Escape to These 4 Towns for a Romantic Getaway

For anniversaries, mini-moons, or sweet retreats

Updated 03/29/19
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Courtesy of Chatham Bars Inn

When you live in cities like New York, Boston, Philadelphia, and Washington D.C., the weekend getaway is a blissful and very essential retreat. Obviously, these bustling metropolises are built with an electricity that keeps people hooked, but understandably, the buzzy pace warrants a relaxing escape at one point or another. What’s more, in these cities, the getaway crowd can be oddly familiar—ask anyone in New York who frequents Montauk or the Hamptons in the summer and they’ll tell you it’s mostly the same people simply relocated to the beach. The same goes for other popular destinations like Nantucket, Martha’s Vineyard, and the Berkshires—not always the peaceful retreat everyone is looking for. But there’s a solve: smaller neighboring towns that make for relaxing and romantic getaway destinations whether you’re craving a seaside escape, want to explore a historic city, or enjoy a retreat to the mountains. Ranging from short drives to reasonable train rides and couple-hour flights, these towns are the perfect way to enjoy time away with your loved one whether you’re simply escaping the city, celebrating an anniversary, planning a proposal, or taking a mini-moon.

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Chatham, Massachusetts

Courtesy of Chatham Bars Inn

Cape Cod is one of the première getaway towns for East Coasters and Chatham is one of the oldest and most picturesque towns at the southeastern tip the popular peninsula. Known for its delightful beaches and historic landmarks, there’s an enchanting feel to this charming seaside village from the store-lined main street (including the well-known sweet treat mecca, Candy Manor ) to the iconic Chatham Bars Inn . Over 100 years old, the storied resort was originally a luxury hunting lodge and offers 217 guest rooms ranging from luxurious spa suites (which include in-room saunas, steam showers, hydrotherapy tubs, and fireplaces) to charming shingle-style cottages and beautifully restored rooms in the original Main Inn. A romantic way to spend a weekend with your S.O., the resort is also an idyllic spot for a serene bachelorette getaway or destination wedding, boasting a private beach, exceptional spa, recreational activities from golf to ocean excursions (including seal and whale watching), and best of all, an eight-acre farm that supplies sustainably grown produce for the resort’s exceptional restaurants, decks, and lounges, led by Chef Anthony Cole. For a true farm-to-table experience, guests are able to forage for produce at the resort’s farm, take part in cooking classes, and attend alfresco family-style dinners in the summer as well as traditional New England-style clambakes.

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Portsmouth, New Hampshire

Carl Heyerdahl

Portsmouth is an utterly pleasant coastal town in New Hampshire, about an hour and a half drive from Boston and approximately five hours by car from New York City. With picturesque streets and a maritime feel, a diverse range of boutique hotels, culinary experiences, and seafaring activities are available from The Hotel Portsmouth to the nearby The Wentworth Inn (which has an unbeatable pre-fixe brunch). For the perfect weekend, spend a few hours relaxing at the not-too-crowded beach, enjoy a sail through the Piscataqua River then stroll the bridge which connects New Hampshire and Maine, and explore the charming downtown area’s assortment of shops, restaurants, and bars with everything from drinks to bites and local seafood—Book & Bar, Row 34, Raleigh are just a few top spots. Likewise, for the buzzy coffee shop Breaking New Grounds and local brunch haunts such as The Friendly Toast and Popovers On The Square.

Portsmouth is also a major destination for brides-to-be. Madeleine's Daughter Bridal is the go-to bridal salon with the most extensive gown selection in New England including collections from Pronovias, Haley Paige, Anne Barge, and many more. Brides from neighboring towns and cities, including Boston, schedule private appointments with stylists in the private (and very beautiful) bridal suites.

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Charleston, South Carolina

Courtesy of Explore Charleston

For foodie couples willing to catch a quick flight, Charleston, South Carolina is the definition of a charming getaway—by plane, it’s less than two hours from Washington D.C. and just over two hours from New York City. With so much to do and see, the southern town is an extremely popular destination for bachelor and bachelorette parties, but you can have a romantic weekend just the same with the right itinerary. To stay, the historic Belmond Charleston Place offers gorgeous rooms with a stately appeal, plus, a luxurious spa where you can enjoy rejuvenating treatments with your S.O. in the couples rooms, followed by a swim in the reflection pool. Or, check out the buzzy new Hotel Bennet for a luxurious and centrally located stay with expansive city views that overlook Charleston’s iconic Marion Square.

For a quintessential afternoon of sightseeing, stroll through the cobblestone streets of the French Quarter neighborhood and take in historic architecture from the famous pastel homes of Rainbow Row to the breathtaking mansions that line the Waterfront Park and White Point Garden (if not by foot, riding bikes is a fun and active way to take in the area while a horse-drawn carriage tour is a romantic way to learn about the city rich history). For a bit of shopping, Hampden Clothing on King Street offers a well-curated assortment of designer and contemporary labels while Gwynn's of Mount Pleasant (which is a quick drive over the scenic Arthur Ravenel Jr. Bridge) offers a similar assortment, though with private shopping suites where you can sip champagne between try-ons. A tour of the Magnolia Plantation and Gardens is another romantic way to spend an afternoon while a sunset sail via the Schooner Pride is the ultimate way to see the city skyline.

With an explosive culinary scene, the restaurant options in Charleston are seemingly endless, though, not-to-be-missed standouts include Melfi's, Millers All Day, Le Farfalle, Husk, The Grocery, McCrady's Tavern, Rodney Scott's BBQ, and Poogan's Porch.

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Windham, New York

Courtesy of Eastwind Hotel

About two and a half hours north of Manhattan, Windham is a small mountain town nestled in the Catskills. Known for skiing at the Windham Mountain Resort, this quaint town is the ultimate location when you want just enough, but not too much to do. Attracting more buzz in recent years, it’s a great getaway in both summer and winter, especially if you’re into hiking and snow sports. To stay, the Eastwind Hotel & Bar is a darling hillside boutique hotel surrounded by a lush landscape with expansive views of the mountains. Whether you choose to stay in one of the unique insulated Lushna cabins (with a close-by wood barrel sauna and hot tub) or in the main lodge with a cozy-chic aesthetic that draws upon the property’s history as a bunkhouse for hunters, fly fishermen, and outdoor enthusiasts, you can spend the entire weekend on property enjoying the salon-style cocktail bar, fireplace, and activities that range from game nights to a Saturday night-only chef's menu-style dinner with wine pairings and homemade weekend breakfasts or venture out and explore the town’s local shops and cuisine—The Windham Local, Ze Windham Wine Bar, and Neapolis Pizzeria & Grille are worthwhile spots. If you have a car, Gaskins and Phoenicia Diner are two close by hits, each about 40 min from the Eastwind.

To get to Windham, LINE bus offers a direct route, dropping of at the Eastwind hotel and whilst in town, there is a complimentary shuttle service to get around via an app.

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