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Top Greece Romantic 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

Santorini, Greece
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

Santorini, Greece
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
$151
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

Santorini, Greece
5.0 (268)

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 (268)
from
$186
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

Santorini, Greece
4.9 (292)

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 (292)
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

Santorini, Greece
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
$151
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

Saronic Gulf Islands, Greece
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
$172
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
Santorini, Greece
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
$928
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
Santorini, Greece
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 2h Photoshoot with a photographer & transportation

Photo shooting to the best island spots by local professional photographers. Your professional photographer will pick you up from your hotel and together you will …More

5.0 (40)

Santorini 2h Photoshoot with a photographer & transportation

Photo shooting to the best island spots by local professional photographers. Your professional photographer will pick you up from your hotel and together you will...

2 hours • Hotel pickup offered • Free Cancellation
5.0 (40)
from
$410
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

Santorini, Greece
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
$189
Zakynthos Sunset Tour

Small group and private tours are the best way to experience a sunset! Your personal driver is a local guide and he will drive you …More

Zakynthos, Greece
4.9 (25)

Zakynthos Sunset Tour

Small group and private tours are the best way to experience a sunset! Your personal driver is a local guide and he will drive you...

3 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.9 (25)
from
$64
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and …More

Rhodes, Greece
5.0 (18)

Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and...

4 hours • Free Cancellation
5.0 (18)
from
$1,095
Sunset Cruise Athens Riviera – Half Day Swimming&BBQ onBoard

Step aboard a traditional wooden boat and sail along the breathtaking Athenian Riviera. Enjoy two refreshing swimming stops in crystal-clear waters and savor a fresh …More

Athens, Greece
5.0 (25)

Sunset Cruise Athens Riviera – Half Day Swimming&BBQ onBoard

Step aboard a traditional wooden boat and sail along the breathtaking Athenian Riviera. Enjoy two refreshing swimming stops in crystal-clear waters and savor a fresh...

5 hours • Free Cancellation
5.0 (25)
from
$128
Wine Tasting and Romantic sunset in Monolithos

Take the chance to experience the idyllic Aegean sunset from the medieval castle of Monolithos after having wine-tasting at the prominent wine region of Ebonas. …More

Rhodes, Greece
5.0 (15)

Wine Tasting and Romantic sunset in Monolithos

Take the chance to experience the idyllic Aegean sunset from the medieval castle of Monolithos after having wine-tasting at the prominent wine region of Ebonas....

7 hours • Hotel pickup offered • Free Cancellation
5.0 (15)
from
$451
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

Santorini, Greece
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
$88
Temple of Poseidon & Cape Sounion Half-Day or Sunset Private Tour

Experience the Athenian Riviera and the Temple of Poseidon at Cape Sounion on a private half-day or sunset tour. Enjoy a comfortable drive in a …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece
4.9 (10)

Temple of Poseidon & Cape Sounion Half-Day or Sunset Private Tour

Experience the Athenian Riviera and the Temple of Poseidon at Cape Sounion on a private half-day or sunset tour. Enjoy a comfortable drive in a...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (10)
from
$63
Sunset Kayak Adventure in Milos to Colorful Klima

Push off from Lagada Beach in Adamas and dip your paddle into Milos’ unbelievably clear water. As you kayak north, you’ll hug the island’s rocky …More

Likely to Sell Out
Likely to Sell Out
Milos, Greece
5.0 (8)

Sunset Kayak Adventure in Milos to Colorful Klima

Push off from Lagada Beach in Adamas and dip your paddle into Milos’ unbelievably clear water. As you kayak north, you’ll hug the island’s rocky...

3 hours • Free Cancellation
5.0 (8)
from
$88
Athens Riviera Private Sunset Cruise with Drinks & Bites

Step aboard Sofia Star 1, our luxury 52ft sailing yacht, and experience the Athenian Riviera in total privacy. This 4-hour private sunset cruise is designed …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece
5.0 (2)

Athens Riviera Private Sunset Cruise with Drinks & Bites

Step aboard Sofia Star 1, our luxury 52ft sailing yacht, and experience the Athenian Riviera in total privacy. This 4-hour private sunset cruise is designed...

4 hours • Free Cancellation
5.0 (2)
from
$1,871
Romantic Luxury Sunset sailing

Sailing by the castle, en route to the historic natural bay of Zeus Island. Imagine a serene evening, nestled in a secluded bay, where the …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
4.5 (4)

Romantic Luxury Sunset sailing

Sailing by the castle, en route to the historic natural bay of Zeus Island. Imagine a serene evening, nestled in a secluded bay, where the...

