15 Sailing Trips in Crete to Plan a Week Around

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The smooth start: boarding at Cafe Marina in Heraklion

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

A small-group sail from Heraklion to Dia Island in Crete with swimming, snorkeling, paddleboarding, and a Mediterranean meal plus unlimited drinks.

“Perfect friendly Crew. Nice Katamaran. Good drinks and delicious food. It was my third time with this company. Sofia, Giannis and our Captain Petros are a super Crew. I will make the Dia Tour again. I love it sooooo much. Thank you Guys. Nicole”

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Cruises & Boat Tours, Dia Island Cruises, Lunch Experiences, Sailing, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Sail from Heraklion to Dia Island on a luxury yacht with snorkeling, unlimited drinks, and lunch, plus optional fishing.

“The trip was excellent and relaxing, especially because our captain and co-captain were very informative and friendly. Overall great experience and the food was amazing too!”

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Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing, Tour Reviews

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

3.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing, drinks, and a Greek meal, with optional sunset views.

“This was a fabulous trip. The staff were very friendly and committed to making sure everyone had a good time. They boat was fantastic and their were enough activities to keen everyone entertained during the cruise. Food was fantastic too. Highly recommend this tour to anyone in Heraklion for the day.”

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Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing, Snorkeling Tours, Snorkeling Tours in Heraklion, Tour Reviews

Heraklion: Dia Island Sailing Cruise with Snorkeling

4.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, drinks, and Greek food on a small group cruise.

“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if I was doing it again, I would book the whole day! Highly recommend this experience! So worth it. 🤍 A big Thank you!!!!!! 🇬🇷 Best ever. Oh & the food was simple, but great! & we had lovely music for the whole tour, good ambiance!!!! +++5 stars ✨”

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Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing, Tour Reviews

Sailing Cruise to Dia Island with Meal and Water Activities

5.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, and a shrimp linguini lunch with wine and beer included.

“Our excursion to Dia Island from the port in Heraklion was very enjoyable. About an hour from port, the captain anchored the boat in a small bay off the island. There were two small beaches there. Once arriving, we had 3-4 hours of free time for all sorts of water activities (snorkeling, paddle boarding, swimming off the boat in the bay) Lunch was served (pasta with shrimp, fresh fruit, etc). This was a great vacation activity, especially for kids. Thoroughly enjoyable.”

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Balos & Gramvousa Tours, Balos & Gramvousa Tours in Kissamos, Cruises & Boat Tours, Kissamos Tours, Sailing, Tour Reviews, VIP

Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

6.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229

Luxury catamaran day trip from Kissamos to Balos lagoon and Gramvousa island, with open bar, swim gear, and free transfers.

“Spectacular cruise and brilliant crew We had a truly amazing cruise to Balos and Gramvousa. The crew Dimitri, Jessica and Giannis were brilliant, very welcoming and knowledgeable. They provided first class hospitality throughout the day, great food, drinks and entertainment. They were great with my son who got to try fishing and S/U paddle boarding. Balos and Gramvousa are spectacular, the views, beaches, snorkelling made this the highlight of our trip to Crete. Would highly recommend this.”

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Cruises & Boat Tours, Dia Island Cruises, Half-Day, Private, Sailing, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

7.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459

Private 4.5-hour sail from Heraklion to Dia Island with snorkeling, fishing gear, paddleboards, drinks, fruit, and optional meal.

“It was a great experience. Best skipper team with Haris and Thomas. Thank you for an unforgettable trip! In August the sea is very rough from noon to afternoon, you should be a bit seaworthy ;)”

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Cruises & Boat Tours, Drinking Tours, Evening Experiences, Rethymno Tours, Sailing, Sunset Cruises, Tour Reviews

Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

8.Sunset Catamaran Cruise – Sushi & Open Bar

★★★★★★★★★★4.8 · 446 reviews · 3.5 hours · from $100

Rethymno sunset catamaran with open bar and sushi. Swim, SUP, snorkel, then watch the Cretan sunset from a pink flamingo float. 3.5 hours.

“The staff were all friendly and accommodating, making sure that our experience was special. The view was amazing and the sunset was spectacular.”

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Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Lunch Experiences, Sailing, Tour Reviews

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

9.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing, and a Mediterranean lunch with unlimited drinks in a small group.

