Sailing in Crete packs some of Europe’s best Mediterranean adventures into manageable day trips. Small-group catamaran cruises give you the most bang for your buck, combining swimming stops, local food, and uncrowded deck space. My favorite tours leave from the old harbor of Heraklion – they’re well-organized and include everything from snorkel gear to authentic Greek lunch spreads.
The sunset trips are particularly memorable, especially when the coastline glows orange and you’re sipping local wine. For families or groups, half-day trips to Dia Island offer the perfect mix of history and leisure. Private sailing lets you set your own pace, though it’s pricier.
The best tours nail three things: knowledgeable local crews, stops at hidden coves, and fresh-cooked meals onboard. Most operators offer free cancellation and hotel pickup – smart for flexible travel plans.
Let’s check out the top sailing tours worth your time and money.
Good To Know
- Small-group luxury catamaran cruises with swimming, snorkeling, fishing, and paddleboarding, featuring Greek cuisine and complimentary drinks.
- Sunset and evening cruises offering breathtaking coastal views, traditional Cretan snacks, and drinks like Prosecco.
- Guided and private full-day cruises with 100% recommendation rates, catering to groups of up to 8 people.
- Half-day and premium sailing experiences to Dia Island, including snorkeling and stand-up paddleboarding.
- Luxury yacht cruises featuring fine dining and coastal views, accommodating up to 20 travelers.
Small-Group Luxury Catamaran Cruise to Dia Island – Crete
On a sunny morning in Crete, travelers embark on a small-group luxury catamaran cruise to the enchanting Dia Island.
Recommended by 96% of past guests, this cruise offers a personalized experience capped at just 10 people.
The day’s activities include swimming, snorkeling, fishing, and stand-up paddleboarding, all while enjoying Greek cuisine like salads, pasta with shrimp, and chicken with oranges.
Complimentary drinks, including Raki and quality white wine, add to the relaxing atmosphere.
With onboard restrooms, Wi-Fi, and a convenient meeting point, this cruise provides exceptional service and beautiful scenery, though some travelers note occasional overcrowding at the destination.
Read our full review: Small-Group Luxury Catamaran Cruise to Dia Island – Crete Review
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Sunset Cruise – Yachting Tour on Catamaran Heraklion, Crete
Travelers embark on a sunset cruise along the coast of Heraklion, Crete, aboard a luxurious catamaran. This small-group tour is capped at 10 people, ensuring an intimate experience.
The evening includes traditional Cretan snacks, drinks, and water sports like swimming, snorkeling, and stand-up paddleboarding around the idyllic isle of Dia. Guests are welcomed with a glass of Prosecco and can enjoy alcoholic beverages, soft drinks, and use of snorkeling equipment throughout the cruise.
With a 90% traveler recommendation and a Badge of Excellence, this sunset tour offers breathtaking views, a relaxing atmosphere, and the opportunity to take in the local culture.
Read our full review: Sunset Cruise – Yachting Tour on Catamaran Heraklion, Crete Review
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Crete Yacht Cruises 8-Hours Guided Cruise in Agios Nikolaos
For those seeking a comprehensive Cretan yachting experience, the Crete Yacht Cruises 8-Hour Guided Cruise in Agios Nikolaos delivers an exceptional journey.
Priced at $1,709.28 per group of up to 8 people, this 7-hour private cruise offers a 100% recommendation rate based on 35 glowing reviews.
Guests can enjoy a delicious Cretan-style lunch prepared by the captain’s wife, along with unlimited soft drinks, water, beer, and wine.
The cruise also provides snorkeling equipment and is accessible for wheelchair users, strollers, and service animals.
With a free cancellation policy and the option to reserve now and pay later, this cruise is a must-consider for those seeking an unforgettable Cretan sailing experience.
Read our full review: Crete Yacht Cruises 8-Hours Guided Cruise in Agios Nikolaos Review
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Half-Day Sailing Trips to Dia Island
Situated just a short distance from Crete’s northern shore, the Half-Day Sailing Trips to Dia Island offer visitors a chance to explore the enchanting island of Dia.
This 4.9-star rated activity includes a skipper, snorkeling equipment, fishing gear, and a delectable lunch featuring roasted chicken, rice, and a Greek salad.
Passengers can also enjoy refreshments like soft drinks, white wine, and bottled water.
The trip allows for swimming in the turquoise waters and returns to the starting point in Heraklion.
With a maximum group size of 10 travelers, this wheelchair and stroller-accessible activity is priced from $90.81 per person and offers flexible booking and cancellation options.
Read our full review: Half-Day Sailing Trips to Dia Island Review
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Day Private Sailing Cruises to Balos Lagoon, Gramvousa Island and More.
Explore the enchanting Balos Lagoon and Gramvousa Island on a private sailing cruise operated by Mikros Naftilos Cruises.
