The 15 Best Guided Sailing Days Around the World

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

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

★★★★★★★★★★4.9 · 3,114 reviews · 2 hours · from $41Top of the fleet

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

2.2 Hour Lisbon Sunset and Wine Sailing Tour

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

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

3.Lisbon: Sailing Tour on the Tagus River

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

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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Funchal: Sunset Sailing Tour

4.Funchal: Sunset Sailing Tour

★★★★★★★★★★4.7 · 2,144 reviews · 3 hours · from $58

Sail from Funchal with up to 20 people on a relaxed evening trip led in English or Portuguese. Look for dolphins and whales, stop to swim or snorkel beneath Cabo Girão, and watch the sunset from the sea. Drinks are included, but food, transport, and shoes on board are not.

“Victor and Bruno were great. Victor really cared for our daughter who was a bit scared initially as the sea was not flat. Very attentive to everyone onboard and the scenery was amazing!”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

5.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147

Spend 10 hours circling Milos and visiting Polyaigos, with swim stops at Gerakas and Kleftiko, snorkel gear, lunch, snacks, and drinks included. Guides such as Dora, Niki, and Alexandra share island stories, while the crew adjusts the route when wind makes the northern coast rough.

“Best trip we have ever been on! The boat was amazing, the food was amazing (we were fed fresh yummy food multiple times and there was unlimited drinks). Our tour guide Dora was amazing, very friendly and knowledgeable about the tour stops. She made the tour great! Couldn’t recommend enough, she even taught us traditional Greek dances - amazing vibes and very fun. The tour stops were amazing, 3 amazing places to swim. Kleftiko is a must visit, swimming into the caves is a highlight! - 10/10 would recommend, worth the money!”

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Sailing Tour through the Laguna de los Siete Colores

6.Sailing Tour through the Laguna de los Siete Colores

★★★★★★★★★★5.0 · 1,521 reviews · 3 hours (approx.) · from $40

Join a small English-speaking group for a three-hour sailing trip on Bacalar’s Seven Colors Lagoon. Crews may include captains such as Irving, Zazil, Leo, or Leandro, depending on the day. You’ll visit Cenote Negro, Pirate Canal, and Bird Island, with two swim stops, seasonal fruit, beer, and water included.

“This was a highlight of our trip to Bacalar! Leondro and Cecile were fabulous - super friendly, explained a ton about the Laguna and the town of Bacalar itself. They took us to less busy spots to swim - at one point it was literally like we had a private lake to ourselves! We appreciated their commitment to protecting the lagoon, as that is a shared value, and why we booked a sailing tour specifically. One note - bring lots of protective gear as the boat isn’t covered and sunscreen use (even biodegradable/reef safe) isn’t allowed in the lagoon.”

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4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

7.4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

★★★★★★★★★★5.0 · 1,465 reviews · from $145

Spend four hours aboard a 48-foot catamaran from Providenciales, with beach pickup, reef snorkeling, lunch, drinks, and a stop at Half Moon Bay or Little Water Cay. The crew, including guides such as Ross, Jay, Reggie, and Willie, helps beginners in the water and points out fish, reefs, and native rock iguanas.

“Awesome snorkeling and overall experience! Fun and informative, great crew who were great with young and old! Highly recommend!”

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Barcelona Helicopter, Sailboat & Old Town Private Walking Tour

8.Barcelona Helicopter, Sailboat & Old Town Private Walking Tour

★★★★★★★★★★5.0 · 1,395 reviews · 4 hours (approx.) · from $513

Start with guides such as Jimena, Carlos, Han, or Oscar in Barcelona’s Old Town and Eixample, then travel by boat to the heliport for a roughly six-minute flight over Port Vell, Barceloneta, and the Olympic Port. Expect plenty of walking, a small helicopter holding three people, and a public boat ride rather than a private sail.

“Great tour! Great information on the walking tour, the helicopter ride was transformative, and the boat ride can be taken at a different time as well.”

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Lisbon: Champagne Sailing Tours

9.Lisbon: Champagne Sailing Tours

★★★★★★★★★★4.9 · 1,366 reviews · 2 hours · from $58

Join Nigel and his crew aboard the 15-meter yacht Mara for a relaxed two-hour sail from Doca de Santo Amaro. Cruise past Belém Tower, Christ the King, Commerce Square, and Alfama while enjoying Portuguese champagne, wine, beer, soft drinks, and homemade snacks. The small group, usually no more than 12 people, keeps the trip personal.

