WORLDWIDE · SAILING YACHT CHARTERS

Where to Sail: the 15 Best Sailing Yacht Charters

116 trips  ·  from $37 a seat

Engines off, canvas up, and a boat that heels. These 15 sailing charters are compared on crew, group size, how long you are actually under sail, and what the day costs.

Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks - Sailing past Belém’s monuments
Lisbon Yacht Cruises, Luxury Yacht Cruises, Luxury Yacht Cruises in Portugal, Portugal Yacht Cruises, Sailing Yacht Charters, Sailing Yacht Charters in Portugal, Sunset Yacht Cruises, Sunset Yacht Cruises in Portugal, Tour Reviews, Tours, Yacht Cruises

Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks

1.Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks

★★★★★★★★★★5.0 · 1,109 reviews · 2 hours (approx.) · from $61 a seat Our pick

Sail Lisbon’s Tagus River aboard a 50 to 58-foot yacht with Captain Sebastian, Tiago, or another multilingual guide. Expect a safety briefing, landmark commentary, two drinks, Portuguese cheese and chouriço, and sunset views of Belém Tower, the 25th April Bridge, Alfama, and more. Bring a jacket, since the river gets cool after sunset.

“A must do when visiting Lisbon. We had a fantastic time. The boat was very nice, and our captain and guide were very knowledgeable and a pleasure to speak with touring our tour. Highly recommend!”

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Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks - Belém’s monuments from the water
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Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks

2.Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks

★★★★★★★★★★5.0 · 703 reviews · 2 hours (approx.) · from $46 a seat Best value

Spend about two hours sailing from Belém with a captain and host aboard a comfortable 50-foot yacht. You’ll pass Belém Tower, the Discoveries Monument, the 25th of April Bridge, Alfama, and more while guides such as Sebastian, Tiago, José, and Chris share Lisbon stories in several languages. Two drinks and Portuguese cheese are included.

“Great trip on a yacht along the river. Small group x 2 hours. Sebastian the Captain was most welcoming. Very safe ! Wine and nibbles as well!”

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Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests) - Falésia Beach from below the clay cliffs
Luxury Yacht Cruises, Luxury Yacht Cruises in Portugal, Portugal Yacht Cruises, Sailing Yacht Charters, Sailing Yacht Charters in Portugal, Sunset Yacht Cruises, Sunset Yacht Cruises in Portugal, Tour Reviews, Vilamoura Yacht Cruises, Yacht Cruises

Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests)

3.Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests)

★★★★★★★★★★5.0 · 383 reviews · 2 hours 30 minutes (approx.) · from $60 a seat

Set sail from Vilamoura for 2.5 hours along the Algarve coast. Your skipper points out Falésia’s clay cliffs, a tiny sea-access beach, and Albufeira’s sandy-to-rocky divide. Expect a welcome drink, Portuguese cheese, chorizo, toast, music, and a relaxed group of no more than 12 people.

“Was a great experience and both crew members were lovely and chatted away and made the experience even better. They pointed out sights along the way and even gave us information on Portugal's history. They also asked us about ourselves and made the full experience really enjoyable. Would definitely come again simply for the crew”

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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef - Dinner begins with drinks and shared appetizers
Cabo San Lucas Yacht Cruises, Dining Experiences, Dinner Yacht Cruises, Luxury Yacht Cruises, Luxury Yacht Cruises in Cabo San Lucas, Luxury Yacht Cruises in Mexico, Mexico Yacht Cruises, Sailing Yacht Charters, Tour Reviews, Yacht Cruises

Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

4.Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

★★★★★★★★★★4.5 · 290 reviews · 3 hours (approx.) · from $199 a seat

Sail from Cabo San Lucas at 5:00 pm toward Land’s End, the Arch, and Lovers Beach, then enjoy cocktails, appetizers, and dinner aboard a luxury yacht. The relaxed cruise allows up to 40 people, with an open bar, onboard restroom, and sunset views. Expect a shared sailing experience, not a private chef charter.

“The staff is amazing. The ambience is excellent. The boat is beautiful. The food is cold. You had no choice in what to eat and they threw it at you no appetizer no dessert all the alcohol you want again the service was excellent.”

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Day sailing Skiathos Skopelos with lunch on Rainbow yacht - Tsougria gives you the first swim
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Day sailing Skiathos Skopelos with lunch on Rainbow yacht

5.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

★★★★★★★★★★5.0 · 262 reviews · 7 hours (approx.) · from $163 a seat

Join Yannis and Angelica aboard Rainbow yacht for a relaxed seven-hour sailing day from Skiathos. Swim at Tsougria, Panormos, and a Skopelos beach, see the Mamma Mia coast, and enjoy a Greek meal cooked on board. Cold drinks, wine, beer, coffee, fruit salad, and time for snorkelling are included.

