Sailing Trips in North America

Set out from Cabo San Lucas on a private 2-hour sunset cruise highlighting some of the coastline's most iconic sights. Board a power catamaran for a leisurely cruise along the Cabo coast, sailing past landmarks such as Lovers Beach and the photo-worthy golden-hued Arch, which looks even more spectacular in the evening light. Watch the sun slowly disappear below the horizon with your friends and family while basking in the natural beauty of your surrounds.

This classic private tour showcases the Manhattan skyline and the natural beauty of a stunning sunset! Depart from North Cove Marina near the iconic Freedom Tower and set sail on a tour that highlights the Brooklyn Bridge, Statue of Liberty and more. Pack food and drinks to ensure a memorable evening as you take in stunning views of one of the world's most dynamic cities!

Sail the seas around Seattle on this private, 3-hour adventure to Puget Sound. Climb aboard the S/V Kingsley and set sail from the Shilshole Bay Marina with an experienced captain leading the way. Learn how to sail or simply sit back and enjoy the view. See an abundance of marine wildlife, the downtown Seattle skyline - including the iconic Space Needle - plus incredible views of the Olympic Mountains, featuring majestic Mount Rainier in the distance.

Cruise the bay and find yourself beneath the Golden Gate Bridge on a 2.5-hour Sunday morning eco sailing tour from Sausalito. Take in fantastic views of San Francisco and Alcatraz while gliding through the bay, and look for native marine life like porpoises and seals with the help of an onboard naturalist.

See Lady Liberty in style during this sailing cruise onboard a wooden schooner built in classic, 1920s style. Walk the teak deck and find your place under the massive white sails of the America 2.0. Set sail through Lower Manhattan to take in epic skyline views on your way to the Statue of Liberty.

Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.

See the skyline and architectural shapes of New York City during this sailing cruise along the Hudson River. Board the elegant sailboat with wooden floors and soaring white sails. Take a seat and feel the wind in your face as you sip wine, beer, and champagne while looking out over iconic sights like the Brooklyn Bridge, Statue of Liberty, Battery Park and more.

See one of the world's most recognizable New York City landmarks in sailing style on this sunset cruise onboard a classic schooner. See the iconic skyline of Lower Manhattan as the vessel sails onward toward Ellis Island and Lady Liberty herself. Sip champagne or cocktails as the sunset casts colorful lights on the city.

A gorgeous island known for its pristine beaches and world-class snorkeling Lana'i is an incredible but sometimes difficult-to-reach destination. This Maui sailing trip offers one of the best tours for getting there. Not only is this full-day sail a great chance to check out healthy coral reefs with provided snorkeling equipment, but it's also packed with inclusions such as breakfast, lunch, and drinks.

See the best of New York City aboard a historic sailing ship on this cruise around New York Harbor. Choose from two afternoon departure times. Enjoy incredible views of the Manhattan skyline, plus landmarks like One World Trade Center, the Empire State Building, the Statue of Liberty, Ellis Island and much more. Help raise the sails or even take a turn navigating the ship.

Cruise around San Diego bay aboard an authentic 1992 America's Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America's Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.

See the best of New York City aboard a historic sailing ship on this 75-minute, daytime cruise around New York Harbor. Enjoy incredible views of the Manhattan skyline, plus landmarks like One World Trade Center, the Empire State Building, the Statue of Liberty, Ellis Island and much more from the water.

See New York City from the waters of the Hudson River on your own private motorboat tour. Enjoy two hours of sightseeing with stops at the Brooklyn Bridge, Freedom Tower (One World Trade Center) and Statue of Liberty. Bring your group of up to six people along with your own food or drink for this exclusive New York boating experience. Your tour departs from a convenient location in lower Manhattan.

Sail to Isla Mujeres from Cancun for a full day of fun in the sun. Stop for snorkeling in the clear waters of the Mexican Caribbean, then head to a private beach club on Isla Mujeres. Enjoy a buffet lunch spread, and have time to hang out at North Beach or go shopping downtown. After your time on the island, sail back to Cancun, with a tequila party and spinnaker flight (weather permitting) along the way. Your tour includes a buffet lunch with unlimited drinks and use of snorkel equipment.

Get out on the waters of Lake Union in a sailboat with a professional captain for a 2-hour intro to sailing lesson. With a small group, learn the ropes of of sailing a small vessel, including sailing theory and safety while enjoying views of the Seattle scenery. Multiple departure times offered throughout the day.

Enjoy a private sailing trip on a 40 foot Beneteau sailboat. Customize your own trip with Captain Bill, who's always game to give an impromptu sailing lesson to adventurous passengers - you can even take the helm or help work a wench. Or, just sit back, relax, and take in the sights. Choose a northern or southern route to highlight Miami classics like the skyline, MIllionaire's Row, and the magnificent Vizcaya estate.

Awaken your senses to the stunning sights and sounds of a Banderas Bay sunset on a tranquil 3-hour sunset cruise from Puerto Vallarta. Sip a cosmopolitan cocktail and nibble on premium cheese as your stylish Beneteau sailboat cruises on the calm waters of Banderas Bay; watch the setting sun sink into the crystal clear Pacific Ocean and absorb the impossibly romantic atmosphere of this enchanting excursion.

Watch the evening lights come on around the San Francisco Bay on Sundays during a 2-hour sunset sail from downtown Sausalito. Cruise aboard a handsome schooner that passes landmarks such as the Alcatraz Island, Crissy Field, Fort Mason, Fisherman's Wharf, Coit Tower, Angel Island, the Golden Gate Bridge, and the Bay Bridge.

See New York City from a rare perspective on a cruise through the Hudson River, with views of the skyline at sunset. As you sail past quintessential landmarks such as One World Trade and the Statue of Liberty, enjoy three drinks on the house (choice of wine, beer, champagne, or soda). The option to bring your own picnic dinner makes this a popular choice for date night or entertaining guests.

Admire San Francisco and its surrounding sights from the water on a San Francisco Bay sailing cruise. On board a catamaran, you'll sail past the iconic Golden Gate Bridge, legendary Alcatraz Island and the hamlet of Sausalito. Take advantage of great photo ops while you soak up the sea breeze during this 90-minute tour.