Category Santorini Sailing Trips

Santorini · SANTORINI SAILING TRIPS

The Top 15 Santorini Sailing Trips, Ranked

23 reviewed

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Pickup, Port, and Boarding Rules That Save You Stress

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Volcano sailing and the hot springs swim near Palea Kameni

2.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95Best value

Sunset Oia catamaran cruise with hotel pickup, hot springs and beach swims, snorkeling gear, and onboard BBQ with wine and soft drinks.

“Our Santorini family cruise was an unforgettable experience filled with beauty, adventure, and relaxation. From the moment we set sail, the views of the caldera and whitewashed villages perched on the cliffs were breathtaking. The boat was comfortable and family-friendly, making the journey enjoyable for both adults and children. We explored hidden beaches, swam in crystal-clear waters, and even got the chance to dip into the famous hot springs near the volcano. The kids loved every moment – from spotting fish in the sea to enjoying delicious Greek food on board. The sunset was truly magical – watching the sun slowly sink into the Aegean from the water was the…”

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Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer - Sailing Past the Volcano and Watching Landmarks From the Sea

Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - What you will actually do on the water for five hours

4.Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145

Santorini catamaran sailing with hotel pickup, hot springs swim, Red and White Beaches, and an on-board BBQ with unlimited drinks.

“Such a beautiful and relaxing way to see the island. Highly recommend while in Santorini! Trip included a delicious meal and wine/beer.”

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Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer - White Beach swim time plus a full Greek BBQ on board

5.Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 422 reviews · 5 hours (approx.) · from $133

Luxury Santorini catamaran cruise with hotel transfers, BBQ, open bar, and three swim stops at the hot springs, White Beach, and Red Beach.

“Staff was extremely friendly fly on the boat and we were very well fed!! It’s a smaller boat at the front so not a lot of room to way out and be on your own space, when we got to the point to board the boat we were left waiting for a while because different boats were loading and off loading, it was just a bit random and isn’t mentioned when booking! Other than that it’s a great way to swim in the amazing waters and see the coastline would definitely recommend”

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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

Santorini Caldera Sailing Tour with BBQ Lunch and Drinks - Where pickup fits into the plan (Vlychada Marina, not just “meeting somewhere”)

6.Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $229

Sail Santorini’s caldera by catamaran with swimming, volcanic islands, and a BBQ seafood lunch plus unlimited drinks, with hotel pickup.

“The crew made it very enjoyable. They made sure everyone had enough food and drink. The tour itself was beautiful. The lunch was absolutely delish. I loved it.”

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Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer) - The Caldera Cruise Portion: lighthouse views and volcanic-side sailing

7.Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

★★★★★★★★★★5.0 · 215 reviews · 5 hours (approx.) · from $157

Small-group Santorini catamaran with hotel pickup, Red and White Beach swims, hot springs snorkeling, and a Greek BBQ with drinks.

“Had the best on the water with this group!! Saw so many highlights, amazing Bbq lunch and really loved the crew. Shared our different cultures and love of Greece. A perfect day!!”

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Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers

Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers - Red Beach for sightseeing and a refreshing swim

Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Price and what you get for about $96

Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included

Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included - The Value Secret: Transfers, Drinks, and Dinner in One Bundle

10.Private Sunset Sailing Tour with Dinner, Drinks &Transfer included

★★★★★★★★★★5.0 · 145 reviews · 5 hours (approx.) · from $650

Private Santorini sunset sailing with transfers, unlimited drinks, and dinner. See Red and White beaches, Thirassia, and the caldera.

“George was a terrific host, captain and guide! His boat was very comfortable - much better than a standard catamaran- and he took us to unique spots and a terrific swimming area where it was less crowded. Our meal was delicious and we really enjoyed his knowledge of Santorini and the sea. Highly recommend this tour! Well worth the money!”

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Private Motor Yacht Cruise with BBQ, Open Bar & Transfers

Private Motor Yacht Cruise with BBQ, Open Bar & Transfers - Getting to Vlihada Marina: timing, pickup, and cruise-ship reality checks

11.Private Motor Yacht Cruise with BBQ, Open Bar & Transfers

★★★★★★★★★★5.0 · 144 reviews · 5 hours (approx.) · from $1,149

Private 5-hour Santorini yacht cruise with BBQ, open bar, Red and White Beaches, volcano hot springs, plus sunset on afternoon trips.

“We ported into Santorini and took the cable car up the cliff. We then walked into town and found Spiriakos travel, which is where we would get picked up and taken to the port for our private yacht excursion. On the way, Dominic explained different sites and even stopped at the winery for a great view of the Caldera. Once we got to the marina, we met our captain Hector and his partner Fayez sp?. The yacht was extremely nice, as were Victor and Fayez. We stopped at three places to snorkel and swim. The second one was the thermal bay by the volcano with the warm waters. It was…”

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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

Deluxe Santorini Sailing with BBQ and Drinks Shared Tour - Price and what makes it feel worth $193.57

12.Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

★★★★★★★★★★5.0 · 137 reviews · 5 hours (approx.) · from $193

Deluxe shared catamaran sailing in Santorini with hotel pickup, BBQ, unlimited drinks, and stops at Red Beach, White Beach, and volcanic islands.

“Beautiful catermeran. Friendly and professional crew who offered excellent service. Fabulous sunset tour with the family sailing around Santorini. It was advertised so we were expecting a bbq. There were 2 on board but unfortunately not. The food was delicious but pre prepared earlier that day. Fortunately we brought our towels as they were not provided as mentioned. With a couple of exceptions overall a fantastic day and would highly recommend.”

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Sunset Caldera Sailing Cruise

Sunset Caldera Sailing Cruise - Red Beach and White Beach, your quick photo stops with real character

13.Sunset Caldera Sailing Cruise

★★★★★★★★★★5.0 · 96 reviews · 5 hours (approx.) · from $151

Small-group Santorini sunset sailing from Vlychada, volcanic sights, Greek meal and unlimited drinks, hotel pickup, swims and snorkeling.

“Great folks ran this. Just was a bit cold the day we went. The cooked a great lunch and had great wine to drink.”

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Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included

Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included - Crossing between volcanoes for hot springs and lighthouse sightlines

Santorini Caldera: Sunset Sailing Cruise with Meal

Santorini Caldera: Sunset Sailing Cruise with Meal - Getting Picked Up: The Coach Ride That Sets the Rhythm

15.Caldera: Sunset Sailing Cruise with Meal

★★★★★★★★★★4.8 · 65 reviews · from $131

5-hour Santorini sunset sail with transfers, caldera views, Red and White Beach stops, swimming and snorkel, and a seafood barbecue with wine.

“This was so fun! I picked this tour because it was an actual sailboat and not a catamaran. The very competent crew had the sails up for most of the trip. It was awesome! We stopped for swimming twice. One of the swimming stops was at the hot springs, which was a nice experience. Swimming in almost hot ocean water near piles of volcanic rock was a very unique experience. That was definitely the highlight for me. The crew also dropped anchor here and fed us a delicious meal. We also had unlimited wine and beer. Yiannis, who is the company/boat owner picked us up from our hotel and dropped…”

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