Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Key West Wind & Wine Sunset Sail Key West Sail, Snorkel, Kayak with Sunset Option Key West Backcountry Safari Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor 1-Hour Interactive Pirate Cruise (arrive 30 minutes early) 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: Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup Waikiki Turtle Snorkeling Adventure(8am) Half-Day Luxury Sailing Experience in Tulum with Open Bar Half Day Oahu Combo Adventure: Bike, Sail and Snorkel 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 →

2.5 hr Sailboat Tour aboard Orion's Child

Cool Shore Excursions Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. …More

Fort Myers, USA

5.0 (92)

2.5 hr Sailboat Tour aboard Orion's Child

Cool Shore Excursions Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel....

2 hours 30 minutes Free Cancellation

5.0 (92)

from
$130

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

5.0 (359)

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation

5.0 (359)

from
$125

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic …More

New York City, USA

4.9 (75)

New York City Sunset Sail to the Statue of Liberty

Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic...

2 hours Free Cancellation

4.9 (75)

from
$90

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA

4.9 (220)

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours Free Cancellation

4.9 (220)

from
$221

Puerto Vallarta Adults-Only Luxury Sunset Sail

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium …More

Puerto Vallarta, Mexico

4.8 (440)

Puerto Vallarta Adults-Only Luxury Sunset Sail

Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium...

3 hours Free Cancellation

4.8 (440)

from
$99

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

4.9 (64)

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation

4.9 (64)

from
$760

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a …More

Bacalar, Mexico

5.0 (432)

Private sailing tour of Bacalar Lagoon

Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a...

3 hours Free Cancellation

5.0 (432)

from
$240

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes …More

Cabo San Lucas, Mexico

4.9 (71)

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes...

2 hours 30 minutes Free Cancellation

4.9 (71)

from
$600

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

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

5.0 (338)

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...

3 hours Free Cancellation

5.0 (338)

from
$27

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - …More

Hilton Head Island, USA

5.0 (125)

Private Hilton Head Sunset Sailing Tour with Dolphin Watching

This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island -...

2 hours Free Cancellation

5.0 (125)

from
$525

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along …More

Big Island of Hawaii, USA

4.9 (480)

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

4 hours 30 minutes Free Cancellation

4.9 (480)

from
$179

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious …More

Tulum, Mexico

4.7 (407)

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar

Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious...

2 hours Hotel pickup offered Free Cancellation

4.7 (407)

from
$89

Key West Sail and Snorkel Day Trip from Fort Lauderdale

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from …More

Fort Lauderdale, USA

3.4 (14)

Key West Sail and Snorkel Day Trip from Fort Lauderdale

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from...

15 hours Free Cancellation

3.4 (14)

from
$149

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

San Diego, USA

5.0 (85)

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes Free Cancellation

5.0 (85)

from
$125

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

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered …More

5.0 (40)

Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

2 hours 30 minutes Free Cancellation

5.0 (40)

from
$116

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

Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

Key West, USA

4.9 (40)

Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation

4.9 (40)

from
$124