Top Crete Sailing

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

4 hours 30 minutesFree Cancellation

4.9

(153)

from US$36

Private Sail in Chania

(38)

from US$419

Feel the sun on your face and the breeze in your hair on this leisurely sailing catamaran cruise from Heraklion to the uninhabited island of Dia. Enjoy activities from snorkeling and stand-up paddle boarding (SUP) through to fishing and sunbathing in a group no larger than 20. As well as onboard Wi-Fi, your package includes a Mediterranean lunch with drinks: online booking means there’s no need to negotiate terms.

Heraklion: Dia Catamaran Cruise Mediterranean Meal & Water Fun

5 hoursFree Cancellation

There's no better way to experience Crete's stunning coastline than by gliding through crystal clear waters on a yacht. Take a cruise to the uninhabited island of Dia, where you can explore and make the most of the beautiful sea with equipment provided for paddleboarding, snorkeling, and fishing. There's also the option to sunbathe as your comfortable yacht gently bobs in the turquoise waters. Plus, you'll feel pampered with a delicious lunch of Greek food, fresh fruit, and drinks.

Dia Island Sailing Cruise with Meal and Water Activities

5 to 6 hoursFree Cancellation

4.7

(529)

from US$96

Sail away from Heraklion’s touristy center on this all-inclusive day cruise to Dia Island. Only reachable by boat, Dia Island is one of the few uncrowded destinations left near the city. Board the catamaran to reach the island's secluded bays, where you can swim, paddleboard, or simply relax on deck. A Mediterranean seafood lunch is prepared on board, and an open bar with soft drinks, wine, and beer runs throughout the day.

Luxury Catamaran Cruise All-Inclusive & OnBoard Chef | Top Rated!

5 hours 30 minutesFree Cancellation

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 island lasts about an hour, offering tranquility, captivating sea views of the Cretan Sea, space for sunbathe on the comfortable and spacious deck and a chance to learn about eco-sailing and marine life. For those interested, our skilled skipper can guide you in sailing activities where you can take part in the sailing aspect of the journey. Upon arrival at Dia, we anchor at pristine wind protected coves with crystal- clear, turquoise waters, where you can enjoy swimming, use the diving equipment provided, or simply relax. Alternatively you can stay onboard and enjoy all the amenities that it has to offer. You can sunbathe on the deck, or socialize in the shaded cockpit, where you’ll find comfortable sofas with large, plush cushions.

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

5 hours 30 minutesFree Cancellation

By our sailing boats "Izabela" and "Poseidon" we organise day cruises to Gramvousa and Balos. Our journey starts from Kissamos Port. After about 90 minutes of cruising, we will reach our first destination, the lagoon of Balos, one of the most beautiful beaches over the Europe. The turquoise water invites you to swimming and snorkeling. We will spend next two hours there, while you can enjoy the beach and relax. We will have a pleasure to offer you traditional and light Cretan lunch on board. Our next stop is the island of Imeri Gramvousa. There you can enjoy the beautiful beach and take a bath in the crystal clear water. On top of the island, you will find an old Venetian Castle. The views from there are really breath taking. Then we will head back. Anytime that the wind will be enough we will be experience sailing. On board you have for your disposal a cabin to rest or sleep, bathroom with shower. We provide snorkeling equipment. Ofered drinks are water, soft drinks, beer and wine.

(20)

from US$78

Balos Lagoon Kissamos Shared Sailboat Tour Experience

Discover a new perspective of Chania on a captivating sailing cruise. Meet at Old Venetian Harbour and embark on a journey around the gulf of Chania. Along the way, pause at two enchanting destinations. First, drop anchor at the island of Ag.Theodori, a protected haven teeming with vibrant birdlife. Then, venture to the secluded paradise of Maherida, boasting stunning turquoise waters. Indulge in traditional Cretan snacks, fresh fruits, and refreshing drinks from the open bar.

