Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 3Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More

Seattle Sailing Harbor Tour
-
North America
-
Superb470 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour,... More

Afternoon Windjammer Cruise Along the Coast of Portland Maine
-
North America
-
Superb182 reviews4.6
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More

Boston Harbor Sunset Sail Tour
-
North America
-
Superb132 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Afternoon Sail & Snorkel to the Captain Cook Monument
-
North America
-
Superb701 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
Free Cancellation
(Saving 16% )

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-
North America
-
Superb275 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
Free Cancellation
(Saving 16% )
Puerto Vallarta, Luxury Sunset Sailing
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More

Puerto Vallarta, Luxury Sunset Sailing
-
North America
-
Superb382 reviews4.7
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
Tall Ship Silva Sailing Cruise Ft. a Live Musician
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More

Tall Ship Silva Sailing Cruise Ft. a Live Musician
-
North America
-
Exellent288 reviews4.2
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
Pirate Ship Sunset Dinner and Show in Los Cabos
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Pirate Ship Sunset Dinner and Show in Los Cabos
-
North America
-
Exellent610 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Waikiki Sunset Cocktail Sail with Open Bar
-
North America
-
Superb522 reviews4.8
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
Panama City Beach Sunset Catamaran Sail on The Privateer
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Panama City Beach Sunset Catamaran Sail on The Privateer
-
North America
-
Superb698 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
-
North America
-
Superb806 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
-
North America
-
Superb176 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour

El Cielo Snorkel by Private Boat
-
North America
-
Superb327 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour
New York Sunset Schooner Cruise on the Hudson River
Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More
Private Tour

New York Sunset Schooner Cruise on the Hudson River
-
North America
-
Superb219 reviews4.9
Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....
Private Tour

Key West Dolphin and Snorkel Experience
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More
Free Cancellation
Private Tour
(Saving 15% )

Key West Dolphin and Snorkel Experience
-
North America
-
Exellent311 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Free Cancellation
Private Tour
(Saving 15% )
Panama City Beach Sunset Sail on The Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Private Tour

Panama City Beach Sunset Sail on The Footloose Catamaran
-
North America
-
Superb431 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour

Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Free Cancellation
Private Tour
(Saving 10% )

Key West Afternoon Reef Snorkeling with Open Bar
-
North America
-
Exellent394 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Free Cancellation
Private Tour
(Saving 10% )
2-Hour Private Luxury Boat Tour in New York City
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More
Private Tour

2-Hour Private Luxury Boat Tour in New York City
-
North America
-
Superb87 reviews5
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....
Private Tour
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Private Tour

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
-
North America
-
Superb39 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Private Tour
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Private Tour

2-Hour Sunset Sail on the San Francisco Bay
-
North America
-
Superb386 reviews4.7
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Private Tour