Recommended by 97% of travelers, this 4.9/5 rated experience offers a relaxing journey aboard the Mikros Naftilos. Enjoy a delicious regional lunch and unlimited drinks as you take in the stunning views.
The crew’s local knowledge ensures safe swim spots, and amenities like a restroom, shower, and beach towels provide convenience.
This private tour for your group is priced at $1,281.96 per group of up to 10 people.
Positive reviews highlight the professionalism and hospitality of the crew, as well as the beautiful sailing experience and breathtaking scenery.
Read our full review: Day Private Sailing Cruises to Balos Lagoon, Gramvousa Island and More. Review
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Private Full-Day Sailing Tour With Greek Lunch From Chania – Crete
Embarking on a private full-day sailing tour from Chania, Crete, allows visitors to enjoy the region’s captivating history and natural beauty.
For $213.66 per person, this all-inclusive experience includes a delectable local lunch, snorkeling equipment, and an open bar featuring beer, wine, and more.
Guests can explore historic sites like Fortezza and Cape Drapano lighthouse, as well as swim and snorkel in sheltered waters.
With a 100% recommendation rating from 32 travelers, the tour is led by a welcoming and knowledgeable host, Captain Nikos, who ensures a perfect balance of cruising and activities.
The tour starts and ends at the convenient meeting point in Souda, making it easily accessible for both locals and visitors alike.
Read our full review: Private Full-Day Sailing Tour With Greek Lunch From Chania – Crete Review
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Heraklion Half Day Sailing Cruise to Dia Island
Visitors seeking a half-day sailing adventure can discover the picturesque Dia Island from Heraklion, Crete. This popular 4.6-rated tour includes amenities like snorkel gear, paddle boards, and complimentary snacks and drinks.
The cruise departs from the Cafe Marina, with pickup available upon request. The small group size of up to 10 travelers ensures an intimate experience. Passengers consistently praise the kind, attentive guides and the comfortable, knowledgeable captains.
However, some reviewers caution about potential overbooking issues. The Heraklion Half Day Sailing Cruise to Dia Island offers a scenic and positive sailing experience for €74.78 per person, with free cancellation up to 24 hours in advance.
Read our full review: Heraklion Half Day Sailing Cruise to Dia Island Review
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Premium – Day Sailing Catamaran Trip in Group, Rethymno, Crete
A premium day sailing catamaran trip in Rethymno, Crete, offers an exceptional opportunity to explore the stunning coastline and crystalline waters of the region.
Operated by DanEri Yachts, this 4.5-star rated experience accommodates a maximum of 30 travelers for a comfortable journey.
The trip includes a range of inclusions, from alcoholic beverages and traditional Greek cuisine to the use of snorkeling and water sports equipment.
Guests have praised the beautiful scenery, friendly staff, and relaxing atmosphere, though some have noted minor wait times for drinks.
With a Badge of Excellence and free cancellation, this premium sailing experience is highly recommended for travelers seeking a memorable day on the water in Crete.
Read our full review: Premium – Day Sailing Catamaran Trip in Group, Rethymno, Crete Review
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Crete Sailing Trip From Hersonissos
This sailing trip from Hersonissos, Crete, offers travelers a chance to explore the scenic St. George’s Bay and Stalis aboard a traditional wooden boat.
The 3.8-rated experience includes swimming and snorkeling at two popular spots, as well as an on-board BBQ lunch.
While the friendly crew and beautiful natural settings receive praise, some guests have critiqued the value, citing concerns over food quality and overcrowding.
The trip isn’t wheelchair accessible but is stroller-friendly.
Travelers should also note health restrictions and the 24-hour cancellation policy.
Read our full review: Crete Sailing Trip From Hersonissos Review
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Agios Nikolaos Evening Catamaran Cruise in Mirabello With Dinner
Travelers seeking a picturesque evening on the Mediterranean can embark on the Agios Nikolaos Evening Catamaran Cruise in Mirabello, which sails around the stunning Gulf of Mirabello and Spinalonga.
This small-group tour accommodates a maximum of 20 guests, providing a more intimate experience. The cruise includes a delicious Greek-style dinner, alcoholic and non-alcoholic beverages, and use of equipment like stand-up paddleboards and snorkeling gear.
Reviewers praise the attentive staff and relaxing atmosphere, though some note a crowded feeling and limited food selection.
Read our full review: Agios Nikolaos Evening Catamaran Cruise in Mirabello With Dinner Review
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Day Sea Excursion on Catamaran Heraklion to Dia With Full Menu
Those seeking a full-day excursion on the Mediterranean can embark on the Day Sea Excursion on Catamaran from Heraklion to the uninhabited island of Dia.
This luxury yacht cruise offers fine dining and impressive coastal views. Guests can enjoy snorkeling, swimming, and sunbathing upon arrival at Dia, and take in the sunset on the return journey.
