Best results for
Sailing in Wellfleet, MA
Showing 1-12 of 12 results
Sunset Sailing Charter in Harwich
A private evening sail with room for your own refreshments
4.8 • 134 reviews
Private 2-Hour Sailing Charter in Harwich
Set sail privately with your group on Pleasant Bay
4.8 • 134 reviews
14' Catamaran Rental on Pleasant Bay
Take the helm of a forgiving catamaran for easy bay sailing
4.8 • 134 reviews
Private Sailing Lesson in Harwich
Learn sailing fundamentals with private on-water instruction
4.8 • 134 reviews
2-Hour Sunset Sail in Provincetown
Sail Provincetown at sunset on the historic Schooner Hindu
Sail Boston Harbor on the Cutter Bloodhound
Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival
Bloodhound Daysail In Provincetown
Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard
Sunset Sail in Provincetown
Watch Provincetown’s shoreline glow from a classic Victorian yacht
Private Sailing Charter in Provincetown
Charter a private sail in Provincetown for up to 34 guests
Sail Boston Harbor on the Historic Schooner Hindu
Sail Boston during Sail Boston 2026 on the restored Schooner Hindu
90-Minute Private Schooner Charter in Provincetown
Private classic schooner sail with lighthouse and cove views