Water Activities in South Dennis, MA

Paddle Sengekontacket Pond with a private guide tailored to your group

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

Set out on a private captain-led motorboat outing with your group

Set sail privately with your group on Pleasant Bay

Paddle a Cape Cod inlet at your own pace

Share a private motorboat charter as you watch for whales off Cape Cod

Explore Martha’s Vineyard waters with your group

Watch Provincetown’s shoreline glow from a classic Victorian yacht

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

Set your own course for a private outing on the water

Paddle a Cape Cod inlet at your own pace

Build foundational paddling skills with an ACA-certified guide

Charter a private sail in Provincetown for up to 34 guests

Take the helm of a forgiving catamaran for easy bay sailing

Get Cape Cod gear delivered for two days of self-guided exploring

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

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

Private classic schooner sail with lighthouse and cove views