Greece · SAILING TRIPS IN CRETE

The 12 Best Sailing Trips in Crete

12 tours  ·  ★★★★★★★★★★ 4.9 average  ·  from $35

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Sailing out of Heraklion: what the first stretch feels like
Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Our pick

Luxury sailing from Heraklion to Dia Island with snorkeling, drinks, and lunch on shared trips, plus private options for more control.

“Wonderful early evening on the water with passionate captain and first mate. Vibes were exactly what we were looking for to get out on the water. Would definitely book again!”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Meeting point and getting on your boat without stress
Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Half-Day, Private, Sailing, Sailing Trips in Crete, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

2.Private Half-Day Sailing Trip to Dia Island

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

Private half-day sailing from Heraklion to Dia Island with swimming, snorkeling, fishing, paddleboarding, unlimited drinks, and optional onboard meal.

“We loved the staff (captain and co-captain). It was really relaxing and the lunch was great. They had all the equipment for snorkelling and even moved the boat closer to the beach, so that we could swim to it. Such a great day! Thank you”

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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - The boat and crew experience, cabins, gear, and how the day stays easy
Balos & Elafonisi Boat Trips, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

3.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa, with Cretan lunch onboard, swimming, snorkeling, and castle views on a small-group cruise.

“The captain and Jo were wonderful. They took good care of our family. The tasty foods, the company, and Balos/Gramvousa Island were all great. We really enjoyed seeing their sailing experiences. You can definitely trust their sailing capabilities. Highly recommend this excursion.”

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Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated! - The onboard food plan: brunch, salads, lunch, and dessert
Catamaran Cruises, Catamaran Cruises in Crete, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Drinking Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews, VIP

Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

4.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145Top rated

Luxury catamaran cruise from Iraklio to Dia Island with open bar, Mediterranean lunch, snorkel and SUP gear, about 5.5 hours.

“What a day Amazing food as a first Amazing boat Amazing staff Amazing day and amazing trip 20/10 thanks again . Check out my page for some photos also @seriouslyscrumptiouseats”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - From Epimenidou 19 to the Harbor: Getting Started Without Stress
Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Sailing, Sailing Trips in Crete, Snorkeling, Snorkeling in Crete, Tour Reviews

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

5.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36

Sail from Heraklion to Dia Island for snorkeling, lunch, drinks, and a sunset return option on a small yacht group.

“This was a truly fantastic experience that my wife and I enjoyed thoroughly! First, we appreciated all the communication before the day of our trip, with all the practical information regarding the trip, which made the preparations and planning simple and easy. We felt the duration of 4.5 hours worked very well. The trip itself is awesome in all respects and definitely something one should do if they visit the area of Heraklio. The sailing experience is exciting, the water at Dia is marvelous, the meal is delicious, and the staff is amazing! Our captain and co-captain were Markos and Magda and each of them was the perfect combination of…”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - The first hour in Heraklion: sailing energy and a simple start
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Heraklion: Private Full-Day Sailing Trip to Dia Island

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Heraklion start, a quick Rocca a Mare photo stop, then you’re off
Catamaran Cruises, Catamaran Cruises in Crete, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Drinking Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews

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

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

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Heraklion to Dia Island on a small-group catamaran with snorkel and SUP gear, Wi-Fi, premium lunch, and open-bar drinks.

“The trip was pleasant enough but compared to similar trips taken elsewhere in Greece, this was very poor value for money at £120 pp. The departure port was moved from Hersonisos to Heraklion which cost us an extra 160 Euros in taxi fares for the six of us. The trip itself was uninteresting and just involved sailing straight to Dia island where anchor was dropped to take a dip from boat. Lunch was only adequate at best. Then sailed straight back to port with no other stop offs. This was certainly an overpriced trip for what was on offer.”

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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Price and value: what your $235.83 actually buys
Balos & Elafonisi Boat Trips, Catamaran Cruises, Catamaran Cruises in Crete, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Sailing, Sailing Trips in Crete, Tour Reviews, VIP

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

8.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

★★★★★★★★★★5.0 · 116 reviews · 7 hours 30 minutes (approx.) · from $235

Luxury catamaran cruise from Kissamos to Balos Lagoon and Gramvousa with snorkeling, SUP, open bar, and a full Mediterranean lunch.

“If you’re looking for a way to explore Balos and Gramvousa, but want to avoid having to trek there or taking the ferry, do this!! It was such a stress free day and the boat was lovely. Balos and Gramvousa were absolutely stunning. It was so nice to basically explore it all alone. This trip is timed to avoid the ferry onslaught of people at both locations. Also, the food is stellar! I would definitely do this trip again and totally recommend it! Also, I love swimming and this trip gave me plenty of time to swim and snorkel in the Aegean!”

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Panormo: Luxury Catamaran Cruise with Lunch & Open Bar - The boat setup: sunbeds, shade, and onboard comfort that really helps
Catamaran Cruises, Catamaran Cruises in Crete, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Drinking Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews, VIP

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Heraklion start, a quick Rocca a Mare photo stop, then you’re off
Catamaran Cruises, Catamaran Cruises in Crete, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Drinking Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews

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

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

★★★★★★★★★★4.9 · 42 reviews · 6.5 - 8.5 hours · from $176

Luxury catamaran day to Dia Island, Crete with premium lunch, open bar, snorkeling gear, SUP and small-group service. $176.

“The catamaran looks so new and classy! Very friendly and accommodating staff. Super tasty food, and there are plenty of things to do! Everyone on board loved it! We all made new friends and had amazing time! The best yacht cruise I ever had! Thank you, guys!”

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Kissamos: Balos and Gramvousa Private Sailing Trip with Meal - Balos Lagoon: white sand, snorkel-ready water, and real downtime
Balos & Elafonisi Boat Trips, Crete Boat Trips, Crete Tours & Activities, Cruises & Boat Tours, Private, Sailing, Sailing Trips in Crete, Tour Reviews

Kissamos: Balos and Gramvousa Private Sailing Trip with Meal

11.Balos and Gramvousa Private Sailing Trip with Meal

★★★★★★★★★★4.8 · 41 reviews · 8 hours · from $931

Private sailing from Kissamos to Balos Lagoon and Gramvousa Island, with snorkeling gear and onboard Cretan lunch for groups up to 10.

“It was a fantastic day on the water with Christopher. Everything was timed perfectly with 2 hours at each stop to swim or explore. The views were amazing on this trip and lunch was excellent.”

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From Chania: Fully Private Sailing Cruise with Meal & Drinks - The Crew Makes It Feel Like Your Day, Not a Schedule
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From Chania: Fully Private Sailing Cruise with Meal & Drinks

12.Fully Private Sailing Cruise with Meal & Drinks

★★★★★★★★★★5.0 · 18 reviews · 7 hours · from $883

Private sailing cruise from Chania with onboard snorkeling, swims in secluded coves, and a freshly cooked 3-course meal plus drinks for up to 4.

“Excellent day. Swam in beautiful clear waters. Sailed in open waters. It would have been good to have had some snorkelling gear, but other than it was superb. Lunch was delicious. It was cooked on the boat with local food. The skipper and his crew were lovely.”

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