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 →

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for …More

Oahu, USA

4.9 (1,014)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Shore Excursions TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for...

2 hours Free Cancellation

4.9 (1,014)

from
$55

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 (982)

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 (982)

from
$79

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

Key West, USA

4.9 (977)

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours

4.9 (977)

from
$109

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for …More

Oahu, USA

4.8 (953)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes Free Cancellation

4.8 (953)

from
$85

Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of …More

Big Island of Hawaii, USA

4.9 (856)

Sunset and Manta Ray Snorkel Adventure

Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of...

2 hours 15 minutes Free Cancellation

4.9 (856)

from
$155

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in …More

Maui, USA

4.8 (836)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours Free Cancellation

4.8 (836)

from
$213

Sailing Tour through the Lagoon of the 7 Colors

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee …More

Bacalar, Mexico

4.9 (825)

Sailing Tour through the Lagoon of the 7 Colors

Sail with people who share your passion for adventure! You will explore fascinating places along the lagoon of the 7 colors. Our small groups guarantee...

3 hours Free Cancellation

4.9 (825)

from
$41

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin …More

Cabo San Lucas, Mexico

5.0 (815)

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas

✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin...

3 hours Free Cancellation

5.0 (815)

from
$90

Cabo San Lucas Sunset Sailing Shared Cruise

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San …More

Cabo San Lucas, Mexico

4.9 (797)

Cabo San Lucas Sunset Sailing Shared Cruise

Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San...

2 hours Free Cancellation

4.9 (797)

from
$90

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines …More

Key West, USA

4.8 (750)

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...

2 hours 30 minutes (approx.) Free Cancellation

4.8 (750)

from
$90

Sunset Dolphin Sail Aboard the Privateer Catamaran

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, …More

Panama City Beach, USA

4.8 (750)

Sunset Dolphin Sail Aboard the Privateer Catamaran

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer,...

2 hours Free Cancellation

4.8 (750)

from
$43

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner …More

Big Island of Hawaii, USA

4.8 (744)

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner...

1 hour 30 minutes Free Cancellation

4.8 (744)

from
$141

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the …More

Special Offer

Key West, USA

4.9 (739)

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

6 hours (approx.) Free Cancellation

4.9 (739)

~~$200~~
$169

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain …More

Big Island of Hawaii, USA

4.9 (737)

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain...

3 hours Free Cancellation

4.9 (737)

from
$136

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut …More

Seattle, USA

4.9 (726)

Evening Colors Sunset Sail Tour in Seattle

Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut...

2 hours Free Cancellation

4.9 (726)

from
$88

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk …More

Hilton Head Island, USA

4.9 (720)

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk...

1 hour 30 minutes Free Cancellation

4.9 (720)

from
$48

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our …More

Big Island of Hawaii, USA

5.0 (713)

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our...

4 hours Free Cancellation

5.0 (713)

from
$189

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA

4.9 (684)

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

3 hours Hotel pickup offered Free Cancellation

4.9 (684)

from
$90

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from …More

San Francisco, USA

4.9 (659)

San Francisco Bay Sailing Cruise

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from...

1 hour 30 minutes Free Cancellation

4.9 (659)

from
$65