(13)

from US$156

4 to 7 hoursFree Cancellation

Sailing Cruises Chania

(94)

from US$434

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, semi-private atmosphere as you cruise along Crete’s stunning northern coast. Swim in crystal-clear waters, snorkel, try paddleboarding, or simply relax and sunbathe on deck. Enjoy a freshly prepared Cretan lunch including seafood or vegetarian pasta, Greek salad, and fruit salad, paired with unlimited local white wine, beer, soft drinks, and water. The friendly local crew will make you feel at home, sharing stories, laughs, and even singing to dolphins if they appear! Choose to meet at Heraklion Port or add optional transfers from nearby areas like Malia, Hersonissos, Analipsi, Gouves, and more. Whether you're traveling solo, with a partner, or in a group, this is a truly authentic and unforgettable way to experience the sea, nature, and heart of Crete.

Sailing Trip to Dia Island - All Inclusive

6 to 8 hoursFree Cancellation

4.9

(73)

from US$90

Likely to Sell Out

Immerse yourself in Crete’s crystal-clear seas with ease and without the expense of a private charter on this sail-and-snorkel trip from Hersonissos. Board a traditional wooden boat and cruise the waters of St. George’s Bay and Stalis. Visit two snorkel hotspots that would be hard to access independently, snorkel and swim at each, and enjoy a BBQ lunch and fruit platter on deck. Snorkeling gear is provided for your use, so there’s no need to bring your own equipment.

Sailing Trips with Cretan Sailing

4 hoursFree Cancellation

3.8

(100)

from US$54

Near Chania—on the Greek island of Crete—lies Balos Lagoon, home to crystal-clear waters and pristine sandy beaches. Swim, snorkel, and relax under the warm Mediterranean sun away from the crowds on this full-day small-group catamaran cruise stopping at the lagoon and Gramvousa Island, where you’ll find an old pirate fortress. Hotel pickup is available, and departures are offered on two catamarans with different group sizes.

Balos Shared Catamaran Cruise (small groups up to 10 or 22ppl)

7 hoursFree Cancellation

4.8

(54)

from US$144

Embark on an unforgettable sunset shared cruise aboard our elegant and luxury Nautitech 46 Fly Catamaran, departing from Kissamos Port. Your exclusive experience begins with a 5pm embarkation, setting the stage for a remarkable journey to the renowned Balos beach. Our destination is the breathtaking Balos lagoon, where we will anchor, allowing you ample time to immerse yourself in its turquoise waters. Throughout the cruise, you will be treated to a selection of delightful snacks, fresh fruits and refreshing alcoholic drinks, ensuring a truly comfortable and enjoyable evening at sea.

Sunset Balos Catamaran luxury *small* group cruise+cocktail

4 hoursFree Cancellation

(5)

from US$144

An afternoon cruise allows you to avoid the peak heat of the day and soak in the gentle, golden light of the late afternoon. And for those who love sunsets, it all concludes with a stunning, radiant display as the sun dips below the horizon. Our luxury catamaran is stylish, refined, and built with your comfort in mind. Whether you prefer stretching out on a sunbed or unwinding in a shaded area, there’s always an ideal place for you to relax and savor every moment. You’ll savor a selection of delicious Cretan bites and appetizers, a variety of sushi rolls, and a welcome glass of Prosecco — all included. Throughout the entire cruise, you can enjoy espresso, tea, water, soft drinks, as well as local Greek white wine and beer, available whenever you like. You can try stand-up paddleboarding, explore underwater life while snorkeling, or simply drift on an inflatable noodle. And of course, our iconic pink flamingo float is always there for your next unforgettable photo moment.

Chania Sunset Catamaran Cruise from Souda Port

3 hours 30 minutesFree Cancellation

Set sail on Boat STELLA for an unforgettable journey across the sparkling waters of the Aegean Sea with a shared group program cruise to Balos Lagoon and Gramvousa Island. Departing from Kissamos Port, this sailing adventure offers the perfect blend of relaxation, exploration, and authentic Cretan flavors. Move to the hot spots at the Lagoon of Balos and Gramvousa Island when it is less crowded and avoid the big ferries. Explore the magic world of sailing with the help of an experienced crew. Swimming in privacy around the boat and not at the crowd beach As you bask in the serenity of this paradise, indulge in the Magic Gastronomic of Simplicity in a delicious traditional Cretan lunch freshly prepared onboard keep your staff and change your dressing at inside cabins out side sitting area well protected with tents and spray hood.

