Island hopping · SAILING & YACHT CHARTERS

The 15 Best Sailing & Yacht Charter Days in the World

64 tours  ·  from $33 a head

Under sail you reach the anchorage the day boats motor past. These 15 cover shared sailing days and whole-boat charters, priced per head where they can be, with crew, route and how much of it is actually sailing.

Hurghada: 3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch - Pickup from Hurghada can take time
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Hurghada: 3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch

1.3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch

★★★★★★★★★★4.7 · 4,609 reviews · 8 hours · from $47Our pick

Cruise from Hurghada to Orange Bay, Giftun and Magawish with two snorkeling stops, dolphin watching and meals on board. Guides such as Fouad, Ahmed, Saef and Ashraf help swimmers of different abilities. Expect a lively group boat, clear water, seafood lunch and a sunset return.

“We had a great day with Tito and the other crew members! The marine life we saw when snorkelling was amazing and the guides/crew were fabulous and a lot of fun. Thank you, we had a wonderful time !”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why the 14-person limit changes the day
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

2.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Your English-speaking crew, including a certified captain, serves shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks, with time for swimming, snorkeling, paddleboarding, and sunset sailing.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - Three hours aboard a 54-foot catamaran
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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

3.Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

★★★★★★★★★★5.0 · 2,100 reviews · from $119Top rated

Spend three hours aboard The VI Cat, a 54-foot catamaran sailing from Marriott Frenchman’s Cove to Little Buck Island. Snorkel with green sea turtles and reef fish, then enjoy snacks, music, and drinks. Captains Serena and Dave and crew members such as Nick, Isaac, and Porscha help keep the trip safe and relaxed.

“Sam was the best mate on the boat! Her service, personality, friendliness, and hospitality, cannot be matched! we had a phenomenal trip! The VI cat is where it’s at!”

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Icacos Island Catamaran Day Sail from Fajardo - Choosing Between Icacos and Palominitos
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Icacos Island Catamaran Day Sail from Fajardo

4.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140

Board East Island Excursions’ catamaran at Puerto del Rey for a six-hour sail to Icacos or Palominitos. Expect reef snorkeling, floating belts, a deli buffet, rum drinks, and a friendly crew. Captains Jose and Carlos are among the crew members praised for careful service.

“1000000/10 would recommend! Everyone was so nice and inviting. The beaches were gorgeous and the snorkeling was great. Unlimited drinks with the most delicious juices + rum. Lunch spread was perfect.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island’s clear water and limited shore access
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

5.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Choose a 3.5 to 6.5-hour shared or private yacht trip from Heraklion to Dia Island, with swimming, snorkeling, paddleboards, fishing gear, lunch, and drinks. The one-hour coastal option stays near Heraklion and includes drinks but no island stop or water activities.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Leaving Gouvia Marina for the northeast coast
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

6.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Set out from Gouvia Marina with a skipper such as Ari, Savvas, or Tasos for a relaxed five-hour cruise along Corfu’s northeast coast. Swim at Barbati and Gialiskari, try a supervised cliff jump, explore a blue cave, and enjoy sandwiches, fruit, and soft drinks aboard a small yacht for up to 12 people.

“Amazing day out! A small sail boat with only 12 people and an amazing guide”

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4-Hour Sailing Tour of Lobos Island from Fuerteventura - Swimming, snorkelling, kayaking, and paddleboarding
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4-Hour Sailing Tour of Lobos Island from Fuerteventura

7.4-Hour Sailing Tour of Lobos Island from Fuerteventura

★★★★★★★★★★5.0 · 785 reviews · from $75

Join FuerteCharter in Corralejo for a four-hour catamaran trip to Lobos Island. You get hotel pickup in Corralejo, a crew-led island visit, swimming, snorkelling, kayaking, paddleboarding, seafood paella, and unlimited soft and alcoholic drinks. Crew members such as Mark and Juliette are praised for friendly service.

