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 →

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

Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

Key West, USA

4.8 (438)

Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours

4.8 (438)

from
$109

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 Luxury Yacht Charters, BYOB & Dolphins

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the …More

Charleston, USA

5.0 (430)

Private Luxury Yacht Charters, BYOB & Dolphins

We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the...

2 hours 30 minutes Free Cancellation

5.0 (430)

from
$525

2-Hour Sunset Sail on the San Francisco Bay

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step …More

San Francisco, USA

4.8 (422)

2-Hour Sunset Sail on the San Francisco Bay

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step...

2 hours Free Cancellation

4.8 (422)

from
$129

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers …More

Big Island of Hawaii, USA

4.8 (419)

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutes Free Cancellation

4.8 (419)

from
$159

St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, …More

St Augustine, USA

4.8 (418)

St. Augustine Live Music Sail with Drinks & Sunset Option

Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised,...

1 hour 45 minutes Free Cancellation

4.8 (418)

from
$66

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a …More

Fort Lauderdale, USA

5.0 (401)

Fort Lauderdale Sailing Charter

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a...

4 hours Free Cancellation

5.0 (401)

from
$95

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with …More

San Francisco, USA

4.8 (396)

1.5-Hour San Francisco Bay Sailing Tour

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with...

1 hour 30 minutes Free Cancellation

4.8 (396)

from
$99

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous …More

San Jose del Cabo, Mexico

5.0 (390)

Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar

Cruise aboard a private sailboat for just you and your group into the Sea of Cortes. Enjoy great photo opportunities as you pass by the famous...

4 hours Hotel pickup offered Free Cancellation

5.0 (390)

from
$1,799

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Big Island of Hawaii, USA

4.8 (384)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes Free Cancellation

4.8 (384)

from
$109

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as …More

San Diego, USA

5.0 (371)

Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as...

2 hours 30 minutes Free Cancellation

5.0 (371)

from
$119

2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

La Jolla, USA

5.0 (370)

2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes Free Cancellation

5.0 (370)

from
$119

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern …More

Key West, USA

5.0 (369)

Key West Sunset Sail Aboard Legendary Schooner Appledore

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...

2 hours Free Cancellation

5.0 (369)

from
$99

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey …More

Monterey & Carmel, USA

4.8 (366)

Monterey Bay Whale Watching

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey...

2 to 3 hours Free Cancellation

4.8 (366)

from
$70

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

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

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine …More

Cozumel, Mexico

4.9 (341)

El Cielo Snorkel by Private Boat

- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine...

4 hours Free Cancellation

4.9 (341)

from
$500

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