USA Sailing Trips

385 Results
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
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
Private Luxurious Sailing Cruise in San Diego Bay

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll …More

La Jolla, USA

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll...

2 hours Free Cancellation
5.0 (13)
from
$2,700
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while …More

Oahu, USA

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes Free Cancellation
5.0 (13)
from
$53
Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

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

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes Free Cancellation
5.0 (12)
from
$149
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
Rosé Golden Hour Sunset Sail

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with …More

Hilton Head Island, USA

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with...

2 hours Free Cancellation
4.8 (12)
from
$80
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
Captain Steve's Sailing Experience on Long Island

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, …More

Long Island, USA

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience,...

2 hours
5.0 (11)
from
$550
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, …More

Mount Pleasant, USA

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran,...

2 hours Free Cancellation
5.0 (11)
from
$63
Private Daytime Sailing Cruise on Lake Champlain (6 Passengers)

Enjoy a sailing experience like no other as you cruise Lake Champlain guided entirely by the wind—making every journey unique. Along the way, your captain …More

Likely to Sell Out
Likely to Sell Out
Burlington, USA

Enjoy a sailing experience like no other as you cruise Lake Champlain guided entirely by the wind—making every journey unique. Along the way, your captain...

2 hours
5.0 (11)
from
$550
Sunday Brunch Sail in Greenport

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see …More

Long Island, USA

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see...

2 hours Free Cancellation
5.0 (10)
from
$175
Tiki Pub Amazing Dolphin Eco Adventure

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and …More

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

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and...

1 hour 30 minutes Free Cancellation
4.9 (10)
from
$60
Wednesday Happy Hour Sunset Sail - Drinks Included

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha …More

Mount Pleasant, USA

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha...

2 hours Free Cancellation
5.0 (10)
from
$76
Key West Nighttime Full Moon Sail

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or …More

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

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or...

1 hour 30 minutes Free Cancellation
5.0 (10)
from
$89
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
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
Sailing Charter

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend …More

Likely to Sell Out
Likely to Sell Out
Port Angeles, USA

Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend...

1 to 3 hours Free Cancellation
5.0 (9)
from
$240
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 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
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

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