Photo Credit: Alison Shaw

Martha’s Vineyard, an idyllic island off the coast of Massachusetts, is one of the best vacation spots of the summer, hands down. But what few actually realize is that Indian summer is actually the best time of year to visit “The Vineyard.” You’ll find less crowds, fewer tourists and find it easier to make reservations at the creme de la creme of restaurants. Here, we’ve decided to showcase Edgartown, the largest and most affluent of the Vineyard’s sectors. Won’t you join us?

STAY

Imagine kicking back with a glass of wine in hand from a rocking chair as the sun sets in an explosion of reds, pinks and purples. You don’t have to say a word to anyone around you: you are content. That is what you’ll take away from an experience at The Harbor View Hotel,  a gem of a property located at the very tip of North Water St. in Edgartown. This property still has touches of its 19th century roots—it’s been around since 1891—though has been updated with modern amenities to make your stay more enjoyable; it is more timeless yet extremely comfortable.

The extremely luxe traveler will request a cottage instead of a room in the hotel’s main building. We recommend you request Cottage 24 in particular: it’s spacious, measuring in at roughly 1500 square feet, has multiple porches, both great lawn and pool views as well as stellar views of Edgartown Harbor. VIPs who don’t necessarily want to meet and mingle also have the use of a private elevator for the utmost privacy. In the cottage you’ll also find a refrigerator, dish washer, washer and dryer, Keurig coffee maker and the very Vineyard-esque outdoor shower (try it, it’s a must), all set among The Harbor View’s beach chic decor.

On property you’ll also find the Lighthouse Grill, a contemporary New England grill, which is a great spot for breakfast or dinner thanks to its ocean views and buffet-style brunch (Sunday brunch is a must) and Henry’s Hotel Bar; a nautically-themed boite that’s great for lunch, tapas and cocktails alike.

In terms of amenities, Angelenos will be pleased to discover that there is an on-site gym, as well as a heated pool, yoga and morning fitness walks as well as access to local bike and jogging trails; there is also a golf course nearby.

The Harbor View Hotel, 131 N Water St, Edgartown, MA 02539, (508) 627-7000

DINE

You’re not at a loss for fine dining options in Edgartown: the problem here is that there are too many great options to choose from. The most ambient option is The Terrace at The Charlotte Inn. This Relais & Châteaux eatery owned and operated by Culinary Institute of America-trained Chef Justin Melnick is the very height of elegance. After walking down a tree-lined street you’ll enter The Charlotte Inn, which feels both glamorous and extremely old world. You’ll then be quietly ushered into the elegant conservatory dining room of The Terrace, which, with its crisp white linens, Limoges china, polished silver and brass accoutrements, and soft candlelight, will make you feel like you’ve wandered into a Jane Austen novel. Soak up the romance and attention to detail in an atmosphere of Edwardian-era elegance, as you savor dishes like pan-seared Hudson Valley foie gras, with chilled berry compote, grilled brioche and wine syrup and cornmeal crusted sole filet with Sardinian couscous salad, olives, tomatoes and celery greens. The wine list is a mixture of French, Italian and Napa favorites.

We also love the romantic vibe of Alchemy Bistro & Bar, a great people-watching spot (regardless of time of day) featuring chef Giordano Smiroldo’s New American take on Vineyard favorites. If we have one recommendation, it’s the fried oysters, though you’ll love the freshness and presentation of the local fluke crudo, which is prepared with Holland chile, lemon, borage flower and Ranieri olive oil. The chicken liver crostini with shiitake and pancetta and ribeye with black garlic butter, red onions, broccoli rabe and herb crushed Yukon cream are other standouts. In terms of cocktails, we recommend The JayBird Swizzle—dark and spiced rums with housemade falernum and orange; the ambitious will order a pitcher over a single cocktail.

Other great options include chef Noah Kincaid‘s elegant fare at Atria, Detente, fan-favorite Chesca’s and l’etoile.

The Terrace at The Charlotte Inn, 27 S Summer St, Edgartown, MA 02539, (508) 627-6227

Alchemy Bistro & Bar, 71 Main St, Edgartown, MA 02539, (508) 627-9999

PLAY

Though the Vineyard is known for its beaches—South Beach, Lucy Vincent and Aquinnah are among the best—life can’t always be a beach, can it? If you’d rather partake in other activities, indulge in an ocean-inspired spa treatment at Edgartown’s darling Sea Spa. This full-service spa offers everything from hair treatments to nails to massages, though we’ve discovered that its facials and body treatments are absolutely divine. Get a kick out of asking for the Sea Maiden’s Delight, a treatment which soothes and rebalances sensitized, summer-ized skin, reduces redness and heals with a blend of neroli, rose, chamomile and plant extracts of blueberry and licorice. Our skin was, quite literally, glowing like Ariel’s afterwards. The spa also offers an option for men with its Triton’s Facial, which eliminates impurities, accelerates skin repair, and neutralizes the skins pH balance. After your day of indulging, head over to the numerous art galleries and shops in Edgartown to pick up some special pieces or some Lilly Pulitzer. If you’re staying at The Harbor View, you might want to hop and skip over to the nearby Lighthouse, which is actually open for tours until 6 p.m.