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Top Santorini Romantic Tours

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Santorini Tours

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

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet …More

4.9 (218)

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

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (218)
from
$151
Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

The sunset sailing trip is unique experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious vessel and one of its kind …More

4.9 (375)

Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

The sunset sailing trip is unique experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious vessel and one of its kind...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (375)
from
$150
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into …More

5.0 (274)

Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (274)
from
$185
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour. …More

4.9 (293)

Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour....

5 hours • Hotel pickup offered • Free Cancellation
4.9 (293)
from
$220
Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious vessel …More

4.9 (212)

Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious vessel...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (212)
from
$150
Santorini Wine Tour: Visit 3 Local Wineries with Tastings

Morning Tour Visit: Roussos Winery - Koutsogiannopoulos Winery Museum - Venetsanos Winery Afternoon Tour Visit: Venetsanos Winery - Roussos Winery - Aroma Avlis Winery A …More

4.7 (149)

Santorini Wine Tour: Visit 3 Local Wineries with Tastings

Morning Tour Visit: Roussos Winery - Koutsogiannopoulos Winery Museum - Venetsanos Winery Afternoon Tour Visit: Venetsanos Winery - Roussos Winery - Aroma Avlis Winery A...

3 hours 30 minutes • Free Cancellation
4.7 (149)
from
$171
Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

Likely to Sell Out
Likely to Sell Out
4.9 (53)

Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (53)
from
$926
Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number …More

Likely to Sell Out
Likely to Sell Out
5.0 (17)

Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (17)
from
$217
Santorini Private Romantic Tour with Wine Tasting & Dinner

Fall in love all over again — in the most romantic place on Earth. Discover Santorini’s most intimate and magical spots, enjoy a wine tasting …More

5.0 (26)

Santorini Private Romantic Tour with Wine Tasting & Dinner

Fall in love all over again — in the most romantic place on Earth. Discover Santorini’s most intimate and magical spots, enjoy a wine tasting...

6 hours • Hotel pickup offered • Free Cancellation
5.0 (26)
from
$188
Santorini Day-trip Semi private 4-5hour

Α unique experience so that you can experience every beauty of our island !! Create unique memories! 5-hour tour of Santorini with an expert guide …More

4.6 (14)

Santorini Day-trip Semi private 4-5hour

Α unique experience so that you can experience every beauty of our island !! Create unique memories! 5-hour tour of Santorini with an expert guide...

5 hours • Hotel pickup offered • Free Cancellation
4.6 (14)
from
$87
Dreamy Flying Dress Photoshoot in Santorini

Indulge in a One-of-a-Kind flying dress experience with our exclusive private photo session, capturing stunning images against the backdrop of Santorini's breathtaking landscape. Our experienced …More

5.0 (11)

Dreamy Flying Dress Photoshoot in Santorini

Indulge in a One-of-a-Kind flying dress experience with our exclusive private photo session, capturing stunning images against the backdrop of Santorini's breathtaking landscape. Our experienced...

1 hour
5.0 (11)
from
$452
Εxplore The Beaches Of Santorini

Whether you are a first-time visitor to Santorini or your time is quite limited, you don’t need to worry about anything! Spend your time relaxing, …More

5.0 (3)

Εxplore The Beaches Of Santorini

Whether you are a first-time visitor to Santorini or your time is quite limited, you don’t need to worry about anything! Spend your time relaxing,...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$81
Εxplore The Beaches Of Santorini

Either you are a first-time visitor to Santorini or your time is quite limited, you don’t need to worry about anything! Spend your time relaxing, …More

5.0 (1)

Εxplore The Beaches Of Santorini

Either you are a first-time visitor to Santorini or your time is quite limited, you don’t need to worry about anything! Spend your time relaxing,...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$397
Round trip transfer For Oia

Oia: We created this service Why the most famous Santorini village should not be missing from your list What comes to your mind when you …More

4.3 (8)

Round trip transfer For Oia

Oia: We created this service Why the most famous Santorini village should not be missing from your list What comes to your mind when you...

