USA Sailing Trips

Private Sailboat Charter on San Francisco Bay

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita, …More

Likely to Sell Out
Likely to Sell Out

Fall and winter typically provide lighter breezes on SF Bay. Great days on the Bay. 3 hour PRIVATE Charter with a unique experience aboard Carmelita,...

3 hours Free Cancellation
5.0 (9)
from
$995
Private Statue of Liberty Sailing Tour

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory, …More

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

Experience a luxury sailing adventure! Enjoy a spacious deck lounge, sun pad, cabin lounge with table seating for six, Bluetooth sound system, luxury wraps, lavatory,...

2 hours
5.0 (14)
from
$800
Champagne Dolphin Sail and Reef Snorkel

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with …More

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

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours
5.0 (10)
from
$109
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
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
Public Sunset Picnic Boat Cruise on Lake Champlain

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain aboard the charming Buttercup for a two-hour sunset picnic cruise. This unique experience invites you to bring your own food...

2 hours Free Cancellation
5.0 (7)
from
$95
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
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
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
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
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
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
Private Daytime Sailing Cruise on Lake Champlain 12 Passengers

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain aboard the classic Friendship Sloop, where stunning views of the Adirondack and Green Mountains await. This private two-hour cruise accommodates...

2 hours
5.0 (4)
from
$800
Private Daytime Picnic Boat Cruise (Up to 6 Passengers)

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same. …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Set sail on Lake Champlain for a one-of-a-kind adventure where the route is guided entirely by the wind—ensuring no two cruises are ever the same....

2 hours
5.0 (2)
from
$550
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

Likely to Sell Out
Likely to Sell Out
Cocoa Beach, USA

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
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment …More

Miami, USA

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment...

3 to 30 minutes Free Cancellation
4.9 (12)
from
$600
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
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

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