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Top Crete Sailing Trips

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Crete Tours

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

Sail to Dia Island: A Boutique Yacht Experience in Paradise Sun, blue waters, and good food—these are the things that define Greece, and Crete in …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
5.0 (225)

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

Sail to Dia Island: A Boutique Yacht Experience in Paradise Sun, blue waters, and good food—these are the things that define Greece, and Crete in...

4 hours 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (225)
from
$88
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun

Join us for a semi-private morning cruise from Heraklion aboard a sleek, modern catamaran. Your adventure begins with a warm welcome from our crew. As …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
4.9 (240)

Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun

Join us for a semi-private morning cruise from Heraklion aboard a sleek, modern catamaran. Your adventure begins with a warm welcome from our crew. As...

5 hours • Free Cancellation
4.9 (240)
from
$130
Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

Our brand-new luxury catamaran is elegant, sophisticated, and designed for your ultimate comfort. With a small-group setting, this cruise offers an intimate and personalized experience, …More

Likely to Sell Out
Likely to Sell Out
4.9 (117)

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

Our brand-new luxury catamaran is elegant, sophisticated, and designed for your ultimate comfort. With a small-group setting, this cruise offers an intimate and personalized experience,...

6 hours 30 minutes • Free Cancellation
4.9 (117)
from
$148
Ag. Nikolaos Catamaran to Spinalonga - Gourmet Meal & Water Toys

Step aboard our luxury catamaran and leave the ordinary behind. Start your day with espresso, tea, detox water, and a light brunch crafted by a …More

Likely to Sell Out
Likely to Sell Out
5.0 (92)

Ag. Nikolaos Catamaran to Spinalonga - Gourmet Meal & Water Toys

Step aboard our luxury catamaran and leave the ordinary behind. Start your day with espresso, tea, detox water, and a light brunch crafted by a...

5 hours • Free Cancellation
5.0 (92)
from
$126
Dia Island Sailing Cruise with Meal and Water Activities

Sail with us to the exotic Dia Island on our large and comfortable sailing yachts. Our journey begins at the Heraklion Old venetian port. After …More

Heraklion, Greece
4.8 (472)

Dia Island Sailing Cruise with Meal and Water Activities

Sail with us to the exotic Dia Island on our large and comfortable sailing yachts. Our journey begins at the Heraklion Old venetian port. After...

5 to 6 hours • Hotel pickup offered • Free Cancellation
4.8 (472)
from
$93
Rethymno: Sunset Catamaran Trip - Sushi & Open Bar

We invite you to step away from the everyday and join us for an unforgettable evening at sea aboard our luxury catamaran. As the sun …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
4.7 (115)

Rethymno: Sunset Catamaran Trip - Sushi & Open Bar

We invite you to step away from the everyday and join us for an unforgettable evening at sea aboard our luxury catamaran. As the sun...

3 hours 30 minutes • Free Cancellation
4.7 (115)
from
$89
Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

This morning cruise from Rethymno to Georgioupoli Bay unfolds into a day of scenic adventure. Crystal-clear waters, golden beaches, and lush coastal hills stretch along …More

Likely to Sell Out
Likely to Sell Out
4.9 (122)

Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

This morning cruise from Rethymno to Georgioupoli Bay unfolds into a day of scenic adventure. Crystal-clear waters, golden beaches, and lush coastal hills stretch along...

6 hours 30 minutes • Free Cancellation
4.9 (122)
from
$168
Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

We invite you to step away from the everyday and join us for an unforgettable evening at sea aboard our luxury catamaran. As the sun …More

Likely to Sell Out
Likely to Sell Out
4.9 (80)

Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

We invite you to step away from the everyday and join us for an unforgettable evening at sea aboard our luxury catamaran. As the sun...

3 hours 30 minutes • Free Cancellation
4.9 (80)
from
$83
Luxury Catamaran Cruise All-Inclusive & OnBoard Chef | Top Rated!

Experience Crete on the top-rated, most luxurious catamaran with EOS Yachts. An exclusive cruise to mythical Dia island featuring a freshly prepared fine dining Mediterranean …More

5.0 (192)

Luxury Catamaran Cruise All-Inclusive & OnBoard Chef | Top Rated!

Experience Crete on the top-rated, most luxurious catamaran with EOS Yachts. An exclusive cruise to mythical Dia island featuring a freshly prepared fine dining Mediterranean...

5 hours 30 minutes • Free Cancellation
5.0 (192)
from
$139
Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys

Join us for an unforgettable luxury catamaran cruise from Agios Nikolaos across the sparkling waters of Mirabello Bay. Sail past the legendary island of Spinalonga, …More

Likely to Sell Out
Likely to Sell Out
4.8 (78)

Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys

Join us for an unforgettable luxury catamaran cruise from Agios Nikolaos across the sparkling waters of Mirabello Bay. Sail past the legendary island of Spinalonga,...

5 hours • Free Cancellation
4.8 (78)
from
$146
Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

There’s a place not far from Panormo Port where sheltered coves, clear waters, and stunning rocky landscapes create a peaceful escape. This is Bali Bay, …More

5.0 (75)

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

There’s a place not far from Panormo Port where sheltered coves, clear waters, and stunning rocky landscapes create a peaceful escape. This is Bali Bay,...

