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Top Heraklion Sailing Trips

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Heraklion 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
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
4.9 (241)

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 (241)
from
$130
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

4.8 (476)

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 (476)
from
$79
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
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
$88
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

4.9 (115)

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 (115)
from
$78
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

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
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
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
$1,021
Daily cruises to Dia Island with All -Inclusive Meal and drinks

Experience a Unique Sailing Adventure and savor our All-inclusive authentic Mediterranean menu, unlimited fragrant white wine, soft drinks and bottled water. The journey to the …More

Likely to Sell Out
Likely to Sell Out
4.9 (36)

Daily cruises to Dia Island with All -Inclusive Meal and drinks

Experience a Unique Sailing Adventure and savor our All-inclusive authentic Mediterranean menu, unlimited fragrant white wine, soft drinks and bottled water. The journey to the...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.9 (36)
from
$75
Private Luxury Sailing Trips to Dia Island

Why not try a new, unforgettable experience! The uninhabited island of Dia is just 6 NM away but also worlds apart from the hustle and …More

Likely to Sell Out
Likely to Sell Out
4.7 (21)

Private Luxury Sailing Trips to Dia Island

Why not try a new, unforgettable experience! The uninhabited island of Dia is just 6 NM away but also worlds apart from the hustle and...

6 hours • Hotel pickup offered • Free Cancellation
4.7 (21)
from
$498
SAILING DAY 4.5-5h & SUNSET 3 or 4.5-5h from Hersonissos CRETE

The minibus picks you up outside your hotel and takes you to the port in Gouves, where the boat leaves. DAY & SUNSET of 4.5-5h: …More

4.8 (24)

SAILING DAY 4.5-5h & SUNSET 3 or 4.5-5h from Hersonissos CRETE

The minibus picks you up outside your hotel and takes you to the port in Gouves, where the boat leaves. DAY & SUNSET of 4.5-5h:...

3 to 5 hours • Hotel pickup offered • Free Cancellation
4.8 (24)
from
$104
Luxury escape Sailing, shared from Hersonissos or Heraklion port

Looking for an Escape? On a yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and …More

4.8 (6)

Luxury escape Sailing, shared from Hersonissos or Heraklion port

Looking for an Escape? On a yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and...

7 hours • Hotel pickup offered • Free Cancellation
4.8 (6)
from
$104
Catamaran Sailing Trip - All Inclusive

Join a unique catamaran adventure from Heraklion to the beautiful, unspoiled Dia Island. Sail in comfort and style aboard a spacious catamaran, enjoying a relaxed …More

4.7 (21)

Catamaran Sailing Trip - All Inclusive

Join a unique catamaran adventure from Heraklion to the beautiful, unspoiled Dia Island. Sail in comfort and style aboard a spacious catamaran, enjoying a relaxed...

5 to 6 hours • Hotel pickup offered • Free Cancellation
4.7 (21)
from
$121
Private Sailing Cruise to Dia Island with Meal & 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

4.7 (10)

Private Sailing Cruise to Dia Island with Meal & 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 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (10)
from
$778
Full Day Private Luxury Escape Sailing

Immerse yourself in the serene ambiance of island life aboard a luxurious yacht, surrounded by breathtaking views and attentive crew. Savor the delightful Mediterranean cuisine, …More

5.0 (4)

Full Day Private Luxury Escape Sailing

Immerse yourself in the serene ambiance of island life aboard a luxurious yacht, surrounded by breathtaking views and attentive crew. Savor the delightful Mediterranean cuisine,...

8 hours • Hotel pickup offered
5.0 (4)
from
$1,391
Sunset Sail & Gourmet dinning

Escape the ordinary and expand your horizon! A Breath of Fresh Air! Enjoy moments of tranquility, soak up the sun, float in sparkling azure waters …More

5.0 (1)

Sunset Sail & Gourmet dinning

Escape the ordinary and expand your horizon! A Breath of Fresh Air! Enjoy moments of tranquility, soak up the sun, float in sparkling azure waters...

