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 →

Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful …More

Baltimore, USA

5.0 (28)

Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful...

1 hour 30 minutes Free Cancellation

5.0 (28)

from
$75

Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

4.9 (58)

Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation

4.9 (58)

from
$75

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

5.0 (5)

Baltimore Inner Harbor BYOB Sunset Sail on the Unforgettable

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$75

Baltimore Harbor Evening Sail on the Unforgettable

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city …More

Baltimore, USA

4.6 (5)

Baltimore Harbor Evening Sail on the Unforgettable

Enjoy a beautiful time on the water as you sail through beautiful Baltimore Harbor, take in the gorgeous scenery of the skyline as the city...

1 hour 30 minutes Free Cancellation

4.6 (5)

from
$75

Baltimore Harbor Moonlight Sail on the Summer Wind

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the …More

Baltimore, USA

5.0 (3)

Baltimore Harbor Moonlight Sail on the Summer Wind

Find your own slice of paradise on this 1.5-hour moonlight sail around Baltimore Harbor. Listen to music inspired by the Caribbean as you enjoy the...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$75

2 Islands in 1 Day: Contoy & Isla Mujeres, Snorkeling + Open Bar

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single …More

Cancun, Mexico

4.3 (6)

2 Islands in 1 Day: Contoy & Isla Mujeres, Snorkeling + Open Bar

What makes this tour unique? Unlike most tours that visit only one island, our experience takes you to two stunning Caribbean islands in a single...

8 hours Free Cancellation

4.3 (6)

from
$76

Boat Ride to the Arch with Snorkeling in Cabo

This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marine experts. Your guide and captain …More

Cabo San Lucas, Mexico

5.0 (186)

Boat Ride to the Arch with Snorkeling in Cabo

This is more than a sightseeing cruise — it's a chance to see Cabo through the eyes of local marine experts. Your guide and captain...

2 hours 30 minutes Free Cancellation

5.0 (186)

from
$76

Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha …More

Mount Pleasant, USA

5.0 (10)

Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours Free Cancellation

5.0 (10)

from
$76

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy nature away from crowds while enjoying an on …More

Bacalar, Mexico

5.0 (107)

Laguna Grill - Private Boat with on-board BBQ and Drinks Included

One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy nature away from crowds while enjoying an on...

4 hours Free Cancellation

5.0 (107)

from
$77

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • …More

Key West, USA

4.6 (432)

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours Free Cancellation

4.6 (432)

from
$77

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both …More

Key West, USA

4.8 (550)

Key West Reef Snorkel & Sail Adventure

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hours Free Cancellation

4.8 (550)

from
$79

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention …More

Key West, USA

4.9 (984)

Sunset Sail in Key West with Beverages Included

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...

1 hour 30 minutes Free Cancellation

4.9 (984)

from
$79

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply …More

Destin, USA

5.0 (1)

Original Cruisin Tikis Shark Tooth and Sea Shell Scavenger Hunt

This interactive experience is perfect for families, kids, and anyone who loves the thrill of the hunt—whether you’re spotting shark teeth, collecting shells, or simply...

3 hours

5.0 (1)

from
$79

Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra …More

Puerto Vallarta, Mexico

4.8 (316)

Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch

Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra...

6 hours Free Cancellation

4.8 (316)

from
$79

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish …More

Cozumel, Mexico

4.9 (256)

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (256)

from
$79

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty …More

Honolulu, USA

4.7 (242)

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hours Free Cancellation

4.7 (242)

from
$79

Discovering Isla Mujeres on a Double Decker Catamaran

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar …More

Cancun, Mexico

4.3 (9)

Discovering Isla Mujeres on a Double Decker Catamaran

Start your day with a hotel pickup or directly at the marina, then head out to open sea through the spectacular mangrove channels. The bar...

7 hours Free Cancellation

4.3 (9)

from
$79

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, …More

Punta Sam, Mexico

5.0 (1)

Cancun Half Day Sailing Cataman Cruise to Isla Mujeres

Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing,...

4 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$79

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. …More

Mazatlán, Mexico

3.8 (4)

City Tour & Beach Club All Inclusive W Horse Ride & Water Sports

Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages....

5 hours Hotel pickup offered Free Cancellation

3.8 (4)

from
$79

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran …More

Key West, USA

4.8 (3,837)

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) Free Cancellation

4.8 (3,837)

from
$80