Cape Cod Boat Rentals & On the Water Experiences

A man and woman sit closely together, wrapped in a dark blanket, relaxing on the deck of a sailboat with water and the shoreline near the Wequassett resort in the background. — On the Water Experiences

Experiences Overview

Wequassett Dock

Go Beyond the Shore with Down Cape Charters

Just steps from the dock at Wequassett, Down Cape Charters invites you to experience Cape Cod from the water—where private sailing, whale watching, Chatham Harbor & Seal Cruises, and Nantucket day trips unfold against a backdrop of breathtaking coastline. Whether setting out for adventure or a leisurely escape, each journey offers a refined perspective on the Cape’s natural beauty.

Visit Down Cape Charters & Boat Rentals for more information.

A man and woman sit on a boat, smiling and clinking champagne glasses, enjoying luxurious On the Water Experiences with sparkling sunlight in the background.

Come Sail Away

Step aboard Maria, a classic luxury daysailer, and experience Pleasant Bay at its most captivating. Offered exclusively as private charters, each outing invites you to relax and take in the beauty of the water. As day turns to evening, there’s nothing quite like a sunset sail, when golden light fades into the horizon and the bay settles into a quiet, effortless glow.

Set Sail

A group of seals rest closely together in shallow water, with one seal in the foreground facing the camera—capturing a serene moment of on the water experiences.

Chatham Harbor & Seal Discovery

Experience Cape Cod from the water on a Chatham Harbor & Seal Tour, a favorite for guests of all ages. With daily group departures and private charter options, each outing offers a relaxed introduction to the coastline.

Cruise past windswept dunes, spot seals along the sandbars, and take in views of working fishing piers, historic landmarks, and classic waterfront homes—an effortlessly Cape Cod perspective.

Explore More

A humpback whale lifts its tail flukes above the ocean’s surface, water splashing around the edges—an unforgettable highlight for those seeking unique Water Experiences.

Whale Watching

Set out on a private whale watch experience, an intimate alternative to the larger vessels found across Cape Cod. Depending on the season, sightings may include humpback, finback, and minke whales, along with seals, porpoises, gannet birds, and ocean sunfish. Offered June through Columbus Day, each journey offers a rare chance to witness the extraordinary marine life of our coastal waters up close.

Reserve your spot

A small lighthouse stands on a narrow strip of land by the water, offering unique On the Water Experiences, with people nearby and numerous sailboats anchored in the harbor in the background.

Nantucket Day Trip

Set out on a private Nantucket day trip, where your captain transports you and up to 12 guests across the Atlantic to the island’s iconic shores. Along the way, take in sweeping coastal scenery, passing lighthouses, and the chance of spotting seals. Upon arrival, enjoy the day at your own pace—stroll cobblestone streets, explore boutiques and galleries, dine at seaside restaurants, or set off by bike or guided tour. Your captain remains on call and will be ready for your return, ensuring a seamless journey from shore to island and back again.

Plan Your Trip

Private Fishing Charter on Cape Cod

Set out with an experienced captain on a private half-day charter and explore these renowned fishing grounds. From Nauset Beach to Monomoy Island and into Nantucket Sound, the focus is on striped bass and bluefish—two of the East Coast’s most sought-after catches. In the shoulder season, black sea bass and false albacore add to the experience.

Welcoming all ages and skill levels, each outing is thoughtfully tailored to your group—whether you prefer a focused day of fishing or a more relaxed approach that blends time on the water with coastal sightseeing.

Visit Down Cape Charters & Boat Rentals for more information.

Let's Go Boating

Discover the water at your own pace with Hobie catamarans, kayaks, and stand-up paddleboards, each offering a different way to experience the beauty of the bay.

Have you always wanted to learn to sail? There’s no better setting. Our experienced instructors offer thoughtful, personalized guidance, introducing the fundamentals with ease and confidence—so you can feel at home on the water from the very first moment.

Experience Cape Cod by Water

Located on 27 acres of gardens, salt marshes and woodlands, this family-friendly Five-Star resort has one of Cape Cod's best locations overlooking Pleasant Bay and the Atlantic Ocean.

Caldwell Family
August 2019

On the Water Experiences