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Tours Europe GreeceSantorini

Santorini Sailing Tours & Trips

190 Santorini trips. Tours from 65 tour companies. 333 reviews. 4/5 avg rating.

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Rushing in the Cyclades: A trip to Athens, Paros & Santorini

By Eros and Psyche Travel

preferred

5/5 Excellent

27 reviews

Private Guided

Why we love them

The husband-and-wife team behind Eros and Psyche specializes in couples' travel to Greece.

Lodging level

Luxury - 5 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Acropolis, Akrotiri, Athens, Parthenon, Santorini

Highlights

Tasting authentic Greek flavors in a fun and relaxing environment.
Catching one of the famous Santorini sunsets from the caldera cliffs.
Enjoying swimming and snorkeling in the deep blue waters of the Aegean.
Marveling at breathtaking views of the rural landscape from your private balcony.
Taking guided tours around the Acropolis & the Acropolis Museum.

Themes

Cultural, Sailing

What travelers are saying

"We always felt taken care of if we had any questions or changes needed, and we felt so relieved to have most of the logistics all planned for us on our honeymoon to Greece so we could relax and enjoy!"

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-12%$1,165

7 days From$1,023

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The best of Cyclades: Athens, Paros, Naxos & Santorini

By Eros and Psyche Travel

preferred

5/5 Excellent

27 reviews

Private Guided

Why we love them

The husband-and-wife team behind Eros and Psyche specializes in couples' travel to Greece.

Lodging level

Luxury - 5 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Acropolis, Akrotiri, Athens, Parthenon, Santorini

Highlights

Admiring the vast historical interest of Athens
Catching a romantic sunset in the magical Portara of Naxos
Reveling in the comfort of the high-end mattresses and plush bedding.
Relaxing and sunbathing at the impressive swimming pools of the hotels.
Discovering the beauty of the Cyclades islands through a sailing trip in Santorini.

Themes

Cultural, Sailing

What travelers are saying

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-12%$1,748

14 days From$1,534

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Giving in the hype: Athens, Mykonos & Santorini

By Eros and Psyche Travel

preferred

5/5 Excellent

27 reviews

Private Guided

Why we love them

The husband-and-wife team behind Eros and Psyche specializes in couples' travel to Greece.

Lodging level

Luxury - 5 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Acropolis, Akrotiri, Athens, Mykonos, Parthenon, Santorini

Highlights

Cherishing romantic moments on the most beautiful beaches of the country.
Delighting in a sunset wine experience in Santorini.
Taking guided tours around the Acropolis & the Acropolis Museum.
Enjoying caldera views from your luxury suite in Santorini.

Themes

Cultural, Sailing

What travelers are saying

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-12%$1,230

9 days From$1,080

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Yolo Yachting - Santorini to Mykonos

By Sail in Greece

preferred

4.7/5 Excellent

100+ reviews

Small Ship Cruise

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Visits

Mykonos, Santorini

Highlights

World famous clubs and wild parties (Mykonos)
Memorable adventures
Traditional vintage cruise ships
Experienced local tour leader

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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-36%$529

8 days From$339

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Yolo Yachting - Mykonos to Santorini

By Sail in Greece

preferred

3.9/5 Great

100+ reviews

Small Ship Cruise

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Flexible schedule

Visits

Mykonos, Santorini

Highlights

Drive to fascinating Mykonos Island
Explore Paros which is famous for its water sports with wind surfing
Enjoy the Aegean archipelago of Paros
Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

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-36%$529

8 days From$339

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YOLO CRUISE - Mykonos to Santorini

By Sail in Greece

preferred

3.2/5 Average

100+ reviews

Small Ship Cruise

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Flexible schedule

Visits

Mykonos, Santorini

Highlights

Drive to fascinating Mykonos Island
Explore Paros which is famous for its water sports with wind surfing.
Enjoy the Aegean archipelago of Paros
Explore Santorini

Themes

18 - 30's, 50 plus, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

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-42%$516

8 days From$299

Health Safety

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Mykonos Cruise

By Sail in Greece

preferred

4.6/5 Excellent

100+ reviews

Group Tour

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Visits

Delos, Mykonos, Santorini

Highlights

It is best suited for ‘young at heart’ travellers looking for an adventurous Greece sailing trip
some of the most iconic island stops in a round-trip from Athens
blend of on-shore cultural
historical sightseeing
coastal relaxation

Themes

National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

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-100%$558

8 days

Inquire

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Yachting in Greece

By ROW Adventures

premier

5/5 Excellent

81 reviews

Small Ship Cruise

Why we love them

They’ve been recognized by major travel publications for their pioneering adventure travel expertise that spans back to their founding in 1979.

