Sailing trips · SAILING TRIPS

Sailing Trips: The 15 Best in the World

371 trips  ·  from $10 a head

The trips worth crossing a bay for: sails actually raised, an anchorage worth swimming off, and a crew who tell you what the wind is doing. These 15 are priced per person, with the length of the swim stop and what is included on board spelled out.

Malaga: Catamaran Sailing Trip with Sunset Option - The Alboran Sea at golden hour
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Malaga: Catamaran Sailing Trip with Sunset Option

1.Catamaran Sailing Trip with Sunset Option

★★★★★★★★★★4.4 · 8,613 reviews · 1 - 1.5 hours · from $16Our pick

You’ll sail from Malaga for 1 to 1.5 hours aboard a spacious catamaran, watching the sun drop behind the mountains and the city lights appear. Choose a standard cruise or add a romantic light show. Cava is available with the selected option, and live music runs on some summer departures.

“Awesome! Was a very calm day too and weather was excellent too, would recommend to everyone of all ages too. Try it.”

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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

2.Oslo Fjord Sightseeing Cruise by Sailing Ship

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

Sail Oslo Fjord for two hours aboard a heated traditional ship with blankets, a bar, and commentary in 13 languages through the Oslo Fjord Guide app. See Hovedøya, Dyna Lighthouse, the Opera House, and Munch Museum, then choose a Bygdøy stop for museums such as Fram.

“It was an amazing Tour. It was alit of fun and the views were just awesome.”

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Valencia: Sailing Catamaran Cruise with Sunset Option and DJ - A relaxed route along Valencia’s coast
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Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

3.Sailing Catamaran Cruise with Sunset Option and DJ

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

Join Mundo Marino for a 60 to 90 minute catamaran cruise along Valencia’s coast. You’ll see the City of Arts, Miquelet, and city skyline from the Mediterranean. Choose a daytime or sunset departure, with cava at sunset and a DJ on selected Wednesday sailings.

“What a wonderful experience for the money! The catamaran was big enough for seating and the staff friendly. It was a great way to spend the evening. The cost is amazingly small for the activity.”

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Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks - The first hour: cliffs, caves, and Costa Brava views
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Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks

4.Catamaran Sailing Cruise with BBQ and Drinks

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

Join Catamarans Sensation Costa Brava for a four-hour cruise from Lloret de Mar. Sail past cliffs, caves, beaches, and fishing villages, then anchor for swimming, snorkeling, a BBQ, and drinks. Morning trips suit families, while afternoon and Saturday departures bring a livelier adults-only atmosphere.

“Excellent morning/early afternoon at sea. Food was good as was the choice of drink. Loved jumping into the sea from the boat and swimming with the fishes.”

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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - The Key West sights from the water
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

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

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

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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Los Cabos Luxury Sailing, Snorkel and Lunch Cruise - Santa Maria Bay or Playa El Chileno
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Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

6.Los Cabos Luxury Sailing, Snorkel and Lunch Cruise

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

Spend about four hours aboard a small sailing boat from San Jose del Cabo, with a maximum of 16 people. Cruise past El Arco, snorkel at Santa Maria or Chileno Bay, use paddleboards, and enjoy lunch, snacks, and an open bar. Crew names vary, with Joe, Poncho, Cesar, Israel, and Michelle praised for warm service.

“This experience was truly exceptional. Despite the weather not being ideal, the captain and crew went above and beyond to ensure everyone on board was comfortable and enjoying themselves. Their attentiveness, friendliness, and overall service made the trip feel seamless. A highlight of the excursion was unexpectedly spotting whales along the way, which added a memorable bonus to the day. The food and drinks were consistently great, and the atmosphere onboard stayed lively and fun throughout the journey. The views of the Arch were stunning, and we had plenty of time to swim and relax in the water. Overall, it was a fantastic trip, and I would highly recommend it…”

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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly - Snorkeling near Cancun, with weather in charge
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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

7.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 catamaran with lunch, an open bar, snorkeling when conditions allow, and free island time. Choose a family-friendly or adults-only departure, but confirm the exact boat and pickup details. Guides such as Enrique, Christina, Judy, and Abraham have earned praise for attentive service.

“Enrique and the crew made our Isla Mujeres trip unforgettable on 2/9/26! From drink service to local tips, they waited on us hand and foot. Great food, even better vibes—pure paradise. 10/10, ask for this team! 🌊🍹🌞”

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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink - From the Monument to the Discoveries to Belém Tower
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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

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

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

Join PalmaYachts for a two-hour Tagus River sail from Belém, limited to 10 people. Guides such as Benny, Miguel, João, and Telma share Lisbon’s stories while you pass Belém Tower, Commerce Square, Christ the King, and the 25 de Abril Bridge with a drink in hand.