The all-inclusive experience features local grilled fish, wine, beer, and traditional Cretan dishes. Amenities include snorkeling and SUP equipment, fishing rods, and WiFi.
With a maximum of 20 travelers and a 92% recommendation rate, this excursion provides an excellent day at sea.
Read our full review: Day Sea Excursion on Catamaran Heraklion to Dia With Full Menu Review
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Southern Crete Private Sailboat Cruise With Lunch From Sfakia
Set out on a private sailing adventure along Crete’s southern coastline, departing from the picturesque town of Sfakia.
This full-day excursion takes you to stunning destinations like Sweet Water Beach, Marmara Beach, and the charming village of Loutro. Enjoy swimming, sunbathing, and optional snorkeling throughout the day.
With a private yacht, you’ll savor a local lunch, snacks, and refreshments while taking in the breathtaking views. The experience is highly recommended, boasting a 5.0 rating from 208 reviews.
Amenities include shaded areas and a cabin for relaxation. Meeting at Sfakia Port, this non-refundable activity is priced from $1,057.62 per group of up to 9 guests.
Read our full review: Southern Crete Private Sailboat Cruise With Lunch From Sfakia Review
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Chania Sailing Cruise, Swim, Snorkel, Lighthouse & Harbor Tour – Crete
The Chania Sailing Cruise, Swim, Snorkel, Lighthouse & Harbor Tour – Crete offers captivating sailing experiences around the Gulf of Chania, Crete, Greece.
Rated 5 stars with a Badge of Excellence, this tour departs from the Old Venetian Harbour and includes stops at the Island of Ag. Theodori for swimming and the stunning Maherida beach.
Onboard, guests enjoy traditional Cretan snacks, fresh fruits, and drinks from the open bar, as well as use of snorkeling equipment and sea towels.
Lunch is included on 7-hour cruises. Pickup from accommodations is available for an additional fee, and the tour concludes back at the meeting point.
Operated by Sailing Exploring & Driving Creta, the experience starts at €720.00 for up to 2 people.
Read our full review: Chania Sailing Cruise, Swim, Snorkel, Lighthouse & Harbor Tour – Crete Review
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Morning Catamaran Experience From Hersonissos. Cruise in Group
Travelers seeking a morning of relaxation and exploration can enjoy the Morning Catamaran Experience from Hersonissos, Crete.
This 91% recommended cruise takes guests on a journey to Dia Island, with a capacity of up to 20 passengers. Activities include sunbathing, swimming, snorkeling, stand-up paddleboarding, and fishing, with all necessary equipment provided.
The onboard experience features a healthy Mediterranean lunch and an array of beverages, including alcoholic drinks.
Wheelchair accessibility, proximity to public transportation, and a flexible cancellation policy make this experience convenient and accessible.
Priced from $154.90 per person, the Morning Catamaran Experience is an ideal way to enjoy Crete’s natural beauty and serenity.
Read our full review: Morning Catamaran Experience From Hersonissos. Cruise in Group Review
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Balos Sailing Cruises offer a shared small-group experience that allows travelers to explore the stunning Balos Lagoon in Crete.
The 4.5-hour cruise on a catamaran accommodates up to 14 passengers, providing an intimate setting to take in the breathtaking coastal views.
The trip includes local snacks, seasonal fruits, and a variety of drinks, along with a provided lunch.
Snorkeling equipment is available, and guests can relax on sea towels and in swimsuits supplied by the operator.
With an overall rating of 4.6/5 based on 20 reviews, this cruise is a popular choice for those seeking a memorable sailing adventure in Crete.
Read our full review: Balos Sailing Cruises Shared in Small Group Review
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Agios Nikolaos Morning Catamaran Cruise in Mirabello With Lunch
For those seeking a serene morning sail along the stunning Mirabello Bay, the Agios Nikolaos Morning Catamaran Cruise offers an exceptional experience.
Guests aboard this 4.9/5-rated tour can expect a delightful array of inclusions, from welcome drinks and a Greek-inspired lunch to snorkeling gear and water sports equipment.
The cruise departs from Agios Nikolaos marina at 9:30 AM, providing wheelchair accessibility and Wi-Fi on board.
With a maximum capacity of 20 travelers, this intimate experience allows guests to bask in the beauty of Crete’s coastline.
While a few guests noted minor issues with portion sizes and communication, the overwhelming majority raved about the attentive crew, comfortable boat, and overall enchanting atmosphere.
Read our full review: Agios Nikolaos Morning Catamaran Cruise in Mirabello With Lunch Review
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Private Sailing Trips to Dia Island
With a 4.6-star rating based on 19 reviews and a Badge of Excellence, private sailing trips to Dia Island offer Crete visitors an exceptional opportunity to explore the island’s picturesque coastline.
