For the 50+ Traveler
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“Girls just want to have fun.” Cyndi Lauper’s hit is the mantra of overworked women seeking out time to relax and have fun with their besties. When you carve out some getaway fun time, the New England region has everything from sophisticated shows and fine dining to beachfront rentals and drag shows. There is a girls’ getaway weekend just waiting to happen.

Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.

Set Sail To Provincetown

Grab the Provincetown Ferry and leave your car and your work-a-day worries behind. Quirky and flamboyant, a weekend getaway in Provincetown, P-town to the locals, has shopping, great food, raucous entertainment, and fun in the sun. Stroll down Commercial Street popping in and out of cute shops. Linger at the beautiful art galleries that sell local artists’ work and discover that perfect piece you have been hunting. Walk down the pier and join a whale-watching expedition. When night falls head over to the Crown and Anchor for a comedic drag show. Laughter is the best medicine, and you will have all you need to cure what ails you. For a toes-in-the-sand stay, check out this Boatyard Luxury Waterfront Apartment that sleeps eight with four bedrooms. Is there anything more relaxing than staying right on the beach? The third-floor apartment has a deck overlooking the sand and the ocean views beyond.

Pro Tip: You don’t need a car when visiting P-town. Everything is within walking distance. For help planning your getaway, check out The Best Things To Do In Provincetown, MA: Where To Stay, Eat, and Play.

Spa Retreat, Lenox, Massachusetts

Canyon Ranch offers guests a luxurious, all-inclusive getaway. Their Lenox, Massachusetts, wellness resort is located in the heart of the Berkshires. You can simply relax in wonderful self-pampering or get out and push your physicality to the max. Whatever path you choose, you will feel grounded and centered when the weekend is over. Each participant can choose their own “pathway” during the stay. The diverse offerings include the Personal Discovery Pathway, Optimal Health Exploration Pathway, Outdoor Escape Pathway, and several others. Each pathway has a central theme and activities tailored to your every need. Additionally, there are over 35 activities that happen each day included in your stay. Choose from yoga classes, wellness talks, workouts, hikes, and creative classes to make up your own unique experience. At the end of the day, join your gal pals for a beautifully prepared dinner and lively conversation where you can come together to share your wellness journey.

Pro Tip: Canyon Ranch also has wellness resorts in Tucson, Arizona; Woodside, California; and Las Vegas, Nevada, and offers programs that explore the location along with catering to your health and well-being.

Elegant Country Inn

The Woodstock Inn, located in Vermont, is synonymous with classic country elegance. The resort resides in the quintessentially quaint town of Woodstock. Exquisitely appointed rooms, luxurious fine dining, and a verdant rural location take you miles from your work-a-worries. This is the spot to slow down, reflect, and replenish.

Spend the day experiencing rejuvenating treatments in the spa, don your hiking boots and explore the Green Mountains, learn a new sport -- fly fishing, play a round of golf, or just relax and immerse yourself in a great novel. The Woodstock Inn has a pre-packaged Girlfriends’ Getaway and all you need to sign up!

Pro Tip: Beautiful anytime of year, the Woodstock area is spectacular in autumn. For more information about Woodstock, see our tips for The Best Things To Do In Woodstock, Vermont.

Shopping in Portland, Maine.

Shop Till You Drop

Situated on the jagged Maine coastline, Portland is a quaint seaside town perfectly located between two major shopping extravaganzas. Just 50 miles north of Kittery, Maine, home to a wide array of outlet stores and 20 miles south of Freeport, home to L.L.Bean, Portland is a nice resting spot for shopping-all-weekend getaways.

Portland is a beautiful harbor city with amazing restaurants, making it the perfect place to gather after a long day of hunting for the shopping find of the trip. Live your best girls’ getaway life and stay at Cornelia, a waterfront penthouse rental that sleeps four. With clean modern lines, gorgeous harbor views, and an industrial loft feel, you can relax in luxury after a day browsing the sales racks.

Shopping at the Kittery Outlets requires comfy sneakers and a good map. The outlets are spread across Route 1 in cluster malls. You will need your car to traverse the groups of stores. However, the malls offer everything from Adidas to Yankee Candle. You will surely find some great buys and enjoy bargain hunting with your girlfriends.

