USA Sailing Trips

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 …More

Likely to Sell Out
Likely to Sell Out
Brooklyn, USA

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
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 …More

Likely to Sell Out
Likely to Sell Out
Key Largo, USA

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
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
LA: Yacht Private Trip -1 hour (1 ticket covers 1-6 ppl

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and …More

Likely to Sell Out
Likely to Sell Out
Long Beach, USA

You may bring 1-6 people on this activity. One ticket covers you and your guests, you have the Yacht to yourselves, just your group and...

1 hour
4.6 (8)
from
$255
Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$98
2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours Free Cancellation
5.0 (4)
from
$1,495
Luxury Sunset Sail on Serendipity Catamaran in Charleston

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local …More

Charleston, USA

Set sail for an unforgettable 2-hour sunset cruise on the Serendipity Catamaran, departing from Seabreeze Marina in downtown Charleston. Enjoy stunning waterfront views and local...

2 hours Free Cancellation
5.0 (26)
from
$150
San Diego's first ever Family Sailing Tours

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put …More

Likely to Sell Out
Likely to Sell Out
La Jolla, USA

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put...

2 hours 30 minutes Free Cancellation
5.0 (6)
from
$975
Private Charter Day Sail For up to 6 People

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to …More

Likely to Sell Out
Likely to Sell Out
Salem, USA

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to...

1 hour 30 minutes Free Cancellation
5.0 (7)
from
$225
Two Hour Scenic Sail on the Liberty Clipper

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island …More

Likely to Sell Out
Likely to Sell Out
Long Island, USA

A voyage aboard the 125' Schooner Liberty Clipper offers a unique opportunity to connect with maritime history while exploring the stunning views of Long Island...

2 hours Free Cancellation
5.0 (9)
from
$69
Newport Sunset Sail on Classic Sailboat

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on …More

Newport, USA

Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on...

1 hour 30 minutes
4.8 (57)
from
$74
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes Free Cancellation
4.5 (50)
from
$110
Private Catamaran: Snorkel, Swim and Dolphin Watching

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take...

3 hours Free Cancellation
5.0 (1)
from
$465
Private Sailing Charter: Up to 24 Passengers

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco …More

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

Our classic sailing yachts are the perfect venue for your group! Treat your family and friends to a spectacular private sail around the San Francisco...

1 hour 30 minutes
5.0 (2)
from
$1,425
Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours Free Cancellation
5.0 (6)
from
$276
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Key West, USA

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours Free Cancellation
5.0 (2)
from
$1,595
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation
5.0 (2)
from
$1,200
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

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

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
Fort Myers: Tiki Pub VIP Private Tropical Sandbar Getaway Cruise

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything...

3 hours Free Cancellation
5.0 (2)
from
$599
Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation
4.9 (58)
from
$75

Frequently Asked Questions

These answers are based on answers previously given to Key West Private Charters customers' questions.

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