Balos Beach and Gramvousa island shared group Sailing Cruise

(7)

from US$234

Step aboard our luxury catamaran and leave the ordinary behind. Start your day with espresso, tea, detox water, a protein shake, and a light breakfast bowl crafted by a nutritionist. Relax on deck as we sail through Mirabello Bay past the mythical Cave of Barbarossa to the historic Spinalonga Island. Enjoy Mediterranean-inspired light snacks and unlimited drinks served by our attentive crew. Dive into adventure with the inflatable slide, sea scooter, water tube, kayak, or SUP, or explore underwater with mask and fins. Capture memories on our pink flamingo float. Back on board, savor a fresh Cretan lunch made from local, organic ingredients, with seasonal dessert. After lunch, unwind on deck or continue water activities as we sail back to port. Return refreshed, inspired, and full of unforgettable memories. Book now for a perfect day of adventure, relaxation, and healthy, gourmet dining.

Ag. Nikolaos Catamaran to Spinalonga - Gourmet Meal & Water Toys

5 hoursFree Cancellation

Set sail on Sailing Boat STELLA or on Sailing Yacht ELECTRA for an unforgettable journey across the sparkling waters of the Aegean Sea with a private program cruise to Balos Lagoon and Gramvousa Island. Departing from Kissamos Port, this sailing adventure offers the perfect blend of relaxation, exploration, and authentic Cretan flavors. Move to the hot spots at the Lagoon of Balos and Gramvousa Island when it is less crowded and avoid the big ferries. Explore the magic world of sailing with the help of an experienced crew. Swimming in privacy around the boat and not at the crowded beach, enjoy traditional fresh food cooked on board and served in ceramic tableware at the outside cockpit, keep your staff and change your dressing inside cabins outside sitting area well protected with tents and spray hood.

Balos Beach and Gramvousa Island Private-Sailing with Lunch

(1)

from US$653

Full Day PRIVATE Cruise out of Kissamos Port to BALOS beach and GRAMVOUSA island Check in: 10am embarkation in Kissamos port Check out: 5pm disembarkation in Kissamos port Description of the cruise: As soon as you embark, we will start our trip to the beautiful Balos beach for our first stop, anchoring, for swimming and relaxation. You will have enough time to swim and explore the seabed if you wish as we will provide you the necessary snorkeling equipment. Then we will sail across, to Gramvousa island, for the next stop. In this second stop you will have the opportunity to visit the old pirate fortress on the top of the hill. Included: Snacks, fruits drinks and lunch will be offered during the cruise to complete a beautiful day on the sea.

Balos Catamaran Private Sailing Cruise with Lunch

7 hoursFree Cancellation

Panormo: Luxury Sunset Catamaran Cruise Sushi & Open Bar

(5)

from US$3,116

Per group

3 hours 30 minutesFree Cancellation

(39)

from US$102

Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

3 hours 30 minutesFree Cancellation

If you’re looking for a unique way to explore the beautiful coastline of Chania, a half day cruise on one of our sailing yachts is the perfect choice. Our cruises offer a relaxed and comfortable way to experience the stunning scenery and crystal-clear waters of the Cretan Sea. Our sailing yachts are equipped with all the necessary amenities to ensure that you have a comfortable and enjoyable experience. You’ll be able to relax on the spacious deck, soak up the sun and enjoy the gentle sea breeze as we sail along the coast. Our yachts also have a shaded seating area where you can escape the heat and enjoy a refreshing drink. Whether you’re travelling, alone, with friends or family, a half day cruise on one of our sailing yachts is a fantastic way to spend a day in Chania. Our yachts are suitable for all ages, so everyone can enjoy the experience. You’ll create memories that will last a lifetime as you sail along the stunning coastline of Chania and take in the breathtaking views.

Chania shared Sailing cruise in a small group

4 hoursFree Cancellation

Escape the crowded beaches and join us for a lazy day cruise to the island of Dia. You can enjoy a swimming stop in the crystal clear waters. You can swim in the small bay, wading on the shallow waters of the beach and making sand castles with your children, or go snorkeling and visit the small beautiful church, that can be reached by a small path. Boat trip to Dia will be an excursion you will never forget. The Island is a perfect place to relax. We sail for the Dia Island in the noon , we spend the afternoon on the island and we return at the Sunset time back to Heraklio. Your trip to Dia Island will surely be a memorable one.

