North America Sailing Trips

North America 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 123 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 37 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

Luxury Sailing and Snorkeling Cruise in Cabo San Lucas

5 star rating: Highly Recommended 32 Reviews

Enjoy a luxury sailing and snorkeling adventure aboard a modern sailing yacht. You will be able to enjoy snorkeling the beautiful Cabo San Lucas bay. This ...  Read more

Location: Cabo San Lucas, Mexico
Duration: 3 hours

From USD $74.00

Los Cabos Luxury Sunset Sail

4.5 star rating: Recommended 29 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

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 $215.00

Luxury Sailing and Snorkeling in the Riviera Maya Including Lunch

5 star rating: Highly Recommended 2 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 ...  Read more

Location: Playa del Carmen, Mexico
Duration: 4 hours

From USD $109.00

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sail boat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous Arch, Land's ...  Read more

Location: Cabo San Lucas, Mexico
Duration: 4 hours 30 minutes

From USD $1,099.00

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

Royal Feast Dinner Sail

5 star rating: Highly Recommended 11 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

Cabo Sunset Sailing Cruise

5 star rating: Highly Recommended 6 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 ...  Read more

Location: Cabo San Lucas, Mexico
Duration: 2 hours

From USD $74.00

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

Catamaran Eco-Adventure with Kayaking Tour and Snorkeling

5 star rating: Highly Recommended 1 Review

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

Isla Mujeres Sailing and Snorkel Cruise from Cancun

4.5 star rating: Recommended 10 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

Oahu Combo Adventure: Bike, Sail and Snorkel

5 star rating: Highly Recommended 36 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

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 12 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 $73.50

Half-Day Sailing Trip to Isla Mujeres from Cancun

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

Location: Cancún, Mexico
Duration: 4 hours 30 minutes

From USD $65.00

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

Isla Mujeres Afternoon Sailing Tour

5 star rating: Highly Recommended 1 Review

Explore the beautiful waters of the Caribbean Sea during this 4-hour cruise aboard a luxury sailing yacht. Depart Cancun in the afternoon and sail along Isla ...  Read more

Location: Cancun, Mexico
Duration: 4 hours

From USD $70.00

Day Sailing on Banderas Bay

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

Location: Puerto Vallarta, Mexico
Duration: 6 hours

From USD $108.99

Isla Mujeres Sailing Adventure from Riviera Maya

Enjoy an amazing sailing journey to Isla Mujeres in a catamaran. You'll go snorkeling and have lots of fun. Explore Isla Mujeres and shop at the souvenir ...  Read more

Location: Playa del Carmen, Mexico
Duration: 10 hours

From USD $90.00

Romantic Sunset Sail

5 star rating: Highly Recommended 2 Reviews

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

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

Caribbean Combo - Sailing, Snorkeling and Sunset

4.5 star rating: Recommended 27 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 reef ...  Read more

Location: Cozumel, Mexico
Duration: 3 hours 30 minutes

From USD $50.99

Private 30 Feet Sailing Experience in Los Cabos

5 star rating: Highly Recommended 1 Review

Enjoy a private sailing boat in Cabo San Lucas that offers snorkeling in tropical waters with colorful friendly fish, smooth and romantic sunset sailing and ...  Read more

Location: Cabo San Lucas, Mexico
Duration: 3 hours

From USD $440.00

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
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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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