These private excursions provide a chance to sail, swim, fish, and snorkel in the crystal-clear waters of St. George’s Bay. The trips include fishing gear, unlimited refreshments, and snorkeling equipment.
Guests can also opt for added luxuries like lunch, champagne, and birthday treats for an additional fee.
The experience starts and ends at the Cafe Marina in Heraklion, with pickup service available from various locations across Crete for a small charge.
Priced from €365 for groups of up to 6, these private sailing trips are a must-do for those seeking an unforgettable encounter with Crete’s natural beauty.
Read our full review: Private Sailing Trips to Dia Island Review
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Sailing Day on the Island of Dia With Departure From Heraklion
Departing from the Cafe Marina in Heraklion, Crete, this sailing day adventure allows visitors to explore the picturesque island of Dia.
Equipped with snorkeling gear, guests can enjoy refreshments like snacks, drinks, and alcoholic beverages while sailing.
With a 90% recommendation rate and 4.5-star reviews, this trip offers private transportation and a maximum group size of 10 travelers.
While not wheelchair accessible, the experience is conveniently located near public transportation.
Cancellations can be made up to 24 hours in advance with a full refund.
At $90.81 per person, this sailing excursion provides a memorable day on the water with positive feedback on hospitality and the quality of homemade meals.
Read our full review: Sailing Day on the Island of Dia With Departure From Heraklion Review
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From Heraklion Crete: Semi Private 5.5 Hours Morning Sailing Trip to Dia Island
This semi-private sailing excursion from Heraklion provides a memorable 5.5-hour morning adventure to the picturesque island of Dia.
The small group of up to 10 travelers will set sail from the Venetian Port, with all fuel, fees, and taxes included. Snorkeling equipment, snacks, and drinks are provided, making it a comfortable and carefree experience.
The highly-rated tour, operated by Cretan Yachts, features a skilled crew and ample opportunities to spot marine life and collect shells.
With free cancellation up to 24 hours prior, it’s an enticing option for those seeking a relaxing yet engaging sailing trip in Crete.
Read our full review: From Heraklion Crete: Semi Private 5.5 Hours Morning Sailing Trip to Dia Island Review
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Private Full Day Sailing Trip to Dia Island
The Private Full Day Sailing Trip to Dia Island offers a captivating adventure for those seeking a more personalized and immersive sailing experience in Crete.
Priced at $555.52 for up to 10 people, this private cruise departs from Heraklion and sails to the picturesque Dia Island.
Guests can enjoy a range of activities, including swimming, paddleboarding, and snorkeling, while indulging in a delicious lunch and refreshing beverages.
With a 5.0 rating and a 100% recommendation from previous travelers, this experience promises an unforgettable day on the Cretan waters, showcasing the region’s stunning natural beauty and allowing guests to truly enjoy the serene atmosphere.
Read our full review: Private Full Day Sailing Trip to Dia Island Review
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South Crete: Private 5-Hour Snorkeling & Sailing Tour With Lunch
For travelers seeking an immersive and adventurous way to explore the stunning southern coast of Crete, the South Crete: Private 5-Hour Snorkeling & Sailing Tour with Lunch offers an unparalleled experience.
Rated 4.6 out of 7 reviews, this private tour takes guests on a sailing cruise with a professional, certified crew. Participants can snorkel, stand-up paddleboard, and enjoy a customizable meal, all while surrounded by Crete’s natural beauty.
The tour includes equipment, drinks, and free transfers within a 5km radius of Agia Galini. With an eco-friendly route and a max capacity of 8 people, this experience is ideal for nature lovers seeking an intimate, unforgettable day on the water.
Read our full review: South Crete: Private 5-Hour Snorkeling & Sailing Tour With Lunch Review
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6-Hour Private Sailing Trips From Heraklion to Island of Dia
Departing from the vibrant Venetian Port in Heraklion, the 6-Hour Private Sailing Trip from Heraklion to Dia Island offers a captivating escape from the crowds.
Guests can enjoy snorkeling with the provided equipment and visit a picturesque church on Dia Island. The trip also allows for beach relaxation and swimming in a small bay.
With a 5.0 rating based on 5 reviews, this private sailing experience is a must-try for those seeking an exclusive and memorable adventure in Crete.
Operated by Cretan Yachts, the trip is priced at $662.35 per group of up to 10 participants, with free cancellation up to 24 hours beforehand.
Read our full review: 6-Hour Private Sailing Trips From Heraklion to Island of Dia Review
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The Sum Up
Crete offers a variety of exciting sailing experiences, from luxurious catamaran cruises to private sailing trips. Whether you want to explore Dia Island, witness a stunning sunset, or snorkel in the crystal-clear waters, there’s something for every type of traveler. With knowledgeable guides and customizable itineraries, you’re sure to have an unforgettable sailing adventure in this beautiful Mediterranean destination.