things to do in South Dennis, MA

Hear Nantucket’s Quaker and maritime stories at landmark stops

Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.

Explore by bike with delivery, helmets, locks, and baskets

Pick up a kayak or paddleboard at Scorton Creek and explore at your own pace

Rent a kayak or paddleboard and explore State Beach from the water

Share a Chatham Harbor motorboat cruise and look for seals

Rent a 52cm road bike with helmet and lock for 24 hours to 1 month

Discover the dune landscape that has inspired generations of artists and writers

Share a whale watch trip from Provincetown and split the boat with other travelers

Pick up a bike in Oak Bluffs and ride the island your way

Fish Cape Cod waters on a 4.5-hour private charter for up to 6

See Pleasant Bay, Chatham, and the Lower Cape from above

Reserve a performance road bike in advance for your Edgartown ride

Trace Nantucket’s Quaker and maritime past on a private narrated ride

Seasonal tastings and local tales on a relaxed walk through Chatham

Pick up a kayak or paddleboard at Lawrence Pond and explore at your own pace

Reserve your kayak online and enjoy a full day on the water with included gear and basic instruction

Cruise Chatham Harbor privately and watch for seals with your group

E-bike rental for 24 hours to 1 week, with helmet and lock

Take in the dunes from an open-air Ford Bronco

Explore Stellwagen Bank's whale feeding and nursing grounds by private boat

Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.

See Monomoy seals up close on a small-group harbor cruise

Aerial views of Chatham, Orleans and Cape Cod National Seashore