3 hours • Free Cancellation
4.3 (8)
from
$58
Surprise Proposal Photoshoot in Santorini

Choosing our photoshoot company for a surprise proposal in Santorini ensures an experience tailored to create timeless memories of this special moment. With a deep …More

5.0 (2)

Surprise Proposal Photoshoot in Santorini

Choosing our photoshoot company for a surprise proposal in Santorini ensures an experience tailored to create timeless memories of this special moment. With a deep...

1 hour
5.0 (2)
from
$428
Santorini Roundtrip transport For oia

Oia: We created this service Why the most famous Santorini village should not be missing from your list What comes to your mind when you …More

3.0 (5)

Santorini Roundtrip transport For oia

Oia: We created this service Why the most famous Santorini village should not be missing from your list What comes to your mind when you...

3 hours • Hotel pickup offered • Free Cancellation
3.0 (5)
from
$58
Santorini Waves of Passion

Couples Massage-Brunch-Wine Tasting-Private Rib Indulge in a couples’ massage, savor a brunch by the Black Beach, enjoy a wine tasting with caldera views, and end …More

Likely to Sell Out
Likely to Sell Out

Santorini Waves of Passion

Couples Massage-Brunch-Wine Tasting-Private Rib Indulge in a couples’ massage, savor a brunch by the Black Beach, enjoy a wine tasting with caldera views, and end...

