USA Sailing Trips

USA Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Catamaran 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 121 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 ...  Read more

Location: Maui, Hawaii
Duration: 5 hours

From USD $117.52

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 36 Reviews

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

Location: Eleele, Hawaii
Duration: 5 hours

From USD $158.94

Royal Feast Dinner Sail

5 star rating: Highly Recommended 10 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

From USD $189.00

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 34 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 $120.00

Small-Group San Diego Sunset Sailing Excursion

5 star rating: Highly Recommended 9 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 ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Catamaran Sail and Snorkel on Oahu

Enjoy a 4-hour sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Snorkel among millions of fish at 2 different ...  Read more

Location: Honolulu, Hawaii
Duration: 5 hours

From USD $139.00

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 175 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

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

5 star rating: Highly Recommended 44 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 ...  Read more

Location: Eleele, Hawaii
Duration: 7 hours

From USD $205.00

Luxury Catamaran Cruise from Oahu

4 star rating: Recommended 28 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 alongside ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours

From USD $69.00

Catamaran Eco-Adventure with Kayaking Tour and Snorkeling

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 ...  Read more

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

From USD $123.63

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 10 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

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 27 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

Half-Day Cruise with Kayaking and Snorkeling

5 star rating: Highly Recommended 11 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 ...  Read more

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

From USD $85.99

Classic Sailboat Afternoon Harbor Tour

Small group sailing tours on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours circle the harbor using traditional sailing methods for ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $107.00

Whalewatch Sail Lahaina

4.5 star rating: Recommended 7 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 ...  Read more

Location: Lahaina, Hawaii
Duration: 2 hours

From USD $57.01

All Inclusive Water Adventure 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

Private Sailing Charter in Miami

5 star rating: Highly Recommended 4 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. ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $425.00

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

5 star rating: Highly Recommended 6 Reviews

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

From USD $140.00

Romantic Sunset Sail

5 star rating: Highly Recommended 1 Review

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

From USD $149.00

Key West Sail and Snorkel Day Trip from Fort Lauderdale

4.5 star rating: Recommended 2 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. ...  Read more

Location: Fort Lauderdale, Florida
Duration: 15 hours

From USD $149.00

Private Sailing Trip on Biscayne Bay with Professional Photographer

5 star rating: Highly Recommended 1 Review

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 ...  Read more

Location: Miami, Florida
Duration: 4 hours

From USD $595.00

Island Adventure Snorkel Kayak and Eco Tour

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 ...  Read more

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

From USD $96.70

Monterey Bay Sailing Cruise With Wine

4.5 star rating: Recommended 5 Reviews

Bring your loved ones, small groups, and even your dog (we are pet friendly) to join us for a memorable 1- or 2-hour sailing cruise within the most bio-dense, ...  Read more

Location: Monterey, California
Duration: 1- or 2-hour

From USD $39.00

90 Min Key West Harbor Sail

This 90 minute sailing trip in Key West is the best way to experience the water with friends and/or family when time is of the essence!  The captain helps ...  Read more

Location: Key West, Florida
Duration: 90 minutes

From USD $255.38

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 37 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
Viewing 1 of 5

Page: 1 | 2 | 3 | 4 | 5 | Next

Only Show: Airboat Tours | Brunch Cruises | Catamaran 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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