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Tours Europe GreeceSantorini

Santorini Sailing Tours & Trips

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

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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 trip is unbelievably fantastic. Two of the best rides of my life, were on this tour. The guides were very good and this was just the start, when we met them, at the hotel in Cortina. Cortina was the site of the 1956 Olympics, and is a small pretty village. Nothing was open the two nights we were there, so probably bad timing. Hotel was a typical ski village hotel, good Italian/German food, and very comfortable. Second day of biking was up an old railroad spur that is now a ski trail about 15-20 K up to a mountain pass called Cimabanche Pass, which is beautiful. We rode up in a snow storm, then rain, then finally clear skies. This was the number two best ride of my life. Starting out from the hotel in Cortina, up the old spur, through single track bike trails, past babbling brooks, up to this fabulous mountain pass. This is now where the fun starts. Mostly downhill on paved roads very little traffic, at good speeds, through the most spectacular valleys you would ever see on a bike ride. Breathtaking. It had to end back at the hotel for a big dinner. The best ride of my life was the last biking day out of Merano. We were bused up 1500 K, about 85-90 miles to Lake Resia, high up in the Dolomites, then rode around the lake, down, back to Merano. High mountain peaks, many valleys,small towns, many grape growing farms, scenery, the best, and cool brisk weather. This was truly a great bike tour, one I will never forget. The trip is rated easy, but maybe easy/moderate is closer. The Hotel in Merano is excellent, middle of old town, modern, has a thermal bath, rooms were very good. The town of Merano is a must see if in the area, small, beneath the high mountains of the Dolomites, good restaurants, lots of tourists."

Trip dates & details

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7 days From$3,845

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Greek Island Hopper

By Interrailing Packages

Local Expert

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

4.8/5 Excellent

100+ reviews

Self-Guided / Independent Tour

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Athens, Mykonos, Santorini

Highlights

Discover the captivating capital of Greece, exploring the ancient history, and modern charm.
Experience the ultimate vacation in stunning Mykonos
Visit Santorini
Greek island hopping

Themes

Cultural, High Adventure, Nature & Wildlife, Sailing, Photography

What travelers are saying

"Los funcionarios de Interraling son excelentes personas y atienden las inquietudes a tiempo y con amabilidad. Nos ayudaron a organizar nuestras vacaciones familiares en Europa, de acuerdo a nuestras solicitudes, las cuales llenaron todas nuestras expectativas. Gracias a ustedes disfrutamos al máximo este viajes. Las salidas de los trenes fueron en el horario previsto y los hoteles buenos y bien ubicados."

Trip dates & details

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-26%$2,121

14 days From$1,571

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Sailing Greece - Mykonos to Santorini

By G Adventures

preferred

2/5 Disappointing

100+ reviews

Small Ship Cruise

Why we love them

They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Mykonos, Paro, Santorini

Highlights

Explore the beautiful southern cyclades by sailboat
Stop at small off-the-beaten-path islands along the way
Relax on white-sand beaches
Try your hand at sailing (or just relax on the deck)
Stroll through local villages and sample traditional greek food and wine

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details

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-29%$1,881

8 days From$1,343

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Sail Greece: Santorini to Mykonos

By Intrepid Travel

premier

4.8/5 Excellent

100+ reviews

Small Ship Cruise

Why we love them

They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Akrotiri, Mykonos, Santorini

Highlights

Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean and sleeping aboard a yacht
The blue and white villages of Santorini may cling to the rim of an ancient volcano, but the only fire you’ll see is in the island’s magnificent sunsets
In the sleepy fishing villages of the Small Cyclades islands, you’re more likely to break bread with a local than a tourist
A taste of rural life on the large island of Navos is a mix of historic neighbourhoods and Kitron liqueur
Stylish Mykonos is a place where Europe’s chic and beautiful come to play – offering an exclusive, boutique feel to the island

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details

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-41%$2,210

8 days From$1,301

Health Safety +

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Greece Sailing Adventure: Cyclades Islands

By Intrepid Travel

premier

5/5 Excellent

100+ reviews

Small Ship Cruise

Why we love them

They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Mykonos, Santorini

Highlights

A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Themes

Small Ship Cruise, Sailing

What travelers are saying

Trip dates & details

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-41%$3,096

10 days From$1,814

Health Safety +

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Sail Greece: Mykonos to Santorini

By Intrepid Travel

premier

4.5/5 Excellent

100+ reviews

Small Ship Cruise

Why we love them

They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Mykonos, Santorini

Highlights

What better way to tour the iconic Cyclades Islands than by yacht? Swim in the Aegean Sea off the side of the boat and let the waves rock you to sleep each night
Chic waterfront bars line the beaches of Mykonos, serving authentic Greek food and cocktails as the sun goes down. This is a great place to eat well and relax
Wedged between the dramatic cliffs of Amorgos, the 11th-century monastery of Moni Hozoviotissis is a unique site for exploration
Santorini has some of the most distinctive and attractive landscapes in the world. Pass bleached-white villages that cling to plunging cliffs and along the rim of a volcano
The remote Small Cyclades islands are chock-full of tavernas serving fresh seafood, far away from tourists and the rest of the world

Themes

Small Ship Cruise, Sailing

What travelers are saying

Trip dates & details

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-39%$2,210

8 days From$1,347

Health Safety +

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Sailing Greece - Santorini to Athens

By G Adventures

preferred

4.8/5 Excellent

100+ reviews

Small Ship Cruise

Why we love them

They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Aegina, Athens, Hydra, Mykonos, Paro, Santorini

Highlights

Relax on white-sand beaches and swim in brilliant turquoise water
Test your hand at sailing or just relax on the deck
Wander through whitewashed villages
Taste traditional greek food and wine
Hike to spectacular viewpoints

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

Trip dates & details

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-46%$3,674

15 days From$1,967

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Sailing Greece - Santorini to Santorini

By G Adventures

preferred

4.8/5 Excellent

100+ reviews

Small Ship Cruise

Why we love them

They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Mykonos, Paro, Santorini

Highlights

Sail through the pristine waters of the greek islands aboard a yacht
Capture the ultimate greek snapshot on santorini
Wander through whitewashed villages on paros
Enjoy the party on mykonos
Discover venetian architecture on naxos

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

Trip dates & details

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-38%$2,407

10 days From$1,504

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Santorini Reviews & Ratings

4/5 Great

333 Reviews

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Trusted Customer

Oct 2023

Written on

Greek Island Wanderer

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

Tour: Greek Island Wanderer

Lesley

Oct 2023

Written on

Greek Island Wanderer

The walks were particularly lovely

Tour: Greek Island Wanderer

Cynthia

Oct 2023

Written on

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...

Tour: Greek Island Wanderer

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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 191 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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