Top North America Sailing Trips

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 148 Reviews

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

Location: Maui, Hawaii
Duration: 5 hours

From USD $117.52

Luxury Sailing and Snorkeling Cruise in Cabo San Lucas

5 star rating: Highly Recommended 72 Reviews

Enjoy a luxury shared sailing and snorkeling adventure aboard a modern, luxurious 38 or 42 foot sailing yacht on a 3-hour shared cruise. Light lunch, ice-cold ... 

Location: Cabo San Lucas, Mexico
Duration: 3 hours

From USD $84.00

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 53 Reviews

Sail the majestic Na Pali Coast and witness its beauty with 4,000-foot cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles and ... 

Location: Eleele, Hawaii
Duration: 5 hours

From USD $169.61

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

5 star rating: Highly Recommended 53 Reviews

Sail past the soaring Na Pali sea cliffs on this 7-hour snorkeling adventure, and discover the secrets of the "Forbidden Island" when cruising the ... 

Location: Eleele, Hawaii
Duration: 7 hours

From USD $229.34

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 191 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 ... 

Location: San Francisco, California
Duration: 90 minutes

From USD $45.00

Key West Island T'ing: Sail, Snorkel and Kayak Adventure

5 star rating: Highly Recommended 95 Reviews

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and snorkeling the perfect way to spend a fun day in the sun. ... 

Location: Key West, Florida
Duration: 6 hours

From USD $112.00

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

5 star rating: Highly Recommended 30 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 ... 

Location: Newport, Rhode Island
Duration: 2 hours

From USD $98.00

Los Cabos Luxury Sunset Sail

4.5 star rating: Recommended 53 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 ... 

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

From USD $89.00

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 27 Reviews

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys. You'll cruise out to a ... 

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $86.00

Cabo Sunset Sailing Cruise

5 star rating: Highly Recommended 20 Reviews

Enjoy a 2-hour sunset cruise aboard a luxury sailing yacht. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San ... 

Location: Cabo San Lucas, Mexico
Duration: 2 hours

From USD $84.00

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 31 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 spot ... 

Location: Key West, Florida
Duration: 4 hours

From USD $95.59

Sunset & Dolphin Catamaran Cruise in Panama City Beach

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the  Island Time sailing catamaran which departs from Treasure Island Marina in Panama City ... 

Location: Panama City Beach, Florida
Duration: 2 hours

From USD $32.10

Island Adventure Snorkel Kayak and Tour

4 star rating: Recommended 6 Reviews

Discover a different side of Key West as you explore a secluded paradise in the Florida Keys backcountry on this Island Adventure. Tucked away between mangrove ... 

Location: Key West, Florida
Duration: 4 hours 30 minutes

From USD $106.37

New York City Sunset Sail

5 star rating: Highly Recommended 6 Reviews

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as ... 

Location: New York City, New York
Duration: 2 hours

From USD $55.00

Schooner Sunset Sail on Charleston Harbor

5 star rating: Highly Recommended 4 Reviews

Experience sunset on Charleston Harbor with a 2-hour cruise on a classic 84-foot tall ship. Witness a kaleidoscope of colors over one of the oldest cities in ... 

Location: Charleston, South Carolina
Duration: 2 hours

From USD $55.12

All Inclusive Water Adventure Excursion in Key West

5 star rating: Highly Recommended 9 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 ... 

Location: Key West, Florida
Duration: 6 hours 30 minutes

From USD $129.00

2-Hour Sunset Sail on the San Francisco Bay

5 star rating: Highly Recommended 7 Reviews

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous ... 

Location: San Francisco, California
Duration: 2 hours

From USD $65.00

Statue of Liberty Tall Ship Sailing Cruise

5 star rating: Highly Recommended 124 Reviews

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day. You will enjoy breathtaking views ... 

Location: New York City, New York
Duration: Varies

From USD $38.25

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 ... 

Location: Hanalei, Hawaii
Duration: 4 hours

From USD $212.27

Half-Day Sailing Trip to Isla Mujeres from Cancun

5 star rating: Highly Recommended 32 Reviews

Enjoy a half-day sailing trip in the Caribbean Sea. Stop to snorkel in the beautiful waters and enjoy snacks on board. Spend free time on the beautiful Isla ... 

Location: Cancún, Mexico
Duration: 4 hours 30 minutes

From USD $65.99

Private Sail from Cabo with Snorkeling, SUP, and Semi-Private Beach

4 star rating: Recommended 2 Reviews

PRIVATE DAY AND SUNSET TOURS ONLY This 4-hour private cruise for up to 12 passengers is like having your own boat and crew for half a day. Leave from ... 

Location: Cabo San Lucas, Mexico
Duration: 4 hours

From USD $640.00

Luxury Sailing and Snorkeling in the Riviera Maya, Including Lunch

4.5 star rating: Recommended 8 Reviews

This is Riviera Maya's ultimate day-sailing adventure. Aboard a luxurious sailing catamaran, you'll explore some of the most beautiful offshore locations along ... 

Location: Playa del Carmen, Mexico
Duration: 4 hours

From USD $109.00

America's Cup Afternoon Sail

4 star rating: Recommended 1 Review

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis ... 

Location: Hilton Head Island, South Carolina
Duration: 90 minutes

From USD $34.95

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 41 Reviews

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

Location: Waikiki, Oahu
Duration: 5 hours 30 minutes

From USD $120.00

Coastal Sailing Adventure in Wrightsville Beach

Take a 2.5 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 ... 

Location: Wrightsville Beach, North Carolina
Duration: 2 hours

From USD $80.00
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