Ever longed for the days to grab your buddies or pack up the family and take on the open road, Chevy Chase style? We’re hitting the open road this summer and making our way from coast to coast.

First stop: Coastal New England

Sorry VT—we’ll have to check you out another time, we hear fall is quite nice—we’re making our way down the coast.

Bar Harbor, ME—is actually on Mt. Desert Island and is quintessential New England—think “lobsta” rolls (say it like a local!) and Whoopie pies.

A short drive away is Acadia National Park, which is perfect for exploring! Drive up Cadillac Mountain (the tallest mountain on the East Coast) or hike over to Thunder Hole and enjoy the thunderous sounds of the Atlantic. The Jordan Pond House has been serving popovers since 1890 and is an Acadian tradition.

A short day trip will take you to the eastern most point in the USA: Lubec, ME.

Stay: Bar Harbor Manor: the perfect base to explore Acadia, downtown Bar Harbor and a day-trip further Downeast!


Portland, ME—Visit a great example of a working waterfront and get lunch or dinner at DuckFat for some life-altering fries and what Jetsetter refers to as one of America’s finest milkshakes. (Tip: the lines are long and they don’t take reservations. In a hurry? Make your order to go and picnic at the park across the street).

Stay: Downtown Portland has all your major hotels. Staying in Freeport, ME is another great option, only 15 minutes from Portland and is a quaint coastal location in itself (with some classic New England shopping nearby).


Hampton Beach, NH—was recently voted one of the top 10 boardwalks in the US. Hampton Beach outranks Atlantic City…and doesn’t even have a traditional boardwalk. It’s fun just the same – the Midway is packed with pizza, fried dough and, of course, seafood.

Stay: For over 100 years, Ashworth By the Sea has been welcoming beach guests as the premiere area hotel.

Further south in MA—you can channel your inner prep. Don your Nantucket Reds and see life like a Kennedy on beautiful Cape Cod.

While the “Cape” is divided into sections that resemble a flexed arm (upper, mid, lower and outer), it’s worth a day’s drive to see them all. Dotted with white-frame, clapboard homes, each town has its own vibe, but all offer breathtaking beaches and views of the Atlantic.



Hyannis, MA—Technically, mid-Cape (the muscle), this area probably has the most draw due to the Kennedy history and mystique. While you cannot actually visit the compound, you can get pretty close (it’s on Merchant Ave. in Hyannisport), but what’s more interesting is the John F. Kennedy Hyannis Museum situated downtown. Admission is $10 or under, and many programs are free. Take a short walk across the street and grab lunch at Spanky’s Clam Shack, right on the harbor.

If you’re beaching it, we recommend Craigville Beach in nearby Centerville. It’s a great stretch of sand, has plenty of shells for beachcombers, as well as a bathhouse and snack bars across the street.

Stay: Travelling with the kids? The Cape Codder Resort has a newly renovated indoor waterpark, heated outdoor pool and plenty of fun activities throughout the summer, plus it’s a short drive to area beaches.



Chatham, MA—Located on the lower-Cape (the elbow), this quaint village is a little more quiet. Its walkable Main Street has many locally-owned shops, gorgeous seaside homes and summer rentals.

Check out the Chatham Light and Lighthouse Beach or take in a baseball game. The Chatham Anglers are part of the popular Cape Cod Summer Baseball League. The Cape Cod Museum of Natural History is a short drive away in nearby Brewster.

Have lunch at The Squire, a family-friendly restaurant and bar, then pop into the Candy Manor for homemade fudge and treats.

Stay: Voted one of Cape Cod Life’s Best Hotels and Resorts, the Chatham Bars Inn offers luxurious, oceanfront accommodations and cottages, poolside cabanas, fine dining and plenty of activities.


People on a whale watching expedition spot the tail of a whale from the boat

Provincetown, MA—All the way at the tip on the outer Cape is P-town, as it’s called, an eclectic and artistic seaside area and vacation destination for the LGBT community. About 4,500 acres of the town itself are owned by the National Park Service, which operates the Cape Cod National Seashore.

If you’re not beach-going, take in some people-watching and shopping along Commercial Street or make your way down to MacMillan Wharf and hop on a whale watch cruise.

Dinner anyone? Check out The Lobster Pot. And order…what else? A traditional spot, it’s located close to the water and has a laid-back, friendly atmosphere.

Stay: Bed and Breakfast Inns abound, each offering their own aesthetic.



Martha’s Vineyard, MA—A short ferry ride away (approx. 45 minutes from Woods Hole, MA) and you’re on island time. You can see all of the island in a day, (by tour bus, bike, scooter or Jeep rental), but we prefer an open-ended journey…

Divided into six towns, each are remarkably diverse. Edgartown is the oldest English settlement on the island and the county seat. It’s peppered with white captain’s houses, preppy shops and big churches…easy to walk in, difficult to find parking in the summer season. Grab a snack and sit atop the pier and watch the ferry go back and forth to Chappaquiddick Island.