Lodging level

Premium - 4 star

Physical level

Easy

Trip pace

Flexible schedule

Visits

Athens, Delos, Santorini

Highlights

Explore the island of Homer
Visit Santorini
Visit Paros, one of the most beautiful islands of the Cyclades
Explore Myconos - the most cosmopolitan island with dazzling white houses
Visit the church of PARAPORTIANI is considered to be an architectural masterpiece

Themes

High Adventure, Small Ship Cruise, Sailing

What travelers are saying

"I have travelled with ROW numerous times, including four trips on the Rogue River. Every trip has been wonderful and every person associated with ROW has been nice, knowledgeable, professional and fun. The Rogue is a great river and the trip is an excellent one for two people or a large group—and I have done both. I’ve taken both of my kids, one time each, and have organized groups of colleagues twice; most recently in 2019 when 14 of us gathered. The guides at ROW are great and help to make the trip very enjoyable. The scenery, lodging and the wonderful outdoors including warm air and refreshing water, make for a wonderful escape from the everyday routine. The fact that this trip offers beds and indoor plumbing is a nice benefit and allows those who have an aversion to camping a chance to see the wilderness. I have recommended ROW and the Rogue trip more times than I can count and my group has already reserved our trip for 2021. What are you waiting for?"

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-19%$2,085

8 days From$1,695

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Explore

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Greek Island Wanderer

By Explore!

premier

4.6/5 Excellent

100+ reviews

Small Group Tour

Why we love them

They explore a place beyond the typical tourist traps and offer exciting activities that bring the “wow factor” intrepid travelers want.

Lodging level

Premium - 4 star

Physical level

Moderate

Trip pace

Full schedule

Visits

Acropolis, Akrotiri, Athens, Delos, Moni , Mykonos, Paro, Santorini

Highlights

Island hopping between the Cyclades Islands of Syros, Paros, Santorini and Naxos
Visit gleaming waterfront harbours, rocky coves and sandy beaches
Explore the historic capital city of Athens with the chance to visit the Acropolis

Themes

Cultural, Hiking & Walking

What travelers are saying

"Great trip. My only reservation about the leader was that he tended to walk fast & didn’t look behind to see if everyone was keeping up. I nearly got lost on a few occasions The itinerary was good but I’d like a bit more time in scenic areas to look around, not 5 minutes for a photo then a full 30 minute stop later on at a service station for a toilet stop. Also we got into hotels quite early say 4pm whilst we could have arrived later & stopped a bit more on the way We will book on more Explore trips in the future"

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-18%$3,160

14 days From$2,600

Health Safety +

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Walking on the Greek Islands

By Exodus Travels

premier

4.2/5 Great

100+ reviews

Small Group Tour

Why we love them

With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Balanced schedule

Visits

Athens, Santorini

Highlights

Discover the three islands of Naxos, Santorini and Paros
Gentle walks through idyllic scenery and remote villages
Enjoy delicious local Greek cuisine

Themes

Cultural, Hiking & Walking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

Trip dates & details

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-28%$2,828

8 days From$2,025

Health Safety +

Generous cancellation

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Greece: Sparta, Monemvasia & the Peloponnesian Peninsula

By VBT Bicycling Vacations

premier

4.9/5 Excellent

100+ reviews

Group Tour

Why we love them

Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.

Lodging level

Premium - 4 star

Physical level

Extreme

Trip pace

Full schedule

Visits

Athens, Crete, Santorini

Highlights

Uncover the treasures of the hillside medieval gem of Mystras, the Byzantine Empire’s cultural capital for nearly a millennium, with an expert archaeologist-guide.
Savor the recipes and the flavors of ancient Byzantine cuisine during a special dinner.
Walk through the maze of alleyways in the medieval castle town of Monemvasia, a crossroads of civilizations with Byzantine, Frankish, Venetian, and Ottoman influences.
Cruise around the monolithic Rock of Monemvasia.
Join a taverna owner on a shrimp-harvesting excursion, then join him for a cooking lesson and prepare garidopetoules—a savory shrimp pancake.

