Skip to content
Sailing: Crewed and bareboat sailing charters, day sails, and multi-day cruising.

Sailing · Connecticut

Sailing in Connecticut

4 operators across Connecticut.

Connecticut boating

Connecticut's whole southern border is water, the sheltered reach of Long Island Sound, running from the busy harbors of Stamford and Norwalk in the west to the old maritime towns of Mystic and Stonington in the east. Cruisers work quiet coves and drop into coastal villages, with well-equipped marinas along the way offering transient slips, repairs, and provisions. The Sound's protected waters make easy work of family outings, sail days, and powerboat runs, with Long Island's shore an easy hop across.

Then there's the Connecticut River, a different trip entirely: navigable for many miles above its mouth at Old Saybrook, winding past Essex and Chester and a run of green hills and small-town waterfronts. River marinas tend to be quieter than the Sound's busier ports, often with excellent amenities and a tucked-away feel. Between salt water and fresh, the state covers day-trippers and long-haul cruisers alike.

About sailing

Crewed and bareboat sailing charters, day sails, and multi-day cruising.

Quick facts

Best season
May through October

Operators

Sailing charters

Loads the full map of every listing on this page. We leave it off by default so the page opens fast on mobile data.

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

Free tools

Your free outdoor toolkit

In your pocket

Take every launch with you.

Free, no account needed. Ramps, marinas, marine conditions, and maps in your pocket.

  • Every marina and boat ramp in your pocket

  • File a float plan and ETA before you cast off

  • Harbor and inlet webcams before you tow

  • GPS tracking that keeps recording beyond cell coverage

The Boating Hubs app dashboard

For operators

Run your boating business?
Launch your branded surface.

Get your own branded surface in the Boating Hubs app and a directory listing in minutes. Bookings, digital waivers, and your whole operation live in one cockpit.