip! She paid attention to every detail, provided thoughtful recommendations, and kept everything organized from start to finish. Her communication was excellent, and she made the entire planning process stress-free. I highly recommend her! 😊

Hotel Reviews
Secret Path Luxury Villas
Santorini
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Cosmos Boutique Hotel
Naxos
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Urban Stripes Athens
Athens
Authenticity & Character
Location
Staff
Cleanliness & Comfort
The hot water in the shower was scarce.
Local specialist: Angela (Angeliki) Giannioti
Angela (Angeliki)
Angela (Angeliki) Giannioti
Local specialist in Greece | Replied on Jun 11, 2026

Thank you so much, Stacey, for your kind words and for trusting me with your Greece journey.

It was a pleasure helping bring your trip to life, and I'm delighted to hear that the planning process felt smooth and stress-free. Creating personalized experiences and taking care of the details so travelers can simply enjoy the journey is exactly what I strive for.

Thank you again for your trust, and I hope the memories from Greece stay with you for years to come.

Wishing you many more wonderful adventures ahead!

Warm regards,
Angela

Greece is Timeless
Greece | Jun 1 - Jun 10, 2026

Leroy
Leroy R.
Ashburn, VA | Reviewed on Jun 11, 2026
Our 10-day journey through Greece was the perfect way to celebrate our 20th wedding anniversary. From the moment we arrived until our final sunset in Santorini, every detail was thoughtfully planned by Marianna, who created an experience that balanced history, culture, adventure, relaxation, and unforgettable memories. Over the course of our trip, we visited Athens, Milos, and Santorini, accumulating an impressive 101,721 steps along the way. Somewhere between climbing the Acropolis,... Read more

Our 10-day journey through Greece was the perfect way to celebrate our 20th wedding anniversary. From the moment we arrived until our final sunset in Santorini, every detail was thoughtfully planned by Marianna, who created an experience that balanced history, culture, adventure, relaxation, and unforgettable memories.

Over the course of our trip, we visited Athens, Milos, and Santorini, accumulating an impressive 101,721 steps along the way. Somewhere between climbing the Acropolis, wandering the historic streets of Athens, exploring the breathtaking beaches of Milos, enjoying food tours through local neighborhoods, sailing through the Santorini caldera, and completing the famous caldera hike, I began to appreciate the wisdom of the Greek philosophers. Socrates encouraged us to examine life. Greece gave us 101,721 opportunities to do exactly that.

Athens was the perfect introduction to Greece. Standing atop the Acropolis and looking across a city that has shaped Western civilization for thousands of years was both humbling and inspiring. Our food tours introduced us to the flavors that define Greek culture, where every meal felt less like dining and more like participating in a tradition that has been passed down through generations.

Milos captured our hearts with its authentic charm and stunning natural beauty. We spent hours exploring picturesque villages, relaxing on extraordinary beaches, and discovering hidden corners of the island. One of the highlights was visiting the beautiful castle overlooking the island, where the panoramic views of the Aegean Sea created one of those rare moments that no photograph can fully capture.

Santorini provided a spectacular finale. Sailing through the caldera offered a unique perspective of the island’s dramatic volcanic landscape, while the caldera hike rewarded us with some of the most breathtaking views we have ever experienced. Every turn seemed to reveal another scene worthy of a postcard.

Beyond the scenery and historic sites, what impressed us most were the Greek people themselves. Everywhere we traveled, we met individuals who were deeply proud of their heritage and genuinely eager to share it. Whether speaking with local guides, restaurant owners, shopkeepers, or fellow travelers, we experienced a level of warmth and hospitality that made us feel welcomed rather than simply accommodated. Their love for their history was contagious, and their stories brought every destination to life.

Of course, no trip to Greece would be complete without experiencing its culinary staples. Fresh seafood, local cheeses, traditional pastries, olive oil, and dishes prepared from recipes perfected over generations became highlights of our daily adventures. Every meal was an opportunity to learn something new about the culture.