Vineyard Haven/Tisbury hosts The Black Dog Tavern and The Black Dog Bakery as well as plenty of places to pick up a sweatshirt with the signature black dog.

West Tisbury hosts a more rural landscape and peaceful charm. Stop into Alley’s General Store for penny candy and just about anything else. Just up the road, up-island, as they say, past stone walls and grazing sheep, you’ll find Chilmark: home to the postcard-perfect fishing village of Menemsha.

Don’t miss whimsical Oak Bluffs, with its nightlife, rustic Flying Horses Carousel where riders can capture a brass ring, arcades and souvenir shops. Once home to religious retreats, you’ll find brightly-colored “gingerbread houses” in the Methodist Campground that now serve as summer homes and rentals.

At the westernmost tip of the island, you’ll find Aquinnah, home to the historic Gay Head Lighthouse and Native-American culture.

Stay: Go traditional and book a romantic room at The Kelley House in Edgartown. It’s close to shopping, sightseeing and excellent restaurants. Want more peace and quiet? Try The Outermost Inn in Aquinnah. Situated on the red-clay Gay Head Cliffs, the Inn offers luxe rooms, a farm-fresh dining room and outdoor bar. Private beaches down a walking path are perfect for watching the sun set.




Newport, RI—where summer has been a verb since the Gilded Age. Visit the “Cottages” of Bellevue Avenue or pretend to be in KJP’s posse and grab a drink and an Adirondack chair at the Lawn at Castle Hill Inn while you watch the yachts sail by. Take a walk along the Cliff Walk or visit Fort Adams (and see where Dylan went electric!)

Stop by the White Horse Tavern, for a signature Dark & Stormy—it’s the oldest tavern in the country, operating continuously since 1673.

Newport also has its own Vineyards, Brew House and Rum Distillery (Newport was once a pirate’s haven during the rum running days)…and check out the Newport Tower in Touro Park…some say it was built by Vikings but you can draw your own conclusions.

Stay: In high season (summer) hotels book fast, the Hotel Viking is perfectly situated to explore downtown Newport, beaches and mansions!


Block Island, RI
(aka New Shoreham). Ferries run from Galilee, RI, New London, CT and Montauk, Long Island (NY) during the summer (only the Galilee ferry is year-round). Arriving in Old Harbor, you’ll see Victorian hotels, small storefronts and plenty of al fresco dining…there’s a laid-back vibe that you’ll notice the second you step foot onto the island. What you won’t find on the Block are ANY chains, stores or restaurants—this is probably the only town in New England without a Dunkin’ Donuts!

Head over to Town Beach for family-friendly fun…gentle surf with boogie board, chair and umbrella rentals right at the beach. Adults may enjoy Ballard’s where servers are happy to dish up lobster rolls, frozen treats and brews right to your beach chair!

Adults and kids should take a walk to Abrams Animal Farm. You wouldn’t expect there to be an exotic animal sanctuary on such a small island…but there is! There are only 200 zeedonks in the world…and now is your chance to see one!

The island is small and walkable, but there are also bike, moped & Jeep rentals. Taxis are also plentiful and will even give guided tours during the slow hours.

Venture to New Harbor for amazing sunsets and seafood at the Oar, or enjoy a farm-to-table feast at the Manisses Restaurant. Mohegan Café boasts the island’s only brewery…if you’re lucky, the Apricot Ale will be on tap.

Stay: Hotels & Inns book quickly in the summer high season; beware, many of the historic properties do not offer air conditioning or elevators, so be certain to check ahead! The Blue Dory is a wonderful inn with the best cookies in town! They even have pet friendly rooms & cottages (and most have AC). Hotel Manisses has been fully restored with AC rooms throughout…my trip is booked for August! See you there!


Mystic, CT—a colonial seaport town that embraces its heritage. Visit the Seaport and learn about Mystic’s whaling & shipbuilding history. You can also board the last wooden Whaler in the world.

Perhaps you’ve seen the 80’s movie that bears its name? Now you can grab your own slice of heaven at Mystic Pizza.

Ever thought about having cocktails with a whale? Painting with penguins? Head over to Mystic Aquarium where both are possible!

Stay: You can find many of your favorite hotel brands in Mystic, near the village & seaport…or stay at the Whaler’s Inn in downtown for a more coastal flavor—the attractions are all within a 10-minute drive. (Note: there’s no elevator at the Whaler’s Inn.)

Which of these destinations have you visited? Where else do you recommend? Tell us in the comments below.


  1. You need to recommend how long to stay , or how long each place would take to adequately visit on this trip.

    • KHall Reply

      Mary, that’s a great point! Having visited most of these places, I would say that each location could be done as a daytrip…however, 2-3 days in each location would give you adequate time to explore, relax and enjoy! Thanks for reading!

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