6 hours • Free Cancellation
from
$1,068

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
An Unforgettable Santorini Sailing Experience
New York City
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour
L6217YFannah, Sep 2026
An Unforgettable Santorini Sailing Experience
Our last day in Santorini turned into the best day of our entire trip thanks to Santorini Sailing! This excursion was so much fun from start to finish. The crew was amazing, friendly, and hardworking, making sure everyone felt welcome and had a wonderful time.We actually sailed, and it was absolutely incredible! From the beautiful atmosphere and friendly people to the music and delicious food, we couldn’t have asked for anything more. It was the perfect way to end our time in Santorini.I highly recommend Santorini Sailing to anyone visiting the area. It was an unforgettable experience and truly one of the highlights of our trip!
Read more
What a dream!
New York City
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour
ericajO3918QJ, Sep 2026
What a dream!
Oh my gosh was it a great time! The playlist was so fun, the food was delicious, the views were extraordinary! My only gripe was I wish it was longer or we had more time for stops in the crystal clear blue waters! The crowd was perfect which was about 20 of us and the staff was so friendly. I can’t recommend enough
Read more
Perfect Tour
New York City
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks
L5070YOnicholasc, Sep 2026
Perfect Tour
Great experience. The staff was fun and knowledgeable. The food was excellent. We had an amazing sunset. I would definitely recommend.
Read more
Fon tour guide was amazing
New York City
Santorini Private Romantic Tour with Wine Tasting & Dinner
rickd826, Sep 2026
Fon tour guide was amazing
Fon our tour guide was amazing he made our day extra special was like traveling with family.we loved Fon had so much fun spending our day with him .I would highly recommend him to anyone 💕💕💕💕
Read more
Santorini Sunset cruise and dinner
New York City
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks
Explorer17345682562, Sep 2026
Santorini Sunset cruise and dinner
Experience was wonderful. Captain and crew made the tour exciting and fun!!
Read more
Highly recommend it!
New York City
Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)
Ola_Z, Sep 2026
Highly recommend it!
Absolutely loved our experience. From beginning to end. The driver for our transfer picked us up from our designated location bang on time. The boat was ultra clean and well appointed and the crew were adorable and super professional, including George and Dimitris. The food was amazing and the swimming stops breathtaking. You cannot miss this Santorini experience.
Read more
1/2 day cruise on a boat
New York City
Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer
William_H, Sep 2026
1/2 day cruise on a boat
Very friendly crew, great food. Wonderful experience The scenery was beautiful and the experience traveling with a small group was perfect
Read more
Must do in Oia Santorini!
New York City
Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer
dshendri, Sep 2026
Must do in Oia Santorini!
Amazing sunset boat cruise!!!! The boat was amazing and so was the staff. The food was also top notch! We were on the second largest boat of their fleet of 40 and it couldn't have been better from a wonderful pickup to the end and drop off. They have snorkeling equipment and floating foam noodles if you wish to swim. The boat wasn't crowded and we enjoyed meeting many others on board.Thank you to Evie, Marios, Ellie and Chris for an amazing day/evening on the water!
Read more
Awesome catamaran trip
New York City
Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer
Kath-Aama, Sep 2026
Awesome catamaran trip
The Lagoon 500 was a beautiful boat and the crew was very friendly. I especially liked Elena’s fun personality.
Read more
We had an increadible...
New York City
Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer
Chris_J, Sep 2026
We had an increadible...
We had an increadible trip, culminating with a wonderful dinner (grilled on the boat) and watching the sunset from Ammoudi Bay! The captain and crew were excellent! Highly recommend!!!
Read more
Must do in Santorini
New York City
Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)
wyattk510, Aug 2026
Must do in Santorini
Highlight of our trip! George, Ina, and Alex were incredible and made the experience so memorable. Kostas was a great captain and the boat (Sunset Nexus) was clean, spacious, and comfortable. The stops were so fun and everyone had an amazing time.
Read more
A unanimous decision...
New York City
Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1
Winifred_L, Aug 2026
A unanimous decision...
A unanimous decision (myself, husband, and three young adult children) that this private sailing boat cruise was THE HIGHLIGHT of our Greece trip!! Beautiful scenery, delicious dinner, gorgeous sunset, refreshing waters for swimming and wonderful company from our skillful charismatic captain Spiros and crewmate Annie. Thank-you for a perfect evening.
Read more
Sunset sailing
New York City
Santorini Caldera Private Sailing Boat Cruise
James_P, Aug 2026
Sunset sailing
We had a great time sailing at sunset. I would especially recommend this if you actually like to do some sailing. The captain/crew were very knowledgeable and friendly. They prepared a great dinner for us as well. Great experience!
Read more
Total Vibe
New York City
Dreamy Flying Dress Photoshoot in Santorini
taylorsL2545QH, Aug 2026
Total Vibe
The flying dress photoshoot was a total vibe! Locations were private and picturesque, and the results are magazine level. Everything exceeded my expectations book it for an unforgettable memory!
Read more
Fun, and Tasty!
New York City
Santorini Wine Tour: Visit 3 Local Wineries with Tastings
Nanine_V, Aug 2026
Fun, and Tasty!
Our guide, Maria, was lovely! She was very knowledgeable about not just the Vineyards and the wine, but also taught us so much about the history of Santorini! The wineries we went to had high quality wine and the people there were informative and friendly! Our driver, Dimitri, was charming and friendly as well. The entire experience was memorable and fun!
Read more
Best family vacation we’ve ever taken!
New York City
Santorini Caldera Private Sailing Boat Cruise
artie205, Jul 2026
Best family vacation we’ve ever taken!
Our two families just returned from a week sailing the Cyclades on the Golden Star (Caldera Yachting) and it was hands down the best trip we’ve ever taken. We traveled with our 10 and 12-year-olds, and our crew, Captain Ilias and Georgia, were just absolutely fantastic with them and made the whole experience unforgettable.Having Georgia on board was a total game-changer. She made two huge, delicious meals a day using all fresh, local ingredients. We had two pescatarians in our group and she accommodated them perfectly with things like shrimp pasta, baked mussels, and amazing whole roasted fish. It was so nice not having to stress about where to eat—we could just enjoy the islands and come back to a home-cooked family-style meal on the deck.Captain Ilias really knows his stuff. He taught us so much about the area, the geology, and sailing, but what we appreciated most was how he adjusted the trip based on the weather. When the water got rough one day, he used his network of other captains to find a safe spot at a tiny fishing port in Naxos. We ended up at this amazing little farm-to-table taverna where the kids ate local lamb and we could literally see the sheep grazing right by the patio.Ilias also gave us great advice on land. He told us to take the bus up to the Chora in Ios, which had exactly the white-washed, bougainvillea-filled, cat-friendly Greek alleys we were hoping for. Antiparos town was another favorite stop just for wandering around the beautiful shops and streets.The kids' absolute favorite part was when Ilias anchored near Paros, took us out on the tender, and brought us to an uninhabited island. We had a pristine beach completely to ourselves for the afternoon just to swim and jump off the boat.If you are thinking about doing a family charter in Greece, definitely request the Golden Star with Ilias and Georgia. We are already trying to figure out when we can go back!
Read more
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