From Ulysses S. Grant in 1874 to Barack Obama in 2016, few vacation spots have captured the hearts of America’s presidents quite like Martha’s Vineyard. With its historic streets and idyllic coastline, it’s easy to see why: set to the calls of sea gulls and breaking waves, this presidential favorite is truly the epitome of a New England hideaway.
For visitors who want to experience the island in all its glory, one of the best ways to do so is from the back of a scooter. Escape with that special someone, rent a two-wheeler from Sun & Fun Rentals, and “set sail” on a two-day journey through the east side of the island. Our suggestions:
Where to Sleep
The Winnetu Inn & Resort
Named Top 100 Resorts in the World, Top 25 in the USA, and Top 20 in New England by Conde Nast Traveler, Winnetu makes it easy to unwind after a day of exploring Martha’s Vineyard. The hotel offers elegant rooms, spacious suites, and family-friendly private residences, all available now for reservations during the 2016 season.
Harbor View Hotel
The historic Harbor View Hotel is rated one of the best in New England and feels more like a home away from home than an ordinary hotel. Located right in the heart of Edgartown, rooms at the hotel are light and open, reflecting the beachy atmosphere seen out the window.
8:00 a.m. | Breakfast of Champions
After a lovely French press at Winnetu Inn, hop on your rented scooter and zip over to the quaint Art Cliff Diner for a quality breakfast spread. There are several items on the menu that get rave reviews, but we suggest the Corned Beef Hash 'n' Eggs and Spicy Chicken Hash guaranteed to tantalize your taste buds.
10:00 a.m. | Beach Days of Summer
The Vineyard’s sprawling beaches are perfect for swimming, or lounging in the sand with a good book for that matter. Today, you are going to savor the sun’s rays at Inkwell Beach in Oak Bluffs, where you’ll find shallow blue waters to take a dip. Lay out your blanket, apply some sunscreen, and soak in the beauty of the beach grasses swaying in the breeze.
1:00 p.m. | Lunchtime is Calling
A great spot to grab some equally great grub is the Offshore Ale Co. Open year round since 1997, Offshore serves satisfying bar food and a flavorful selection of brews to wash down your lunch. The Lobster Role is packed with the tender meat tossed with a small bit of mayonnaise.
3:00 p.m. | A Real-life Gingerbread House
A quick drive on your scooter takes you to Oak Bluffs, where you’ll find a fairytale land of gingerbread cottages. There are over 300 houses painted in an array of colors, a big tourist draw for photo opportunities. Each dainty house is adorned in detailed trimmings and embellishments seen around roofs and windows.
7:00 p.m. | Best Chowda Eva
With its creamy broth and tender—not chewy—clams, clam chowder is undoubtedly the state soup of Massachusetts, if there is such a thing. For the local answer to New Englanders’ eternal question—who has the best chowder?—look no further than Martha’s Vineyard Chowder Company. It’s rated best on the island among locals and tourists alike, and absolutely worth a visit.
9:30 p.m. | Late-night Cravings
Finish your day with arguably the best donuts you’ll ever taste at Gourmet Café and Bakery’s Back Door Donuts in Oak Bluffs. You might think, “aren’t donuts normally a breakfast treat?” Yes, but Back Door serves up their sugary confections from 7:30-12:58 a.m.
8:00 a.m. | A Dose of Caffeine
Begin the day with a delectable coffee at Carol McManus’ Espresso Love in downtown Edgartown. Savor an assortment of scones, muffins, and croissants, or sink your teeth into the Church St. Bagel complete with an egg, cheddar cheese, lettuce, tomato, and an avocado.
10:00 a.m. | Beach Therapy
It’s Martha’s Vineyard, so of course you’re going to the beach two days in a row. This time, you’ll head over to South Beach in Edgartown. In 2013, Travel & Leisure named the beach one of the world’s best beaches and most vacationers would certainly agree.
1:30 p.m. | Relax & Refuel
By now you are going to need some flavorful energy to continue your island adventures. The Wharf Pub offers diners a pub atmosphere for a quick bite and a baseball game in the back, or family restaurant atmosphere in the front.
2:30 p.m. | Creatively Inspired
With landscapes like the ones you see in “The Vineyard,” chances are you’ll be feeling creatively inspired. Art galleries are peppered throughout the island, displaying detailed pieces of art, including the Old Sculpin Gallery—a once whale oil factory—and The Christina Gallery—a traditional, expressionist gallery.
6:30 | Wine Down
After a quick scooter ride back to your hotel to freshen up, a delicious dinner awaits. Détente isn’t your average casual seafood locale, but rather a fine dining bistro right down to the white table cloths. Sip on wines from around the world and dine on local modern fare.
8:30 | Sunset Views
Depending on how long you decide to dine, and what month you are visiting, a sunset at the Edgartown Lighthouse is not one to miss. The colors look as if they have been painted on the sky, almost too perfect to be real. Don’t forget your camera!