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Top 10 Best North America Sailing Trips

Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 19
 

2.5-hour Guided Sailboat Tour

(5 of 181 reviews)

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More

Start From $118.00
 
2.5-hour Guided Sailboat Tour Likely to Sell Out

2.5-hour Guided Sailboat Tour

  • North America
  • Superb181 reviews5

2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....

    Start From $118.00
 
 

Private Key West Sandbar and Paddle by Boat

(4.9 of 36 reviews)

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More

Free Cancellation
Private Tour
Start From $600.00
 
Private Key West Sandbar and Paddle by Boat Likely to Sell Out

Private Key West Sandbar and Paddle by Boat

  • North America
  • Superb36 reviews4.9

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Private Statue of Liberty Sailing Tour

(5 of 14 reviews)

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, and curated amenities. Fully staffed by USCG licensed captain a... More

Free Cancellation
Private Tour
Start From $860.00
 
Private Statue of Liberty Sailing Tour Likely to Sell Out

Private Statue of Liberty Sailing Tour

  • North America
  • Superb14 reviews5

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with tabl....

    Free Cancellation
    Private Tour
    Start From $860.00
 
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.8 of 16 reviews)

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More

Free Cancellation
Private Tour
Start From $279.95
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests Likely to Sell Out

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • North America
  • Superb16 reviews4.8

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Free Cancellation
    Private Tour
    Start From $279.95
 
 

The Finest Private Yacht Experience in Cabo

(4.6 of 23 reviews)

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some of the best things to do in Cabo such as whale watching and bathing on soothing crystal waters... More

Free Cancellation
Private Tour
Start From $782.32
 
The Finest Private Yacht Experience in Cabo Likely to Sell Out

The Finest Private Yacht Experience in Cabo

  • North America
  • Superb23 reviews4.6

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30....

    Free Cancellation
    Private Tour
    Start From $782.32
 
 

Private Morning Sail, Dolphin and History Tour on Mystique

(5 of 84 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More

Free Cancellation
Private Tour
Start From $525.00
 
Private Morning Sail, Dolphin and History Tour on Mystique Likely to Sell Out

Private Morning Sail, Dolphin and History Tour on Mystique

  • North America
  • Superb84 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private Therapy Sailing Adventure

(4.8 of 42 reviews)

Old Plank Adventures: Sail into a Deep Relaxed State LUXURY THERAPEUTIC SAILING & AQUATIC EXPEDITIONS Experience the enchanting Mediterranean lifestyle along the stunning SoCal Riviera, where the soothing rhythms of the Pacific O... More

Free Cancellation
Private Tour
Start From $400.00
 
Private Therapy Sailing Adventure Likely to Sell Out

Private Therapy Sailing Adventure

  • North America
  • Superb42 reviews4.8

Old Plank Adventures: Sail into a Deep Relaxed State LUXURY THERAPEUTIC SAILING & AQUATIC EXPEDITION....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

Boat ride to the Arch and Snorkel

(5 of 127 reviews)

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a smooth ride through the Sea of ​​Cortez Our guide and captain who are biologists will share interesting and professional infor... More

Free Cancellation
Private Tour
Start From $80.27
 
Boat ride to the Arch and Snorkel Likely to Sell Out

Boat ride to the Arch and Snorkel

  • North America
  • Superb127 reviews5

Check these must-do Cabo activities off your list and spend a proper day in the sun, relaxing on a s....

    Free Cancellation
    Private Tour
    Start From $80.27
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 21 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • North America
  • Superb21 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Deluxe Day Sail in San Diego

(5 of 57 reviews)

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • North America
  • Superb57 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

(5 of 14 reviews)

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to make t... More

Free Cancellation
Private Tour
Start From $1,535.50
 
Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free Likely to Sell Out

Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free

  • North America
  • Superb14 reviews5

Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sur....

    Free Cancellation
    Private Tour
    Start From $1,535.50
 
 

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

(4.8 of 40 reviews)

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Free Cancellation
Private Tour
Start From $57.24
 
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport Likely to Sell Out

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

  • North America
  • Superb40 reviews4.8

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....

