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.
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.
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.
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, .
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.
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
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.