The time between summer ending and the Holiday season kicking off can begin to feel long and drawn out. The sun is setting earlier, it’s getting a bit of a chill in the air, and your mind is already thinking about the upcoming holiday season. Why not get away for a long weekend to an easily accessible destination on the East Coast? A quick flight and you’re in rest and relaxation for a much deserved break! 

1. Savannah, GA 

Savannah is the perfect destination for a relaxed weekend getaway if you’re looking for amazing southern hospitality, a stellar cocktail, and beautiful views of the Savannah River. To eat you must get reservations at The Grey, which was opened in a former Greyhound station. The James Beard Award-winning chef Mashama Bailey and John O. Morisano opened the doors in 2015 and it’s still one of the best tables in town. The focus is on local produce, seafood and meat, typically giving an upscale twist to southern classics. After dinner, Leopold’s Ice Cream is the perfect stop to satisfy that craving for a little something sweet. 

Where to stay: Perry Lane Hotel, A Luxury Collection or Thompson Savannah

2. Key West, FL

One of my favorite locations, as I lived in Key West for three years! With sunshine, watersports, outdoor bars, and delicious food, there’s something for everyone. While everyone knows the more famous spots, such as Sloppy Joe’s Bar, it’s the small local places you really want to find. One of my favorites is Mary Ellen’s Bar, located on a small side street. The boozy coffee slushie is perfect for cooling off after walking downtown in the Key West Heat. The Bloody Mary Bar at Rams Head Southernmost is one of the best additions to your brunch. My all-time favorite bar is Southernmost Point Bar, where you can get in some great people-watching and enjoy the perfect Key West weather. 

Where to stay: Casa Marina Key West

3. Middleburg, VA 

A beautiful town in horse country, Virginia, you’ll be surrounded by the Blue Ridge Mountains, expansive rolling hills, and tranquil pastures. With historic sites, gourmet restaurants, and award-winning wineries, there’s no reason not to take the 45 minute drive from Dulles Airport to the stunning area. To make the stay even more special, book a room at the Salamander Resort, to really enjoy everything the area has to offer. With a 22-stall horse stable, you can take a trail ride through 25 acres of property dedicated to entry-level equestrian use. If you’d rather admire the horses from afar you can relax with other activities, such as yoga and spa treatments. Adventure out to Greenhill Winery and Vineyards, or RdV Vineyards, for old-world inspired blends. 

Where to stay: Salamander Resort & Spa

4. Kennebunkport, ME 

Over 100 years ago, Kennebunkport became one of the first resort areas on the Maine Coast, and today it’s a great place to visit all year. Visit the small shops downtown to pick up a gift (or something for yourself), before heading to Mabel’s Lobster Claw for the quintessential Maine lobster roll. If craft beer is up your alley, Batson River Brewing and Distilling is a must-stop. While they’ve opened locations across the state, KPT is the original and still a favorite stop. For an upscale dinner away from the bustle, try Earth at Hidden Pond – where they grow most produce on-site and have a menu that will blow you away. Staying at this beautiful property is also highly recommended. However, staying at the White Barn Inn is amazing as well, and you won’t want to miss the dinner served in their restaurant. 

Where to stay: White Barn Inn, Auberge Resorts Collection or Hidden Pond

5. Burlington, VT 

Who doesn’t dream of seeing the changing leaves in Vermont over the autumn season? With direct flights from New York, Philadelphia, and Washington D.C., Burlington is the perfect place to base yourself. You can spend the morning biking around Lake Champlain, then head to the Ben & Jerry’s factory for a tour and tasting. For locally-sourced food and Vermont cheese, visit Hen of the Wood by chef Eric Warnstedt. For a more casual evening, head over to American Flatbread for wood-fired pizza and locally made craft beer.

Where to stay: Hotel Champlain Burlington, Curio Collection by Hilton 

No matter where you travel, spend a long weekend away for some rest and relaxation. Let the small town atmosphere of these recommendations relax you and head back home refreshed and ready for the holiday season!