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Top USA Sailing Trips

375 Results
Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Key West, USA

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation
5.0 (4)
from
$1,070
Portland Tall Ship Private Charter on Casco Bay

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the …More

Portland, USA

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the...

2 hours Free Cancellation
from
$1,069
Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to …More

Oahu, USA

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to...

1 hour 30 minutes Free Cancellation
from
$1,000
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 Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully …More

San Diego, USA

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$975
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 Sailing Trip on Monterey Bay

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline, …More

Monterey & Carmel, USA

Discover the stunning beauty of Monterey Bay aboard your own private sailing charter. This experience caters to all ages and interests. Venture along the coastline,...

2 hours Free Cancellation
5.0 (1)
from
$965
Private Swim, Snorkel & Sail on the Daydreams Sailboat

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area …More

Panama City Beach, USA

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area...

3 hours Free Cancellation
5.0 (33)
from
$963
Key West Private Charter: Sandbar and Snorkeling

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a …More

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

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a...

4 hours
5.0 (20)
from
$950
Private Charleston Harbor Catamaran Sail

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a …More

Mount Pleasant, USA

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a...

2 hours 30 minutes Free Cancellation
5.0 (29)
from
$950
Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours Free Cancellation
5.0 (25)
from
$900
Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours Free Cancellation
5.0 (11)
from
$900
Up to 34Pax Bachelorette Party Boat & Yacht Rental Miami

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a …More

Miami, USA

Price Includes up to 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +1250 reviews on Google with a...

3 hours Free Cancellation
5.0 (19)
from
$899
Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of …More

Panama City Beach, USA

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of...

1 hour 30 minutes Free Cancellation
from
$857
Golden Hour Escape: Private Sunset Sail in Coastal Maine

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined …More

Kennebunkport, USA

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined...

2 hours Free Cancellation
5.0 (23)
from
$849
San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is …More

San Diego, USA

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is...

2 hours 30 minutes Free Cancellation
5.0 (4)
from
$810
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
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 Sunset Sail of NYC Skyline and Statue of Liberty

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your …More

Jersey City, USA

Discover NYC from a completely different perspective on a private sailboat charter during sunset hours when the views are even more spectacular. You and your...

2 hours Free Cancellation
5.0 (2)
from
$800
Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, …More

San Diego, USA

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines,...

2 hours
5.0 (2)
from
$800

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