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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
Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
5.0 (221)

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 (221)
from
$89
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun
Likely to Sell Out
Likely to Sell Out
Heraklion, Greece
4.9 (238)

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 (238)
from
$132
Dia Island Catamaran – Premium Lunch, Open Bar, Small Group
Likely to Sell Out
Likely to Sell Out
4.9 (116)

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 (116)
from
$150
Balos Shared Catamaran Cruise (small groups to 22ppl)
Likely to Sell Out
Likely to Sell Out
Chania, Greece
4.8 (89)

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 (89)
from
$142
Ag. Nikolaos Catamaran to Spinalonga - Gourmet Meal & Water Toys
Likely to Sell Out
Likely to Sell Out
4.9 (88)

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
4.9 (88)
from
$128
Dia Island Sailing Cruise with Meal and Water Activities
Heraklion, Greece
4.8 (469)

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 (469)
from
$94
Rethymno Catamaran Cruise: Healthy Lunch & Open Bar
4.9 (119)

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 (119)
from
$171
Luxury Catamaran Cruise All-Inclusive & OnBoard Chef | Top Rated!
5.0 (191)

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 (191)
from
$141
Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys
Likely to Sell Out
Likely to Sell Out
4.8 (77)

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 (77)
from
$148
Heraklion: Morning/Sunset Sailing Experience-Dia Island & Lunch
4.8 (165)

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 (165)
from
$95
Rethymno: Sunset Catamaran Trip - Sushi & Open Bar
Heraklion, Greece
4.7 (109)

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 (109)
from
$90
Catamaran Cruise Heraklion to Dia, Dinner, Drinks & Hotel Pickup
Likely to Sell Out
Likely to Sell Out
4.9 (64)

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 (64)
from
$131
Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar
Likely to Sell Out
Likely to Sell Out
4.9 (75)

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 (75)
from
$84
Panormo: Luxury Catamaran Cruise with Lunch & Open Bar
5.0 (73)

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 (73)
from
$150
Sailing Cruises Chania
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
$205
Sailing Trip to Dia Island - All Inclusive
Heraklion, Greece
4.9 (111)

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 (111)
from
$80
Heraklion: Full Day Sailing Experience-Dia Marine Area with Lunch
Heraklion, Greece
4.9 (74)

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 (74)
from
$116
Private luxury Escape free drinks & Meals Cruise
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
$1,044
South Crete: Small group Full Day/ Sunset Sailing & Lunch
4.9 (46)

South Crete: Small group Full Day/ Sunset Sailing & Lunch

Our crew will meet you at Agia Galini port and welcome you on board, where you will be given a briefing about safety and boat...

5 to 7 hours • Hotel pickup offered • Free Cancellation
4.9 (46)
from
$106
Heraklion: Sunset Luxury Cruise with Sushi and Open Bar
Likely to Sell Out
Likely to Sell Out
4.7 (42)

