USA Sailing Trips

New York City Sunset Jazz Sail aboard Clipper City

Sail toward the sun dipping behind the Statue of Liberty and return with the skyline glittering before you—a view that never gets old, no matter …More

New York City, USA

Sail toward the sun dipping behind the Statue of Liberty and return with the skyline glittering before you—a view that never gets old, no matter...

1 hour 45 minutes Free Cancellation
4.7 (90)
from
$102
Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation
5.0 (57)
from
$599
San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

San Diego, USA

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes Free Cancellation
4.9 (55)
from
$55
Private Sunset Sail in San Diego Up to 6 guests

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking …More

La Jolla, USA

Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking...

2 hours Free Cancellation
5.0 (74)
from
$99
Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic …More

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

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hours Free Cancellation
4.9 (18)
from
$90
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in …More

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

2 hours Free Cancellation
5.0 (22)
from
$160
Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More

Key West, USA

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$600
St Augustine Nights of Lights Viewing Boat with Live Music

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset …More

St Augustine, USA

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset...

1 hour 45 minutes (Approx.) Free Cancellation
4.9 (64)
from
$72
Golden Gate Bridge Sailing Tour

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views …More

San Francisco, USA

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views...

2 hours Free Cancellation
4.9 (52)
from
$129
Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation
4.9 (72)
from
$65
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
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
South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have …More

Oahu, USA

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes Free Cancellation
4.8 (26)
from
$48
2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours Free Cancellation
5.0 (17)
from
$245
Spectacular Afternoon Sail on San Diego Bay

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or …More

La Jolla, USA

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or...

2 hours Free Cancellation
5.0 (24)
from
$150
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
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours Free Cancellation
4.8 (37)
from
$250
Private Afternoon Harbor Cruise on Kismet for parties up to 20

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history …More

Charleston, USA

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history...

2 hours Free Cancellation
5.0 (30)
from
$1,549
Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Key West Private …More

Charleston, USA

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Key West Private...

2 to 4 hours Free Cancellation
5.0 (35)
from
$575
Private Morning Sail in San Diego up to 12 guests $975

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little …More

San Diego, USA

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little...

2 hours 30 minutes Free Cancellation
5.0 (34)
from
$81
Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback …More

Oahu, USA

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hours Free Cancellation
5.0 (21)
from
$150

Frequently Asked Questions

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

Recent tour reviews
Activity name

USA Tours
Attractions
Guides
Calendar