Cape Cod Rail Trail
Lindsay Buckley They say the best things in life are free, something that certainly applies to this long, winding trail that spans 27.5 miles from Yarmouth all the way to Wellfleet. With vistas of ponds, cranberry bogs, and wildlife sanctuaries — not to mention an eclectic mix of specialty stores and cafés to recharge when the going gets tough — there’s plenty to see and do along the way. Major expansions and upgrades planned for the next few years, meanwhile, mean you’ll never get bored by the scenery. 3488 Main St., Brewster, MA 02631, mass.gov/locations/cape-cod-rail-trail.
Respoke
These shoes were made for walking — in only the coolest of places. Former fashion stylist Michael Tonello has repurposed his collection of designer silk scarves into handcrafted espadrilles that are now sold in specialty stores across the country. Snag them right here in P-town at the flagship boutique, where you’ll also find similarly made clothing and accessories. 145 Commercial St., #3, Provincetown, MA 02657, respoke.com.
Añejo
Trade your mimosas for margaritas at this brunch hot spot, which serves up creative Mexican cuisine with a Cape twist (see: the quahog rellenos and chipotle-laced lobster bisque). Dine beneath a centuries-old weeping beech tree at the Hyannis outpost, or sit back and people-watch, Paloma in hand, from the Falmouth location’s patio — either way, you’ll find a fun atmosphere that makes every Sunday feel like a party. Multiple locations. anejo.cc.
Winnetu Oceanside Resort
Courtesy Photo The Winnetu takes the prize this year not only for its comfort, charm, and amenities such as poolside cabanas and front-lawn clambakes, but also for its new programming. The resort’s Over-Sand Beach Day package includes a bottle of prosecco, a picnic lunch, and a permitted Jeep waiting to take you on a romp to one of the island’s outer beaches. Signature oyster tours and kayaking expeditions, meanwhile, round out the summer adventures. 31 Dunes Rd., Edgartown, MA 02539, winnetu.com.
Moshup Beach
New England Images by Allan Wood/Alamy Stock Photo We’ve finally ditched the masks. Now it’s time to … ditch the clothes, too? Embrace the Roaring Twenties on this remote stretch of sand and boulders at the foot of the Gay Head Cliffs, where nudity is the norm (though you’ll at least want to bring a pair of sturdy, waterproof shoes for the 10-minute walk from the public Philbin Beach parking lot). Once you get comfy with the clothing-optional dress code, you’ll be able to marvel at the vibrant clay that makes up the cliffs surrounding the beach. Just don’t touch: The natural treasures, sacred among the native Wampanoags, are under environmental protection to thwart erosion. 71 Moshup Trail, Aquinnah, MA 02535, .
Mikel Hunter Fine Art & Apparel
As overused as the word “curated” may be in the retail industry, there’s simply no other way to describe the one-of-a-kind fine art, clothing, accessories, and jewelry hand-selected by owner Mikel Hunter, a veteran of both the fashion and gallery worlds. Small-batch designer duds? Check. Paintings by collectible emerging artists? Check. Everything and anything unexpected? Double check. 11 Winter St., Edgartown, MA 02539, mikelhunter.com.
Galley Beach
Elizabeth Cecil Close your eyes and imagine an open-air restaurant with tables right on the sand and canvas canopies that flutter in the gentle sea breeze. No, it’s not the scene at some all-inclusive Caribbean resort — it’s dinner at Galley Beach, where every table has a prime view of Nantucket Sound. At sunset, diners often leave their shoes under the table and walk barefoot to the water’s edge for photo ops beneath a painted sky, making this the perfect spot to celebrate the end of yet another beautiful day on Nantucket. Be sure to check out the new, reservation-only prix-fixe bar menu, offered only during that wonderfully languid time between lunch and dinner, but be forewarned: You may still be there by dark. 54 Jefferson Ave., Nantucket, MA 02554, galleybeach.net.
Polpis Bike Path
Looking for a post-quarantine quad challenge with the best views on the island? Stretching from the Old South Road rotary all the way to ’Sconset, this 9.5-mile paved route is it. Once you’ve cruised past the sky-blue inlets of oyster farms and mile upon mile of emerald-green moors buzzing with songbirds, soothe those achy muscles with an icy drink from the Sconset Market, or refuel with an ice cream (or two). An easy and quick pedal from there to the Sankaty Head Light offers an unforgettable view of the Atlantic. Nantucket, MA
Current Vintage
Donning yoga pants on the mainland is one thing, but what you wear on Nantucket is an entirely different ball game. The bolder and more colorful the print, the better — and Current Vintage, a boutique vintage clothing and home-goods store in downtown Nantucket, is here with everything you need to look island-chic. Proprietor Elisabeth English has put together a collection of vibrant, hard-to-find apparel that’s classy, not costume-y (think: Emilio Pucci and vintage Lilly Pulitzer, originally known as the Lilly), along with wine, cheeses, and other goodies you’ll surely want to bring back home. 4 Easy St., Nantucket, MA 02554, currentvintage.com.