“We had a lovely day in beautiful places, with nice food and nice company! We absolutely recommend this experience”

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From Vilamoura: Sunset Tour on a Luxury Sailing Yacht - Sailing toward Falésia and Albufeira
Algarve Yacht Cruises, Luxury Yacht Cruises, Luxury Yacht Cruises in Portugal, Portugal Yacht Cruises, Sailing Yacht Charters, Sailing Yacht Charters in Portugal, Sunset Yacht Cruises, Sunset Yacht Cruises in Portugal, Tour Reviews, Tours, Yacht Cruises

From Vilamoura: Sunset Tour on a Luxury Sailing Yacht

6.From Vilamoura: Sunset Tour on a Luxury Sailing Yacht

★★★★★★★★★★4.7 · 249 reviews · 2.5 hours · from $58 a seat

Set out from Pontoon Q in Vilamoura for a 2.5-hour sunset cruise toward Albufeira. You will see Falésia Beach and Tomato Beach from the water, enjoy aperitifs and one welcome drink, and listen to music aboard a comfortable sailing yacht. Guides speak English, Portuguese, and Spanish. Some departures include time for a swim.

“Fantastic sailing trip, great guide, friendly service, and great value for money”

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Alcudia: Sailing Yacht Excursion with Wine & Tapas - The first hour on Badia de Pollença
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Alcudia: Sailing Yacht Excursion with Wine & Tapas

7.Alcudia: Sailing Yacht Excursion with Wine & Tapas

★★★★★★★★★★4.4 · 236 reviews · 4 hours · from $147 a seat

Spend four hours aboard a 14-meter sailing yacht from Alcudia with skipper Jörn and the Romantic Sailing crew. Cruise Badia de Pollença, stop at Cala en Gossalba for swimming, snorkeling, SUP, and homemade tapas, then take the helm if conditions allow. Wine, beer, soft drinks, photos, and equipment are included.

“Es war das perfekte Geburtstagsgeschenk für meinen Mann. Die Zeit war rundum gelungen. Vielen Dank an dieser Stelle an Jörn, dessen Art als Guide und Käpten den Tag zu einem tollen Erlebnis für uns gemacht hat :)”

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Private Sailing Yacht Charter by Independence from Koh Samui - Choosing between sunset, half-day, and full-day sailing
Private Yacht Charters, Sailing Yacht Charters, Thailand Yacht Cruises, Tour Reviews, Yacht Cruises

Private Sailing Yacht Charter by Independence from Koh Samui

8.Private Sailing Yacht Charter by Independence from Koh Samui

★★★★★★★★★★5.0 · 215 reviews · whole boat $1,112, up to 6

Sail privately from Koh Samui aboard the 52-foot Independence yacht with up to six people, a skipper, hostess, chef, open bar, seafood meals, snorkeling gear, and beach stops. Choose a sunset, half-day, full-day, or Angthong National Marine Park route. Crew members including Luca, Nok, A, and Rong are known for warm, attentive service.

“First class food and excellent attentive staff. We were amazed how our chef could provide such wonderful gourmet food from a tiny kitchen! Safety was paramount and we felt safe throughout. Having the yacht to ourselves made my friend's Read more”

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Private Sailboat tour in Cabo San Lucas with Papillon Yachts - Meeting at the Marina and riding from your hotel
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Private Sailboat tour in Cabo San Lucas with Papillon Yachts

9.Private Sailboat tour in Cabo San Lucas with Papillon Yachts

★★★★★★★★★★5.0 · 198 reviews · 3 hours (approx.) · whole boat $800, up to 6

Spend about three hours on a private Papillon Yachts sailboat for up to six people. Cruise past Cabo’s Arch and sea lions, stop near Médano Beach, and use the included snorkel gear and paddleboards. Your crew serves quesadillas, guacamole, fruit, and an open bar, with roundtrip transport included.

“Great crew! Very attentive / flexible to what we wanted to do. Appreciated having a photographer on board so we could just enjoy ourselves”

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Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group) - Anthony Quinn Bay: the first big view
Greece Yacht Cruises, Rhodes Yacht Cruises, Sailing Yacht Charters, Sailing Yacht Charters in Greece, Tour Reviews, Yacht Cruises

Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

10.Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

★★★★★★★★★★5.0 · 197 reviews · 6 hours (approx.) · from $120 a seat

Spend about six hours on a small sailing yacht from Rhodes, stopping at Anthony Quinn, Traganou, and Ladiko bays for swimming, snorkeling, or sunbathing. Lunch-style cold dishes, fruit, wine, beer, soft drinks, and water are included. Captains and crew, including George, Dimitri, Despina, Luca, and Yannis, have been praised for warm, capable service.

“Excellent motor yachting experience… Captain Yannis (aka Poseidon) was an excellent host and cook and being a small group experience shared some excellent company for the day… but people must be prepared for yachting experience with waves and all!”

