Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Private Luxury Yacht Charter aboard Tu Enamorado Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Luxury Yacht 58 ft for up to 20 people 4 hrs Private Cruise Swim with Dolphin Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs View all Tours with Instant Confirmation →

Q: I need a ride! Which North America Sailing Trips have Hotel Pickup?

No problem. These North America Sailing Trips include Hotel Pickup: Private Cruise Swim with Dolphin Private Romantic Sailing Sunset Experience Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Private Luxury Sunset Sail in San Jose del Cabo Marina Private Luxury Yacht Charter with Snorkeling in Los Cabos View all Tours with Hotel Pickup →

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 →

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service …More

Punta Sam, Mexico

4.7 (88)

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar

*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service...

2 hours Hotel pickup offered Free Cancellation

4.7 (88)

from
$89

Isla Mujeres Plus by Albatros Catamarans

Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise …More

Cancun, Mexico

4.0 (211)

Isla Mujeres Plus by Albatros Catamarans

Delight all your senses aboard a boat that will take you to one of the best islands in the world, swim in the impressive turquoise...

7 hours Free Cancellation

4.0 (211)

from
$89

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while …More

Long Island, USA

5.0 (18)

Sunset Sail Aboard the Liberty Clipper

Set sail into the golden hues of sunset on the 125' Schooner Liberty Clipper. This 2-hour adventure lets you glide through the tranquil waters while...

2 hours Free Cancellation

5.0 (18)

from
$89

Cabo Sunset Tour with Dinner and Open Bar

If you are in Cabo wanting to make memories that last a lifetime then this is the one for you. Watch the sunset as it …More

Cabo San Lucas, Mexico

5.0 (1)

Cabo Sunset Tour with Dinner and Open Bar

If you are in Cabo wanting to make memories that last a lifetime then this is the one for you. Watch the sunset as it...

2 hours 15 minutes Free Cancellation

5.0 (1)

from
$89

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the …More

Cancun, Mexico

5.0 (1)

Afternoon Catamaran to Isla Mujeres: Snorkel, Open Bar & Sunset

This is one of the few afternoon catamaran experiences available in Cancun. Discover Isla Mujeres on a relaxed afternoon catamaran tour from Cancun. Avoid the...

7 hours Free Cancellation

5.0 (1)

from
$89

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy …More

Key West, USA

5.0 (5)

Key West Night Cruise aboard Schooner America 2.0

Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy...

1 hour 45 minutes Free Cancellation

5.0 (5)

from
$89

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

Key West, USA

5.0 (10)

Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation

5.0 (10)

from
$89

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut …More

Seattle, USA

4.9 (726)

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut...

2 hours Free Cancellation

4.9 (726)

from
$88

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to …More

Oahu, USA

4.6 (10)

Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes Free Cancellation

4.6 (10)

from
$85

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we …More

San Diego, USA

4.8 (2,472)

San Diego Whale Watching Cruise

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we...

4 hours Free Cancellation

4.8 (2,472)

from
$85

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests, …More

Burlington, USA

5.0 (49)

Public Daytime Sailing Cruise

Experience the beauty of Lake Champlain from a unique perspective aboard classic Friendship Sloops, Friend Ship and Wild Rose. With a maximum of 10 guests,...

2 hours

5.0 (49)

from
$85

Private Sunset Sail in San Diego up to 12 guests

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be …More

San Diego, USA

5.0 (73)

Private Sunset Sail in San Diego up to 12 guests

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be...

2 hours 30 minutes Free Cancellation

5.0 (73)

from
$85

Tall Ship Adventure aboard the Schooner Californian with General Admission

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 …More

San Diego, USA

4.3 (6)

Tall Ship Adventure aboard the Schooner Californian with General Admission

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984...

4 hours

4.3 (6)

from
$85

All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience. Explore …More

Punta Sam, Mexico

3.9 (27)

All Inclusive Caribbean adventure, reef snorkeling, Food & Drinks

Admire the peaceful waters of the Caribbean Sea, aboard a catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience. Explore...

8 hours Hotel pickup offered Free Cancellation

3.9 (27)

from
$85

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. …More

San Diego, USA

4.1 (7)

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon....

4 hours

4.1 (7)

from
$85

Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

Escape to paradise on this all-inclusive catamaran tour to Isla Mujeres, one of the Caribbean's most beautiful destinations. Sail across crystal-clear waters, enjoy unlimited drinks …More

Punta Sam, Mexico

3.0 (1)

Sail To Isla Mujeres By Catamaran Buffet And Drinks Included

Escape to paradise on this all-inclusive catamaran tour to Isla Mujeres, one of the Caribbean's most beautiful destinations. Sail across crystal-clear waters, enjoy unlimited drinks...

8 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$85

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

Discover the perfect Caribbean getaway on this all-inclusive catamaran adventure from Cancun to Isla Mujeres. Dive into an unforgettable snorkeling experience at the beautiful El …More

Punta Sam, Mexico

Catamaran Sail with Snorkeling and Beach Club of Isla Mujeres

Discover the perfect Caribbean getaway on this all-inclusive catamaran adventure from Cancun to Isla Mujeres. Dive into an unforgettable snorkeling experience at the beautiful El...

8 hours Hotel pickup offered Free Cancellation

from
$85

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for …More

Oahu, USA

4.8 (953)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes Free Cancellation

4.8 (953)

from
$85

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time …More

Oahu, USA

4.8 (598)

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time...

1 hour 30 minutes Free Cancellation

4.8 (598)

from
$85

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own …More

Honolulu, USA

4.9 (363)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours Free Cancellation

4.9 (363)

from
$84