Gated Getaway in Charming Cape Cod Town

A 19th-century whaling commander once kept quarters in the Captain's House, a charming New England federal-style building that rests within the gates of the Brass Key Guesthouse property in vibrant Provincetown. Today, the whaler's house has been renovated and sports American antiques and elegant upholstery, a salt-glazed pottery collection, board games, and a rooftop deck that overlooks a vast patio with an infinity-edge pool. Surrounding the pool are a small sector of suites, cabanas, guesthouses, and other charming buildings—each possessing a unique character that exemplifies Brass Key's keen attention to detail in creating a romantic, relaxing atmosphere for its shore-side getaway.

After a day sipping complimentary poolside beverages or kicking back in the in-ground hot tub, guests can retire to their well-appointed chamber. In rooms with queen-size beds, windows may peek out to the interior courtyards, the harbor, or the neighboring streets, and most bathrooms come with European body-spray showers. Meanwhile, a cozy fireplace warms up many king rooms, where guests may wash off in a dual-control shower or reenact famous typhoons in the jacuzzi tub. Come evening, toweled-off tenants can join in the resort's social hour to sip complimentary wines and beers and nibble on complimentary cheeses and crudités. When the sun rises over the ocean in the morning, an expansive awning covers guests as they nosh an expanded continental breakfast near the property's surrounding English gardens.

The nearby Shui Spa welcomes guests to apply a credit toward any treatment or massage. The spa menu touts transformative treatments such as the chardonnay facial ($109), which exfoliates weathered countenances with a 20% multi-fruit-acid complex designed to fortify faces with essential nutrients and antioxidants before topping off the treatment with a glass of local wine. Complexly knotted shoulders may unfurl with a deep-tissue massage ($129 for 50 minutes), which employs an arsenal of strokes and tenderizing techniques to whisk away aches and painful muscle memories.

Provincetown: Progressive Peninsular Merriment

Provincetown—once the signing site of the Mayflower Compact by the Pilgrims—has established itself as an artists' colony and a premier LGBT-friendly community. Commercial Street runs parallel to the harbor shoreline and brandishes everything from fine dining to beachside takeout, and an array of galleries, boutiques, cafés, and a vibrant nightlife sing inviting siren songs to sojourners.

Whitecapped ocean waters and accessible beaches fence in Provincetown on three sides. Bicycles may be rented in town to explore the breathtaking National Seashore. A quick pedal 1 mile into the countryside reveals Herring Cove Beach, where sightseers gather each evening to catch dazzling views of the sun as it puts on scuba gear and submerges into the horizon.

More than 125 wines swish in their bottles at the nearby Bistro at Crowne Pointe, where culinary engineers creative fare in an intimate 40-seat setting. Their fresh-seafood-centric menu carries a flavorful spread of small and large plates.