Sailing

Build team racing skills and strategy on Long Island Sound

Charter the 60-foot Oyster Sloop CHRISTEEN for a private cruise

Charter the Ida May for a private sail with up to 44 guests

Build your sailing skills with instructor-guided time on Oyster Bay Harbor

Step aboard CHRISTEEN to see harbor sights and learn its story

Learn the basics aboard a relaxed harbor sail led by a certified instructor

Sail past Fajardo’s islands as the sun sets behind El Yunque

Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

Sail the Delaware River at sunset with a USCG-licensed captain

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

Watch Provincetown’s shoreline glow from a classic Victorian yacht

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 guests

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Private Delaware River day sail for up to six guests

Private classic schooner sail with lighthouse and cove views

Take the helm on a hands-on private sail around Grand Marais Harbor

Build hands-on skills for independent coastal sailing on larger boats

Get a taste of sailing with hands-on time at the helm