East Coast Summer Weekend Getaways

filed under: Travel Guides

Do you work somewhere with summer Fridays? If so, I bet they started last Friday! Summer Fridays are the perfect excuse to extend weekends and embark on a few East Coast summer weekend getaways. The East Coast has some amazing gems that are absolutely made for summer travel. A few of the destinations I’m sharing below are at the very top of my list of favorite places so I know you will find this post insightful and inspiring. It’s time to let your summer wanderlust soar!

P.S. a few other seasonal travel posts I’ve written include quick spring getaways, three fall road trips, and the five best winter weekend getaways on the East Coast.

Summer Weekend Getaways for the East Coast

Nantucket, MA

Take my word for it, it doesn’t get more magical than summertime on Nantucket! Nantucket is such a fantastic getaway for East Coasters because it is so seasonal and thus really shines Memorial Day through Labor Day. However, don’t discount September on Nantucket either… it is still warm and much less crowded! For a little island that is only 15 miles long, there is a ton to do on Nantucket. The beaches on Nantucket are glorious and all offer something different as seen in my guide to Nantucket beaches!

Four other activities I also highly recommend are 1) window shopping for clothing, accessories, art, antiques, nautical home decor, and trinkets in town 2) spending an afternoon eating, drinking, and listened to music at Cisco Brewery (there is a free shuttle from town + it’s family friendly!) 3) sailing on the Endeavor (it’s BYOB) and 4) the Whaling Museum! When it comes to dining, don’t miss Cru (the oysters + lobster rolls = wow!), Galley Beach, Millie’s, Black Eyed Susans, and The Juice Bar (for ice cream!).

Nantucket is the perfect destination if you’re looking for beach summer vacation rentals! I can’t recommend renting though Great Point Properties enough – I’ve used them and they are fabulous! If you’re interested in a hotel, then consider Harborview, 76 Main, Greydon House, The Roberts Collection, or White Elephant. P.S. you can fly directly onto the island easily from Boston, New York City, Washington DC, and Charlotte.

Watch Hill, RI

It doesn’t get more New England than Watch Hill, Rhode Island. If you’re looking for a relaxing, beautiful, slow-paced beach town, then Watch Hill is for you! The jewel of Watch Hill is without a doubt The Ocean House. It is one of the most magical hotels you will ever step foot in with the most vibrant charm and character as well as the most stunning grounds and views. If you want the charming vibe of The Ocean House but don’t want to pay the pricey bill, then consider stay down the road at The Weekapaug Inn. Be sure to enjoy their farm to table restaurants and weekly lobster bakes.

In Watch Hill, spending a day at the beach is a must! Visit Napatree Beach, East Beach, or Carousel Beach. Visit the Watch Hill Lighthouse and the Watch Hill’s Flying Horse Carousel, which is the oldest operating carousel in the United States. Dine at the delicious Ten Sandwiches, The Cooked Goose, Olympia Tea Room, Manunuck Oyster Bar, and Sift Bake Shop. Don’t forget to act like a local and visit family-owned St. Clair’s for an ice cream cone! Last but not least, shop at Savoy Books, Island Outfitters, Highpoint Home, J.McLaughlin, and Bay Breeze Interiors.

Sag Harbor, NY

Sag Harbor is a true gem among all the towns in the Hamptons. I think it has the most quintessential American feel of all the Hamptons towns on Long Island and is just so beautiful + friendly (they have parades on the summer holidays!). Sag Harbor is so fun to visit in the summer for people who live on the East Coast for a number of reasons, the weather is stunning, the food is delicious, there are a surprising number of activities, and the hydrangeas are blooming!

Of all the small towns I’ve been to in America, Sag Harbor is at the top! Spend a day bopping on and off Main Street for art galleries, restaurants, coffee shops, yoga studios, and shopping at Goop, Goldie, Harbor Books, and Monc XIII. Visit one of my favorite casual seafood restaurants, Dockside Grill, by the water and top it off with ice cream at Big Olaf’s. Visit the beautiful Wölffer Estate for wine tasting. If you’re in town on a summer Friday or Saturday, then visit the Wölffer Wine Stand for their summer sunset events. When it comes to somewhere to stay, definitely check out the iconic American Hotel and the coastal cool Baron’s Cove. If you’re seeking a vacation rental, then check out Luxury Retreats, Out East, or Hamptons Rentals.

