Top North America Sailing Trips

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 142 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 51 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

Luxury Sailing and Snorkeling Cruise in Cabo San Lucas

5 star rating: Highly Recommended 70 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

Los Cabos Luxury Sunset Sail

4.5 star rating: Recommended 49 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

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

5 star rating: Highly Recommended 51 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 23 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

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

Luxury Sailing and Snorkeling in the Riviera Maya Including Lunch

4.5 star rating: Recommended 7 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

Cabo Sunset Sailing Cruise

5 star rating: Highly Recommended 19 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

Half-Day Sailing Trip to Isla Mujeres from Cancun

5 star rating: Highly Recommended 23 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 Customizable Sailing Tour in Cancun

5 star rating: Highly Recommended 13 Reviews

Enjoy a private sailing tour for just you and your party aboard a 44-feet sailboat Bavaria which offers the opportunity to visit wonderful places that can only ... 

Location: Cancun, Mexico
Duration: Flexible

From USD $515.00

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

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

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

5 star rating: Highly Recommended 1 Review

This 4-hour private cruise for up to 12 passengers is like having your own boat and crew for half a day. Leave from Cabo San Lucas marina in the morning and ... 

Location: Cabo San Lucas, Mexico
Duration: 4 hours

From USD $500.00

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

Schooner Appledore Key West Cruise

5 star rating: Highly Recommended 10 Reviews

Enjoy a day sail or sunset sail around Key West on the Appledore II. Stretch out and relax to the sounds of internationally renowned chanteyman Geoff Kaufman, ... 

Location: Key West, Florida
Duration: 2 hours

From USD $39.00

Private Boat Charter Tour in Cozumel

5 star rating: Highly Recommended 1 Review

Enjoy a 4 to 4 1/2 hour private boat excursion tailored for just you with your friends and family and enjoy an extraordinary day in Cozumel. Climb aboard the ... 

Location: Cozumel, Mexico
Duration: 4 hours

From USD $475.00

Caribbean Combo - Sailing, Snorkeling and Sunset

4.5 star rating: Recommended 30 Reviews

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

Location: Cozumel, Mexico
Duration: 3 hours 30 minutes

From USD $51.00

Sunset Whale Watch

5 star rating: Highly Recommended 4 Reviews

Enjoy a 2-hour sailing adventure. Part of the reason Maui has been voted the world’s #1 island year after year is due to the breathtaking sunsets and the ... 

Location: Kaanapali, Hawaii
Duration: 2 hours

From USD $78.23

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

Teralani Sunset Maui Cocktail Sail

4.5 star rating: Recommended 17 Reviews

This relaxing Maui cocktail cruise takes you between the islands of Lanai and Molokai, for a stunning picture-perfect sunset. Unwind with your favorite ... 

Location: Maui, Hawaii
Duration: 2 hours

From USD $73.50

Day Sailing on Banderas Bay

4.5 star rating: Recommended 12 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 ... 

Location: Puerto Vallarta, Mexico
Duration: 6 hours

From USD $108.99

Aloha Sunset Sail

Enjoy a beautiful sunset like a kama’aina (local resident), as you set sail along Kauai’s sunny south shore listening to the classic mellow sounds of Hawaii’s ... 

Location: Eleele, Hawaii
Duration: 2 hours

From USD $90.67

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 ... 

Location: Cabo San Lucas, Mexico
Duration: 4 hours

From USD $1,399.00

Sail Trip to Isla Mujeres from Playa del Carmen

4.5 star rating: Recommended 4 Reviews

Discover a beautiful island where you will be able to take walks along the beach and snorkel in the clear waters.

Location: Playa del Carmen, Mexico
Duration: 12 hours

From USD $80.00
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