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Top 10 Best North America Sailing Trips

Found 755 Sailing Trips activities in North America. Sort by Popularity. - Page 8
 

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

(5 of 36 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More

Free Cancellation
Start From $89.00
 
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise Likely to Sell Out

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

  • North America
  • Superb36 reviews5

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....

    Free Cancellation
    Start From $89.00
 
 

New York City Sunset Sail to the Statue of Liberty

(4.8 of 68 reviews)

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More

Free Cancellation
Start From $90.12
 
New York City Sunset Sail to the Statue of Liberty Likely to Sell Out

New York City Sunset Sail to the Statue of Liberty

  • North America
  • Superb68 reviews4.8

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....

    Free Cancellation
    Start From $90.12
 
 

Sightseeing Day Sail around Boston Harbor

(4.8 of 542 reviews)

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More

Free Cancellation
Start From $66.54
 
Sightseeing Day Sail around Boston Harbor Likely to Sell Out

Sightseeing Day Sail around Boston Harbor

  • North America
  • Superb542 reviews4.8

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....

    Free Cancellation
    Start From $66.54
 
 

Isla Mujeres, Cancún Private Sunset Trip

(5 of 81 reviews)

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the sunset and experience the moment. We are here to bring you the the quality service you so rightly deserve. Our adored crew ensure... More

Free Cancellation
Private Tour
Start From $450.00
 
Isla Mujeres, Cancún Private Sunset Trip Likely to Sell Out

Isla Mujeres, Cancún Private Sunset Trip

  • North America
  • Superb81 reviews5

Our tours are suited to your needs, as we want you to enjoy yourself, to simply let go, to watch the....

    Free Cancellation
    Private Tour
    Start From $450.00
 
 

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

(5 of 33 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated ... More

Free Cancellation
Private Tour
Start From $575.00
 
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique Likely to Sell Out

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

  • North America
  • Superb33 reviews5

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

    Free Cancellation
    Private Tour
    Start From $575.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 398 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Private Tour
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • North America
  • Superb398 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 146 reviews)

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Free Cancellation
Private Tour
Start From $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • North America
  • Superb146 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 62 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • North America
  • Superb62 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.6 of 37 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Free Cancellation
Private Tour
Start From $109.95
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • North America
  • Superb37 reviews4.6

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 50 reviews)

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More

Free Cancellation
Private Tour
Start From $1,413.61
 
Private Oahu Sunset Charter with Tasting and Drinks Likely to Sell Out

Private Oahu Sunset Charter with Tasting and Drinks

  • North America
  • Superb50 reviews5

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....

    Free Cancellation
    Private Tour
    Start From $1,413.61
 
 

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

(5 of 199 reviews)

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More

Free Cancellation
Private Tour
Start From $800.00
 
Private Sailboat tour in Cabo San Lucas with Papillon Yachts Likely to Sell Out

Private Sailboat tour in Cabo San Lucas with Papillon Yachts

  • North America
  • Superb199 reviews5

Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....

    Free Cancellation
    Private Tour
    Start From $800.00
 
 

Fort Lauderdale Sailing Charter

(5 of 391 reviews)

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More

Free Cancellation
Private Tour
Start From $150.00
 
Fort Lauderdale Sailing Charter Likely to Sell Out

Fort Lauderdale Sailing Charter

  • North America
  • Superb391 reviews5

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Classic Key West Schooner Sunset Sail with Full Open Bar

(4.9 of 230 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
  • Superb230 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
 
 

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

(4.9 of 230 reviews)

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More

Free Cancellation
Private Tour
Start From $120.00
 
Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams Likely to Sell Out

Snorkel, Swim & Dolphin Sightseeing Sail Aboard the Daydreams

  • North America
  • Superb230 reviews4.9

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

(4.9 of 51 reviews)

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More

Free Cancellation
Private Tour
Start From $64.00
 
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms Likely to Sell Out

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

  • North America
  • Superb51 reviews4.9

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....

    Free Cancellation
    Private Tour
    Start From $64.00
 
 

Lāna'i Coast Snorkel and Sail

(5 of 30 reviews)

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More

Free Cancellation
Private Tour
Start From $216.22
 
Lāna'i Coast Snorkel and Sail Likely to Sell Out

Lāna'i Coast Snorkel and Sail

  • North America
  • Superb30 reviews5

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....

    Free Cancellation
    Private Tour
    Start From $216.22
 
 

Cabo San Lucas 34ft Private Yacht with Drinks Included

(5 of 30 reviews)

Set sail from Cabo San Lucas Marina on a private 34ft Formula yacht for an unforgettable 2-hour coastal cruise. As you glide past iconic landmarks like El Arco and Lover’s Beach, the professional captain and crew ensure a smooth... More

Free Cancellation
Private Tour
Start From $850.00
 
Cabo San Lucas 34ft Private Yacht with Drinks Included Likely to Sell Out

Cabo San Lucas 34ft Private Yacht with Drinks Included

  • North America
  • Superb30 reviews5

Set sail from Cabo San Lucas Marina on a private 34ft Formula yacht for an unforgettable 2-hour coas....

    Free Cancellation
    Private Tour
    Start From $850.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 37 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb37 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $192.17
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 10 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • North America
  • Superb10 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

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 $149.40
 
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 $149.40
 
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