Top North America Sailing Trips

633 Results
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such …More

San Diego, USA

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such...

1 hour 30 minutes Free Cancellation
4.6 (549)
from
$38
Morning Charleston Harbor Sail Lux Catamaran Shade and Seating

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in …More

Mount Pleasant, USA

Ready to escape the everyday and experience Charleston from a whole new perspective? Step aboard the Charleston's premier 50-foot catamaran. Designed for stunning views in...

2 hours Free Cancellation
5.0 (2)
from
$38
Toronto Tall Ship Boat Cruise

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat, …More

Toronto, Canada

This is your chance to experience Toronto's only tall ship boat cruise! Sail aboard the historic 'Tall Ship Kajama,' a traditional 165-foot, 3-masted schooner boat,...

2 hours Free Cancellation
4.4 (668)
from
$37
Slow Sailing Bacalar Experience with snack and drinks

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help …More

Bacalar, Mexico

Step aboard our sailboat and experience Bacalar in most authentic and sustainable way - powered mainly by the wind. By choosing to sail, you help...

3 hours Free Cancellation
4.9 (17)
from
$37
Tour Sailing boat 4 Hours

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush …More

Bacalar, Mexico

We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped with bathroom for emergencies. Surrounded by lush...

4 hours Free Cancellation
4.8 (28)
from
$36
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along …More

Fort Lauderdale, USA

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...

1 hour Free Cancellation
4.9 (1,532)
from
$35
Private Paddle Tour at Sunrise

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity …More

Bacalar, Mexico

With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity...

3 hours Free Cancellation
5.0 (128)
from
$32
Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch

Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. Enjoy a premium national open bar while sailing to …More

Cancun, Mexico

Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. Enjoy a premium national open bar while sailing to...

7 hours Hotel pickup offered Free Cancellation
from
$29
Sunrise by Paddle or Kayak with Floating Picnic

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic …More

Bacalar, Mexico

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic...

3 hours Free Cancellation
5.0 (338)
from
$27
Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor

Why This is a "Must-Do" Experience: Unrivaled Views: Get up close to the Arch and see the diverse marine life, including tropical fish and occasionally …More

Likely to Sell Out
Likely to Sell Out
Cabo San Lucas, Mexico

Why This is a "Must-Do" Experience: Unrivaled Views: Get up close to the Arch and see the diverse marine life, including tropical fish and occasionally...

3 hours 30 minutes Free Cancellation
5.0 (11)
from
$27
Paddle at Dawn with visit to Cenotes and Islands

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic …More

Bacalar, Mexico

Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic...

3 hours Free Cancellation
5.0 (95)
from
$23
Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give you a real caribbean experience. Discover …More

Likely to Sell Out
Likely to Sell Out
Cancun, Mexico

This is the most complete tour to Isla Mujeres on board a Catamaran with all the inclusions to give you a real caribbean experience. Discover...

8 hours Free Cancellation
5.0 (4)
from
$20
Speedboat and Snorkeling Adventure in Cancun

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and serenity. Hop into a 2-passenger speedboat and zip around the stunning …More

Cancun, Mexico

Explore the vibrant Cancun jungle with an exhilarating water adventure that combines speed and serenity. Hop into a 2-passenger speedboat and zip around the stunning...

2 hours 30 minutes Free Cancellation
4.3 (3)
from
$16

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