“Ilis and Vaso were our guides and we were really pleased with their hospitality. They were very welcoming, ensured we were looked after and had the best possible experience. Food was really lovely and great variety of drinks available on board. They had a paddling board and snorkelling masks available for everyone for when we stopped off to swim. Would recommend, 10/10 experience.”

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Chania Tours, Cruises & Boat Tours, Sailing, Tour Reviews

Kolimvari: Sailing Cruise with Meal & Water Activities

10.Kolimvari: Sailing Cruise with Meal & Water Activities

★★★★★★★★★★4.7 · 390 reviews · 5 hours · from $129

Sail from Kolimvari to Agioi Theodoroi for swimming, snorkeling and SUP, with a 3-course Crete meal and unlimited drinks.

“Loukas & Jason were lovely hosts, the boat was a great size for the group of 11 that we had. loved the paddle boarding and jumping off the side of the boat. fab value for money, Jason is an excellent chef and Loukas an excellent captain. we had a lot of fun and would definitely recommend this over the larger tours!”

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Cruises & Boat Tours, Evening Experiences, Hersonissos & Malia Tours, Sailing, Sunset Cruises, Tour Reviews

Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks

11.Sunset Catamaran Cruise with Snacks and Drinks

★★★★★★★★★★4.8 · 328 reviews · from $90

3.5-hour Hersonissos sunset catamaran with open bar, snacks, swimming, snorkeling, SUP, and a golden-hour sail along Crete’s coast.

“Loved everything about this trip! Wonderful experience from start to finish, something we will never forget! Hosts were lovely and friendly, food/drink was great, music was awesome too! We had enough time to jump and swimming in the sea and also enough time to enjoy the beautiful sunset! The most relaxing boat trip I’ve ever been on, highly recommend to anyone don’t hesitate to book it! Thanks for the wonderful experience, Monika,Tim &Oliver”

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Cruises & Boat Tours, Rethymno Tours, Sailing, Tour Reviews

Rethymno: Sailing Catamaran Cruise with Meal & Drinks

12.Sailing Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.7 · 285 reviews · from $164

New catamaran from Rethymno to swim near Georgioupoli, with snorkel gear, SUP, unlimited drinks, and a Mediterranean lunch.

“Absolutely gorgeous outing. We sailed to two beautiful coves outside of Rethymno and swam, snorkeled, and paddle boarded while the staff prepared lunch. We were served a cheese tray, Greek salad, avocado salad, pasta with garlicky tomato sauce with prawns, grilled orange chicken, pita bread, and an assortment of desserts. They even provided a birthday cake for one lucky guest. The white wine and beer were unlimited and the staff were very attentive with refills. The coves where we swam were absolutely GORGEOUS. They had that beautifully blue water that you think of when you picture Crete. There’s not a lot of shade on a catamaran, so keep that in…”

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Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Lunch Experiences, Sailing, Tour Reviews

Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

13.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Small-group sailing from Heraklion to Dia Island with crystal coves for snorkel, SUP and wildlife, plus organic lunch and wine.

“We had amazing time on this trip. Crew were very helpful and friendly. Amazing view from the sailing boat. We stopped in very beautiful shore, where we could swim in the sea and have relaxing time. Served food was also great. All in all 100 percent I would recommend this experience. Maybe I would suggest taking a day time trip, because it gets a bit chilly in the evening. But even in the cold weather I had a good time.”

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Cruises & Boat Tours, Dia Island Cruises, Evening Experiences, Heraklion Tours, Sailing, Snorkeling Tours, Snorkeling Tours in Heraklion, Sunset Cruises, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

14.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63Best value

Heraklion to Dia Island sunset catamaran with snorkel time, paddleboard, food and drinks, and up to 7 hours on Crete.

“Amazing, lovely time in the water, the snorkelling kits and paddle board added to the fun. Great wine on deck too!”

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Cruises & Boat Tours, Sailing, Tour Reviews

Sailing trip to the Top Coasts of Crete, Daily/Multi-day

15.Sailing trip to the Top Coasts of Crete, Daily/Multi-day

★★★★★★★★★★5.0 · 221 reviews · 7 hours (approx.) · from $1,197Top rated

Private sailing day on Crete’s south coast, visiting Loutro, Glika Nera and Marmara for cave swims, snacks and shade.

“Beautiful, non-touristy sailing trip. Swam in some amazing caves. Visited a village that you can only access by boat or hiking. A day we will never forget!!”

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