On the water · SAILING TRIPS

Sailing Trips Around the World: The 15 Best

140 tours  ·  from $12 a head

Under sail is slower, quieter and completely dependent on wind. These 15 say whether the engine does most of the work, how much crewing you are expected to do, and what happens on a flat day.

Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship - Starting at Rådhusbrygge 3 beside City Hall
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Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship

1.Oslo Fjord Sightseeing Cruise by Sailing Ship

★★★★★★★★★★4.5 · 5,790 reviews · 2 hours · from $39Our pick

Sail Oslo Fjord for two hours aboard a traditional heated sailing ship with blankets, a bar, and commentary in English or through an app in 13 languages. You can get off at Bygdøy at 12:20 PM to visit museums, then rejoin the boat at 2:50 PM. Guides such as Karen and Captain Pete have helped make some sailings especially lively.

“A beautiful traditional sailing ship. The weather wasn’t really on our side, but the activity was interesting. It would be great to make the menu and drinks a bit more varied.”

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Valencia: Sailing Catamaran Cruise with Sunset Option and DJ - Choosing your seat on the catamaran
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Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

2.Sailing Catamaran Cruise with Sunset Option and DJ

★★★★★★★★★★4.1 · 4,270 reviews · 1 hour - 90 minutes · from $17Best value

Join Mundo Marino at Valencia’s port for a 1 to 1.5-hour catamaran cruise along the Mediterranean coast. Choose a daytime sailing or sunset departure with cava. Selected summer Wednesday sailings add a live DJ, while the boat’s bar sells drinks and snacks.

“The sunset was incredible and the crew was very friendly. The only thing would be nice to have is making music louder that’d add up to the atmosphere ☺️”

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Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks - Two hours at anchor for swimming and snorkeling
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Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks

3.Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks

★★★★★★★★★★4.5 · 3,812 reviews · 4 hours · from $59

Board at Lloret de Mar’s beach promenade for a four-hour Costa Brava cruise. You’ll sail past cliffs, caves, beaches, and fishing villages, then stop for swimming, snorkeling, floating-mattress fun, and a self-service BBQ. Morning trips suit families, while afternoon and Saturday departures bring a more adult party mood, with lively crew members such as Julio helping set the tone.

“It was very well run, the staff were extremely pleasant and helpful. It was very good value as there was plenty to eat and drink. We had a wonderful swim off the boat, and the music was good. They looked after us well as we were a couple of oldies amongst the younger passengers.”

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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - From 205 Elizabeth Street to open water
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

4.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Sebago’s large Key West catamaran, sailing past Mallory Square, Fort Zachary Taylor, and Sunset Key. Your ticket includes an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, chef-selected hors d’oeuvres, and live music from local performers. Arrive early for a good bow seat, and bring a sweater for cool or windy evenings.

“Fun crew and drinks were plenty. There is enough room for everyone and the boat was well handled. Highly recommend this one.”

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Los Cabos Luxury Sailing, Snorkel and Lunch Cruise - Leaving the marina with El Arco in view
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Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

5.Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

★★★★★★★★★★5.0 · 3,515 reviews · 4 hours (approx.) · from $149Top rated

Spend four hours aboard a luxury sailboat from San Jose del Cabo, visiting Santa Maria Bay or Chileno Bay for snorkeling and paddleboarding before lunch with an open bar. Expect a small group of up to 16, views of El Arco, and crew members such as Cesar, Israel, Michelle, Joe, and Captain Poncho depending on the departure.

“Service and experience was good. It would have been better if we actually put up the sails and tools advantage of the wind on the way back in the afternoon”

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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly - What the cruise is really like on the water
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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

6.Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

★★★★★★★★★★4.5 · 3,418 reviews · 5 hours 30 minutes (approx.) · from $129

Sail from Cancun to Isla Mujeres on a half-day catamaran cruise with hotel pickup, open bar, onboard lunch, snorkeling when conditions allow, and island free time. The bilingual crew, including guides such as Enrique, Christina, Judy, and Abraham, keeps the trip lively. Choose a family-friendly or adults-only departure, but confirm the details carefully.