As Aristotle wrote, “Pleasure in the job puts perfection in the work.” That perfectly describes Marianna’s approach to planning this trip. Her attention to detail, responsiveness, and thoughtful recommendations transformed a vacation into a once-in-a-lifetime anniversary celebration.

We returned home with incredible memories, a deeper appreciation for Greece’s remarkable history and culture, and 101,721 steps worth of stories. For anyone considering a journey to Greece, I cannot recommend Marianna and Kimkim highly enough.

Hotel Reviews
Agali Houses
Firostefani 00

Agali Houses delivered a flawless experience from check-in to check-out. The hospitality was exceptional, with a team that was welcoming, attentive, and genuinely committed to making every moment special. The rooms were stunning. Spacious, elegant, and beautifully designed, they perfectly captured the charm and aesthetics of Santorini while providing every modern comfort imaginable. Every detail was thoughtfully considered, creating an atmosphere that felt both luxurious and relaxing. The sunsets were simply unforgettable. Somehow, each evening’s view seemed even more breathtaking than the one before. Watching the sun melt into the Aegean Sea became the highlight of every day and a memory we will cherish for years. The room offered every creature comfort we could ask for, making it easy to unwind and enjoy the beauty surrounding us. Each morning, breakfast was a wonderful bonus, featuring fresh, delicious selections that started every day on the perfect note. Agali Houses is more than just a hotel. It is an experience defined by beauty, comfort, and world-class hospitality. If you’re visiting Santorini and looking for an unforgettable stay, this is the place.

Authenticity & Character
Views, Staff Attentiveness, Quality is unmatched!
Location
Perfect, you could stay in the hotel and not leave and you would have the best vacation of your life. Each night a sunset or spectacular than the last.
Staff
Staff were great! I need reservations, I received the best seat at the restaurant. The staff will make you feel as though you are the star!
Cleanliness & Comfort
En Milo
Milos
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Perianth Hotel
Athens

Absolutely amazing location and the hospitality to match. The accommodation was perfect, and a chocolate left on our bed each night made us feel special. Great location near everything and breakfast was fantastic each morning.

Authenticity & Character
Location
Center of everything you want to do or visit.
Staff
Cleanliness & Comfort
Staff was amazing!
Activity Reviews
Flavors of Athens Food Tour
Flavors of Athens Food Tour
Athens
Quality of Experience
Food
Guides, Drivers and Staff
Transport
Athens Highlights
Athens Highlights
Athens
Quality of Experience
P
Guides, Drivers and Staff
Transport
Local specialist: Marianna Loupou
Marianna
Marianna Loupou
Local specialist in Athens | Replied on Jun 11, 2026

Dear Leroy,

Reading your beautiful words truly made my day! I’m so honored that your 20th anniversary in Greece was filled with memorable moments, laughter, and discovery and 101,721 steps is incredible!

Thank you so much for trusting me with such an important milestone. Knowing that this journey gave you both moments to reflect, laugh, and explore together is the highest compliment I could receive. Greece has a way of inspiring the soul and I’m so happy it left its mark on yours.

Thank you again and I wish you all the very best!

Warmest wishes,
Marianna

My Daughter and I have just returned from the...
Greece | Jun 1 - Jun 8, 2026

K
Katrina D.
United Kingdom | Reviewed on Jun 10, 2026
My Daughter and I have just returned from the most amazing vacation to Greece that was booked through KimKim and was organised and taken care of 100% by Eirini.
We have loved Mamma Mia the movie and show since we saw it, my Daughters dream has been to go to Skiathos and Skopelos so Eirini made it happen. We explained what we wanted and Eirini came back with the most amazing trip that we have ever been on. Every step of the way was perfect starting off in Athens bring picked up from...
Read more