6 hours 30 minutes • Free Cancellation
5.0 (75)
from
$148
Catamaran Cruise Heraklion to Dia, Dinner, Drinks & Hotel Pickup

Join us for a semi-private afternoon cruise from Heraklion aboard a sleek, modern catamaran. Set sail to Dia Island and enjoy water activities — swim, …More

Likely to Sell Out
Likely to Sell Out
4.9 (66)

Catamaran Cruise Heraklion to Dia, Dinner, Drinks & Hotel Pickup

Join us for a semi-private afternoon cruise from Heraklion aboard a sleek, modern catamaran. Set sail to Dia Island and enjoy water activities — swim,...

5 hours • Free Cancellation
4.9 (66)
from
$129
Sailing Trip to Dia Island - All Inclusive

Join a small-group sailing adventure from Heraklion to the beautiful, unspoiled Dia Island. With a maximum of 10 guests on board, you’ll enjoy a relaxed, …More

Heraklion, Greece
4.9 (114)

Sailing Trip to Dia Island - All Inclusive

Join a small-group sailing adventure from Heraklion to the beautiful, unspoiled Dia Island. With a maximum of 10 guests on board, you’ll enjoy a relaxed,...

6 to 7 hours • Hotel pickup offered • Free Cancellation
4.9 (114)
from
$79
Heraklion: Morning/Sunset Sailing Experience-Dia Island & Lunch

Traveling is about exploring new places, meeting people, sharing experiences, learning about history, and above all having fun. Our sailing tours are designed based on …More

4.8 (169)

Heraklion: Morning/Sunset Sailing Experience-Dia Island & Lunch

Traveling is about exploring new places, meeting people, sharing experiences, learning about history, and above all having fun. Our sailing tours are designed based on...

4 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.8 (169)
from
$93
Balos Shared Catamaran Cruise (small groups to 22ppl)

There are not enough words to describe the beauty of Balos beach… on our yachts you will enjoy the crystal-clear waters of this western, amazing …More

Chania, Greece
4.8 (92)

Balos Shared Catamaran Cruise (small groups to 22ppl)

There are not enough words to describe the beauty of Balos beach… on our yachts you will enjoy the crystal-clear waters of this western, amazing...

7 hours • Hotel pickup offered • Free Cancellation
4.8 (92)
from
$139
Private luxury Escape free drinks & Meals Cruise

Looking for an Escape? Leave your comfort zone and embrace nature to the fullest. The best place to start your eco-quest is the island of …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
5.0 (22)

Private luxury Escape free drinks & Meals Cruise

Looking for an Escape? Leave your comfort zone and embrace nature to the fullest. The best place to start your eco-quest is the island of...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (22)
from
$1,028
Sailing Cruises Chania

A Sailing cruise around the gulf of Chania will give your vacations a different view of the city! We set sails every morning at 10am …More

5.0 (98)

Sailing Cruises Chania

A Sailing cruise around the gulf of Chania will give your vacations a different view of the city! We set sails every morning at 10am...

4 to 7 hours • Free Cancellation
5.0 (98)
from
$203
All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

Our luxury catamaran offers spacious elegance and is designed for your complete comfort. It takes you to the uninhabited Dia Island, where you’ll witness the …More

Likely to Sell Out
Likely to Sell Out
5.0 (46)

All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

Our luxury catamaran offers spacious elegance and is designed for your complete comfort. It takes you to the uninhabited Dia Island, where you’ll witness the...

6 hours 30 minutes • Free Cancellation
5.0 (46)
from
$146
Heraklion: Full Day Sailing Experience-Dia Marine Area with Lunch

Traveling is about exploring new places, meeting people, sharing experiences, learning about history, and above all having fun. Our sailing tours are designed based on …More

Heraklion, Greece
4.9 (76)

Heraklion: Full Day Sailing Experience-Dia Marine Area with Lunch

Traveling is about exploring new places, meeting people, sharing experiences, learning about history, and above all having fun. Our sailing tours are designed based on...

7 hours • Hotel pickup offered • Free Cancellation
4.9 (76)
from
$114
Heraklion: Sunset Luxury Cruise with Sushi and Open Bar

Your evening begins with a glass of chilled Prosecco and carefully crafted Mediterranean finger foods as light snacks. After a brief safety briefing, we set …More

Likely to Sell Out
Likely to Sell Out
4.7 (45)

Heraklion: Sunset Luxury Cruise with Sushi and Open Bar

Your evening begins with a glass of chilled Prosecco and carefully crafted Mediterranean finger foods as light snacks. After a brief safety briefing, we set...

