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 →

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, …More

Maui, USA

4.8 (19)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours Free Cancellation

4.8 (19)

from
$279

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and …More

Puerto Vallarta, Mexico

5.0 (2)

Pirate Ship by Day

Start the day enjoying a delicious and complete breakfast Under the Sea, in our Pirate Tavern, aboard an incredible 700-ton Galleon, full of adventure and...

6 hours

5.0 (2)

from
$280

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making …More

Kauai, USA

4.9 (559)

The Nāpali Coast Snorkel Excursion

6 hours Free Cancellation

4.9 (559)

from
$292

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Oahu, USA

5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation

5.0 (17)

from
$300

Private luxury sailing catamaran experience in Bacalar lagoon

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed …More

Bacalar, Mexico

5.0 (4)

Private luxury sailing catamaran experience in Bacalar lagoon

Our Stiletto catamaran stands out due to several unique features: 1. Speed and Stability : Unlike traditional catamarans, the Stiletto combines the thrill of speed...

4 hours

5.0 (4)

from
$303

Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of …More

Cocoa Beach, USA

5.0 (2)

Private Sunset Catamaran Sail in Cocoa Beach

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of...

2 hours Free Cancellation

5.0 (2)

from
$338

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on …More

Fort Myers, USA

5.0 (3)

Fort Myers: Tiki Pub VIP Private Fun in the Sun Dolphin Cruise

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on...

2 hours Free Cancellation

5.0 (3)

from
$349

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a …More

New York City, USA

5.0 (43)

Best Private Luxury Daytime Boat Tour in New York City - 1 Hour

Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a...

1 hour Free Cancellation

5.0 (43)

from
$350

Private Sailing Charters: Island Adventures and Sunset Cruises

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years …More

Folly Beach, USA

5.0 (2)

Private Sailing Charters: Island Adventures and Sunset Cruises

Set sail on a private charter with Water Music Charters, offering an unforgettable experience along Folly Beach and Charleston's vibrant waters. With over 25 years...

2 hours Free Cancellation

5.0 (2)

from
$350

Guided Seattle Sailing Adventure from Bainbridge Island

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we …More

Seattle, USA

5.0 (86)

Guided Seattle Sailing Adventure from Bainbridge Island

Depending on the day, we’ll get up close to seals, explore some beautiful harbors with stunning waterfront homes, and maybe even spot whales. Or we...

2 hours Free Cancellation

5.0 (86)

from
$360

Private Catamaran Sunset Cruise with Dolphin watching

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain …More

Destin, USA

5.0 (4)

Private Catamaran Sunset Cruise with Dolphin watching

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain...

2 hours Free Cancellation

5.0 (4)

from
$360

Private Tour Isla Mujeres excursion in Transparent Boat

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a …More

Isla Mujeres, Mexico

4.5 (2)

Private Tour Isla Mujeres excursion in Transparent Boat

We have a great diversity of marine life, which can be enjoyed throughout our journey thanks to our 100% transparent boat. It will be a...

1 hour Free Cancellation

4.5 (2)

from
$374

Private Sailboat Charter from San Pedro: Port of Los Angeles

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis …More

Los Angeles, USA

5.0 (1)

Private Sailboat Charter from San Pedro: Port of Los Angeles

Experience the beauty of the Pacific Ocean with a private yacht charter in San Pedro, CA. Enjoy a sunset sailing adventure on a Beneteau Oceanis...

2 to 4 hours Free Cancellation

5.0 (1)

from
$380

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting …More

Key Largo, USA

5.0 (2)

SUNSET CRUISE in Key Largo,FL.

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$389

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean …More

Santa Monica, USA

4.8 (49)

Private Therapy Sailing Adventure

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean...

2 to 3 hours

4.8 (49)

from
$400

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to …More

Cabo San Lucas, Mexico

5.0 (8)

Luxury Private Yacht Charter in Cabo San Lucas Mexico

You will take a 2-hour tour of the bay of Cabo San Lucas aboard "Reel Tequila" our 31ft boat with a capacity of up to...

2 hours Free Cancellation

5.0 (8)

from
$400

Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica …More

Santa Monica, USA

5.0 (3)

Old Plank Adventures: Sail into Deep Tranquility

Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica...

2 hours Free Cancellation

5.0 (3)

from
$400

Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

Key West, USA

4.9 (20)

Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes Free Cancellation

4.9 (20)

from
$425

Private Yacht Charter in Cabo for Up to 8 People

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch, …More

Cabo San Lucas, Mexico

5.0 (4)

Private Yacht Charter in Cabo for Up to 8 People

Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch,...

2 hours Free Cancellation

5.0 (4)

from
$429