Take the short drive up to Freeport and experience the L.L.Bean flagship store. Actually, it’s several stores located on an enormous campus in the heart of downtown. The main store has all the great L.L.Bean clothing you love. There are four other storefronts worth a peek: the Outlet; Home; Bike, Boat, and Ski; and Hunting and Fishing. Each store has something unique to offer. Even if you are not in the market for a new canoe, the best backpack, or a plaid sofa, checking out the latest L.L.Bean style is a fun way to spend an afternoon. To learn more about Freeport, visit How To Spend A Fantastic Day In Freeport, Maine: Shopping, Eating, And Relaxing.

Pro Tip: Portland is a foodie town -- bring your appetite and sense of adventure. For some great dining ideas visit Eating Local In Portland Maine: The Best Restaurants To Try. Maine lobster is always a good choice.

Sunset in Portsmouth, New Hampshire.

Pub Crawl

Portsmouth, New Hampshire, is a pretty city on the water. The compact downtown district is filled with shops, restaurants, and breweries. It is a fun place to shop a little, drink a little, and enjoy great company.

The Portsmouth Brewery takes center stage when it comes to brewpubs. Order a flight to sample their wonderful brews. Pair your beverage with some upscale pub grub and start your crawl off with a satisfying meal.

Earth Eagle Brewings offers a kickback, neighborhood vibe with a casual outdoor beer garden. Try their New England Gangsta brew while munching on a hot dog -- the perfect Downeast combo.

At the Thirsty Moose Tap House, you don’t need to wear flannel, but you can if you want. Their on-tap offerings come from around the New England area. From Cisco to Harpoon to Smuttynose, you will find tried-and-true pints along with some unique brew purveyor options. Their seasonal menu offers bites, burgers, and pizzas.

Pro Tip: To fill up your itinerary with activities other than sampling brews, visit How To Spend A Day In Portsmouth, New Hampshire.

Dinner And A Show

If you only have time for a quick getaway, dinner and a show in Boston is a sophisticated way to have some high-brow girl fun in a short timeframe.

Begin your adventure with an elegant dinner at one of Boston’s best restaurants. Ostra, a Mediterranean-inspired seafood restaurant in the Back Bay, is an excellent choice for a stylish evening out. Alternatively, Strega, in the North End, offers exquisite Italian cuisine and an unforgettable dining experience. Advance reservations are required for both of these fine dining establishments.

Boston is home to some historic theaters that host hit Broadway shows. You can peruse all your options for Theatre District Shows to find exactly what you need for a memorable girls’ overnight getaway. Whether you want a kinky comedy, a serious drama, or an old-school musical, you will find a great show that everyone in your group getaway will enjoy.

After the show, rest your head at the Four Seasons Hotel, Boston’s five-star luxury hotel. Elegant and refined, it is the most sumptuous stay for a night with your best girlfriends.

Pro Tip: If you have more time to visit this wonderful city, 11 Things Everyone Should Do In Boston is a good resource for ideas.

Relaxing Beachside Getaway

Gorgeous private beach, your own cabana, drinks served while you tan, and your own villa just steps away. Can’t you almost feel your shoulders relaxing as you consider the possibilities? Ocean Edge Resort in Brewster, Massachusettes, is the perfect luxury seaside girls’ getaway.

Select either the Edinborough or Endicott Villas for accommodations that sleep up to eight guests, and there is enough space for all your gallivanting gal friends. With a spa, restaurant, golf, and private beach steps from your villa, you have everything you need for a relaxing, sun-filled, best friends’ vacation without ever having to leave the resort.

Additionally, Ocean Edge just launched a new, just-in-time-for-summer, pod-cation package “The Crew on the Cape!” The package includes one of their two or three-bedroom villas, a resort activity credit, and a whale-watching tour or sunset cruise perfect for your gal pal pod getaway.

Pro Tip: You can select either the golf-focused villas or the private beach-focused villas. Be sure to discuss the options with their reservation staff.

Getting away with your best gal pals is good for your mind, body, and soul. We rely on our girlfriends to keep us centered and real. Take the initiative, propose a weekend getaway, pick a date, choose your favorite location, and plan an adventure with your girls. You will be so happy you did! For even more inspiration, consider more of our favorite New England getaway ideas:

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