New York has the Hamptons, Rhode Island has Watch Hill and Massachusetts has Cape Cod. Each of these East Coast vacation hot spots has their appeal, but I’ve always been partial to Cape Cod. There’s something almost surreal about the Cape; from the moment you cross Bourne Bridge, a sense of tranquility falls over you. Watching the hustle of the city fade away, you can feel yourself adjusting to the low-key pace of the peninsula.
Sure, you can revel in the luxury of a five-star hotel or feast on fresh seafood at a top-notch fine dining establishment, but no matter where you are, the Cape Cod atmosphere is still low-key, laidback and easygoing. You don’t need to dress in your fanciest designer garb; just show up in a crisp pair of white jeans and wedge heels and you’ll fit right in.
Tucked in between all Cape Cod’s discreet luxury are plenty of hidden gems: think a 25-mile picturesque biking, local-beloved clam shacks and seafood markets as well as secluded ocean-front stays. If you’re heading to the Cape for the first time, or if you just want insider tips, then you’re in the right place. I grew up spending every summer on Cape Cod, and I’ve created the ultimate guide featuring all the must-hit spots on the peninsula. Read on to discover the best of Cape Cod.
Subscribe to Observer’s Lifestyle Newsletter
Where to stay in Cape Cod
Chatham Bars Inn is a stately hotel that still retains that laidback Cape Cod charm, and that’s what makes this one of the most uniquely breathtaking properties on the entire coast. The resort consists of soothing, airy rooms and separate villas, with four restaurants and a private beach. For a proper getaway, splurge on a stay in one of the new Spa Suites. Once you’re settled in and relaxed, venture down to the beach restaurant for a quintessential Cape Cod lunch, consisting of lobster rolls and freshly harvested salads from the resort’s eight-acre farm.
After spending summers at the now-closed Cape Cod Sea Camps, I admittedly may be biased, but Brewster is one of my all-time favorite towns on the Cape. It’s exactly what comes to mind when you try to picture Cape Cod; it’s riddled with antique shops, strawberry farms and quaint inns. The Mansion at Ocean Edge sits atop a big lawn, with croquet set up on the grassy expanse. It’s a grand building, with a red roof and accents flanking the stucco exterior. Inside, there are wings filled with various accommodations, with options for classic rooms, suites or villas. Wander past the tennis courts and swimming pool to the tree-lined wooden bridged path, which leads to an opening where you’ll find a beach bar and sandy bay. Spend the day sipping on cocktails in lounge chairs, or watch the sunset over the bay with a spritz or beer in hand at night. This is more of a rugged luxury vibe, embodying much of what makes a Cape Cod vacation so special and unique. If you’re traveling with family, it’s worth considering booking in at The Villages, a different area of property that boasts renovated two- to four-bedroom villas, for extra space.
Red Jacket Beach Resort is another good family-friendly option for those traveling with children. This mid-Cape property has its own stretch of private beach, with tons of activity programming as well as a spa, bike rentals and both indoor and outdoor pools.
Where to dine in Cape Cod
Brewster Fish House offers some of the freshest seafood on the peninsula, with quintessential Cape Cod ambiance. Dine on homemade lobster rangoons, seared tuna, cured Scottish sea trout and lightly fried local squid, which can be enjoyed indoors or outdoors. Pro tip: Come early or plan to wait, as they don’t take reservations and it tends to fill up fast.
If you’re interested in that white tablecloth, fine-dining experience I mentioned, head over to Dennis Port, to the Ocean House Restaurant. This establishment sits right on the water, so you can watch the tide ebb and flow as you dine on charred octopus, lamb lollipops, grilled oysters and more.
For a casual bite, head to Mac’s. The Chatham location is my personal favorite, as you can sit outside on picnic benches while waiting for your order. The locally caught lobster roll is a classic, complete with a side of coleslaw and fries. If you feel like you’ve already eaten your fill of traditional seafood, try the sushi, tuna poke or fried chicken salad. This mini-chain also has outposts in Provincetown, Wellfleet, Eastham and Denis.
Where to drink in Cape Cod
If you find yourself in Provincetown, head to Commercial Street for a full-on party atmosphere. P-Town is a thriving hub for the LGBTQ+ community, and is laden with historical fixtures. One of our favorites? Old Colony Tap, a dive bar with a jukebox and extensive beer selection.
This tasting room is a fun activity if you want to experience locally distilled spirits; it’s open Fridays, Saturdays and Sundays, and uses only Cape Cod-sourced raw materials and ingredients.
What to do in Cape Cod
At some point, you’re just going to have to embrace being a tourist and take the opportunity to see some whales. If you’re up for it, book a spot on one of the Hyannis Whale Watcher Cruises, which leave from Hyannis. Hopefully, you’ll see a few Humpback, Finback or Minke whales, and maybe even a dolphin. Even if you don’t spot a whale, at least you’ll get to enjoy a few hours out on the water.
If you’re a biking enthusiast, strap on your helmet and hit the scenic Cape Cod Rail Trail, spanning 25 miles and weaving through six different towns on the peninsula. There are various entry points, so you don’t have to max out on distance if you’re not an intensive biker. It also gives you the opportunity to explore different towns on the Cape, including Dennis, Harwich, Brewster, Eastham, Orleans and Wellfleet. Make sure to stop at Cobies Clam Shack in Brewster for a quick bite; the fried clams are such a treat.
Where to shop in Cape Cod
Chatham, Main Street
Chatham’s Main Street is overflowing with charming boutiques, memorabilia shops, antique haunts, home décor stores, bookstores, bustling restaurants and so much more. A few of my favorites include Jackie’s, The Black Dog and Cook’s Nook, and definitely stop at Candy Manor, to treat yourself to some next-level fudge.
While adorable local stores are always great, the Mashpee Commons is your go-to stop for all big box necessities. There’s a Lululemon, L.L. Bean and Pottery Barn, as well as a few smaller boutiques interspersed throughout. Once you finish shopping, head to Bleu for a chic French meal.