3 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (45)
from
$94

Frequently Asked Questions

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

Recent tour reviews
Manos is the Man
New York City
Dia Island Sailing Cruise with Meal and Water Activities
michaelfM5582NB, Sep 2026
Manos is the Man
Manos is one of the coolest people I've ever met. He made the experience a true highlight of our trip. Not only is he an awesome sailor, but he has a heart of gold and is full of some of the most interesting stories and knowledge the world over. 10/10.
Read more
Lovely afternoon and sunset
New York City
Dia Island Sailing Cruise with Meal and Water Activities
Rachel_H, Sep 2026
Lovely afternoon and sunset
The trip was amazing. Stopped for a swim. Had delicious food and drinks and saw the lovely sunset. What more can you wish for?
Read more
What a wonderful experience!
New York City
Heraklion: Morning/Sunset Sailing Experience-Dia Island & Lunch
adrianag173, Sep 2026
What a wonderful experience!
Petros and Redi were an amazing team and made sure we had a fantastic time. The water was absolutely beautiful, and we even went for a swim. As the icing on the cake, we got to see the goats! I highly recommend it without hesitation!
Read more
Snorkel, paddle board, swim or flamingo float, open bar & sushi… yes please!
New York City
Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar
Christopher_H, Sep 2026
Snorkel, paddle board, swim or flamingo float, open bar & sushi… yes please!
We had a wonderful experience and enjoy everything on our sunset cruise had to offer. We were welcomed with warmth & a glass of sparkling wine. Then we enjoyed a charcuterie board twice, a variety of sushi, watermelon and almond cookies… and yes open bar. There were two separate opportunities to swim, snorkel, paddle board or ride their pink flamingo floaty and everyone was having a great time. We have enjoyed similar cruses around the world but none quite like this one, it was the little things for instance they used plastic glassware & dishes and not disposables, the cold cuts were shaped like roses and Cristos our skipper & Danny our deck hand were very attentive and made sure we were safe and having a good time during the entire voyage.
Read more
Salí g day from Crete to Dia Island
New York City
Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
G2479IUluluc, Sep 2026
Salí g day from Crete to Dia Island
Amazing experience. Beautiful boat and amazing crew! Congratulations
Read more
Worthwhile adventure on the water
New York City
Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar
chrislizh2021, Sep 2026
Worthwhile adventure on the water
Pleasant trip in Crete! The crew was particularly helpful and courteous.
Read more
Once in a lifetime Mediterranean Sailing Experience
New York City
Heraklion: Morning/Sunset Sailing Experience-Dia Island & Lunch
AuntieSandra, Sep 2026
Once in a lifetime Mediterranean Sailing Experience
Amazing once in a lifetime experience. Ocean going sailboat piloted by two very experienced and competent sailors. What a great team in commandeering the boat. Sailed through very windy and large wave conditions. What a thrill. Stopped for a swim in beautiful waters at the Island and had an authentic Greek, homemade lunch. All in all, a superb excursion!
Read more
Day cruise
New York City
Panormo: Luxury Catamaran Cruise with Lunch & Open Bar
Justine186332, Sep 2026
Day cruise
Fantastic day cruise the crew , food drinks and experience brilliant.We sailed from Panorama the day was amazing and so relaxing I would definitely recommend it.
Read more
Awesome
New York City
Sailing Trip to Dia Island – All Inclusive
313tatumc, Sep 2026
Awesome
This was fantastic. The guides were incredible and made sure we had everything we needed. The food was great. The swimming spot had some of the prettiest water I have ever seen and some great fish to see snorkeling. I would absolutely do this again.
Read more
Fun times.
New York City
Heraklion: Sunset Luxury Cruise with Sushi and Open Bar
reginafR2278ZU, Sep 2026
Fun times.
Amazing thank you ❤️ would definitely recommend!!
Read more
Bali’s catamaran
New York City
Balos Shared Catamaran Cruise (small groups to 22ppl)
Arthur_B, Sep 2026
Bali’s catamaran
Very nice people, the staff made this such a great experience. The boat was very clean, awesome food and drinks served on board. I highly recommend.
Read more
This was an excellent...
New York City
Balos Shared Catamaran Cruise (small groups to 22ppl)
Me_I, Sep 2026
This was an excellent...
This was an excellent excursion. The staff was very friendly and helpful. The food they provided was delicious.
Read more
It was fantastic. The...
New York City
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun
Leslie_W, Sep 2026
It was fantastic. The...
It was fantastic. The crew was so helpful. The food was delicious. The toys were really fun. I totally recommend this if you like to be on and in the beautiful water
Read more
Great Time
New York City
Panormo: Luxury Catamaran Cruise with Lunch & Open Bar
janbI7724VG, Sep 2026
Great Time
Greate guides and great time.
Read more
Great sailing experience
New York City
Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
CahillDD, Sep 2026
Great sailing experience
Wonderful trip to the island. Marissa and Niko were amazing to watch set sails and sail the boat. Food was very good. Only slight negatives were too many boat's in the small bay and not many fish. Suggestion: put a different color small flag near the ladder to help swimmers without glasses identify which of the several boats anchored in the bay is the one they are on.
Read more
Day trip
New York City
Ag. Nikolaos Catamaran to Spinalonga – Gourmet Meal & Water Toys
carolinekD3818FH, Sep 2026
Day trip
Absolute brilliant day out food and service spot on couldn't ask for a better crew
Read more
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