Themes

Cultural, Cycling & Biking, Nature & Wildlife, Sailing, Photography

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

Trip dates & details

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7 days From$3,845

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Greece Panorama Adventure

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

5/5 Excellent

100+ reviews

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Visits

Acropolis, Akrotiri, Archaeological Museum of Athens, Athens, Epidaurus, Heraklion, Meteora , Mycenae, Olympia, Santorini, Thessaloniki

Highlights

Cook and have lunch with a local family in the Peloponnese
Visit the most important archeological sites of Greece
Experience a speed-boat Private Tour at the sandy beaches of Crete
Hike the Caldera of Santorini
End your trip with a cruise witnessing the most famous sunset of Greece

Themes

Culinary & Wine, Cultural, Education / Learning, Family Friendly, Hiking & Walking, Photography, Scuba Diving

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

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-26%$7,312

19 days From$5,416

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Greece Exclusive: A unique trip to mainland, Santorini & Mykonos

By Greeking.me

preferred

5/5 Excellent

61 reviews

Private Guided

Why we love them

There is no one more passionate or knowledgable about travel to Greece.

Lodging level

Luxury - 5 star

Physical level

Very Easy

Trip pace

Balanced schedule

Visits

Acropolis, Akrotiri, Athens, Corinth, Delos, Delphi, Epidaurus, Mykonos, Parthenon, Santorini, Temple of Apollo

Highlights

Admiring the timeless Parthenon and all other striking monuments of the Acropolis Hill
Standing before the Oracle of Delphi and taking in the mystical ambiance that defines the region
Testing the acoustics of the Epidaurus theater
Basking in the melting sunset of Santorini
Take in the cosmopolitan ambiance of Mykonos

Themes

Culinary & Wine, Cultural

What travelers are saying

""Our trip with Greeking Me completely exceeded our expectations. In booking the trip, Nikos was able to to design our trip exactly to our specifications and it truly was just what we had hoped it would be. We had licensed tour guides for our visits to the Acropolis, ancient Corinth, Nafplio and Mycenae. All three were experts in their field and left no questions unanswered. They were friendly, helpful and we enjoyed our time with each of them. We met our tour leader, Vasiliki on our 2nd night and she, and our driver, Alex, would remain with us until we were dropped off at the airport. We could not not have asked for a better team. We became fast friends and shared many great times together. As we hit inclement weather at the end of our trip, Vasiliki revised our itinerary and added activities that she knew we would enjoy. We fell in love with the mountains of the Peloponnese and visited many of the tiny villages high in the mountains. Our driver, Alex, was from one of these villages, Vytina, and he was kind enough to show us his childhood home, took us for a walk through many beautiful streets and we had lunch at one of his favorite taverns. We all took an unplanned hike up the gorge to the Monastery of Prodomos. An exhilarating (and wet) hike uphill through beautiful forests and breathtaking views. Both of these days were a great part of our trip. The food and wine tasting tours were first rate and we enjoyed each one. Our favorite, however, was the time we spent with Dimitrius and his family at their organic farm and vineyard. After a cooking lesson for cheese bread, we drove up to his vineyards to see his crops. We returned back to his home and had a wonderful Greek feast prepared by his wife and daughter. Others “greats” of the tour: Kapsia caves, simply unbelievable Country cooking class at Arcadiani Agrotourism Collective Church of Agia Theodora What we remember most is the bond we formed with Vasiliki and Alex. They made our trip one we will never forget. They were caring, kind, personable and cared about our every need. Obviously we would recommend this trip to anyone. It was our first trip to Greece, but it won’t be our last.""

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-12%$7,118

12 days From$6,245

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Santorini Reviews & Ratings

4/5 Great

333 Reviews

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Trusted Customer

Oct 2023

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Greek Island Wanderer

Walks were the highlight, especially hike down from hilltop village on Naxos

Tour: Greek Island Wanderer

Lesley

Oct 2023

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Greek Island Wanderer

The walks were particularly lovely

Tour: Greek Island Wanderer

Cynthia

Oct 2023

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Greek Island Wanderer

We had a fabulous Tour Guide who not only looked after us, was very informative but made the holiday lots of fun! We had great weather and a very nice mix of walkin...

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Santorini Tour Selection Trips

Santorini is a common destination for honeymoons - plan a custom trip!
The food in Santorini is heavily seafood based. If you have allergies or an aversion to seafood be sure to let your tour leader know well in advance.
There is much to see beyond the famous postcard destination in the North. Going on a tour will reveal many hidden gems around the entire island that you might not have seen otherwise.
Tours to Greece don't always include Santorini or the islands, and are only focused on the mainland. Be sure to check if you're interested in visiting Santorini!

Additional details

Top Santorini Travel Companies

Intrepid Travel Reviews

G Adventures Reviews

Collette Reviews

Explore! Reviews

Exodus Travels Reviews

Greeking.me Reviews

Eros and Psyche Travel Reviews

Eskapas Reviews

Greece Insiders Reviews

Exoticca Reviews

Topdeck Reviews

Sail in Greece Reviews

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On Travelstride you can find 190 trips to Santorini and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

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