“Great experience and lots of fun. Staff was great and attentive! Christina and Judy were very friendly and entertaining as well as the rest of the crew!”

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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink - Meeting the boat beside the Monument to the Discoveries
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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

7.Daytime/Sunset/Night City Sailboat Tour with Drink

★★★★★★★★★★4.9 · 3,114 reviews · 2 hours · from $41

Join a small group of up to 10 people for a two-hour sail from Belém. Your crew, often including guides such as Benny, Miguel, Telma, or João, shares Lisbon history while you pass Belém Tower, Cristo-Rei, Commerce Square, and MAAT. Choose daytime, sunset, or night sailing, with one drink and water included.

“We actually sailed some. The skipper/guide was knowledgeable and fun, and the crew member was good. The views were good. I recommend the trip”

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2 Hour Lisbon Sunset and Wine Sailing Tour - Portuguese wine, conversation, and the onboard mood
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2 Hour Lisbon Sunset and Wine Sailing Tour

8.2 Hour Lisbon Sunset and Wine Sailing Tour

★★★★★★★★★★5.0 · 2,680 reviews · 2 hours (approx.) · from $66

Join a small group of up to 12 at Lisbon’s Alcântara marina for a two-hour sunset sail. Your skipper handles the boat while you enjoy Portuguese wine, views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and commentary from hosts such as Joe, Henry, JP, or Marta.

“The guide (JP) was very knowledgeable, and the tour was very relaxing. This was such a nice evening getting to know the other riders, and enjoying the atmosphere.”

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Lisbon: Sailing Tour on the Tagus River - Finding the boat at Doca do Bom Sucesso
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Lisbon: Sailing Tour on the Tagus River

9.Sailing Tour on the Tagus River

★★★★★★★★★★4.8 · 2,632 reviews · 1 - 2 hours · from $23

Join a small sailboat or catamaran at Belém’s Doca do Bom Sucesso for a relaxed Tagus cruise. You can help steer with the crew or stretch out on deck. Expect a safety briefing, city views, one drink, water, a light snack, and about 105 minutes on the river. Sunset departures add Lisbon’s skyline in warm evening light.

“I really enjoyed the sailboat tour—the guides were very friendly, and it was a great value for the money.”

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

10.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island aboard a yacht limited to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos provide the sailing, safety guidance, food, and drinks. You’ll swim, snorkel, paddleboard, and eat shrimp linguini with Greek salad before sailing back.

“Fantastic few hours in the Greek sea, lovely crew DELICIOUS food and gorgeous sunset! Love love love”

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Arusun Catamaran Sail with Snorkeling in Aruba - First stop: the Antilla Shipwreck
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Arusun Catamaran Sail with Snorkeling in Aruba

11.Arusun Catamaran Sail with Snorkeling in Aruba

★★★★★★★★★★5.0 · 2,402 reviews · from $63

You’ll cruise from Palm Beach aboard the 65-foot Arusun with a captain and first mate, open bar, snacks, shade, sun, and front nets. After a short zodiac transfer, snorkel at the Antilla Shipwreck and Catalina Bay. Small groups can make this feel relaxed, though music may be lively.

“This trip gave us a nice variety of places to snorkel. The Antilla shipwreck was a bit crowded with swimmers, snorkelers and scuba divers, but the views were amazing. Catalina Bay also offered us great views and we managed to see a sea turtle just as our boat was departing. The drinks and snacks were satisfying, and the crew were great to work with.”

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Dolphin Catamaran Snorkel and Sail with Open Bar - The Rope Swing and Spinning Water Slide
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Dolphin Catamaran Snorkel and Sail with Open Bar

12.Dolphin Catamaran Snorkel and Sail with Open Bar

★★★★★★★★★★4.5 · 2,291 reviews · from $69

Sail from Noord aboard The Dolphin for three hours, with snorkel stops at the Antilla shipwreck and Boca Catalina Bay. The crew provides gear, wraps, fruit, snacks, an open bar, music, a rope swing, and a spinning water slide. Check in with Olga or John at Delphi Watersports by the Hyatt Regency.