“We had a wonderful experience on the sunset sailboat tour - Telma was so friendly and informative as this was our first time on a sailboat like this and she had interesting facts about the sites we passed. We were also given the chance to have our own time and take in our beautiful surroundings so we appreciated this too. Would definitely recommend! ✨”

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2 Hour Lisbon Sunset and Wine Sailing Tour - Setting out past Belém’s waterfront
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2 Hour Lisbon Sunset and Wine Sailing Tour

9.2 Hour Lisbon Sunset and Wine Sailing Tour

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

Meet Joe, Henry, JP, Marta, or another skipper at the Alcântara marina for a two-hour shared sail past Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and more. Portuguese wine, blankets, and skipper commentary are included, but this is a relaxed cruise, not a formal wine tasting.

“Very easy going. The boat was extremely clean and well kept. Our two guides were excellent- very knowledgeable, very friendly and nothing was too much trouble. We had great chats with the other guests and overall it was wonderful. You get fantastic views of the Lisbon ‘coastline’ as well as the 25th April bridge and Sanctuary of Christ the King. I should have tipped them more on departure as it was such a lovely experience”

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Lisbon: Sailing Tour on the Tagus River - Choosing Between a Sailing Boat and Catamaran
Lisbon Sailing Trips, Portugal Sailing Trips, Sailing Trips, Tour Reviews, Tours

Lisbon: Sailing Tour on the Tagus River

10.Sailing Tour on the Tagus River

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

Cruise from Belém past the Discoveries Monument, 25 de Abril Bridge, Christ the King, and Belém Tower. You can help sail or relax with a drink and snack. The crew may share local river knowledge, and sunset trips add glowing views over Lisbon.

“It was a lovely one hour sailing trip across the Tagus to the bridge and back It was slightly windy so on a hot day I’m sure it would be even better. Free beer water and the young skipper and his mate were very good Worth the money and definitely recommend”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Dia Island from the water, not from the beach
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

11.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 protected Dia Island aboard a comfortable yacht with a maximum of 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. Afternoon departures can include a beautiful sunset sail back.

“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”

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Arusun Catamaran Sail with Snorkeling in Aruba - Catalina Bay and the chance of sea turtles
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Arusun Catamaran Sail with Snorkeling in Aruba

12.Arusun Catamaran Sail with Snorkeling in Aruba

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

Spend 2.5 hours aboard the 65-foot Arusun from Palm Beach. Captain Amanda, Ronnie, Gabriel, or Rashim may guide your sail, with two snorkel stops, provided gear, snacks, and an open bar. The boat holds up to 35 people, though some departures are much smaller.

“What a fun trip! The staff was so energetic and welcoming! The boat ride was beautiful and relaxing! We loved the shipwreck snorkel and saw a beautiful sea turtle and tons of fish! Worth it and we will do it again!”

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Dolphin Catamaran Snorkel and Sail with Open Bar - First stop: the Antilla shipwreck
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Dolphin Catamaran Snorkel and Sail with Open Bar

13.Dolphin Catamaran Snorkel and Sail with Open Bar

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

Sail aboard The Dolphin from Noord for a three-hour Aruba cruise with two snorkel stops at the Antilla shipwreck and Boca Catalina Bay. You get fresh gear, wraps, fruit, an open bar, a spinning slide, and rope swing. Crew members including Frederick, Oscar, Rio, Jay, and Brandon have earned warm praise.

“Whole Lotta fun! Catamaran beautiful. Snorkeling, swing and slide were great!! Drinks were good! Had a ball!”

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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar - The route to El Arco and Lover’s Beach
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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

14.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 on a 50-foot boat with up to 16 people. Expect the Arch, Lover’s Beach, sea lions, open-bar drinks, light appetizers, and a relaxed sunset setting. Pickup is available for $10 per person, with a $2 dock fee.

“Very well organized, the comisny was very responsive and accommodating. The pick up was right on time and everything about the logistics went smoothly. The sailboat was beautiful and the crew really great. The food and drink was also delicious! We even got to see whales. I’d highly recommend this sunset sail. It was a really, really great trip! I’d choice this company again and will remember them for the next time we come to Cabo”

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Barcelona Sailing Cruise - Leaving the marina and finding your sea view
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Barcelona Sailing Cruise

15.Barcelona Sailing Cruise

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

Spend 75 minutes aboard a classic Turkish Gulet, choosing between the rooftop, interior lounge, or aft chill-out area. Enjoy one Aperol Spritz, bar service, music, and Barcelona’s skyline from the Mediterranean. Hosts speak Spanish and English, with crew members such as Oriol, Khalid, and Jon praised for friendly service.

“Amazing experience for my cousin and I on the hot summers day we went we ended up feeling relaxed and happy. Aperol was a nice touch.”

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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Waikiki and Diamond Head from the water
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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - The 54-foot catamaran ride
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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Barcelona: Midday or Sunset Sailing with Open Bar and Snacks - What the two-hour route feels like
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Barcelona: Midday or Sunset Sailing with Open Bar and Snacks

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