(4)

from US$120

From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island

5 hours 30 minutesFree Cancellation

4.7

(26)

from US$84

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, or dance under the open sky, you’ll always find your perfect spot. Pleasant music accompanies you throughout the day, creating a joyful atmosphere as you enjoy the journey. Between laughter and melodies, you’ll savor a selection of Cretan snacks, a light brunch, and a delicious lunch — all included. Coffee, tea, water, soft drinks, as well as local Greek white wine and beer, are available throughout the cruise. For those who love a bit of adventure, the sea becomes your playground. Enjoy stand-up paddleboarding, snorkeling, or just relax on one of our inflatable noodles. And don’t forget — our pink flamingo float is always ready for your next perfect photo. We’ve already sailed over 3,653 miles, organized 242 cruises, and welcomed 3,630 happy travelers aboard our yacht. Trust our expertise and embark on this unforgettable journey with us!

Premium Catamaran Cruise to Marathi Bay with Lunch from Chania

6 hours 30 minutesFree Cancellation

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

6 hours 30 minutesFree Cancellation

Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys

(80)

from US$174

Likely to Sell Out

5 hoursFree Cancellation

4.7

(43)

from US$168

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Top Attractions in Crete

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What are people saying about Crete

Heraklion: Pantanassa Sea Playtime

Amer_S, Aug 2025

A must do in Heraklion!

Nice experience. Our skipper Stephanos was very cool and spoke at least 4 languages. He and the co-skipper Mario’s, an excellent chef btw, took us to a secluded area away from the crowds and the water was absolutely amazing! Book with these guys, they know what they’re doing and they will make it fun for you!

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

Daniele_B, Jun 2025

Fantastic day sailing to Dia Island

We had a fantastic time today sailing with Yannis and Alex. It turned out that we were the only family to book the tour this morning so we had a private sailing to Dia Island! They took great care of us from start to finish. They had soft drinks, lemonade, iced tea, annd water available as soon as we took off. They had a Bluetooth speaker for my daughter to play music for us. It was a windy day today and it was clear they are very good sailors. Alex gave us some background on Heraklion and Dia Island and we talked all through the trip to Dia. Once we arrived they got the boat situated and brought out snorkeling gear, pool noodles, and a paddleboard. My daughter wanted to use the paddle board and they made sure she had experience and that she knew the wind would be pushing her toward the shore and that paddling back would be challenging. They also warned her about sea urchins on the floor in the shallows. Alex made us a delicious lunch of Greek salad, bread, pasta with or without shrimp, and a variety of fresh melon for dessert. Wine was offered but we don’t drink so had more soft drinks. We spent a few lovely hours at Dia before heading back to the marina, arriving right on time. I would definitely recommend this excursion. We loved it! It was very convenient for the time our cruise ship was in port tires.

Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

Caroline_M, Jun 2025

Fantastic exerience

A fantastic evening cruise, really chilled and relaxed. We were given plenty of time to swim and use the snorkeling equipment before sitting and watching the beautiful sunset. The crew were really friendly and couldn't do enough for us. The welcome drink, all inclusive other drinks and snacks were an added bonus. I would definitely recommend this trip for anyone visiting Crete.

Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

Robert_H, Jun 2025

Must do while in Crete!

Fantastic day trip with Skipper Christopher. There were 8 of us and the boat provided was a Beneteau 48, which was the perfect size for our party. Christopher welcomed us and we were on our way. We motored around the point and arrived first to the island of Gramvousa where we anchored in crystal clear water about 30 meters from the shore. Some of us swam and others were taken by dingy to the shore. We hiked up to the Venetian fort, taking in the breath taking view. Back on the boat Christopher then served us a tasty lunch of classic Creten dishes along with beer, wine and soft drinks. We then motored over to Balos beach, anchored and swam to shore. It’s everything you read about and more. Mere words cannot fully describe the beauty of this place. After reaching the shore we walked| over to Balos lagoon and enjoyed a swim. Since we were there the first week of June the water was..refreshing! But the closer you swam to shore the warmer the water..and the lagoon was like bath water. After this excursion, headed back to the boat and we motored back to Kissamos. I have to say this day was the highlight of our trip to Crete and I highly recommend it. Christopher did a great job. The only bummer is that we did not actually sail..but that was due to no wind that day..which is entirely out of the control of the operator.