SAILING YACHT CHARTERS

Sailing Yacht Charters: the 15 Best Days Aboard

101 sailings  ·  from $37 a head

A yacht charter is a smaller group, a better boat and a skipper who talks to you. These 15 are compared on the hull, the head-count and whether you are handed a line or handed a drink.

Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks - Starting at Doca de Belém
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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 $61Our pick

Set out from Belém for a two-hour sunset sail on a 50 to 58-foot yacht with a captain and host. You’ll pass Belém Tower, the 25th of April Bridge, Alfama, and Commerce Square while enjoying two drinks and Portuguese cheese. Guides such as Sebastian and Tiago add lively stories in English and other languages.

“Very enjoyable. Knowledgeable and friendly captain. Kept us all informed on the sights and was very entertaining”

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Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks - The Tagus turns Lisbon into one big view
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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 $46Best value

From Doca de Belém, you’ll sail past Belém Tower, the Discoveries Monument, the 25th of April Bridge, Alfama, and more aboard a 50-foot yacht. A captain and host provide commentary in English and other languages, with two drinks and Portuguese cheese included. The group is limited to 14 people.

“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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America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head - What happens during the 90-minute afternoon sail
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America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

3.America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

★★★★★★★★★★4.5 · 504 reviews · 1 hour 30 minutes (approx.) · from $55

Spend 90 minutes sailing Hilton Head aboard a 39-foot America's Cup 12-Meter yacht with Captain Peter and crew. You may help raise the mainsail, grind lines, or take the wheel while enjoying views of Harbour Town, the marina, and the Intracoastal Waterway. Cushioned deck seating, paid drinks, and moderate mobility needs are worth noting.

“Super fun time! Skipper and crew were so caring and wanted to make sure you had the best experience.”

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Private Luxury Yacht Charters, BYOB & Dolphins - Downtown Charleston from the harbor
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Private Luxury Yacht Charters, BYOB & Dolphins

4.Private Luxury Yacht Charters, BYOB & Dolphins

★★★★★★★★★★5.0 · 395 reviews · 2 hours 30 minutes (approx.) · from $499 whole boat, up to 6

Set sail from Ashley River Marina on a private 2.5-hour yacht charter for up to six people. Your captain and first mate handle the sailing while you enjoy Charleston Harbor, Fort Sumter, the Ravenel Bridge, dolphins, and sunset views. Bring drinks and snacks, or request catering.

“Brian and Austin were amazing captains and gave us an incredible and memorable experience to culminate our trip to SC. The sunset sailboat trip was as informative as it was relaxing and the vibe was very chill. They took amazing family photos for us as well. The sunset was the best we’ve ever seen. Would recommend 1000%.”

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Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. - Planning Your Route Around St. Thomas
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Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

5.Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

★★★★★★★★★★5.0 · 386 reviews · from $1,495 whole boat, up to 12

Sail aboard S/Y Pisces, a 47-foot Leopard catamaran, with your own captain and mate from Havensight. Build a half or full-day plan around snorkeling, turtles, beaches, Water Island, Buck Island, and quiet coves. Snorkel gear, floats, water, soda, beer, and rum punch are included for groups of up to 12.

“Such a relaxing and wonderful way to spend the day! Loved snorkeling in areas that we've never gone to. Honeymoon beach is our new favorite spot!”

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Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests) - From Vilamoura Marina toward Falésia Beach
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Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests)

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

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

Set out from Vilamoura Marina for a 2.5-hour sunset sail along the Algarve coast. The skipper points out Falésia Beach, a tiny sea-access beach, and the fishing village of Albufeira. Expect a maximum of 12 people, one welcome drink, Portuguese snacks, music, and possible swimming when sea conditions allow.

“It was a superb Sunset tour, weather was really nice and we did a lot of photos along the way. Even swam in the sea :)”

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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - The Maritime Museum and Star of India
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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

7.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115

Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat, for a 2.5-hour evening cruise on San Diego Bay. The small group, usually limited to six people, keeps the outing personal. You can help with the sailing, watch for sea lions and dolphins, and enjoy beer, white wine, soft drinks, water, and light snacks.

“The boat is very nice but definitely just fits 6 plus Captain Philip. It does get chilly on the water as the sun is starting to set but we came prepared so we were quite comfortable. There was plenty of refreshments on the boat and everything was clean and shiny. I think the Captain knows a lot about the area and could share a lot of info about what you're seeing but he pretty much read his audience and did tell us about a lot of things and was very knowledgeable and always answered our questions but as we were girlfriends (plus my lucky husband) of close to 60 years…”

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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef - Drinks, appetizers, and dinner on the water
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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

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

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

Set sail from Cabo San Lucas at 5:00 pm for a three-hour sunset cruise past Land’s End, the Arch, and Lovers Beach. You’ll enjoy a welcome cocktail, premium open bar, appetizers, dinner with shrimp and beef, and dessert. The boat holds up to 40 people, and the minimum age is 18.