My Daughter and I have just returned from the most amazing vacation to Greece that was booked through KimKim and was organised and taken care of 100% by Eirini.
We have loved Mamma Mia the movie and show since we saw it, my Daughters dream has been to go to Skiathos and Skopelos so Eirini made it happen. We explained what we wanted and Eirini came back with the most amazing trip that we have ever been on. Every step of the way was perfect starting off in Athens bring picked up from the airport and taken to The Foundry suites. We met the beautiful Elena who was our tour guide for the afternoon at the Acropolis and ending at one of the red that Eirini had recommended that we loved.
We were picked up and dropped off to every location along the way. In Skiathos we had a private boat tour around Skopelos and Skiathos stopping along the way to swim if we wished, take in the sights and having an amazing lunch cooked by the captain.
Then a ferry over to Skopelos for three nights staying at Minno and having again an amazing tour of all the Mamma Mia filming sites before enjoying the afternoon on Kastani beach. We had plenty of time to relax even though it was a full on trip. We’ve made the most amazing memories.
I will be booking a holiday again through Kimkim and will be reaching out to Eirini for our next adventure to Greece.

Thank you Eirini for all that you did for us

Hotel Reviews
Elia Ermou Athens Hotel
Athens

Wow, think we had one of the best views in the hotel overlooking the Acropolis

Authenticity & Character
Location
Right where we wanted to be, the vibe was great
Staff
Great check in and the restaurant on the roof was breath taking. Again the views were amazing.
Cleanliness & Comfort
Minno Boutique Hotel & Spa
Skopelos

Absolutely loved this hotel, beautifully decorated. Our room was a really lovely size with lots of storage and a balcony overlooking the harbour and pool.

Authenticity & Character
This is Wyeth I’d expect from a new hotel, modern, but still has the charm of Greece
Location
Not even 10 mins walk into the town
Staff
They need more staff! We had the most amazing welcome from the front desk and there if you ever needed help. The only thing that let the stars down and not receiving a five was the lack of staff around the pool and restaurant. The food was amazing, but It would be great if during breakfast you were able to get your own tea and coffee rather than having to wait for a staff member to order one. It’s all an easy fix
Cleanliness & Comfort
Could not fault it at all
Thalassa Collection Skiathos
Skiathos
Authenticity & Character
Our room was a nice size with a balcony overlooking the gardens. Had everything that you needed just wish they proper coffee in the room and not instant.
Location
It’s a short walk to the port where all the lovely restaurants are, shops etc and the Ferry
Staff
Cleanliness & Comfort
The Foundry Suites
Athens

We loved it here, totally my vibe. Not too far away from the Acropolis. Staff were lovely too

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Mamma Mia & Skopelos Highlights tour
Mamma Mia & Skopelos Highlights tour
Skopelos

What a great tour guide, took us to exactly where we wanted to go and didn’t give us a time limit when we stopped at locations. He also gave us the choice of where we wanted to stop at the beach giving us lots of options of where to go.

Quality of Experience
Guides, Drivers and Staff
Transport
Sailing trip around Skiathos
Sailing trip around Skiathos
Skiathos

Great hosts. Offered drinks and snacks through out our time on board. The lunch that was made for us was amazing.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Acropolis guided tour
Acropolis guided tour
Athens

Elena was the perfect tour guide, such a lovely human being and so knowledgeable about the history of Greece. We really enjoyed our time with Elena.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Eirini Tzoka
Eirini
Eirini Tzoka
Local specialist in Athens | Replied on Jun 10, 2026

Thank you so much for your wonderful review, dear Katrina!
It was truly a pleasure helping you and Hannah plan this special Mamma Mia adventure and I'm so happy to hear that every part of the trip met your expectations and created such memorable memories for both of you.
Knowing that we were able to make your daughter's dream of visiting the Mamma Mia filming locations come true means so much to me. I'll be sure to pass along your compliments to Elena!
I look forward to helping you plan your next Greek adventure whenever you're ready!❤️
Wishing you all the very best,
Eirini

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.