The long wooden dock at Wequassett extended like a forefinger into the peaceful waters of Pleasant Bay. It's like an invitation, beckoning across the bay toward the Cape Cod National Seashore in Massachusetts.
We had a picnic basket in hand -- along with books and beach towels, an umbrella and chairs -- on our way to a remote barrier beach island that didn't exist until 2007, when a storm created a new inlet along Outer Beach.
From the dock at the Wequassett Resort & Golf Club, it's a 20-minute boat ride on the Outer Beach Shuttle. The complimentary charter service is reserved exclusively for registered guests of Wequassett, the five-star resort nestled into the Lower Cape -- or what's known as the "elbow" of Cape Cod, home to the towns of Chatham, Harwich, Orleans and Brewster.

Resort guests can take a shuttle to a remote barrier beach island that didn’t exist until 2007, when a storm created a new inlet along Outer Beach. Photo Credit: Wequassett Resort & Golf Club
It was a gorgeous day on the aptly named Pleasant Bay, and as we traversed the tranquil water, our guide, Cap'n John, shows us his phone's Sharktivity app. The most recent Great White sightings have been added in the past 48 hours. This is a species that tops out about 20 feet in length. Cap'n John looks up from his phone and says, "So, you catch my drift then?"
We're intrepid, but not stupid. Carefully, we disembarked into the bay's shallow water and hiked over the dunes.
A Cape Cod classic

Accommodations at Wequassett include cedar-shingled cottages, villas and signature suites with gas fireplaces and private decks. Photo Credit: Wequassett Resort & Golf Club
For more than a century, Wequassett has been hosting guests at the secluded 27-acre resort along the scythe-shaped shoreline of Pleasant Bay. Originally settled by the Wampanoag people who lived on Cape Cod more than 400 years ago, the word wequassett means "crescent on the water."
Wequassett opened as an inn in 1925 and generations of families return to Pleasant Bay year after year. A member of Preferred Hotels & Resorts' Legend portfolio, the expansive resort recently completed a $12 million multiyear renovation to coincide with the property's centennial. Included in the renovation was a refresh of 113 rooms, villas and cottages.

A $12 million multiyear renovation included a refresh of 113 rooms, villas and cottages. Photo Credit: Wequassett Resort & Golf Club
As we wandered toward our cottage along the red-brick footpaths lined with hydrangeas and rhododendron, I was reminded of the sense of escape so often associated with summer camp. There's a blissful sense of distance from the outside world at Wequassett, and it's easy to feel as if you've arrived in some bucolic natural preserve.
In keeping with the resort's location alongside a federally protected wet zone and seashore, Wequassett's commitment to sustainability includes the restoration of the waterfront, water conservation with Kohler's high-efficiency water fixtures in all guestrooms and water stations located throughout the property that offer purified water with electrolytes. Oyster shells from all Wequassett restaurants are recycled and returned to local waters, thanks to a partnership with the Massachusetts Oyster Project.
Wequassett's collection of accommodations includes the aforementioned cedar-shingled cottages, along with villas, signature suites and specialty rooms. There's also The Mother Goose House, a private home for multigenerational groups and extended stays. The serene interiors evoke a "home away from home" atmosphere, with a nod to the resort's nautical heritage and coastal surroundings. Amenities include gas fireplaces and private decks as well as marble bathrooms with soaking tubs, coffee machines, nightly turndown service and 24-hour in-room dining.
Activities onsite and off

Wequassett’s main pool is flanked by luxury cabanas designed by Sister Parish, the original design firm for the Kennedy White House. Photo Credit: Wequassett Resort & Golf Club
Guests who wish to golf have access to the neighboring Cape Cod National Golf Club, one of the nation's most prestigious 18-hole courses. Ranked as one of the top 20 private courses by Golf Digest, the par 72 championship course is notable for its breathtaking views and smooth fairways. As for tennis, Wequassett's three courts are onsite alongside three pickleball courts. There's also an adults-only lap pool tucked behind a pirate ship playground for children.
Wequassett's main pool is flanked by luxury cabanas designed by Sister Parish, the original design firm for the Kennedy White House. The resort also features a Barbour Borrowing Closet for guests, which includes the brand's signature waxed jackets and Wellington boots that are perfect for autumn walks, cranberry bog tours and clamming on the shore. For guests who wish to travel off-property, Wequassett has paired with both Barbour and BMW, offering luxury outerwear and a choice of luxury vehicles.
Apart from the Outer Beach Shuttle, guests at the resort can partake in a variety of maritime experiences with Down Cape Boating. We were tempted by the Shark Alley Tour, but the company also offers seal tours, charter fishing and sunset sails. Whale watching continues through October.
The food scene

A member of Preferred Hotels & Resorts Legend portfolio, Wequassett first opened as an inn in 1925. Photo Credit: Wequassett Resort & Golf Club
Upon our return from Outer Beach, we headed to dinner at Outer Bar, Wequassett's waterfront restaurant with its signature peaked canopies. As the sun set over Pleasant Bay, we dined on local seafood and listened to live music. Each summer, Wequassett is host to the Cape Cod Jazz Festival, now in its 22nd year.
Wequassett is also home to Twenty-eight Atlantic, the Cape's sole Forbes Five-Star restaurant, where executive chef James Hackney serves a prix fixe menu that features caviar, crudo and lobster cacio e pepe. For off-property dining, we headed down the road to Mac's Chatham Fish & Lobster on Main Street. One of Cape Cod's most popular seafood restaurants, Mac's is notable for its lively vibe and local fish. You're all but guaranteed a good time.
On our final morning at Wequassett, we enjoyed an alfresco breakfast at The Verandahs, the resort's seasonal outdoor restaurant that overlooks Pleasant Bay. The water was completely placid, so still that the boats and birds were reflected like mirror images.
That morning, it was easy to understand why the Wampanoag returned to Wequassett every year -- and why Wequassett remains such a draw for visitors to the Cape.