USA Sailing Trips

377 Results
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

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

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

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
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

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
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

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
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

Likely to Sell Out
Likely to Sell Out

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
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

Likely to Sell Out
Likely to Sell Out
Charleston, USA

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
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

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
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 …More

Key West, USA

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 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

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
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

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
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, …More

Likely to Sell Out
Likely to Sell Out

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
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, …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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

Likely to Sell Out
Likely to Sell Out
New York City, USA

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

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

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

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 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 …More

Key West, USA

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

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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
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

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
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, …More

Savannah, USA

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

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

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