Browse by state
Sailing by State
Crewed and bareboat sailing charters, day sails, and multi-day cruising.
By state
Find sailing charters
Florida
2 listings
California
2 listings
Texas
3 listings
New York
1 listing
South Carolina
2 listings
Washington
1 listing
Maine
3 listings
Maryland
2 listings
Virginia
2 listings
Connecticut
4 listings
Alabama
1 listing
Mississippi
1 listing
Louisiana
3 listings
Michigan
1 listing
Wisconsin
1 listing
Illinois
1 listing
Hawaii
3 listings
Missouri
1 listing
Pennsylvania
1 listing
Keep exploring
More Charters
Resources
More to explore in Sailing
Hand-picked videos and free guides from the community to help you plan your next trip.
Videos worth watching
Hand-picked clips, sorted by what you do.
How I Sail And Sleep Alone At Night FAR Offshore.
Sailing Songbird
Learn How to Sail: A Step-by-Step Guide to SAILING
Josh Post
Sailing Alone 11,500 Nautical Miles Across The Entire Pacific Ocean on a $2400 Sailboat
Sailing Triteia
Kite-Powered Sailboat Aiming to Be the World's Fastest | What The Future
CNET
Uncovering the True Beauty of the Caribbean : An Eye Opening Experience
Sailing Honu Time
How to Sail in 3min
Igor Stropnik
Guides worth reading
Trip briefs, prep checklists, and how-tos. Free to read.
Chesapeake Bay Cruising Season: Wind, Weather & Crowds
May 2026
How to Choose a Charter Operator: Red Flags and Vetting Questions
May 2026
Pacific Coast Cruising Route: San Diego to San Francisco
May 2026
How to Choose a Sailing School for Keelboat Certification
May 2026