“The small group and the great crew made this experience very enjoyable. We loved the tour and can recommend it for every weather. Many thanks to Nigel and his team :-)”

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Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

10.Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

★★★★★★★★★★4.5 · 1,269 reviews · 6 hours (approx.) · from $66

You’ll board the Sea Breeze catamaran at Bugibba Jetty for about six hours of swimming, sun, music, and Maltese coastline views. Blue Lagoon is guaranteed, while Crystal Lagoon, Ghajn Tuffieha, Mellieha Beach, Ramla Bay, or Popeye Village may be added depending on sea conditions. Bring sunscreen, a towel, and arrive early for a good seat.

“I was with my family of 5, and I was worried as a lot of reviews for this and other boat trips said the boats got really crowded. Perhaps we got lucky but the crowds were not too bad when we went and the boat ride was amazing! We got to make a lot of cool stops, swim, use the slide on the boat, and get some cool photos. One thing to note is that they leave at very strict times and the departure dock is a little bit of a walk, so try to find it early (15 minutes early to find should be okay. It's by a little…”

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Sailing Tour through the Lagoon of the 7 Colors

11.Sailing Tour through the Lagoon of the 7 Colors

★★★★★★★★★★5.0 · 1,161 reviews · 3 hours (approx.) · from $37

Set out from Casa China Bacalar for a three-hour lagoon trip with a bilingual guide and a maximum of 16 people. You’ll visit three cenotes, Bird Island, and the Pirate Canal, with time to swim and snorkel. Captains such as David, Abraham, Angelo, and Hugo are praised for friendly service and clear explanations. Fruit drinks, snacks, and three beers per adult are included.

“Great experience with David and Luis. We had a lot of time for swimming, enjoying cenotes, and the laguna ...the only thing: there was no wind!! It was also very good to have the possibility to stay at this place for the afternoon enjoying jumping from the pier.”

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Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks

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

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

Sail the Tagus for about two hours aboard a 50 to 58 foot yacht from Belém. A captain and host explain Lisbon landmarks in English and other languages, while you enjoy two drinks, Portuguese cheese, chouriço, and sunset views. Sebastian, Tiago, and Christina are among the guides who may lead the cruise.

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

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Lisbon: Sailboat Sunset Tour with a Drink

13.Lisbon: Sailboat Sunset Tour with a Drink

★★★★★★★★★★4.9 · 1,044 reviews · 2 hours · from $40

Saildreams takes you from Doca de Alcântara along the Tagus in a boat limited to 10 people. Guides such as Sergio, Mary, and Francisco mix Lisbon stories with relaxed sailing, wine or beer, snacks, and sunset views of Christ the King, Belém Tower, and the Discoveries Monument. Bring a coat: the river breeze can be strong.

“Our guide Mary was a wonderful host and truly made the sunset boat tour a highlight with her engaging commentary. She seamlessly switched between two languages and shared informative stories with great humor. The captain also did an excellent job, calmly guiding us along the Tajo.”

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Rio de Janeiro: Sunset Sailing Tour

14.Rio de Janeiro: Sunset Sailing Tour

★★★★★★★★★★4.8 · 994 reviews · 3 hours · from $75

Set sail from Marina da Glória for three hours around Guanabara Bay, passing Rio’s forts, Boa Viagem Island, and Niterói’s striking contemporary art museum. The small boat carries no more than 12 people, with drinks, snacks, and friendly guides such as Clarisse and Karina. Swimming may be possible when weather and the captain allow.

“This was SO such fun!! Clarisse and the crew made sure everyone on board was well taken care. There was about 10 of us on board and it definitely didn’t feel overcrowded. The drinks were unlimited and the snacks were yummy! Clarisse was the absolute sweetest person and made sure everyone was happy the whole time. An absolute gem! I would HIGHLY recommend this tour! Especially for solo travellers like I was! 5 stars all around!”

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Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks

15.Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks

★★★★★★★★★★5.0 · 976 reviews · 2 hours (approx.) · from $50

Join BYX Best Yacht Xperience for a two-hour sunset sail from Doca de Santo Amaro. Expect a small group of up to 10, Portuguese wine, cheese or chouriço, music, and views of Cristo Rei, Belém Tower, MAAT, and the 25 de Abril Bridge. Crew members including Vasco, Fernando, Manuel, Miguel, and Alfonso have been praised for their stories and friendly style.

“So when we started it was raining and you couldn’t see three feet. BUT! 20 minutes in it cleared up and we ended up having an absolutely gorgeous sunset on the bay. Our guides were super knowledgeable about the city and very funny and friendly as well. Plus, the wine was excellent. I’d highly recommend if you’re visiting Lisbon, it’s great fun and you’ll get wonderful photos”

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