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 →

Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and …More

5.0 (1)

Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$790

2 hours - Private Day Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to …More

St Augustine, USA

5.0 (20)

2 hours - Private Day Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hours Free Cancellation

5.0 (20)

from
$795

Miami Private Yacht Celebration Cruise with Captain

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is …More

Miami, USA

4.7 (52)

Miami Private Yacht Celebration Cruise with Captain

Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is...

4 hours Free Cancellation

4.7 (52)

from
$799

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, …More

New York City, USA

5.0 (14)

Private Statue of Liberty Sailing Tour

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory,...

2 hours

5.0 (14)

from
$800

Private Daytime Sailing Cruise on Lake Champlain 12 Passengers

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates …More

Burlington, USA

5.0 (4)

Private Daytime Sailing Cruise on Lake Champlain 12 Passengers

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates...

2 hours

5.0 (4)

from
$800

Private Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your …More

Jersey City, USA

5.0 (2)

Private Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your...

2 hours Free Cancellation

5.0 (2)

from
$800

Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, …More

San Diego, USA

5.0 (2)

Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines,...

2 hours

5.0 (2)

from
$800

Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht …More

Daytona Beach, USA

5.0 (2)

Private Sailing Charters on La Vie Dansante

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht...

3 hours Free Cancellation

5.0 (2)

from
$800

Private Sailing Experience on Galveston Bay

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to …More

Houston, USA

5.0 (1)

Private Sailing Experience on Galveston Bay

See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to...

4 hours Free Cancellation

5.0 (1)

from
$800

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, …More

San Diego, USA

5.0 (1)

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers,...

2 hours

5.0 (1)

from
$800

Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers …More

San Diego, USA

5.0 (1)

Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers...

2 hours

5.0 (1)

from
$800

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several …More

San Diego, USA

4.0 (3)

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several...

2 hours

4.0 (3)

from
$800

Half-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a …More

Puerto Vallarta, Mexico

5.0 (104)

Half-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta

Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore los arcos area while savoring fresh guacamole and a...

4 hours

5.0 (104)

from
$803

San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is …More

San Diego, USA

5.0 (4)

San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is...

2 hours 30 minutes Free Cancellation

5.0 (4)

from
$810

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will …More

Cabo San Lucas, Mexico

5.0 (17)

Cabo Private Catamaran: Arch, Sea Lions and Beach for Up to 12

Our boat excursions in Cabo San Lucas are the perfect way to explore the wonders of the Sea of Cortez. Our well-trained bilingual crew will...

3 hours 30 minutes Free Cancellation

5.0 (17)

from
$840

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or …More

Halifax, Canada

5.0 (19)

JFarwell Sip & Sail aboard the Reverie

This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or...

1 hour 30 minutes Free Cancellation

5.0 (19)

from
$844

Golden Hour Escape: Private Sunset Sail in Coastal Maine

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined …More

Kennebunkport, USA

5.0 (23)

Golden Hour Escape: Private Sunset Sail in Coastal Maine

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined...

2 hours Free Cancellation

5.0 (23)

from
$849

Cozumel Private Snorkeling and Charter Experience

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting …More

Cozumel, Mexico

5.0 (25)

Cozumel Private Snorkeling and Charter Experience

We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting...

5 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$850

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains …More

Puerto Vallarta, Mexico

5.0 (27)

Private Sunset Sailing Cruise with Drinks in Puerto Vallarta

On this sunset sailing experience you will be able to apreciate a relaxing sunset while you take on stunning views of the Sierra Madre mountains...

3 hours 30 minutes

5.0 (27)

from
$853

Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of …More

Panama City Beach, USA