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Top 10 Best USA Sailing Trips

Found 446 Sailing Trips activities in USA. Sort by Popularity. - Page 9
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 25 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)

Private Catamaran Charter in Waikiki (1-6 Guests)

  • USA
  • Superb25 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
 
 

Sunset Sail Cruise in Key West

(4.9 of 295 reviews)

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Free Cancellation
Private Tour
Start From $95.00
 
Sunset Sail Cruise in Key West

Sunset Sail Cruise in Key West

  • USA
  • Superb295 reviews4.9

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Private Sailing Charter: Up to 24 Passengers

(5 of 1 review)

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco Bay. While our boats are coast guard licensed for 34 passengers, we are limiting... More

Free Cancellation
Private Tour
Start From $1,425.00
 
Private Sailing Charter: Up to 24 Passengers

Private Sailing Charter: Up to 24 Passengers

  • USA
  • Superb1 review5

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a ....

    Free Cancellation
    Private Tour
    Start From $1,425.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 970 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Private Tour
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • USA
  • Superb970 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Private Tour
    Start From $84.99
 
 

Sailing Charters in Wilmington

(5 of 204 reviews)

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for ... More

Free Cancellation
Private Tour
Start From $89.48
 
Sailing Charters in Wilmington

Sailing Charters in Wilmington

  • USA
  • Superb204 reviews5

After a successful first three seasons I am happy to be here for a fourth season!!! Sail in style on....

    Free Cancellation
    Private Tour
    Start From $89.48
 
 

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(4.9 of 1,002 reviews)

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Free Cancellation
Private Tour
Start From $108.91
 
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

  • USA
  • Superb1,002 reviews4.9

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....

    Free Cancellation
    Private Tour
    Start From $108.91
 
 

Public Sunset Picnic Boat Cruise on Lake Champlain

(5 of 4 reviews)

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food and drinks, all while enjoying stunning waterfront views and the company of up... More

Free Cancellation
Private Tour
Start From $95.00
 
Public Sunset Picnic Boat Cruise on Lake Champlain

Public Sunset Picnic Boat Cruise on Lake Champlain

  • USA
  • Superb4 reviews5

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This u....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui

  • USA
  • Superb63 reviews4.6

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Public Sunset Sailing Cruise on Lake Champlain

(5 of 14 reviews)

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendship Sloop. This two-hour cruise offers an unparalleled view of the Adirondack Mountains as you relax and enjoy the charming atmosphe... More

Free Cancellation
Private Tour
Start From $95.00
 
Public Sunset Sailing Cruise on Lake Champlain

Public Sunset Sailing Cruise on Lake Champlain

  • USA
  • Superb14 reviews5

Witness the captivating Burlington sunset while sailing across Lake Champlain on a classic Friendshi....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 129 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail

Polynesian Canoe Sunset Sail

  • USA
  • Superb129 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 59 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Private Tour
Start From $59.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • USA
  • Superb59 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Private Tour
    Start From $59.95
 
 

Wrightsville Beach Sunset Cocktail Sail

(5 of 20 reviews)

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More

Free Cancellation
Private Tour
Start From $150.00
 
Wrightsville Beach Sunset Cocktail Sail

Wrightsville Beach Sunset Cocktail Sail

  • USA
  • Superb20 reviews5

Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....

    Free Cancellation
    Private Tour
    Start From $150.00
 
 

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

(4.5 of 73 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

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach

  • USA
  • Exellent73 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $34.95
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 404 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

1.5-Hour San Francisco Bay Sailing Tour

  • USA
  • Superb404 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
 
 

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

(4.9 of 77 reviews)

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Free Cancellation
Private Tour
Start From $114.00
 
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise

  • USA
  • Superb77 reviews4.9

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....

    Free Cancellation
    Private Tour
    Start From $114.00
 
 

Luxury Camden Sailing Experience

(4.9 of 15 reviews)

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor... More

Free Cancellation
Private Tour
Start From $125.00
 
Luxury Camden Sailing Experience

Luxury Camden Sailing Experience

  • USA
  • Superb15 reviews4.9

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Experience Oceanside Sailing with Whales and dolphins!

(5 of 18 reviews)

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and most comfortable sailboats in the Oceanside harbor. We cater to guests from many of the five star hotels in the area. We serve an up... More

Free Cancellation
Private Tour
Start From $200.00
 
Experience Oceanside Sailing with Whales and dolphins!

Experience Oceanside Sailing with Whales and dolphins!

  • USA
  • Superb18 reviews5

We set sail on a 45 foot, teak filled sailing yacht- Named, Song of David. One of the largest and mo....

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Private Sunset Sail in San Diego Up to 6 guests

(5 of 73 reviews)

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water. Relax while our licensed captain handles... More

Free Cancellation
Private Tour
Start From $297.50
 
Private Sunset Sail in San Diego Up to 6 guests

Private Sunset Sail in San Diego Up to 6 guests

  • USA
  • Superb73 reviews5

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....

    Free Cancellation
    Private Tour
    Start From $297.50
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 103 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • USA
  • Superb103 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 323 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Private Tour
Start From $148.00
 
4-Hour Fort Lauderdale Sailing Charter Likely to Sell Out

4-Hour Fort Lauderdale Sailing Charter

  • USA
  • Superb323 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $148.00
 
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