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 89 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 245 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

Cancun Combo: Chichen Itza Tour plus Isla Mujeres Dolphin Encounter or Catamaran Sail with Snorkeling

4 star rating: Recommended 24 Reviews

Experience the best of the Yucatan on a Cancun combo tour including Chichen Itza and your choice of a Dolphin Encounter, Dolphin Adventure Swim or catamaran ...  Read more

Location: Cancun, Mexico
Duration: 2 days

From USD $135.99

Royal Feast Dinner Sail

5 star rating: Highly Recommended 6 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

Big Island Snorkel Cruise Along Kohala Coast

5 star rating: Highly Recommended 15 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

Los Cabos Luxury Sunset Sail

5 star rating: Highly Recommended 19 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

Private Boat Tour in Playa del Carmen Including Snorkeling

Enjoy a private boat tour in Playa del Carmen tailored for just you and your group. Sail the Caribbean sea and go snorkeling at a reef, admiring wonderful ...  Read more

Location: Playa del Carmen, Mexico
Duration: Flexible

From USD $700.00

Riviera Maya Catamaran Adventure

5 star rating: Highly Recommended 21 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 ...  Read more

Location: Playa del Carmen, Mexico
Duration: 4 hours

From USD $109.99

Champagne Brunch Sail in New York City

5 star rating: Highly Recommended 5 Reviews

Indulge in a classic New York brunch with a twist. Nosh on a plentiful buffet and get your fill on tea and coffee service as well as an open Prosecco bar. ...  Read more

Location: New York, New York
Duration: 2 hours

From USD $94.99

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 29 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

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 ...  Read more

Location: Waikiki, Oahu
Duration: 2 hours

From USD $69.00

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 147 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

Sail Away to Isla Mujeres in Cancun

4 star rating: Recommended 3 Reviews

Sail away through Caribbean waters, with the best crew in Cancun, ¨La Lupita¨, where you can enjoy the best personalized service for ...  Read more

Location: Cancún, Mexico
Duration: 7 hours

From USD $50.00

Catamaran Isla Mujeres Tour

Don´t miss the chance of spending a wonderful day sailing through the Caribbean Sea and to Isla Mujeres in our catamarans. Enjoy the sun and the breeze ...  Read more

Location: Cancún, Mexico
Duration: 7 hours

From USD $82.00

Luxury Sailing and Snorkeling Cruise in Cabo San Lucas

5 star rating: Highly Recommended 12 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

Statue of Liberty Tall Ship Sailing Cruise

4.5 star rating: Recommended 88 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 $29.50

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 23 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

Caribbean Combo - Sailing, Snorkeling and Sunset

4.5 star rating: Recommended 24 Reviews

This Caribbean tour is a combination of all the must do activities in Cozumel! Start with snorkeling the crystal clear turquoise waters at the famous ...  Read more

Location: Cozumel, Mexico
Duration: 3 hours 30 minutes

From USD $47.99

Americas Cup Sailing Racing Experience on Lake Michigan

Sail in beautiful Lake Michigan in between The Shedd Aquarium and Navy Pier, aboard the famous America’s Cupyachts: ‘Stars and Stripes’ and ‘Abracadabra.’  ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $150.00

Morning and Afternoon Half Day Cruise

5 star rating: Highly Recommended 8 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

Lets Go Sailing Today

5 star rating: Highly Recommended 1 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 ...  Read more

Location: Miami, Florida
Duration: Flexible

From USD $425.00

Private Sailing Trip on Biscayne Bay with Professional Photographer

5 star rating: Highly Recommended 1 Reviews

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 $425.00

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 29 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 $84.99

Day Sailing on Banderas Bay

5 star rating: Highly Recommended 10 Reviews

This wonderful sailing tour is the perfect way to spend a day in Puerto Vallarta! Relax on board, sail into the wind, swim in crystal clear blue ...  Read more

Location: Puerto Vallarta, Mexico
Duration: 6 hours

From USD $98.99

Day Sail in Key West by Private Charter

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the ...  Read more

Location: Key West, Florida
Duration: Flexible

From USD $294.99
Viewing 1 of 5

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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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