Top North America Sailing Trips

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Speedboat and Snorkeling Adventure in Cancun Catamaran Sailing and Snorkeling to Isla Mujeres from Cancun Paddle at Dawn with visit to Cenotes and Islands Where Two Seas Meet: Arch Discovery & Free Time at Playa del Amor Sunrise by Paddle or Kayak with Floating Picnic View all Tours with Instant Confirmation →

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 →

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around …More

New York City, USA

4.9 (15)

New York City Live Jazz Sail

Step aboard 105-foot Schooner America 2.0, a modern tribute to the first boat that won the America's Cup in 1851, for a 2-hour sail around...

2 hours Free Cancellation

4.9 (15)

from
$134

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of …More

San Jose del Cabo, Mexico

5.0 (2)

Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas

Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of...

2 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$135

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah. …More

Savannah, USA

5.0 (100)

Two Hour Coastal Sailing Cruise

What makes this tour unique is the custom experience aboard our 43-foot, 27-foot wide trimaran—one of the largest and most stable sailing vessels in Savannah....

2 hours Free Cancellation

5.0 (100)

from
$135

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

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

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Maui, USA

4.8 (213)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours Free Cancellation

4.8 (213)

from
$138

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights …More

Oahu, USA

5.0 (5)

BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$139

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty …More

Kennebunkport, USA

5.0 (66)

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty...

2 hours Free Cancellation

5.0 (66)

from
$139

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

Boat to Isla Espíritu Santo and Balandra

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides on a super comfortable …More

La Paz, Mexico

4.9 (31)

Boat to Isla Espíritu Santo and Balandra

Nothing with sea lions and get to know Espíritu Santo Island and Balandra from another perspective accompanied by MARINE BIOLOGISTS guides on a super comfortable...

6 hours 30 minutes Free Cancellation

4.9 (31)

from
$143

New York Fall Foliage Sail up the Hudson River

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson …More

New York City, USA

4.6 (11)

New York Fall Foliage Sail up the Hudson River

Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson...

3 hours 30 minutes Free Cancellation

4.6 (11)

from
$143

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone …More

5.0 (2)

Sunset Sailboat Cruise on Winyah Bay

As the sun lowers over the bay, the water softens and the sky comes alive. This is a favorite for couples, relaxed evenings, and anyone...

2 hours Free Cancellation

5.0 (2)

from
$145

Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incredible coastal region is home …More

Playa del Carmen, Mexico

5.0 (1)

Sailboat on the Mayan Riviera at sunset

Ready to set sail on a catamaran at sunset? The Riviera Maya is the ideal place to do it. This incredible coastal region is home...

2 hours Hotel pickup offered

5.0 (1)

from
$145

2hr Shared Sailing Experience in Toronto

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to …More

Toronto, Canada

5.0 (24)

2hr Shared Sailing Experience in Toronto

On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to...

2 hours Free Cancellation

5.0 (24)

from
$146

JFarwell Sunset Wine and Cheese Yacht Sailing

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved …More

Halifax, Canada

5.0 (171)

JFarwell Sunset Wine and Cheese Yacht Sailing

Our 45' luxury sailing yacht is one of a kind on the Halifax waterfront. Our hands-on crew love to invite our guests to be involved...

2 hours 30 minutes Free Cancellation

5.0 (171)

from
$146

JFarwell Private Yacht Wine & Cheese Sunset Sail

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine …More

Halifax, Canada

4.9 (18)

JFarwell Private Yacht Wine & Cheese Sunset Sail

This sunset sail is a stunning opportunity to see how Halifax's urban and nature connect. Guests will be greeting with their first Nova Scotia wine...

2 hours 30 minutes Free Cancellation

4.9 (18)

from
$146

3.5 hour Sailing Adventure in Nanoose Bay

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are …More

Vancouver Island, Canada

5.0 (6)

3.5 hour Sailing Adventure in Nanoose Bay

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are...

3 hours 30 minutes Free Cancellation

5.0 (6)

from
$146

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Maui, USA

4.7 (90)

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation

4.7 (90)

from
$148