North America Sailing Trips

North America Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Glass Bottom Boat Tours | Gondola Cruises | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 104 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

From USD $117.52

San Francisco Bay Sunset Catamaran Cruise

5 star rating: Highly Recommended 265 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: 90 minutes

From USD $55.00

Statue of Liberty Tall Ship Sailing Cruise

4.5 star rating: Recommended 106 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 will ...  Read more

Location: New York City, New York
Duration: Varies

From USD $34.99

2 Hour Newport Harbor Sail Aboard Former America's Cup Yacht

5 star rating: Highly Recommended 18 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

From USD $79.00

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 166 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: 90 minutes

From USD $40.00

Luxury Sailing and Snorkeling Cruise in Cabo San Lucas

5 star rating: Highly Recommended 17 Reviews

Enjoy a luxury sailing and snorkeling adventure aboard an inviting and modern sailing yacht. You will enjoy snacks, unlimited drinks and have chance to snorkel ...  Read more

Location: Cabo San Lucas, Mexico
Duration: 3 hours

From USD $74.00

Na Pali and Ni'ihau The Forbidden Island Kauai Snorkel Cruise

5 star rating: Highly Recommended 44 Reviews

Discover the secrets of Hawaii’s legendary Forbidden Island of Niihau and the historical Na Pali Coast in one amazing day. Voyage in style and comfort ...  Read more

Location: Eleele, Hawaii
Duration: 7 hours

From USD $218.67

Los Cabos Luxury Sunset Sail

4.5 star rating: Recommended 24 Reviews

Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes ...  Read more

Location: Los Cabos, Mexico
Duration: 2 hours 30 minutes

From USD $84.99

Royal Feast Dinner Sail

5 star rating: Highly Recommended 8 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 ...  Read more

Location: Maalaea, Hawaii
Duration: 2 hours 30 minutes

From USD $179.00

Riviera Maya Catamaran Adventure

5 star rating: Highly Recommended 24 Reviews

Imagine cruising along the Riviera Maya on a luxury 45 foot (14 meter) catamaran, snorkeling in the crystal clear waters, and lazing in the sun while enjoying ...  Read more

Location: Playa del Carmen, Mexico
Duration: 4 hours

From USD $109.99

Morning and Afternoon Half Day Cruise

5 star rating: Highly Recommended 10 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

From USD $85.99

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 36 Reviews

Set sail from San Diego on this small-group sailing tour! This three-hour adventure on a Catalina-style sailboat is limited to just six people, ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Premium Full Day Excursion in Key West

5 star rating: Highly Recommended 3 Reviews

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

From USD $118.25

Na Pali Snorkel Adventure

We invite you to climb aboard their Kauai-built rigid-hull inflatable “rafts” that will get you to the Na Pali Coast in record time! As we travel down the ...  Read more

Location: Hanalei, Hawaii
Duration: 4 hours

From USD $201.61

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 33 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

From USD $110.00

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 26 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

From USD $95.59

Sunset Sail

5 star rating: Highly Recommended 3 Reviews

Enjoy a 2-hour sailing adventure. Part of the reason Maui has been voted the world’s #1 island year after year is due to the breathtaking sunsets. Sure you ...  Read more

Location: Kaanapali, Hawaii
Duration: 2 hours

From USD $75.88

Luxury Catamaran Cruise from Oahu

4 star rating: Recommended 27 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 ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours

From USD $69.00

Isla Mujeres Sailing and Snorkel Cruise from Cancun

4.5 star rating: Recommended 7 Reviews

Escape Cancun for the day and sail towards Isla Mujeres. Enjoy a relaxing ride, indulge in an open bar and buffet lunch, snorkel in the crystal-clear ...  Read more

Location: Cancun, Mexico
Duration: 7 hours

From USD $75.00

Big Island Snorkel Cruise Along Kohala Coast

5 star rating: Highly Recommended 16 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 ...  Read more

Location: Waikoloa Village, Hawaii
Duration: 3 hours 30 minutes

From USD $146.99

Lakeside Architecture Sail

4 star rating: Recommended 6 Reviews

Join us for a 75 minute sail on Lake Michigan while we explore Chicago's architectural majesty.

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60

Private Tour: Sport Fishing in Cabo San Lucas

4 star rating: Recommended 2 Reviews

Enjoy a private sport fishing tour in Cabo San Lucas. You will be able to do both shore and deep sea fishing and catch some of the following: d orado, ...  Read more

Location: Cabo San Lucas, Mexico
Duration: Flexible

From USD $500.00

Small-Group San Diego Sunset Sailing Excursion

5 star rating: Highly Recommended 4 Reviews

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina-style sailboat ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Teralani Sunset Maui Cocktail Sail

4 star rating: Recommended 8 Reviews

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

Location: Maui, Hawaii
Duration: 2 hours

From USD $71.50

Craft Beer Sailing Cruise in New York City

4.5 star rating: Recommended 9 Reviews

Step aboard one of the largest sailing ships in the US and cruise along New York Harbor while tasting some of New York’s best craft beers. Sip crisp ales and ...  Read more

Location: New York City, New York
Duration: 1-hour and 45-minutes

From USD $74.99
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Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Glass Bottom Boat Tours | Gondola Cruises | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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