4 hours 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$799

Frequently Asked Questions

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

Recent tour reviews
Crete
New York City
Dia Island Sailing Cruise with Meal and Water Activities
Joann_C, Sep 2026
Crete
The crew was awesome. Captain dimetre and George. The cook Richard. All were so nice. Went paddle boarding to the island. Such a beautiful island.
Read more
Amazing!
New York City
Sailing Trip to Dia Island – All Inclusive
Stephanied2527, Sep 2026
Amazing!
Amazing experience! Beautiful isle land and very friendly crew. Would definitely recommend!
Read more
Crete trip
New York City
Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun
Wazzertv, Sep 2026
Crete trip
Brilliant experience. I honestly couldn't find a fault, im so happy we booked this. The crew were amazing. Our deck hand Daniel was a star. He had time for everyone. The yacht was clean and well kept. And it wasnt overcrowded. Highly recommend
Read more
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
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
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
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 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
Sunset cruise
New York City
Rethymno: Sunset Catamaran Trip – Sushi & Open Bar
jackiefL4251UA, Sep 2026
Sunset cruise
Totally amazing! Went with my boyfriend but met lots of wonderful people! Great cove and beach when we stopped - paddle boarding, snorkellling and swimming. Lovely sunset - fantastic part of our holiday in Crete. Thank you xx
Read more
Amazing views
New York City
Rethymno: Sunset Catamaran Trip – Sushi & Open Bar
SienRamboer, Sep 2026
Amazing views
Amazing views, great tour guides
Read more
Views, sun, and water
New York City
Heraklion: Full Day Sailing Experience-Dia Marine Area with Lunch
Steve_S, Sep 2026
Views, sun, and water
What an phenomenal time. The captain and skipper were informed, kind, and very good at their job. I cannot recommend enough.
Read more
Action and romance for water lovers
New York City
Daily cruises to Dia Island with All -Inclusive Meal and drinks
A1281IRannikar, Sep 2026
Action and romance for water lovers
A fantastic trip to the island of Dia by sailboat. We left the harbor at 3:00 PM and returned about 5 hours later around 8:15 PM. The skipper and captain were super nice and gave us very good instructions on how to behave on the boat in quite choppy seas. It was a really exciting experience because the trip was very action-packed. After about 1 hour, we reached a beautiful, blue bay for swimming and snorkeling. During this time, while the guests were in the water, salad, pasta with shrimp, and fruit for dessert were prepared for us, which we could then enjoy with soft drinks and white wine. The return trip into the sunset was also unforgettably beautiful. A great price-performance ratio!
Read more
Dia island experience
New York City
Catamaran Sailing Trip – All Inclusive
Jean_S, Sep 2026
Dia island experience
Great crew , food and drink excellent and cooked from scratch which was impressive. The island and the water was turquoise blue like an ad for Greece. I would highly recommend it
Read more
Absolutely amazing sailing trip – highly recommended! ⭐⭐⭐⭐⭐
New York City
Heraklion: Full Day Sailing Experience-Dia Marine Area with Lunch
Connector15717099859, Sep 2026
Absolutely amazing sailing trip – highly recommended! ⭐⭐⭐⭐⭐
We had an absolutely wonderful day sailing with Tonia and George! From the very beginning, everything was perfect. They were incredibly friendly, welcoming, attentive and made us feel comfortable throughout the entire trip.The sailing itself was beautiful, and the swimming spots were absolutely fantastic. The water was crystal clear and every stop was a highlight of the day. We also really enjoyed the food on board – everything was delicious and made the experience even more special.What really stood out to us, though, was how warm and genuine Tonia and George were. They were always there when we needed something, but at the same time made the whole trip feel relaxed and effortless. You can tell that they genuinely care about their guests and want everyone to have an amazing time.This was definitely one of the highlights of our holiday in Crete. We enjoyed every single minute and would book this trip with Tonia and George again without hesitation.Thank you so much for an unforgettable day! ❤️⛵🌊
Read more
Cool way to spend a day!
New York City
Daily cruises to Dia Island with All -Inclusive Meal and drinks
Kettia_D, Sep 2026
Cool way to spend a day!
Great way to spend a Greek morning or afternoon..This is just a boat trip to the island and back ...you will only see the island from the boat... unless you swim to it. For my favorite part!My crew was the best! It was my mom's first time on a boat and she enjoyed it very much! Thank you so much!
Read more
Amazing booking and experience
New York City
Private luxury Escape free drinks & Meals Cruise
samanthagN2673OA, Sep 2026
Amazing booking and experience
Magda was the best! We arrived early and our boat wasn’t quite ready so she gave us a tour of the surrounding city and it was wonderful!! She’s so kind and easy to talk to. I’d recommend her every time!!
Read more
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