Top USA Sailing Trips

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 145 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

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

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 25 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

Key West Sunset Sail Aboard Schooner America 2.0

5 star rating: Highly Recommended 8 Reviews

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in great views of Mallory Square, Sunset Pier, Sand Key Light ... 

Location: Key West, Florida
Duration: 2 hours

From USD $91.38

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

Whalewatch Sail Lahaina

4.5 star rating: Recommended 8 Reviews

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 ... 

Location: Lahaina, Hawaii
Duration: 2 hours

From USD $57.01

Schooner Appledore Key West Cruise

5 star rating: Highly Recommended 12 Reviews

Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations ... 

Location: Key West, Florida
Duration: 2 hours

From USD $45.97

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

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 189 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

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

Small-Group San Diego Sunset Sailing Excursion

5 star rating: Highly Recommended 16 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 is limited ... 

Location: San Diego, California
Duration: 3 hours

From USD $88.99

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

Schooner Sunset Sail on Charleston Harbor

5 star rating: Highly Recommended 3 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 $57.24

Private Sailing Charter in Miami

5 star rating: Highly Recommended 8 Reviews

A perfect way to enjoy a day is sailing on a beautiful 40 foot Beneteau sailboat on Biscayne Bay in Miami. The most popular charter is a sunset cruise. ... 

Location: Miami, Florida
Duration: Flexible

From USD $425.00

Java Cat Sail, Kayak and Snorkel Charter

5 star rating: Highly Recommended 2 Reviews

Combine three Key West activities on this eco-adventure by chartered catamaran. Sail to the Key West National Wildlife Refuge for a guided kayaking tour of ... 

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

From USD $123.63

Key West Sail and Snorkel Trip from Miami

3.5 star rating: Worth doing 35 Reviews

Whether you’re an experienced snorkeler, or want to try something new and exciting, Key West is the perfect underwater destination. Your sailing and snorkeling ... 

Location: Miami, Florida
Duration: 12 hours

From USD $119.00

Sunset & Dolphin Watching 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 ... 

Location: Panama City Beach, Florida
Duration: 2 hours

From USD $32.10

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

Private Sailing Trip on Biscayne Bay

5 star rating: Highly Recommended 5 Reviews

Set sail on a private 40-ft sailboat for 4 hours on Biscayne Bay with this charter from Miami. Choose from a morning, afternoon or evening sail and enjoy a ... 

Location: Miami, Florida
Duration: Flexible

From USD $425.00

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

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

5 star rating: Highly Recommended 9 Reviews

Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’s Cup Class racing yacht that challenged in 2003 for ... 

Location: San Francisco, California
Duration: 2 hours 30 minutes

From USD $150.00

Key West Sail and Snorkel Day Trip from Fort Lauderdale

4.5 star rating: Recommended 3 Reviews

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 ocean. ... 

Location: Fort Lauderdale, Florida
Duration: 15 hours

From USD $149.00

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 48 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, allowing you a ... 

Location: San Diego, California
Duration: 3 hours

From USD $88.99

1.5-hour San Francisco Bay Sailing Tour

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 ... 

Location: San Francisco, California
Duration: 90 minutes

From USD $49.00
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