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Top 10 Best North America Sailing Trips

Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 3
 

Seattle Sailing Harbor Tour

(4.7 of 470 reviews)

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

Free Cancellation
Start From $49.66
 
Seattle Sailing Harbor Tour

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....

    Free Cancellation
    Start From $49.66
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.6 of 182 reviews)

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

Free Cancellation
Start From $67.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine

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....

    Free Cancellation
    Start From $67.00
 
 

Boston Harbor Sunset Sail Tour

(4.8 of 132 reviews)

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

Free Cancellation
Start From $82.27
 
Boston Harbor Sunset Sail Tour

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 ....

    Free Cancellation
    Start From $82.27
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 701 reviews)

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

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

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....

    Free Cancellation
    Start From $136.19
 
 
-16% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 275 reviews)

-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

Special Offer
Free Cancellation
Start From $83.16
(Saving 16% ) $99.00
 
-16% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

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....

    Special Offer
    Free Cancellation
    Start From $83.16
    (Saving 16% ) $99.00
 
 

Puerto Vallarta, Luxury Sunset Sailing

(4.7 of 382 reviews)

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

Free Cancellation
Start From $99.00
 
Puerto Vallarta, Luxury Sunset Sailing Likely to Sell Out

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....

    Free Cancellation
    Start From $99.00
 
 

Tall Ship Silva Sailing Cruise Ft. a Live Musician

(4.2 of 288 reviews)

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

Free Cancellation
Start From $39.71
 
Tall Ship Silva Sailing Cruise Ft. a Live Musician Likely to Sell Out

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....

    Free Cancellation
    Start From $39.71
 
 

Pirate Ship Sunset Dinner and Show in Los Cabos

(4.3 of 610 reviews)

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

Free Cancellation
Start From $99.00
 
Pirate Ship Sunset Dinner and Show in Los Cabos Likely to Sell Out

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 ....

    Free Cancellation
    Start From $99.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 522 reviews)

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

Free Cancellation
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

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....

    Free Cancellation
    Start From $84.77
 
 

Panama City Beach Sunset Catamaran Sail on The Privateer

(4.8 of 698 reviews)

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

Free Cancellation
Start From $45.00
 
Panama City Beach Sunset Catamaran Sail on The Privateer Likely to Sell Out

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....

    Free Cancellation
    Start From $45.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 806 reviews)

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

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

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....

    Free Cancellation
    Start From $202.59
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(5 of 176 reviews)

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

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming Likely to Sell Out

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....

    Free Cancellation
    Start From $79.00
 
 

El Cielo Snorkel by Private Boat

(4.8 of 327 reviews)

- 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

Free Cancellation
Private Tour
Start From $499.99
 
El Cielo Snorkel by Private Boat Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

New York Sunset Schooner Cruise on the Hudson River

(4.9 of 219 reviews)

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

Free Cancellation
Private Tour
Start From $90.12
 
New York Sunset Schooner Cruise on the Hudson River Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $90.12
 
 

Key West Dolphin and Snorkel Experience

(4.4 of 311 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $59.45
(Saving 15% ) $69.95
 
-15% Key West Dolphin and Snorkel Experience Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $59.45
    (Saving 15% ) $69.95
 
 

Panama City Beach Sunset Sail on The Footloose Catamaran

(4.8 of 431 reviews)

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

Free Cancellation
Private Tour
Start From $45.00
 
Panama City Beach Sunset Sail on The Footloose Catamaran Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Key West Afternoon Reef Snorkeling with Open Bar

(4.5 of 394 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $53.95
(Saving 10% ) $59.95
 
-10% Key West Afternoon Reef Snorkeling with Open Bar Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.95
    (Saving 10% ) $59.95
 
 

2-Hour Private Luxury Boat Tour in New York City

(5 of 87 reviews)

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

Free Cancellation
Private Tour
Start From $499.99
 
2-Hour Private Luxury Boat Tour in New York City Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $499.99
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 39 reviews)

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

Free Cancellation
Private Tour
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.7 of 386 reviews)

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

Free Cancellation
Private Tour
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

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 ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
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