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 →

Private Sail Around New York City and The Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are …More

Jersey City, USA

5.0 (10)

Private Sail Around New York City and The Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are...

2 hours Free Cancellation

5.0 (10)

from
$650

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and …More

Long Island, USA

5.0 (2)

Oyster Bay Two Hour Sailing Experience

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and...

2 hours Free Cancellation

5.0 (2)

from
$650

4th of July Fireworks on Clipper City Tall Ship

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive 4.5-hour experience combines gourmet hors d’oeuvres, open bar, themed cocktails, and live …More

New York City, USA

3.5 (6)

4th of July Fireworks on Clipper City Tall Ship

Celebrate Independence Day in unforgettable style aboard America's largest Tall Ship. This exclusive 4.5-hour experience combines gourmet hors d’oeuvres, open bar, themed cocktails, and live...

4 hours 30 minutes

3.5 (6)

from
$655

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate …More

Cabo San Lucas, Mexico

5.0 (192)

Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling

Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate...

3 hours Free Cancellation

5.0 (192)

from
$660

2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing …More

San Diego, USA

5.0 (188)

2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing...

2 hours Free Cancellation

5.0 (188)

from
$675

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

Key West, USA

4.9 (50)

Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours

4.9 (50)

from
$693

2 Hours Private Sailboat Charter in the San Francisco Bay

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the …More

San Francisco, USA

4.8 (22)

2 Hours Private Sailboat Charter in the San Francisco Bay

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the...

2 hours Free Cancellation

4.8 (22)

from
$695

Private Boat Charter to Johns Pass Shell Key and Egmont Key

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key, …More

St Petersburg, USA

5.0 (4)

Private Boat Charter to Johns Pass Shell Key and Egmont Key

Cruise the beautiful waters of the Tampa Bay area on a private boat charter customized to your group. Explore popular destinations such as Shell Key,...

4 hours Free Cancellation

5.0 (4)

from
$695

Private Classic Sailboat Tour in New York City

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll …More

New York City, USA

5.0 (4)

Private Classic Sailboat Tour in New York City

This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll...

2 hours Free Cancellation

5.0 (4)

from
$700

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, …More

San Diego, USA

5.0 (3)

Deluxe private Sunset & Day Sail

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks,...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$714

Exclusive Isla Mujeres and Cancun Private Yacht Tour

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise …More

Isla Mujeres, Mexico

5.0 (41)

Exclusive Isla Mujeres and Cancun Private Yacht Tour

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise...

4 hours Hotel pickup offered Free Cancellation

5.0 (41)

from
$720

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, …More

5.0 (6)

Chesapeake Bay Private Cruise

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water,...

2 hours 30 minutes Free Cancellation

5.0 (6)

from
$736

The Finest Private Yacht Experience in Cabo

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some …More

Cabo San Lucas, Mexico

4.7 (22)

The Finest Private Yacht Experience in Cabo

This 3hrs activity is the epitome of what the visitors have been coming to Cabo San Lucas for for 30+ years, it consists of some...

3 hours Free Cancellation

4.7 (22)

from
$740

Private Sailing Experience along the Southern Maine Coastline

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you …More

Kennebunkport, USA

5.0 (3)

Private Sailing Experience along the Southern Maine Coastline

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you...

2 to 6 hours Free Cancellation

5.0 (3)

from
$747

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and …More

Panama City Beach, USA

5.0 (3)

Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and...

2 hours Free Cancellation

5.0 (3)

from
$749

6-Hour Sailing Charter from Fort Lauderdale

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have …More

Fort Lauderdale, USA

5.0 (3)

6-Hour Sailing Charter from Fort Lauderdale

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have...

6 hours Free Cancellation

5.0 (3)

from
$750

4-Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully …More

Playa del Carmen, Mexico

5.0 (29)

4-Hour Private Fishing Charter in the Riviera Maya

Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully...

4 hours

5.0 (29)

from
$750

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

Key West, USA

5.0 (1)

Private Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation

5.0 (1)

from
$750

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

4.9 (64)

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation

4.9 (64)

from
$760

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you …More

Puerto Vallarta, Mexico

5.0 (6)

Private Whale Watching Sailing Tour

Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you...

4 hours

5.0 (6)

from
$770