5 to 7 hours • Hotel pickup offered • Free Cancellation
4.5 (4)
from
$694
Rhodes Private Luxury Sunset Cruise,Cocktails & Champagne, wine

Sunset Cruise to Kallithea Springs – Aboard Our Luxury Sailing Yacht Embark on Sailing Edisa for an unforgettable sunset cruise as golden light reflects across …More

Rhodes, Greece
5.0 (12)

Rhodes Private Luxury Sunset Cruise,Cocktails & Champagne, wine

Sunset Cruise to Kallithea Springs – Aboard Our Luxury Sailing Yacht Embark on Sailing Edisa for an unforgettable sunset cruise as golden light reflects across...

3 hours 30 minutes • Free Cancellation
5.0 (12)
from
$920

Frequently Asked Questions

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

Recent tour reviews
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
Great, thanks to George!
New York City
Sunset Kayak Adventure in Milos to Colorful Klima
BarbaraG9977, Sep 2026
Great, thanks to George!
Worth joining, although challenging… George gave very good tipps and information! We enjoyed a lot and it is the best doing it there and in the evening. thanks!!
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
Captain George and first mate George for the win!
New York City
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour
tomfN3747NQ, Sep 2026
Captain George and first mate George for the win!
George and George were the perfect captain and crew Food was excellent, tour very fun and great swimming. Pickup was a problem, arrived 20 minutes late with no call or text to advise in advance and no explanation or apology. Otherwise a great experience with Santorini Sailing
Read more
Amazing and wonderful
New York City
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour
Y7148ISfrancisf, Sep 2026
Amazing and wonderful
Marjorie, Pilot and Billy made our trip absolutely fantastic. They were fun, informative and very attentive to detail. The food was outstanding and the views were unforgettable. Marjorie took several terabytes of beautiful photos for us as well.
Read more
Sailing Edisa
New York City
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne
kaneh713, Sep 2026
Sailing Edisa
Sailing Edisa cannot recommend it enough. Great experience as well as 10/10 hospitality. Food was also amazing and so tasty as the pictures show.We enjoyed it so much we also booked for the following day, however this time we chosen to do the deluxe sunset dinner. This was also fantastic as the views were amazing. We enjoyed so much that we will be visiting again next year for this premium 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
Great private luxery sunset cruise!
New York City
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne
Navigator29611069976, Sep 2026
Great private luxery sunset cruise!
Today, we enjoyed a fantastic private luxury sunset cruise with Sailing Edisa, hosted by Captain Edward and his lovely wife, Isabelle.We received a warm welcome right from the start and were given a fascinating overview of the boat's history. Along the way, we stopped at the Kallithea Springs, where we enjoyed a wonderful swim. Every detail was taken care of—they even provided the necessary swimming gear.After our swim, we were treated to delicious homemade Vietnamese spring rolls, fresh fruit, and a tasty cocktail, all served on a beautifully decorated table. We even got to taste dragon fruit for the first time—a unique fruit grown by Captain Edward himself.Afterwards, we were invited to sit next to the captain and enjoy a glass of champagne as the sun slowly set. It was a truly beautiful moment!And as if that weren't enough, they surprised us with a bottle of delicious wine to celebrate our wedding anniversary. Such a wonderful, thoughtful gesture!Edward and Isabelle make you feel welcome immediately, turning the boat trip into so much more than just an ordinary excursion. Personal service, beautiful moments, great food and drinks, and a stunning sunset.Highly recommended! If you are in Rhodes, you absolutely must experience this cruise.
Read more
Great time!
New York City
Sunset Kayak Adventure in Milos to Colorful Klima
melissagV9289PP, Sep 2026
Great time!
Kayaking with George was awesome! He had many interesting facts about Milos and took lots of pictures for us and made sure we all had a great time. He was a very attentive guide and so friendly. Highly recommend!
Read more
Best Day in Santorini
New York City
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks
sophiegirl0814, Sep 2026
Best Day in Santorini
Bruna, Marjorie, Billy and Pilot gave us an amazing day on the sea! Lunch was freshly cooked and delicious. Towels water and drinks a plenty!
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
Absolutely amazing!
New York City
Sunset Cruise Athens Riviera – Half Day Swimming&BBQ onBoard
meredithe283, Sep 2026
Absolutely amazing!
Smooth ride, not crowded, and great staff, especially Elena. The food was ok, but we didn’t really like the Greek food but we didn’t starve. Loved the free drinks and sight commentary. The captain was friendly and navigated perfectly. We would definitely recommend this trip.
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
Afternoon full of memories
New York City
Sunset Cruise Athens Riviera – Half Day Swimming&BBQ onBoard
christinepL672LQ, Sep 2026
Afternoon full of memories
We had a great afternoon on board our sailing vessel. The weather was a bit cool but the crew made it all worth while. The sea was warm and inviting. The food was amazing and we came home with more than memories, new friends! This is a must do and a great value for your money.
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
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