“Super friendly crew, fabulous food and overall great day. Would highly recommend Frank and his team!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Dia Island: quiet shores and clear water
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

8.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a certified crew, snorkeling gear, SUP boards, fishing equipment, lunch, wine, soft drinks, and raki. You’ll hear island legends, swim in clear water, and return by sail, with sunset departures available.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar - Whitehaven Beach gets a proper three-hour visit
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2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

9.2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

★★★★★★★★★★4.5 · 771 reviews · from $466

Spend two nights aboard Avatar, the Whitsundays’ only commercial sailing trimaran, with up to 26 passengers. Sail from Airlie Beach to Whitehaven Beach and quiet reef spots, snorkel with turtles and fish, and enjoy meals, guiding, and onboard accommodation. Expect simple food and tight sleeping quarters.

“I will try to report the facts, without entering into personal judgment because only bad words will come out. I state, in 7 participants we interrupted halfway through the tour, due to safety and health risk problems as the extremely precarious Read moreAuto-translated”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Dia Island’s quiet northern bays
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Heraklion: Dia Island Sailing Cruise with Snorkeling

10.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a small crew of up to 18 people to uninhabited Dia Island. Expect swimming, snorkeling, paddleboarding, drinks, and food onboard. Ernesto and George are among the crew members, and the half-day or full-day format lets you match the trip to your schedule.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Rhenia for Swimming and the Onboard BBQ
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

11.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia. Explore Delos with an optional guide, then swim, snorkel, and eat a fresh BBQ lunch aboard a spacious gulet. Crew members Dimitri and Thomas are noted for attentive help, while hotel transfers cost extra.

“The sailing trip to Delos and Renia was maybe our favorite activity of our time in Mykonos. It was a good mix of relaxation and activity — enjoying a relaxing drink and lunch on the boat, exploring on our own in Delos, and a refreshing swim at Renia. I would have liked a little bit more time on Delos, but other than that, it was perfect. Staff/crew was very attentive to the needs of all passengers.”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Five hours around Dia’s main cove
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

12.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a professional crew, snorkeling gear, paddleboard, food, drinks, and time to swim. Full-day trips add a second bay and a seafood meal, while half-day trips focus on one cove and sunset sailing.

“Thoroughly enjoyed! nice crew and nice ppl on board”

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Sailing Cruise to Dia Island with Meal and Water Activities - Dia’s church, wildlife, and old Minoan harbor
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Sailing Cruise to Dia Island with Meal and Water Activities

13.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 uninhabited Dia Island with a small crew and time to swim, snorkel, fish, paddleboard, and sunbathe. Lunch includes shrimp linguine, Greek salad, Cretan appetizers, and fruit, with beer, wine, soft drinks, and water. Pickup is available across much of Crete.

“Perfect day sailing and enjoying the sun and sea!!! The crew was great and the food was delicious!!!”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Dia Island and Saint George Bay
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

14.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Join a six-hour small-group sailing trip from Heraklion to Dia Island with up to 10 people. Captains George, Panos, and Vaso share local stories while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with drinks on board.

“We are a family of 5 and were lucky to share the yacht with just another family of 3 and our lovely guides George and Marcos. It was a very hot, still day so we couldn’t actually sail but this meant for beautiful calm waters and exceptional swimming and snorkelling when we got to Dia Island. Lunch was delicious too. All in all a fabulous trip!”

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PRIVATE! | Full Day Charter Boat Trip| Up to 14 | Snorkeling and Islands tour - Carless Reef: the main snorkeling stop
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PRIVATE! | Full Day Charter Boat Trip| Up to 14 | Snorkeling and Islands tour

15.PRIVATE! | Full Day Charter Boat Trip| Up to 14 | Snorkeling and Islands tour

★★★★★★★★★★5.0 · 478 reviews

Spend about eight hours on a private Hurghada boat with your own group, captain, cook, and snorkeling crew. Visit Omo Gamaar and Carless Reef, look for dolphins, and choose an optional island stop. Lunch, drinks, gear, restroom use, and the national park ticket are included.

“We had an amazing day. Capt Mohammed and his 2 crew Yousuf and Ayad were brilliant. We spent whole day out at sea. We saw dolphins and went snorkeling. The captain helped us in the sea as I was nervous and never done before. They prepared a very nice lunch for us also. All in all an amazing day. Highly recommend it.”

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