things to do in South Dennis, MA

See Nantucket's harbor from the water with ice cream for everyone

A family-friendly private harbor outing with ice cream for everyone

Cover more of Martha's Vineyard with pedal-assist power

Cruise comfortably at your own pace on an easy-riding bike

Bring your favorite drinks for a relaxed hour on Nantucket waters

Bring your favorite food and drinks for an evening on Nantucket Harbor

See Nantucket's whaling-era landmarks from the water before the day gets busy

Gather your group for music, drinks, and water views around Nantucket

Cruise Nantucket waters while uncovering the island's whaling-era landmarks

Make Nantucket Harbor your private setting for an evening cruise timed for sunset

Cruise comfortably with a bike built for relaxed riding

Customize a private 4-hour Martha’s Vineyard island tour with flexible stops

Fish Cape Cod Bay on a private 4-hour charter for up to 6 people

Private 3-hour beach cruise for up to six, with snacks and soft drinks included

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

Cruise Provincetown Bay at sunset with snacks and soft drinks

Tour all 6 Martha’s Vineyard towns in 3 hours, with time for photos and a Menemsha stop

Watch Provincetown’s shoreline glow from a classic Victorian yacht

Charter a private sail in Provincetown for up to 34 guests

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Taste Truro Vineyards wines and spirits aboard a historic schooner

Fish Cape Cod Bay on a private 3-hour charter for up to 6

Try fishing in Cape Cod Bay on a 2-hour kids-friendly private charter

Join a 6-hour Cape Cod Bay fishing charter with a licensed captain