    Free Cancellation
    Private Tour
    Start From $57.24
 
 

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

(4.8 of 48 reviews)

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the Captain and passengers for a social sail - or laying on the bow relaxing under the stars, this moonlight sail is ultimate freedom! ... More

Free Cancellation
Private Tour
Start From $73.50
 
JFarwell Moonlight Yacht Cruise from Halifax Waterfront Likely to Sell Out

JFarwell Moonlight Yacht Cruise from Halifax Waterfront

  • North America
  • Superb48 reviews4.8

Experience elevated, laid back nightlife in Halifax. Whether you're gathered at the stern with the C....

    Free Cancellation
    Private Tour
    Start From $73.50
 
 

4th of July Fireworks on Clipper City Tall Ship

(3.7 of 6 reviews)

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive 4.5-hour experience combines gourmet hors d’oeuvres, open bar, themed cocktails, and live music. Sail through New York Harbor a... More

Free Cancellation
Private Tour
Start From $689.16
 
4th of July Fireworks on Clipper City Tall Ship Likely to Sell Out

4th of July Fireworks on Clipper City Tall Ship

  • North America
  • Very Good6 reviews3.7

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive....

    Free Cancellation
    Private Tour
    Start From $689.16
 
 

52' Yacht Rental in Miami Beach with Experienced Captain

(3.6 of 7 reviews)

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +1200 reviews on Google with a 4.9 score guarantee our quality. Our Yacht & Captains are certified & licensed by the USCG, giving you ... More

Free Cancellation
Private Tour
Start From $550.00
 
52' Yacht Rental in Miami Beach with Experienced Captain Likely to Sell Out

52' Yacht Rental in Miami Beach with Experienced Captain

  • North America
  • Very Good7 reviews3.6

Enjoy the day on the water with friends & family in Miami Beach with Dolphin Water Sport. Our +1200....

    Free Cancellation
    Private Tour
    Start From $550.00
 
 

2hr Shared Sailing Experience in Toronto

(5 of 23 reviews)

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More

Free Cancellation
Private Tour
Start From $138.91
 
2hr Shared Sailing Experience in Toronto Likely to Sell Out

2hr Shared Sailing Experience in Toronto

  • North America
  • Superb23 reviews5

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....

    Free Cancellation
    Private Tour
    Start From $138.91
 
 

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

(4.9 of 80 reviews)

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More

Free Cancellation
Private Tour
Start From $73.00
 
Day Sails and Sunset tours on Schooner Surprise in Camden Maine Likely to Sell Out

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

  • North America
  • Superb80 reviews4.9

Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....

    Free Cancellation
    Private Tour
    Start From $73.00
 
 

New York Day Sail to the Statue of Liberty on Schooner America

(4.8 of 66 reviews)

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, elegant and smooth at 105-feet in length with 3600 square... More

Free Cancellation
Private Tour
Start From $60.08
 
New York Day Sail to the Statue of Liberty on Schooner America Likely to Sell Out

New York Day Sail to the Statue of Liberty on Schooner America

  • North America
  • Superb66 reviews4.8

Offering a premium sailing experience, the Schooner America is a tribute to the original America t....

    Free Cancellation
    Private Tour
    Start From $60.08
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.6 of 52 reviews)

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More

Free Cancellation
Private Tour
Start From $34.95
 
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach Likely to Sell Out

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • North America
  • Superb52 reviews4.6

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

Sunset Sail Tour

(4.9 of 90 reviews)

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, engage on this classic 42 ft yacht, that accommodates a 6 passenger maximum for an intimate cruise through the waters of Wrightsvill... More

Free Cancellation
Private Tour
Start From $115.00
 
Sunset Sail Tour Likely to Sell Out

Sunset Sail Tour

  • North America
  • Superb90 reviews4.9

Take a 2.0 hour sailing cruise on a Sparkman and Stephens Sailing Yacht. With your small-group, enga....

    Free Cancellation
    Private Tour
    Start From $115.00
 
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