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 (42)
from
$95

Frequently Asked Questions

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

Recent tour reviews
Fantastic Sailing Cruise on Crete, Greece
New York City
Dia Island Sailing Cruise with Meal and Water Activities
44keviny, Sep 2026
Fantastic Sailing Cruise on Crete, Greece
Captain Kosta and first mate Theodore could not have been more accommodating! Not everyone on our cruise were experienced sailors like myself. If you have never sailed, no worries! They helped get everyone aboard comfortably and then served pastries and coffee. Kosta got the boat out of the slip with ease. As we moved through the harbor, he explained in detail where we were going and how long it would take to get there. Additionally he talked about the history of Crete which I particularly enjoyed. As someone who has been sailing for over 40 years, I can say Kosta is a very capable captain and BONUS…he’s a comedian! Loaded with quick lines, he had us all laughing as we sailed along. He and Theodore were always asking if we wanted a drink…water, soda, wine and beer were plentiful. Once we reached the island of Dia, our swimming destination they skillfully set anchor. They distributed snorkeling equipment, floaty noodles, set up the paddle board and helped those who wanted to get in the water. Then Kosta and Theodore got busy in the galley. They treated us to an excellent home cooked meal! Shrimp linguini, mushroom risotto, Greek and regular salad. They even made a dish for their vegan guest. Our desert was fresh sliced fruits. 6 hours had passed before we tied off back at the harbor. We all had the kind of day that made us all feel it ended too soon! I’ve sailed the Bahamas, St. Maarten, San Diego Bay, Marina Del Ray and back home all around The Lake Erie Islands to Canada and back. This was one of my most memorable sailing experiences!
Read more
Beautiful Scenery & an Unforgettable Sunset
New York City
Dia Island Sailing Cruise with Meal and Water Activities
helenarP4200ZY, Sep 2026
Beautiful Scenery & an Unforgettable Sunset
We had an amazing tour to Dia Island! The food was delicious, the scenery was beautiful, and the crew was incredibly friendly, helpful, and attentive throughout the entire trip. The sunset was absolutely spectacular and made the experience even more special. We highly recommend this tour, definitely an experience worth having!
Read more
Incredible Day Trip 10/10 Would Recommend!
New York City
Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
916amyq, Sep 2026
Incredible Day Trip 10/10 Would Recommend!
We had the most amazing private boat trip to Dia with Marios and George, and we honestly couldn’t recommend them highly enough!From the moment we met them, they were incredibly friendly, welcoming and professional. They were right on time to greet us and immediately made us feel comfortable and looked after throughout the entire trip.When we arrived at Dia, they had a fantastic selection of equipment for water activities, which made the day even more fun. They genuinely went above and beyond to make sure we had the best experience. We didn’t have suitable shoes for going onto the island, but rather than letting that stop us, they came up with a clever makeshift solution so we could take our shoes with us. It was such a small thing, but it really showed how thoughtful and attentive they were.When we returned to the boat, we were greeted with a beautiful selection of fresh fruit that they had prepared for us. Not only was it absolutely delicious, but it was presented so beautifully that, honestly, if the sailing career ever comes to an end, they definitely have a future in food presentation! 😂Marios and George were incredibly knowledgeable, attentive and professional, while still being fun and easy to spend the day with. They made the whole experience feel effortless and genuinely special. We had an unforgettable day and couldn’t have asked for better guides. A huge thank you to Marios and George for making our trip to Dia one of the highlights of our honeymoon. We would 100% recommend them to anyone looking for an amazing boat trip in Crete! ❤️⛵️🌊
Read more
Nice saiking trip
New York City
Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
L9645FXmatthiasr, Sep 2026
Nice saiking trip
Super sailing trip, would definitely recommend it.
Read more
Fun trip
New York City
Ag. Nikolaos Catamaran to Spinalonga – Gourmet Meal & Water Toys
Travel57689347925, Sep 2026
Fun trip
Wonderful experience! Guides were fun and full of energy. Lots of delicious food also. The time went so fast.
Read more
Sailing on Cabrio
New York City
Ag. Nikolaos Catamaran to Spinalonga – Gourmet Meal & Water Toys
markwN5441VC, Sep 2026
Sailing on Cabrio
The crew took great care of us. The boat was in excellent condition, and we enjoyed the experience. We are happy we selected this adventure for our day in Crete.
Read more
Great experience, a must book
New York City
