Top North America Sailing Trips

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

No problem. These North America Sailing Trips include Hotel Pickup: Los Cabos Luxury Sailing, Snorkel and Lunch Cruise Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Waikiki Turtle Snorkeling Adventure(8am) 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 →

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have …More

Fort Lauderdale, USA

4.9 (323)

4-Hour Fort Lauderdale Sailing Charter

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

4 hours Free Cancellation

4.9 (323)

from
$110

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the …More

Oahu, USA

4.9 (322)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes Free Cancellation

4.9 (322)

from
$73

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

Private Sailboat + Captain for a Day Experience

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY Cool Shore Excursions TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride …More

Bacalar, Mexico

5.0 (304)

Private Sailboat + Captain for a Day Experience

RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY Cool Shore Excursions TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride...

3 hours Free Cancellation

5.0 (304)

from
$222

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's …More

Key West, USA

5.0 (292)

Sunset Sail Cruise in Key West

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...

2 hours Free Cancellation

5.0 (292)

from
$102

Suncoast Sailing's Sunset Sailing Experience!

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. …More

St Petersburg, USA

4.9 (285)

Suncoast Sailing's Sunset Sailing Experience!

Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script....

2 hours 30 minutes Free Cancellation

4.9 (285)

from
$70

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under …More

Clearwater, USA

5.0 (284)

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under...

2 hours Free Cancellation

5.0 (284)

from
$80

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This …More

Key West, USA

4.9 (282)

Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours Free Cancellation

4.9 (282)

from
$109

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as …More

Oahu, USA

5.0 (279)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes Free Cancellation

5.0 (279)

from
$51

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far …More

Oahu, USA

4.9 (264)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours Free Cancellation

4.9 (264)

from
$50

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. …More

Miami, USA

4.9 (259)

Miami Private Boat Tour- Millionaire’s Row and Celebration Cruise

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google....

4 hours Free Cancellation

4.9 (259)

from
$150

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA

4.9 (256)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes Free Cancellation

4.9 (256)

from
$45

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner …More

Big Island of Hawaii, USA

4.9 (253)

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner...

3 hours Free Cancellation

4.9 (253)

from
$136

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, …More

Cancun, Mexico

5.0 (251)

Premium Isla Mujeres Tour by Private Catamaran

We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired,...

5 hours Free Cancellation

5.0 (251)

from
$990

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide …More

Cocoa Beach, USA

4.9 (243)

Dolphin Adventure Sail in Cocoa Beach

Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide...

2 hours Free Cancellation

4.9 (243)

from
$51

Private Luxury Catamaran in Tulum with Snacks and Open Bar

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve …More

Tulum, Mexico

5.0 (238)

Private Luxury Catamaran in Tulum with Snacks and Open Bar

It is a private experience, where you can enjoy the Caribbean Sea while our chef cooks exclusive and delicious dishes and our host will serve...

4 hours Free Cancellation

5.0 (238)

from
$2,700

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for …More

Maui, USA

5.0 (226)

Lahaina Maui Sunset Sail on 'Alihilani

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes Free Cancellation

5.0 (226)

from
$127

New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known …More

New York City, USA

4.9 (224)

New York Sunset Schooner Cruise on the Hudson River

Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known...

2 hours Free Cancellation

4.9 (224)

from
$90

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique …More

Honolulu, USA

4.9 (223)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours Free Cancellation

4.9 (223)

from
$67