Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

Q: Got any more North America trip ideas?

We sure do. Check out our curated lists of hand-picked North America Tours. Top 10 North America 2026 Senior-friendly tours North America The best tours and activities for culture lovers in North America Top Day Trips from North America Things to do in North America this summer View all North America Trip Ideas →

Q: What are the most popular styles of Tours and Activities in North America?

Based on our sales data over the past year, the most popular styles of tours and activities in North America are: North America Luxury & Special Occasions North America Luxury Tours North America Tours & Sightseeing North America Kid Friendly North America Cruises, Sailing & Water Tours View all tour styles in North America →

Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of …More

Boston, USA

4.8 (654)

Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...

90 to 120 minutes Free Cancellation

4.8 (654)

from
$54

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first …More

Cozumel, Mexico

4.5 (4)

Crystal Boat Tour with Snorkeling and Drinks in Cozumel

Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first...

1 hour 30 minutes Free Cancellation

4.5 (4)

from
$55

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

4.9 (1,015)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation

4.9 (1,015)

from
$55

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by …More

Hilton Head Island, USA

4.7 (564)

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutes Free Cancellation

4.7 (564)

from
$55

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical …More

Bacalar, Mexico

4.9 (111)

Catamaran Adventure: Sailing and Swimming in the Bacalar Lagoon

Bacalar is the perfect place to live this experience. This wonderful region has the calmest waters in the Caribbean and has the most fascinating tropical...

3 hours Free Cancellation

4.9 (111)

from
$55

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can …More

Newport, USA

5.0 (4)

Scenic Day Sails in Newport Harbor and Narragansett Bay Aquidneck

Set sail aboard Aquidneck on a memorable journey through Newport Harbor and Narragansett Bay, where the winds are perfect for an afternoon adventure. Guests can...

1 hour 40 minutes Free Cancellation

5.0 (4)

from
$55

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or …More

Isla Mujeres, Mexico

4.8 (3,830)

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or...

5 hours 30 minutes Free Cancellation

4.8 (3,830)

from
$55

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

4.9 (55)

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation

4.9 (55)

from
$55

Jungle Tour In Cancun, drive a speedboat through the lagoon

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its …More

Cancun, Mexico

4.3 (3)

Jungle Tour In Cancun, drive a speedboat through the lagoon

Welcome to the most enigmatic activity in Cancun, the famous jungle tour, this is the best and quick way to know Cancun and all its...

3 hours Hotel pickup offered Free Cancellation

4.3 (3)

from
$55

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall …More

Charleston, USA

4.6 (858)

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...

1 hour 30 minutes Free Cancellation

4.6 (858)

from
$56

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to …More

Mount Pleasant, USA

4.7 (11)

Daytime Charleston Harbor Sail - Lux Catamatan w/Bar

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to...

2 hours Free Cancellation

4.7 (11)

from
$56

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana …More

Cocoa Beach, USA

4.9 (206)

Sunset Catamaran Sail in Cocoa Beach

Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana...

2 hours Free Cancellation

4.9 (206)

from
$56

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world …More

Punta Sam, Mexico

4.3 (10)

Snorkeling Adventure in Isla Mujeres

Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world...

8 to 9 hours Hotel pickup offered Free Cancellation

4.3 (10)

from
$59

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a …More

Punta Sam, Mexico

3.9 (35)

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar

Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a...

8 hours Hotel pickup offered Free Cancellation

3.9 (35)

from
$59

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two …More

Mazatlán, Mexico

3.9 (16)

All Inclusive Beach Club, Water Sports, Horse Ride, Food & Drinks

Introducing the ultimate beach getaway - Stone Island! This all-inclusive package offers an unbeatable experience with unlimited drinks, mouth-watering lunch, and your choice of two...

5 hours Hotel pickup offered Free Cancellation

3.9 (16)

from
$59

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel and spend time in the …More

Cancun, Mexico

3.4 (7)

Catamaran to Isla Mujeres

Enjoy the sun and to sail in the Caribean ocean just to discover the amazing Isla Mujeres you will snorkel and spend time in the...

7 hours Free Cancellation

3.4 (7)

from
$59

Key West Afternoon Reef Snorkeling with Open Bar

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key …More

Key West, USA

4.6 (463)

Key West Afternoon Reef Snorkeling with Open Bar

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key...

3 hours Free Cancellation

4.6 (463)

from
$59

Beach Island Shelling Cruise to Keewaydin Island Tour

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River …More

Naples, USA

5.0 (101)

Beach Island Shelling Cruise to Keewaydin Island Tour

Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River...

3 hours Free Cancellation

5.0 (101)

from
$59

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

Fort Myers, USA

5.0 (114)

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours Free Cancellation

5.0 (114)

from
$60

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and …More

4.8 (175)

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and...

2 hours Free Cancellation

4.8 (175)

from
$60