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun
baileyc927, Sep 2026
Great experience, a must book
Transport pick up was a breeze and the crew has been awesome!!! The only negative we’ve had was the clouds, and they made it fun regardless! Would recommend 10/10!
Read more
Catamaran trip around spinalonga with unlimited drinks, food and swimming.
New York City
Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys
barrmorter, Sep 2026
Catamaran trip around spinalonga with unlimited drinks, food and swimming.
Great afternoon/early evening trip out with swimming, food, amazing views you only get from sea of the coast and Spinalonga. Excellent and friendly crew with great food/drink and a giant pink flamingo (what more could you want?!?). They also have loads of other stuff to mess about in the sea with, like paddle boards, snorkels, flippers and under water sea scooters. All that and a slide from the top deck. There were 20 people in total with us and didn't feel crowded at all. Would recommend 100%.
Read more
Worth the money for a smaller trip
New York City
Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys
neilm051969, Sep 2026
Worth the money for a smaller trip
Weren’t sure what to expect but wanted something smaller than the big impersonal party boat trips.Picked up by taxi from hotel and taken to marina where we boarded a very impressive looking catamaran.From start to finish the trip was laid back, informative and enjoyable - 10 couples in total and such a nice atmosphere:Sailed around around Soinalonga island and had a brief history lesson - in time for an actual trip onto the island tomorrowSwam in the Blue Lagoon and first time using an inflatable slide into the sea.Good food too and a couple of beers while the sun set behind us.Worth every Euro
Read more
Perfect half a day trip
New York City
Luxury Catamaran Cruise All-Inclusive & OnBoard Chef | Top Rated!
emmimariar, Sep 2026
Perfect half a day trip
Very nice trip! Friendly and helpnful stuff, good food and drinks! Swimming spot was beautiful and we had enough time! Snorkeling equipments and sup boards were procided😊 Perfect half a day trip. We had a two year old with us, and everything worked perfectly with her as well.Had enough space in the boat. Good toilets!
Read more
So enjoyable!
New York City
Balos Shared Catamaran Cruise (small groups to 22ppl)
suerM2634GF, Sep 2026
So enjoyable!
We had a great time on our trip. We had plenty of time to look around, swim, and snorkeled a bit. The boat ride there was nice and we sat up front and saw some flying fish on the way. Our captain and assistant did a phenomenal job of making us feel comfortable and safe.
Read more
Brilliant
New York City
Balos Shared Catamaran Cruise (small groups to 22ppl)
David_R, Sep 2026
Brilliant
So relaxed. Absolutely brilliant with lovely food, wine, beer, water. Just amazing and a prompt transfer as well. Well worth it.
Read more
Absolute highlight of our vacation
New York City
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun
Jacroy, Sep 2026
Absolute highlight of our vacation
The trip to Dai Island was an absolute highlight of our vacation, delivering the perfect balance of relaxation and high-energy fun.The captain and crew went above and beyond to make our day special. They were incredibly friendly, attentive, and deeply knowledgeable, ensuring every guest felt welcomed and safe throughout the journey. Their warm hospitality truly set the tone for the entire experience.The onboard food was another major standout. We were treated to fresh, Mediterranean-style lunches and snacks that earned high marks from everyone in our group for both quality and flavor. It was a delicious, authentic touch that felt much more elevated than standard boat trip fare.When it came to water activities, the boat was exceptionally well-equipped. The crew kept us entertained with a fantastic variety of gear, including an inflatable water slide that was a hit with everyone, sea scooters, paddleboards, and top-tier snorkeling gear. Whether you wanted to lounge on a paddleboard or zip through the water, there was something for every pace.If you are considering a trip to Dai Island, this experience is worth every penny.
Read more
Good view & experience
New York City
Dia Island Catamaran – Premium Lunch, Open Bar, Small Group
L659ZKericah, Sep 2026
Good view & experience
Had such a great experience here with friends! The lunch was delicious, and the view was absolutely incredible. Definitely a beautiful spot to enjoy good food and good company!
Read more
Recommended trip
New York City
Dia Island Catamaran – Premium Lunch, Open Bar, Small Group
mattdQ2111IE, Sep 2026
Recommended trip
Great experience, beautiful views at Dia island
Read more
Hens on Board
New York City
Rethymno Catamaran Cruise: Healthy Lunch & Open Bar
kylieskyes2023, Sep 2026
Hens on Board
No notes. Could not have been better. Every element was perfection. Highly recommend. Best trip ever
Read more
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