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Top 10 Best North America Sailing Trips

Found 770 Sailing Trips activities in North America. Sort by Popularity. - Page 6
 

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

(4.9 of 347 reviews)

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. ... More

Free Cancellation
Start From $125.00
 
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests Likely to Sell Out

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

  • North America
  • Superb347 reviews4.9

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San ....

    Free Cancellation
    Start From $125.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 300 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • North America
  • Superb300 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Sunset Sailing Cruise in Monterey Bay

(4.8 of 42 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Free Cancellation
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • North America
  • Superb42 reviews4.8

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Start From $95.00
 
 

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

(5 of 41 reviews)

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More

Free Cancellation
Private Tour
Start From $350.00
 
Best Private Luxury Daytime Boat Tour in New York City - 1 Hour Likely to Sell Out

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

  • North America
  • Superb41 reviews5

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....

    Free Cancellation
    Private Tour
    Start From $350.00
 
 

JFarwell Sunset Wine and Cheese Yacht Sailing

(4.9 of 149 reviews)

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved in sailing - take the helm, hoist the sails, or sit back and enjoy the beautiful sights and wines ... More

Free Cancellation
Private Tour
Start From $147.77
 
JFarwell Sunset Wine and Cheese Yacht Sailing Likely to Sell Out

JFarwell Sunset Wine and Cheese Yacht Sailing

  • North America
  • Superb149 reviews4.9

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to i....

    Free Cancellation
    Private Tour
    Start From $147.77
 
 

Spectacular Sunset Sail on San Diego Bay

(5 of 28 reviews)

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharing hidden stories, hands-on sailing, wildlife encounters, and unforgettable vistas of San Diego Bay. Participate or sit back and en... More

Free Cancellation
Private Tour
Start From $120.00
 
Spectacular Sunset Sail on San Diego Bay Likely to Sell Out

Spectacular Sunset Sail on San Diego Bay

  • North America
  • Superb28 reviews5

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharin....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 217 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Private Tour
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • North America
  • Superb217 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Halifax Sunset Cruise Ft. a Live Musician

(4.7 of 48 reviews)

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More

Free Cancellation
Private Tour
Start From $40.79
 
Halifax Sunset Cruise Ft. a Live Musician Likely to Sell Out

Halifax Sunset Cruise Ft. a Live Musician

  • North America
  • Superb48 reviews4.7

Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....

    Free Cancellation
    Private Tour
    Start From $40.79
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 478 reviews)

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 adventure will begin in the turquoise waters... More

Free Cancellation
Private Tour
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • North America
  • Superb478 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Private Tour
    Start From $179.27
 
 

New York City Sailboat Day Cruise to the Statue of Liberty

(4.9 of 159 reviews)

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

Free Cancellation
Private Tour
Start From $60.08
 
New York City Sailboat Day Cruise to the Statue of Liberty Likely to Sell Out

New York City Sailboat Day Cruise to the Statue of Liberty

  • North America
  • Superb159 reviews4.9

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 532 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Private Tour
Start From $55.00
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb532 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

(4.9 of 835 reviews)

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More

Free Cancellation
Private Tour
Start From $120.00
 
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas Likely to Sell Out

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

  • North America
  • Superb835 reviews4.9

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 241 reviews)

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More

Free Cancellation
Private Tour
Start From $109.00
 
Classic Key West Schooner Sunset Sail with Full Open Bar Likely to Sell Out

Classic Key West Schooner Sunset Sail with Full Open Bar

  • North America
  • Superb241 reviews4.9

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 2 reviews)

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More

Free Cancellation
Private Tour
Start From $130.00
 
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise Likely to Sell Out

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • North America
  • Superb2 reviews5

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

San Francisco Bay Sailing Cruise

(4.9 of 640 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Private Tour
Start From $72.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • North America
  • Superb640 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Private Tour
    Start From $72.00
 
 

Afternoon Windjammer Cruise Along the Coast of Portland Maine

(4.6 of 186 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
Private Tour
Start From $69.00
 
Afternoon Windjammer Cruise Along the Coast of Portland Maine Likely to Sell Out

Afternoon Windjammer Cruise Along the Coast of Portland Maine

  • North America
  • Superb186 reviews4.6

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to e....

    Free Cancellation
    Private Tour
    Start From $69.00
 
 

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

(4.9 of 460 reviews)

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More

Free Cancellation
Private Tour
Start From $129.00
 
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling Likely to Sell Out

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling

  • North America
  • Superb460 reviews4.9

This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....

    Free Cancellation
    Private Tour
    Start From $129.00
 
 

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

(4.9 of 252 reviews)

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Partic... More

Free Cancellation
Private Tour
Start From $80.00
 
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach Likely to Sell Out

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

  • North America
  • Superb252 reviews4.9

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

(4.7 of 475 reviews)

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More

Free Cancellation
Private Tour
Start From $625.00
 
Private Fishing Trip Likely to Sell Out

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

  • North America
  • Superb475 reviews4.7

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 751 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Private Tour
Start From $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • North America
  • Superb751 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Private Tour
    Start From $141.57
 
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