Top North America Sailing Trips

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 →

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

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

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

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

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

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-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

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

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

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, …More

Savannah, USA

5.0 (7)

Private Sailing Charter in Savannah GA

Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding,...

2 hours Free Cancellation

5.0 (7)

from
$650

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

Private Charter: Shell Island Snorkeling & Dolphin Adventure

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this …More

Panama City Beach, USA

4.8 (32)

Private Charter: Shell Island Snorkeling & Dolphin Adventure

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this...

3 hours Free Cancellation

4.8 (32)

from
$641

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn …More

Brooklyn, USA

5.0 (9)

Private Sailing Charter in Brooklyn

Are you ready to set sail on a one-of-a-kind tour of New York Harbor? We've got an unforgettable adventure waiting for you! Departing from Brooklyn...

2 hours Free Cancellation

5.0 (9)

from
$630

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to …More

Cabo San Lucas, Mexico

4.8 (538)

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico

Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to...

8 hours

4.8 (538)

from
$625

El Cielo Cozumel snorkel by Private Boat

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private …More

Cozumel, Mexico

4.8 (133)

El Cielo Cozumel snorkel by Private Boat

Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private...

4 hours Free Cancellation

4.8 (133)

from
$625

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes …More

Cabo San Lucas, Mexico

4.9 (71)

Private Cabo San Lucas Sunset Cruise on 33´ sailboat

You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes...

2 hours 30 minutes Free Cancellation

4.9 (71)

from
$600

Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More