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Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group - First Pakleni Islands swim stop
Croatia Yacht Cruises, Hvar Yacht Cruises, Island Yacht Cruises, Island Yacht Cruises in Croatia, Sailing Yacht Charters, Sailing Yacht Charters in Croatia, Tour Reviews, Yacht Cruises

Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

11.Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

★★★★★★★★★★4.5 · 194 reviews · 4 hours (approx.) · from $90 a seat

Sail from Hvar to two bays around the Pakleni Islands aboard a small yacht with up to eight people. Your skipper sets the route around the weather, provides sailing tips and local stories, and anchors for swimming and snorkeling. Bring lunch and drinks, then use the onboard fridge, WiFi, and restroom during this relaxed four-hour outing.

“The pickup by the green lantern was smooth and efficient. The instructions were easy to follow. Although there was no wind, the 2 lads made it interesting and were able to adapt and overcome. The little stories of the local places of interest were entertaining. Safety of our group was important to them. Nice choice of music!”

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From Skiathos Marina: Yacht Sailing Day Trip with Lunch - Skopelos by boat: Kastani and Hovolo
1-Day Tours, Greece Yacht Cruises, Lunch Experiences, Sailing Yacht Charters, Sailing Yacht Charters in Greece, Tour Reviews, Yacht Cruises, Yacht Cruises with Lunch and BBQ, Yacht Cruises with Lunch in Greece

From Skiathos Marina: Yacht Sailing Day Trip with Lunch

12.From Skiathos Marina: Yacht Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 180 reviews · 8 hours · from $175 a seat

Spend eight hours aboard the Marina yacht with skipper Lambros and crew, sailing from Skiathos toward Skopelos. You get breakfast, drinks, towels, snorkeling gear, SUP use, several swim stops, lunch at a local taverna, cave snorkeling near Dasia, and fruit salad at Arkos Island.

“Great day out sailing around Skiathos and Skopelos. The boat was fantastic, the swim stops were amazing with the option to paddleboard too. We also got lucky and saw some dolphins! The lunch at a local taverna was also a highlight. A must do in Skiathos - we will book again if we come back!”

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Yacht Me Up – Private All-Inclusive Cannes Sailing Fever - The Lérins Islands and the day’s main swimming stop
France Yacht Cruises, Sailing Yacht Charters, Tour Reviews, Yacht Cruises, Yacht Cruises with an Open Bar

Yacht Me Up – Private All-Inclusive Cannes Sailing Fever

13.Yacht Me Up – Private All-Inclusive Cannes Sailing Fever

★★★★★★★★★★5.0 · 175 reviews · 3 hours 30 minutes (approx.) · whole boat $624, up to 6

Sail Cannes in a private Dufour 382 with Captain Brice and crew. You’ll pass the Croisette, reach the Lérins Islands, swim near underwater statues, and use a paddleboard, snorkel gear, GoPro, and SeaBob. The package includes snacks, drinks, and a wood-fired pizza, with seafood and custom menus available at extra cost.

“Captain Brice and Hansel were amazing hosts and made us feel very comfortable! Lovely snacks on board and an excellent swimming stop. Highly rexommend”

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Sailing on Historic Schooner Yacht in Salem, MA - Sailing Salem Sound for about two hours
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Sailing on Historic Schooner Yacht in Salem, MA

14.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.)

Set sail from 10 Blaney Street in Salem aboard the classic schooner Malabar for about two hours. You’ll cruise Salem Sound, Marblehead, and nearby islands while the crew explains the vessel and may invite you to help raise the four sails. Captain Seth and crew members such as Kos and Kate bring the boat’s story to life. Drinks are available for purchase onboard.

“Very nice and relaxing experience! The crew were very helpful and welcoming! A very romantic setting for couples as well.”

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Lisbon: 2-Hour Sunset Sailing Tour on Luxury Sailing Yacht - Boarding near the Monument to the Discoveries
2-Hour Experiences, Lisbon Yacht Cruises, Luxury Yacht Cruises, Luxury Yacht Cruises in Portugal, Portugal Yacht Cruises, Sailing Yacht Charters, Sailing Yacht Charters in Portugal, Sunset Yacht Cruises, Sunset Yacht Cruises in Portugal, Tour Reviews, Tours, Yacht Cruises

Lisbon: 2-Hour Sunset Sailing Tour on Luxury Sailing Yacht

15.2-Hour Sunset Sailing Tour on Luxury Sailing Yacht

★★★★★★★★★★4.9 · 171 reviews · 2 hours · from $70 a seat

Spend two hours on the Tagus with Lisbon ByBoat, sailing from Belém past Belém Tower, the 25 de Abril Bridge, Praça do Comércio, Alfama, and São Jorge Castle. A live guide speaks English, Spanish, French, or Portuguese, and you’ll toast the sunset with sparkling wine aboard a handsome yacht.

“i colori di Lisbona visti dal fiume sono spettacolari... aveva ragiobe Pessoa... non si può venire a Lisbona e non fare questa esperienza... e poi un equipaggio così affabile”

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New in Sailing Yacht Charters

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