The 15 Best Sailing Trips to Book, Anywhere

Catamaran Sailing Trips, Catamaran Sailing Trips in Spain, Malaga Sailing Tours, Sailing Tours, Spain Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in Spain, Tour Reviews

Malaga: Catamaran Sailing Trip with Sunset Option

1.Malaga: Catamaran Sailing Trip with Sunset Option

★★★★★★★★★★4.4 · 8,613 reviews · 1 - 1.5 hours · from $16Top of the fleet

Sail from Malaga for 1 to 1.5 hours along the coast as the sun drops behind the mountains. You can sit on the front nets, listen to chillout music, and add a glass of Spanish cava or a romantic light show. English and Spanish crew members are on board. Live music runs on selected Wednesdays, Fridays, and Sundays until mid-September.

“It's always an excellent option, during the day as during sunset!”

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Norway Sailing Tours, Sailing Tours, Tour Reviews

Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship

2.Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship

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

Cruise Oslo’s fjord for two hours aboard a traditional sailing ship with a heated main deck, blankets, bar, and English commentary. The free Oslo Fjord Guide app adds audio in 13 languages. You can leave the boat at Bygdøy to visit a museum, then rejoin it later, though museum admission is separate.

“Well, i acknowledge that it would have been a great experience, if not for the rainy cold weather. The activity providers did their best however to make us cosy, and were friendly. The views were amazing too!”

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Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

3.Valencia: Sailing Catamaran Cruise with Sunset Option and DJ

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

Sail from Valencia’s marina along the Mediterranean coast on a spacious catamaran. Choose a daytime or sunset departure, then settle into cushioned seating or pay extra for the front nets. Sunset trips include a glass of cava, while selected Wednesday sailings feature a live DJ.

“We really enjoyed enjoyed the Catamaran trip, the scenery was beautiful the boat nets were comfy, staff friendly and helpful, a very relaxing experience. it was chilly in November so definadvuse wrapping up warm. The sunset was stunning, but the red purple sky afterwards was incredible... definitely a highlight of our trip! Would love to go back in the summer for a daytime trip.”

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Lloret de Mar: Catamaran Sailing Cruise with BBQ and Drinks

4.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 beachside promenade for a four-hour Costa Brava cruise with swimming, snorkeling, a floating mattress, BBQ, and drinks. Morning departures suit families, while afternoon and Saturday celebration trips bring a stronger party mood. English, Spanish, and French support is available.

“Absolutely amazing unforgettable You cant go wrong with this purchase”

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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

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

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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 $149Best loved

Spend about four hours aboard a small luxury sailboat from San Jose del Cabo, with snacks, an open bar, snorkeling, paddleboards, and lunch. The route may include Santa Maria Bay, Chileno Bay, and El Arco. Crew members such as Cesar, Israel, Michelle, Joe, and Captain Poncho have earned warm praise for friendly service.

“The crew and sailing were fabulous as was the food. Pictures and whale spottings were great. Snorkeling was disappointing and we could not get on the beach where we anchored!! Ugg!”

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Cancun Sailing Tours, Mexico Sailing Tours, Sailing Tours, Tour Reviews

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

7.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 catamaran with hotel pickup, bilingual crew, open bar, light lunch, snorkeling when conditions allow, and free island time. The boat carries up to 60 people. Guides such as Enrique, Christina, Judy, Abraham, and Diego have been praised for friendly service, but pickup times and snorkeling length can vary.

“Amazing staff, beautiful boat and excellent experience. The transfer from our resort was perfectly on time.”

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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

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

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

Spend two hours aboard a small sailboat with a skipper and guide, passing Belém Tower, the Discoveries Monument, MAAT, Alfama, and Christ the King. Choose daytime, sunset, or night sailing. The crew speaks English, Spanish, and Portuguese, serves one drink, and keeps the group to 10 people.

“Benny & Miguel were wonderful hosts. Benny was very informative and gave excellent information. They were very respectful and we received complimentary drinks. They asked to take photos which was very nice and respectful .”

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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

Join a shared sailing cruise of up to 12 people from Lisbon’s Alcântara marina. Your skipper handles the sailing while you enjoy Portuguese wine, views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and a sunset over the Tagus. Guides such as Joe, Henry, JP, and Bruno are praised for friendly conversation and local insight.

“It was a great experience. They upgraded us to a luxury boat free of cost. Excellent customer service. Loved the cruise.”

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Lisbon: Sailing Tour on the Tagus River

10.Lisbon: Sailing Tour on the Tagus River

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

Join a small sailboat or catamaran from Belém’s Doca do Bom Sucesso for a relaxed cruise past the Discoveries Monument, 25 de Abril Bridge, Christ the King, and Belém Tower. You can help sail with no experience or sit back with a drink. The crew, including captains such as Luis, may share useful river and city details.

“A perfect night on the river. The crew was kind and attentive and we had a great time.”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

11.Heraklion: 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 yacht limited to 14 people. You’ll swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. English-speaking crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros, with morning and sunset departures available.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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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 Aruba’s coast aboard *The Dolphin* for two snorkel stops at the Antilla shipwreck and Boca Catalina Bay. Guides such as Frederick, Oscar, Rio, Jay, and Brandon help with the fun, while you get a light wrap-and-fruit lunch, drinks, a rope swing, and a spinning water slide. The three-hour trip leaves from Delphi Watersports near the Hyatt Regency.

“Best snorkeling/catamaran experience we’ve ever been on—and we’ve been on a lot. The vibe was low key and family friendly. Could have had maybe a tad more time at the shipwreck site (that’s where we saw a turtle), but the generous snorkeling time at the next site made up for it. We saw some corals doing a-okay and some unique reef fish. Ending the adventure with the rope swing was awesome! Highly recommend!”

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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 vessel with a maximum of 16 people. You’ll pass Lover’s Beach and El Arco, enjoy unlimited drinks and light appetizers, and watch sunset from the water. Crews have included Tito, Chino, Chava, Aldo, and Ronnie, though assignments vary.

“The sailing was awesome! Gorgeous views. Really good appetizers. Staff was fun and entertaining. Got some great pics.”

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Barcelona Sailing Tours, Sailing Tours, Spain Sailing Tours, Tour Reviews

Barcelona Sailing Cruise

14.Barcelona Sailing Cruise

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

Spend 75 minutes aboard a classic Turkish Gulet, sailing from Barcelona’s port with a complimentary Aperol Spritz, bar service, music, and open views of the coast. Choose the rooftop, interior lounge, or aft chill-out area. Crew members speak Spanish and English. Kids ages 4 to 12 sail free.

“It was so beautiful being on the water! There was plenty of seating. The music playlist was great! The price was very inexpensive for this experience! I got off the boat and almost booked the next ride out.”

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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

Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.

“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”

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