Top North America Sailing Trips

Q: What are the best options for North America Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best North America Sailing Trips are: Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only) Private Sunset Sail in San Diego up to 12 guests Private Sunset Sail in San Diego Up to 6 guests Sail 4hr in the most SECRET Spot of Bacalar and Beach Club. Tiki Pub Glow Party Cruise (Adults only)

Q: What are the best kid-friendly options for North America Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly North America Sailing Trips are: 3 Hour Xpuha-60' Neptunus-Tulum, Playa del Carmen, Riviera Maya 4th of July Fireworks on Clipper City Tall Ship #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Pirate Ship by Day View all kid-friendly Tours →

Q: Which North America Sailing Trips have Instant Confirmation?

North America Sailing Trips with Instant Confirmation include: Private Luxury Yacht Charter aboard Tu Enamorado Private Catamaran from Cancun to Isla Mujeres | For up to 100 pp Luxury Yacht 58 ft for up to 20 people 4 hrs Private Cruise Swim with Dolphin Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs 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: Private Cruise Swim with Dolphin Private Romantic Sailing Sunset Experience Private Luxury Sailing Cruise in Los Cabos with Lunch and Open Bar Private Luxury Sunset Sail in San Jose del Cabo Marina Private Luxury Yacht Charter with Snorkeling in Los Cabos 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 →

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

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

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

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

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

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

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

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

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

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

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

4-Hour Sailing Adventure on The Strait of Juan de Fuca

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water …More

Vancouver Island, Canada

4.8 (26)

4-Hour Sailing Adventure on The Strait of Juan de Fuca

Sailing on Starlight or PrimeTime in the Strait of Juan de Fuca is different each time. From Humpbacks, Orcas, Sea lions, Seals, Eagles and water...

4 hours Free Cancellation

4.8 (26)

from
$132

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Oahu, USA

4.8 (142)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation

4.8 (142)

from
$130

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 (93)

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 (93)

from
$130

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

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views …More

San Francisco, USA

4.9 (52)

Golden Gate Bridge Sailing Tour

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views...

2 hours Free Cancellation

4.9 (52)

from
$129

Isla Mujeres Platinum by Albatros Catamarans

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and relaxation in the Mexican Caribbean. What sets it apart is …More

Cancun, Mexico

4.4 (245)

Isla Mujeres Platinum by Albatros Catamarans

The Platinum Tour is unique because it offers an unparalleled experience of luxury, adventure, and relaxation in the Mexican Caribbean. What sets it apart is...

7 hours Free Cancellation

4.4 (245)

from
$129

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily …More

Cancun, Mexico

4.0 (10)

Catamaran Sail and Snorkeling Tour with Open Bar in Puerto Morelos

Embark on an unforgettable sailing adventure to the Puerto Morelos Reef, part of the Mesoamerican Barrier Reef System, the world’s second-largest coral reef. Departing daily...

7 hours Hotel pickup offered Free Cancellation

4.0 (10)

from
$129

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key …More

Key West, USA

4.9 (1,704)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours Free Cancellation

4.9 (1,704)

from
$127