It’s what we look forward to all year– summer vacation. Although due to the extenuating circumstances of COVID-19, for many of us, summer travel may look a little different this year. With international travel bans and even the risk associated with flying domestically, we must turn elsewhere to fulfill our need for summer R&R. With the reduced risks of traveling by car to towns with exciting outdoor attractions, road trips are looking more and more appealing. Summer 2020 doesn’t have to be a let down! Round up your family or grab a few friends, pack up the car, and get on the road! As an east coast life and leisure connoisseur, let me be your travel guide as you take on the highways and backroads of all the states from Maine down to Florida. Happy traveling!
This trip is perfect for the nature-loving, hippie-souled crowd. Start in Woodstock, NY, the iconic hometown of Woodstock Music Festival. The town itself is quaint and colorful, its streets lined with cafes, specialty shops, bookstores and coffee joints. You won’t need more than a day here, so start early in the morning and head to stop two at sundown.
About 90 minutes north through New York’s Catskill Mountains is Saratoga Springs, a town known for its annual horse races. Whether you’re there for the equestrians or not, Saratoga Springs is a beautiful town with tons of restaurants and boutiques. Spend the night in an Inn or Bed & Breakfast or rent an Airbnb to rest up for your next day of exploring.
After a day or two in Saratoga, take Route 7 through Vermont’s Green Mountain Forest up to Burlington, a free-spirited and ultra-liberal town on the eastern shore of Lake Champlain. Walk along the Champlain waterfront, go brewery-hopping, shop local boutiques, and grab some ice-cream (home of the beloved Ben & Jerry’s)!
Next, head about 30 minutes east to Stowe, Vermont, a top-ranking ski resort town in the Northeast. In the summer, Stowe is a great destination for hiking, shopping farmers’ markets, and swimming in the mountains’ waterfalls and streams.
When there’s Green Mountains, there’s White Mountains. Drive into New England’s White Mountain State, stopping in the Nash Stream Forest. Another great destination for hiking and camping, Nash Stream Forest is the perfect place for some much needed R&R.
Heading back down south, Maine’s Cape Elizabeth is about 3 hours away and just southeast of Portland. Rich with history, lighthouses, and seaside parks, Cape Elizabeth offers the tranquility that Portland doesn’t. Stay in a shorefront Inn and enjoy the sunset over the lighthouses lining the coast and toast to a perfect end to the perfect laid back summer road trip.
Calling all prepsters! This road trip is like something straight out of a Ralph Lauren photoshoot. Start in Larchmont, New York, a small town in Westchester County on the coast of the Long Island Sound. Larchmont has the most beautiful houses (rent one through Airbnb!) in walking distance to their beach and yacht club, as well as their downtown area complete with old-fashioned ice-cream parlors, coffeeshops, cafes and boutiques.
Next, drive about 20 minutes to Greenwich, Connecticut, an affluent town with the best shopping restaurants, Inns, spas and golfing you’ve seen in the Northeast. Enjoy the day living the life of luxury… you’ll never want to leave!
A new state a day keeps the doctor away? I hope so! Trek into Rhode Island to visit the town of Newport, complete with a yacht-filled harbor and beautiful historic mansions. Spend a day on the beach, hiking the shorelines, or relaxing on a boat. This is a lifestyle you’ll want to get used to.
Last stop (and perhaps the preppiest), take a ferry over to Martha’s Vineyard, Massachusetts. An island just south of Cape Cod, the town is only accessible by boat, but don’t worry! You can bring your car! Spend the day admiring the island’s gothic cottages and unique architecture, relaxing on the beach, or dining by the sea. If you’re looking to experience a preppy, luxurious lifestyle this summer, this road trip is perfect for you.
This trip is a personal favorite (mainly because I grew up taking this drive), but also because it’s a gorgeous snapshot of Pennsylvania, New Jersey, and Delaware. Start in New Hope, Pennsylvania, the Greenwich Village of suburbia. This little town, situated on the Delaware River and a walk across the bridge to Lambertville, New Jersey, is known for its progressive views and support of the LGBTQ+ community. Take a stroll around town, enjoying the beautiful and colorfully painted homes, specialty and vintage shops, ice cream parlors and restaurants.
Next stop– the beach. About an hour drive across New Jersey is Asbury Park, an iconic beach town on the Jersey coast made famous by Asbury native, Bruce Springsteen, and his album, “Greetings from Asbury Park.” Known for its beautiful shoreline, beachfront boardwalk with shops and cafes, and The Stone Pony, a popular music venue for indie bands, Asbury Park is the perfect example of why reality show, Jersey Shore, isn’t always accurate.
Two hours south along the shoreline, stop at the southern tip and the objectively most beautiful shoretown in New Jersey, Cape May. Cape May is an affluent seaside resort known for its grand Victorian homes, previous vacation houses for the richest New Yorkers and Philadelphians in the early twentieth century. Spend a day enjoying the beautiful beaches, resorts and spas, quaint downtown area, and historic lighthouses. Cape May is the perfect summer getaway.
Last stop on the Delaware Drive is Rehoboth Beach, Delaware. Just a ferry ride across the Delaware Bay is Rehoboth Beach, one of Delaware’s best beach towns. Rent a house or stay in a hotel, explore the shorefront boardwalk, and dine in beachfront cafes. You’ll never want to leave this mid-Atlantic paradise.
Alexa, play “Take Me Home, Country Roads” by John Denver! This trip is the key to your best southern summer. Start in Shenandoah National Park, Virginia. Hike the Blue Ridge Mountains, (and Shenandoah River), and enjoy a night camping in the area’s beautiful campsites.
Next, head to Asheville, North Carolina, a colorful little town in the western part of the state, not too far from the Tennessee border. Asheville is one of my favorite southern towns, with the cutest coffee shops, bookstores, restaurants, and boutiques. You’ll be happy you made the stop!
Next state: South Carolina! Drive down to the coast and spend a couple days at Hilton Head, South Carolina’s iconic beach resort and golf destination. Enjoy the beaches, take a speedboat out for the day, dine shorefront or try out the gorgeous golf-courses. With the southern charm and state-of-the-art, well, everything, you will never want to leave.
Last stop, Savannah, Georgia! My favorite coastal city the Peach State has to offer, Savannah has the southern charm you crave with beautiful parks, a colorful downtown area, an extensive arts district and so many other attractions to enjoy. The end to your southern road trip will be just peachy!
Florida: America’s east coast paradise. Start in St. Augustine, known for its beautiful Spanish-colonial architecture and beautiful beaches. In addition to exploring historic fortresses in what’s claimed to be America’s oldest city, enjoy the outdoor cafes, rent a paddleboard for the day, or play a game of golf or tennis.
Next stop down the east coast is Key Biscayne. Just off the coast of Miami, Key Biscayne lies between two large parks, each with long beaches, mangroves and tropical forests. Enjoy a day on the beach beside the island’s iconic lighthouse, dine shorefront, or enjoy a drink in a hotel lounge overlooking the ocean. Now this, I could get used to!
Next coast (west coast), and only two hours away through the Big Cypress National Preserve, is Naples. Naples is a city on the Gulf of Mexico known for its high-end shopping and golf courses, white sand beaches, and frequent dolphin sightings! Rent a house, enjoy the beaches, hunt for seashells, and kick back. You’ll never want to leave Naples.
Last stop on the West Coast is Clearwater, three hours north of Naples. Known for its practically constant sunny weather, gulf coast beaches, and you guessed it, clear water, the shorefront in this town is the main attraction. You won’t be disappointed.
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