“Absolutely amazing! From us checking in, to being on the boat, everything was exceptional! Everyone was so nice and friendly. They were welcoming, and the tour itself was awesome. They take you to 2 awesome snorkel spots to see fish and turtles! They serve unlimited drinks and fruit/ wraps for a snack. Highly recommend as an excursion. -Alex”

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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar - What the open bar really adds
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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

13.Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

★★★★★★★★★★5.0 · 2,267 reviews · 2 hours 30 minutes (approx.) · from $109

Sail Cabo San Lucas Bay for 2.5 hours aboard a 50-foot boat, passing Lover’s Beach and El Arco as the sun sets. Your small group gets unlimited drinks, light appetizers, music, and attentive crew service. Hotel pickup is available for $10 per person, with a $2 dock fee at El Arco.

“The staff was excellent. The boat was in great condition and the music was relaxing, and the whole experience was elevated and chill. Not a party pug, which is awesome. Good crowd, and the number of people. I highly recommend. As we saw the other boat we were so thankful we were on this boat. The snacks were yummy.”

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Barcelona Sailing Cruise - What the 75-minute route actually gives you
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Barcelona Sailing Cruise

14.Barcelona Sailing Cruise

★★★★★★★★★★4.4 · 2,230 reviews · 1h 15m · from $20

Spend 75 minutes aboard a classic Turkish Gulet off Barcelona’s coast. Choose the rooftop, interior lounge, or aft chill-out area, enjoy one Aperol Spritz, and order extra drinks or snacks at the bar. English and Spanish-speaking crew members, including Oriol and Khalid on some departures, keep check-in and sailing easy.

“Was an amazing event, thank you to Santiago & Mark. Great hosts”

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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - The Moana Catamaran and the First Drink
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

15.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89

Sail the Waikiki coast aboard the Hawaii-built Moana Catamaran for sunset views, Diamond Head, and a premium cocktail. The crew, including Vivian, keeps service friendly and attentive. From November through May, you may spot humpback whales, and dolphins are possible year-round. Shoes come off before boarding.

“Great trip. Saw humpback whales and a fantastic sunset. Crew was attentive and we all had a lovely time.”

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New in Sailing Trips

★ 4.8Puerto Banús by Sailboat: Discover Marbella’s Luxury CoastFrom $65499 reviews
★ 4.9Best Charming Sailboat Cruise SunsetFrom $70334 reviews
★ 5.0Charming Sailboat Cruise with Port Wine,Sunset OptionFrom $411,978 reviews
★ 4.6Sunset Sailing Cruise on Luxury CatamaranFrom $66342 reviews
★ 4.6Palma de Mallorca: Sunset Sailing Catamaran Trip with DrinkFrom $23613 reviews
★ 4.7Palma de Mallorca: Deluxe Catamaran Sailing Tour with MealFrom $97459 reviews
★ 4.5Fjord Mini Cruise by Wooden Sailing ShipFrom $36503 reviews
★ 4.7Waikiki Sunset Catamaran Sail and SwimFrom $44519 reviews
★ 4.9Sunset Sail Aboard a SchoonerFrom $101344 reviews
★ 4.8Naxos: Sailing Cruise with Lunch & DrinksFrom $188347 reviews
★ 4.7Sunset Sail aboard a Traditional Boat with ProseccoFrom $58286 reviews
★ 4.9Morro Jable: Sailing Boat Excursion with Food and DrinksFrom $117296 reviews
★ 4.5Whitsunday Islands 2-Day Sailing TourFrom $350452 reviews
★ 4.8Marseille: Calanques Sailing Cruise with Lunch and WineFrom $153354 reviews
★ 4.7Marbella: Sailing & Dolphin Watching with Snacks and DrinksFrom $711,062 reviews

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