USA Sailing Trips

USA Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 75 Reviews

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, ...  Read more

Location: Maui, Hawaii
Duration: 5 hours (approx.)

From USD $109.99

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 33 Reviews

Come aboard this Na Pali snorkeling trip where lush valleys and cliffs await. As you head to your destination, your crew will entertain you with stories of ...  Read more

Location: Kauai, Hawaii
Duration: 5 hours 30 minutes (approx.)

From USD $139.99

Royal Feast Dinner Sail

5 star rating: Highly Recommended 5 Reviews

Come aboard Alii Nui, a luxurious sailing catamaran, and experience the Royal Feast Sunset Dinner Sail. Alii Nui and her expert crew treat you to a truly ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours 30 minutes (approx.)

From USD $179.00

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 20 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll ...  Read more

Location: Key West, Florida
Duration: 4 hours (approx.)

From USD $95.59

Whalewatch Sail Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum ...  Read more

Location: Lahaina, Hawaii
Duration: 2 hours (approx.)

From USD $56.51

Big Island Snorkel Cruise Along Kohala Coast

5 star rating: Highly Recommended 14 Reviews

Discover the best snorkeling off the Kohala Coast on this 3.5-hour Big Island snorkel cruise. Aboard a comfortable catamaran, admire Hawaii's postcard-worthy ...  Read more

Location: Waikoloa Village, Hawaii
Duration: 3 hours 30 minutes (approx.)

From USD $146.99

Luxury Catamaran Cruise from Oahu

4 star rating: Recommended 24 Reviews

Take a 2-hour sail through the waters of Hawaii on one of the fastest & most luxurious catamarans in Honolulu. Cruise the coast and open water ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours (approx.)

From USD $69.00

San Francisco Bay Sunset Catamaran Cruise

5 star rating: Highly Recommended 236 Reviews

Enjoy the serene San Francisco Bay at sunset on this evening with the Sunset Cruise aboard a luxurious catamaran. Sail by Alcatraz Island, under the Golden ...  Read more

Location: San Francisco, California
Duration: 1 hour 30 minutes (approx.)

From USD $55.00

Luxury Yacht Cruise of New York Harbor

5 star rating: Highly Recommended 4 Reviews

Take an intimate luxury cruise of New York Harbor and enjoy views of the Statue of Liberty, Ellis Island, Governor's Island, the Brooklyn Bridge, Castle ...  Read more

Location: New York, New York
Duration: 2 hours (approx.)

From USD $68.00

Small-Group San Diego Sailing Excursion

5 star rating: Highly Recommended 26 Reviews

Set sail from San Diego on this small-group sailing tour! Choose from a daytime sail in San Diego Harbor or a sunset sail on the open ocean. This three-hour ...  Read more

Location: San Diego, California
Duration: 3 hours (approx.)

From USD $84.99

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 7 Reviews

This relaxing Maui cocktail cruise takes you between the islands of Lanai and Molokai, for a stunning picture-perfect sunset. Unwind with your favorite ...  Read more

Location: Maui, Hawaii
Duration: 2 hours (approx.)

From USD $71.50

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 27 Reviews

Bike, sail & snorkel on Oahu on this exhilarating combo tour! Explore lush rainforest and sparkling ocean all in one day! Roundtrip Waikiki hotel ...  Read more

Location: Waikiki, Oahu
Duration: 5 hours 30 minutes (approx.)

From USD $110.00

Statue of Liberty Tall Ship Sailing Cruise

4.5 star rating: Recommended 85 Reviews

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day, at twilight or by night. You ...  Read more

Location: New York City, New York
Duration: Varies

From USD $35.09

Key West Sail and Snorkel Day Trip from Fort Lauderdale

Whether you’re an experienced snorkeler or you want to try something new and exciting, you’ll find Key West to be the perfect destination for fun in the ...  Read more

Location: Fort Lauderdale, Florida
Duration: 15 hours (approx.)

From USD $164.99

America's Cup Sailing Adventure on San Francisco Bay: America's Cup Sunset Sail

USA 76 is a unique opportunity to participate in the sailing of an International America’s Cup Class yacht. Sail the official race course from the 2013 ...  Read more

Location: San Francisco, California
Duration: 2 hours 30 minutes (approx.)

From USD $170.00

Morning and Afternoon Half Day Cruise

5 star rating: Highly Recommended 4 Reviews

Don't miss one of the top things to do in Key West! Come enjoy the Florida Keys on this kayaking, snorkeling and sailing adventure. You will cruise out to the ...  Read more

Location: Key West, Florida
Duration: 4 hours 30 minutes (approx.)

From USD $85.99

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 145 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 ...  Read more

Location: San Francisco, California
Duration: 1 hour 30 minutes (approx.)

From USD $40.00

Premium Full Day Excursion in Key West

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing! You will head way back into the Key ...  Read more

Location: Key West, Florida
Duration: 6 hours 30 minutes (approx.)

From USD $118.25

Romantic Sunset Sail

Come aboard Alii Nui and get the Royal Treatment. Alii Nui and her expert crew will treat you to a truly memorable evening. Heavy appetizers and a full, open ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours (approx.)

From USD $139.00

Private Sailing Trip on Biscayne Bay with Professional Photographer

Set sail on a private 40-ft sailboat on Biscayne Bay with this charter from Miami. Choose from an afternoon or evening sail and observe the beautiful sunset ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $639.99

San Diego Half-Day Marine Wildlife Tour with Lunch

Join this guided whale watch tour on a classically restored sailing yacht. Come see marine wildlife in their natural habitat. This is a small group tour, ...  Read more

Location: San Diego, California
Duration: 4 hours (approx.)

From USD $172.84

Newport Harbor Sail Aboard Former America's Cup Yacht

5 star rating: Highly Recommended 11 Reviews

Sail aboard an America's Cup 12-meter yacht for the ultimate Newport nautical experience! This 2-hour Newport Harbor cruise lets you ride in a yacht used in ...  Read more

Location: Newport, Rhode Island
Duration: 2 hours (approx.)

From USD $78.00

Catamaran Sailing Lesson or Boat Rental in Biscayne Bay

4 star rating: Recommended 2 Reviews

Sailing on a sleek catamaran is the best way to explore Miami’s beautiful Biscayne Bay. Whether you want to learn how to sail or want to rent a boat to ...  Read more

Location: Miami, Florida
Duration: Varies

From USD $16.29

Monterey Bay Sunset Appetizer Cruise

Our most-popular and romantic cruise with or without hors d’oeuvres. The appetizer option includes two hors d’oeuvres beginning with brie cheese, sliced pear, ...  Read more

Location: Monterey, California
Duration: 2 hours (approx.)

From USD $89.00

Sail With the Whales from Anaeho'omalu Bay

This tour combines real coastal sailing on a legendary catamaran with the biggest party guests of all...the Humpback Whales! This tour also includes ...  Read more

Location: Waikoloa Village, Hawaii
Duration: 2 hours (approx.)

From USD $99.00
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Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Lunch Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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