Hudson Valley, NY

Sitting only about an hour and a half outside of New York City, Hudson Valley makes for an amazing and easy to get to East Coast weekend getaway. The Catskills area is home to tons of adorable Instagram-worthy boutique hotels, yummy locally focused farm-to-table restaurants, and lots of outdoor activities. You’ll see me heading here at the end of the summer for a wedding… can’t wait! Where to stay you ask. I recommend Audrey’s Farmhouse, Shipley Corner, Rivertown Lodge, Tiger House, Wm. Farmer & Sons, and the Glenmere Mansion. Get a taste of Hudson Valley with a trip to Millbrook Winery for wine tasting or Tuthilltown Spirts for whiskey tasking.

Outdoor enthusiasts will want to take advantage of the delicious summer weather here by visiting the Storm King Art Center, walking the Walkway over Hudson, going hiking in the rolling hills and mountains, and shooting at Orvis Sandanona. Perhaps the best way to experience Hudson Valley is by renting a car and driving from town to town stopping at farm stands, taking in the landscapes, enjoying the historical architecture and estates, antiquing, and feasting at the renowned restaurants. History buffs won’t want to miss the Vanderbilt Mansion and the FDR’s house either.

Saint Michaels, MD

Nestled on Maryland’s Eastern Shore, Saint Michaels is a quaint waterside town with a rich history dating back to the late 1770s. This all-American East Coast small town first came on my radar because I discovered and was interested in taking a weekend getaway to stay at the Inn at Perry Cabin. The Inn at Perry Cabin is a historic hotel property that offers just about everything including a spa, pool, local farm to table food, bikes, tennis, golf, boating, sailing, and gardens. The hotel’s waterfront lawn is dotted with Adirondack chairs and couldn’t be more idyllic. (P.s. it was made famous by the movie Wedding Crashers)! We stayed at the Inn at Perry Cabin for our second wedding anniversary and truly loved the property and experience!

If you stay at the Inn at Perry Cabin then you can boat and sail through the hotel but I also recommend sailing the Chesapeake Bay on Selina II or the Skipjack. Other than the water (and crab cakes!), the main attraction of Saint Michaels is the Chesapeake Bay Maritime Museum. It’s family friendly and paints a great picture of the history of the region. The main drag in town is the historic Talbot street, which is lined with colorful shops, American flags, and plenty of charm. Rum enthusiast will want to tour and sample Maryland made run at the micro rum distillery, Lyon Distilling. Also, be sure to eat and drink at Limoncello (SO yummy!), Agave Arts and Juicing Co., Foxy’s Grille, 208 Talbot, and Ava’s Pizzeria.

Outer Banks, NC

The Outer Banks (also known as OBX) is a beautiful stretch of coastal towns, beaches, and barrier islands on the coast of North Carolina. I don’t recommend much of the south in the summer because it is quite hot and humid but the beaches of North Carolina are north enough that they aren’t quite as bad as South Carolina, Georgia, and Florida… a beach breeze is always a savior too! OBX is 75 miles of protected coastline (the Cape Hatteras National Seashore) so it really is a gem of a destination! When thinking about where to stay, consider the islands of Bodie, Hatteras, Ocracoke, and Roanoke. Each island has different little towns and villages on it.

Bodie Island has both very quiet parts to it with no restaurants etc. On the northern part of the island as well as bustling parts too if on the southern end with hotels, restaurants, and shops. It’s a great place to stay for your first visit to the area! Hatteras Island is known for its surfing, kiteboarding, fishing, and bonfires. It’s great for active family friendly beach vacations. Ocracoke Island has been discovered but it still maintains a very quiet and slow-moving pace of life so it’s great for those looking for total relaxation.

Outer Banks veterans will tell you that the best way to stay is in a beach vacation rental house! I highly recommend using Twiddy or Southern Shores as your rental house resource! A few activities that are musts: beaching, visiting one of the 5 lighthouses (I recommend the Cape Hatteras Lighthouse and Bodie Island lighthouse), horseback riding on the beach, deep sea fishing, cruising the beach in a beach jeep, and enjoying ice cream cones at Sunset Ice Cream. P.S. rent all your beach gear and anything you could possibly need for every water sport at either Kitty Hawk Kites or Ocean Atlantic Rentals.

A Few Other East Coast Summer Weekend Getaways

There are so many amazing options for East Coast summer weekend getaways! The destinations I shared above are ones I’m super familiar with; however, I have a few other spots on my list to visit for the first time or again this summer or a coming summer. I wanted to share these with you because they are also fantastic places to enjoy the lazy days of summer.

Beach destinations… Massachusetts: Cape Code and Martha’s Vineyard. Rhode Island: Newport and Providence. New York: Fire Island and Shelter Island. New Jersey: Cap May. Delaware: Rehoboth. Also, see my Mini Maine Travel Guide for Maine recommendations!

Mountain destinations (so wonderful for road trips!)… Vermont: Manchester, Stowe, and Woodstock. Massachusetts: the Berkshires. North Carolina: Asheville.