Best 95 things to do in Dennis, MA

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 guests

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

Soar up to 600 feet over the sea on a parasailing flight

Rent a Yamaha WaveRunner and cruise Oak Bluffs for 1 hour

Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary

Discover all six Martha's Vineyard towns in a small-group guided bus tour.

Paddle a clear-bottom kayak at night with glow lights on State Beach

Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup

Explore Sengekontacket Pond from State Beach with stable kayaks and a quick on-water intro

Build kayaking and paddleboard skills on a 4-day kids series at Sengekontacket Pond

Build paddling skills at any level with a private lesson

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

Build kayak skills with guided games and exploration for kids

Start your day with a beginner-friendly paddle board fitness class

2-hour Plymouth Harbor party cruise with DJ, onboard bar, and landmark views

Cruise Plymouth Bay at sunset with a classic clambake dinner on board

Nighttime harbor cruise with ghost stories and Plymouth history

Sail into the Plymouth sunset with live music, appetizers, and unlimited drinks

Join a pirate crew mission with treasure maps and water cannons

Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group