“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

9.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

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

Spend about seven hours aboard Rainbow yacht with Yannis, Angelica, and their dog Naya. Swim at Tsougria, Panormos, Skopelos, and other islands, see the coast near Mamma Mia Beach, eat a Greek meal cooked on board, and enjoy wine, beer, soft drinks, water, coffee, and fruit salad.

“We had an amazing day on the rainbow yacht. Lots of stops for swimming and snorkelling, the food was great and we were given plenty of drinks. The hosts were lovely and welcoming. Highly recommend!”

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From Vilamoura: Sunset Tour on a Luxury Sailing Yacht - A gentle run along the Vilamoura and Albufeira coast
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From Vilamoura: Sunset Tour on a Luxury Sailing Yacht

10.Sunset Tour on a Luxury Sailing Yacht

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

Set sail from Vilamoura for 2.5 hours along the Algarve coast toward Albufeira. You’ll pass Falésia and Tomato beaches, enjoy aperitifs and one welcome drink, and watch the sun sink over the water. The yacht has indoor and outdoor seating, a paid bar, music, and sometimes a swim stop. Guides speak English, Portuguese, and Spanish.

“We done the sunset cruise on 25/09/23 and we found it very enjoyable the crew were nice friendly and helpful”

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Alcudia: Sailing Yacht Excursion with Wine & Tapas - Homemade tapas served at sea
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Alcudia: Sailing Yacht Excursion with Wine & Tapas

11.Alcudia: Sailing Yacht Excursion with Wine & Tapas

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

Spend four hours on a 14-meter yacht sailing from Alcudia along the Bay of Pollença toward Cap de Formentor. Your skipper, sometimes Jörn, serves homemade tapas, Spanish wine, beer, and soft drinks. Swim at Cala en Gossalba, use the SUP and snorkel gear, or take the helm while you enjoy the coast from the water.

“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 - What the day feels like from hotel pickup to the pier
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Private Sailing Yacht Charter by Independence from Koh Samui

12.Private Sailing Yacht Charter by Independence from Koh Samui

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

Sail privately from Koh Samui aboard Independence, a 52-foot yacht for up to six people. Skipper Luca and his crew provide hotel transfers, drinks, snacks, water-sports gear, and chef-prepared food. Choose a sunset, half-day, full-day, or Ang Thong National Marine Park cruise, with time for swimming, snorkeling, fishing, or quiet sailing.

“The crew will always be memorable. Extremely nice and helpful. My wife and I chartered the full day experience. You will not go hungry as they feed you plenty. Part of the experience may include getting wet as the Yacht travels to and from your destination. We are very glad we included this experience in our trip to Koh Samui.”

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Private Sailboat tour in Cabo San Lucas with Papillon Yachts - Starting at the Cabo marina
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Private Sailboat tour in Cabo San Lucas with Papillon Yachts

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

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

Sail privately from Cabo San Lucas with a crew such as Captain Martin and guide Jessica, stopping near the Arch and Médano Beach. Your group gets snorkeling gear, paddleboards, an open bar, guacamole, pico de gallo, quesadillas, fruit, and roundtrip transportation. The three-hour outing can include swimming, sailing, whale sightings, and sunset views, depending on conditions.

“This was the best sailing experience. From the beginning when Julio was so flexible to pick us up early, to our awesome and skilled Captain Arturo to every need being met by Alexis. All these guys were more like friends and amigos than a paid tour. The personal time for you and your loved ones make priceless memories. It was like having our own personal sailboat, without all the maintenance!”

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Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group) - Traganou Beach: Open Coast and Clear Swimming
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Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

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

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

Join a six-hour coastal cruise from Rhodes Town to Anthony Quinn Bay, Traganou Beach, and Ladiko Beach. You’ll swim, snorkel, enjoy Greek food, and have drinks aboard a yacht carrying up to 15 people. Captains such as George, Dimitri, Giorgia, and Yannis have been praised for friendly hosting, though boat space and sailing conditions can vary.

“The yacht was slightly chaotic as our skipper was single handed and also provided us with a lovely meal comprising Greek Salad and chicken with fresh bread. He did a great job but the head could have been cleaner. The sail was lovely and we had the chance to swim in all 3 bays. I would recommend this trip but I feel that a 2 person crew would have made the trip even better.”

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Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group - First Pakleni Islands stop: time to swim
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Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

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

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

Leave Hvar’s Riva aboard a comfort sail yacht for four easygoing hours around the Pakleni Islands. With a group of up to eight on the advertised small-group option, you’ll stop at two bays for swimming and snorkeling. Skippers such as Viktor, Alexander, Peter, and Vitor adapt the route to weather. Bring lunch and drinks, with fridge space onboard.

“Vítor was an AMAZING guide! We felt completely safe the entire trip and he was willing to teach us so much about the islands and sailing! Our group was fantastic and had the most fun - it is definitely the highlight of our trip! I truly cannot say enough good things about the whole experience.”

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