Sailing trips · CITY TOURS
Every trip has one free day too few. These 15 city sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
From Long Wharf, you’ll ride a high-speed catamaran to Stellwagen Bank with a naturalist guide, watching for humpback, fin, minke, and pilot whales, dolphins, and seabirds. Expect about 3.5 hours on the water, indoor seating, restrooms, and snacks for purchase.
“Saw a humpback blow and dive several times, including one up close. The narrator was great and enthusiastic.”
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! ✨”
Spend two hours aboard MagicSail with a drink, music, and a live guide in English, Portuguese, or Spanish. Cruise from Belém past the Tower, Discoveries Monument, Praça do Comércio, Alfama, and Christ the King. Guides such as Tiago, Miguel, Paulo, and Isaac add history and humor.
“We took the sailboat cruise on the last day of our trip to Lisbon and it was the perfect end to our vacation. Our tour guides were Mr Miguel and Mr Tiago, both of them were extremely jovial, humorous and kept us all engaged during the cruise. It was a great experience all thanks to our guides. We loved every bit of it and would absolutely recommend everyone to take the cruise- it is one of a kind experience.”
Join DiscoverOasis at Santo Amaro Dock for a relaxed two-hour sail past Praça do Comércio, Alfama, Belém Tower, Cristo Rei, and the 25 de Abril Bridge. Teresa, Manuel, or another multilingual crew member may share local stories while you enjoy wine, beer, water, and simple snacks.
“Excellent tour - Theresa was so welcoming, friendly, and accommodating. The city views were beautiful by boat, and a glass of wine/snacks were provided. Highly recommend!”
Settle into an assigned table aboard a classic 1920s-style yacht and cruise past Lower Manhattan, Governor’s Island, Ellis Island, and the Statue of Liberty. You get indoor comfort, open-deck views, and one included drink. Crew members such as Jacob, Yuri, and Tim have been praised for warm service and helpful photo-taking.
“The boat itself was beautiful and the crew on the boat were so friendly. We could just sit back and relax and enjoy the nice view. Highly recommended for a visit if you’re in NYC!”
Leave Galway City Docks at 9:30 a.m. for Inishmore, the largest Aran Island, with about 4.5 hours to explore by bike, bus, walking, or horse-drawn cart. On the return, cruise past the Cliffs of Moher and a major seabird colony. This is a ferry-style trip, not a fully guided shore tour.
“Very well organised, safe is very friendly and facilities and choice of drinks on board was fantastic. Parking in Galway and getting to the pier was very easy - instructions are very well explained on the ticket. Highly recommend this tour.”
Board the 105-foot Schooner America at Pier 62 for a two-hour sunset sail past Chelsea, Battery Park, Ellis Island, and the Statue of Liberty. A professional crew handles the sailing, and each adult receives one beer, wine, or Champagne. Bring a photo ID and a warm layer.
“So beautiful and fun. Boat is beautiful and was especially nice on a Sunday night as it was only about half full. The crew is super nice and attentive”
Board at Pier 62 for a 90-minute evening cruise around Manhattan. You’ll have an assigned table, one complimentary drink, indoor and outdoor viewing areas, and clear views of the skyline, Statue of Liberty, and Ellis Island. The cruise is not formally narrated, so expect music and sightseeing at an easy pace.
“if you have a good weather night, this is the best experience I feel for New York City. There’s nothing like seeing the skyline from a boat and also the Statue of Liberty and the Brooklyn Bridge. Amazing photos unobstructed. Highly recommended and I will be taking my mom the spring.”
Cruise New York Harbor for 75 to 90 minutes aboard a 1920s-inspired yacht. You’ll have an assigned seat in the climate-controlled salon, access to open decks, and one included drink while passing Lower Manhattan, Governor’s Island, Ellis Island, and the Statue of Liberty.
“Even though it was foggy due to the weather, The tour guides did the best they could at letting the tourists get a good view of the Statue of Liberty.”
Join Paulo for a private two-hour sail on the Tagus, starting beneath the 25 de Abril Bridge and cruising past Belém Tower, Cristo Rei, Praça do Comércio, Alfama, and Lisbon’s hilltop monuments. You’ll hear local stories, enjoy a white or rosé wine, and see Lisbon from the river.
“Paulo was absolutely amazing!! I would definitely recommend this experience! Unforgettable!”
Sail the Gulf of Mexico for two hours aboard the Privateer catamaran, with one complimentary drink, tropical music, sunset views, and a chance to spot dolphins near Shell Island. Captains and crew such as Justine, Mosley, Jason, and Captain J help keep the mood relaxed and social.
“This was so much fun!! Seeing dolphins and having a drink with good music and a sunset!! Would do it again ❤️”
Set sail from Rua da Praia for two hours along the Douro, passing Vila Nova de Gaia and Porto before reaching Foz do Douro for sunset. Expect a welcome drink, music, a comfortable boat, and guides such as Anselmo who share local stories in English, Portuguese, or Spanish.
“Is a most do in porto , such a beautiful experience to see the sunset the guide is extremely nice we had really good drinks and we even saw dolphins ❤️ thank you for everything definitely i would do it again”
Set sail from Old Sacramento for a 90-minute, adults-only party cruise with a live DJ, indoor and outdoor seating, and two fully stocked bars. You’ll pass beneath Tower Bridge and by I Street Bridge while buying cocktails, beer, wine, and snacks onboard. Check in 30 minutes early.
“Did not have an experience because the power went off snd the captain was rude.”
Board a private 42-foot yacht at Rainbow Harbor for a one-hour cruise past the Queen Mary, Long Beach waterfront, beaches, bridges, and Parkers’ Lighthouse. Captain Ryan handles the boat while you bring snacks, drinks, and music for a relaxed day or night outing.
“The private yacht ride was exactly what I hoped it would be. Our guide Ryan was very pleasant and welcoming to me and my friends. The tour he takes you around the ocean area of long beach is also really beautiful!”
Join the 40-foot Footloose for a 90-minute cruise from Bluegreen Bayside Resort. Watch for bottlenose dolphins near Panama City Beach and Shell Island, hear lively facts from the English-speaking crew, and enjoy one complimentary drink. Ryan, Jamie, Marci, and Lamar have led recent departures.
“Toller Trip mit dem Katamaran, guter Musik, Snacks und Getränken. Delfine haben wir sogar im Januar gesehen.”
Pick the boat, the hour on the water or the country.
