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By Brittany Bowker

Tourist or not, it’s easy to get caught up in the midsummer vibes of vacationland along Oak Bluffs Harbor.

“Just one drink,” you may think, enticed by the calypso music and spirited stream of people lining up at Donovan’s Reef next to Nancy’s.

There are three different seating areas at the iconic Nancy’s Restaurant. There’s the downstairs outdoor snack bar, which is an open space with picnic tables, great for families and large groups on the go. Order a range of fried seafood platters, sandwiches, snacks, salads, and an entire selection of Middle Eastern food, pay at the window, grab a buzzer, and find an empty picnic table overlooking the harbor. Jump in line at Donovan’s Reef for a drink to take back to your table.

The second seating option at Nancy’s is the open-air downstairs bar. Here, you’ll order from a slightly different menu from the snack bar, and you’ll have a server. Sit along the bar facing the harbor and you’ll catch some midafternoon rays — and one of the best spots for people-watching. The third seating option is the upstairs dining space, which overlooks the entire harbor.

Nothing screams summer like a fruity frozen drink, and Nancy’s cocktail menu has you covered. There’s, of course, the Dirty Banana ($11), made with fresh ripe banana, chocolate sauce, and rum. There’s the Mango Tango ($11), made with pineapple mango rum, fresh mango chunks, and a passionfruit swirl. Next, a classic Piña Colada ($11), mixed with coconut, light rum, creme of coconut, and pineapple chunks. And there’s another Nancy’s special, Donovan’s Rum Punch ($11), which has light and dark rum, and peach and tropical juices.

For a satisfying dose of apps, order the Mediterranean Sampler ($18.95), which comes with hummus, tabouli, falafel, grape leaves, and pita bread. This is one of the only restaurants on-Island with such a variety of Middle Eastern food. You’ll notice its fresh herby greens and flavorful lentils. For something a little heartier, go with the Scallops Wrapped in Bacon ($14.95). They’re served with an apricot glaze, taste salty and fresh from the sea, and fulfill that surf-and-turf craving we all seem to get when we’re sitting by the water.

Nancy’s is just one of five stops you might be tempted by along Oak Bluffs Harbor. If your time, money, and liver allow for it, it might be worth taking the harborside tour.

Next on the lineup is the Sand Bar and Grill. You’ll recognize it right away, with its beach sand bottom, and faux palm trees scattered about. This is another spot where you’ll notice lots of families, and lots of large drinks — that’s where we honed our focus on phase two of the harbor tour.

Sand Bar’s Menemsha Sunset ($12) is probably the booziest drink on the block. It’s mixed with Bacardi Silver, Captain Morgan Spiced Rum, orange, cranberry, and pineapple juice, and topped with a Myers Dark Rum floater. Sip carefully on this one. A good choice for those with a sweet tooth is the Blue Shark Attack ($11). It has Blue Chair Bay Rum, blue curaçao, pineapple juice, and a school of gummy sharks. The Painkiller ($12) is another loaded option. It’s made with Gosling’s Gold Rum, pineapple and orange juice, and a touch of coconut cream.

Lobsterville Bar and Grille is the Sand Bar’s neighbor, and the next stop on the harbor hop. Lobsterville is located in a pastel teal gingerbread-style house, and has two decks for dining overlooking the harbor. The bar-style seating gives the place an intimate feel — it’s smaller and tends to be less crowded than the other spots along the harbor.

Chef Douglas Hewson cooks with the freshest fish around, and tries to switch up menu options daily. The Ceviche (market price) appetizer has been a bestseller, according to Hewson. It’s made with black sea bass, cooked with peppers and onions, and loaded with flavor. The raw sea bass was cured well and served in a martini glass. Another appetizer worth trying is the Bang Bang Shrimp ($15). It’s a generous portion of rock shrimp dredged in flour and fried crispy. The Bang Bang sauce is a mix of a sweet and sour chili that’s mild and approachably spicy. Each shrimp is the perfect bite size, crunchy, light, and good for sharing. The Pig Wing ($5 each) is a braised pork shank deep-fried and tossed in a chipotle pineapple BBQ sauce. It’s an amalgam of a rib and a wing, and comes off the bone easily. The sauce is tangy, and the meat is dark. The Mini Lobster Roll ($12) comes out cold, tossed lightly in mayo, and is a good alternative to a $30 lobster roll.

Specialty drinks at Lobsterville are just as tasty as they are beautiful. The Martha’s Vineyard Mule ($12) is made with Ketel One Vodka, fresh lime juice, simple syrup, ginger beer, and a lime wedge. The Menemsha Sunset ($12) is made with lemon and orange vodkas, orange juice, sour mix, lime juice, Sierra Mist, and a dash of grenadine. It fades from a deep orange pink to a darker orange, with colors that look a lot like, well, a Menemsha sunset. The Royal Hawaiian ($12) is mixed with Empress gin, pineapple, fresh lemon juice, blueberry vodka, and lemonade. Purple hues sit on the top of a faded yellow mix of juices, and it tastes as sweet as candy.

Coop de Ville is next up on the harbor hop, but it was closed for a great reason the day we visited: The staff was out on the Alabama, celebrating a record-breaking Fourth of July in 2018. Coming up on its 34th season, Coop de Ville is known for its wings and its Tuesday night Lobster Fest, a $16 steal.

Last but not least along the harbor strip is Fishbones Bar and Grille. We took a break from drinks, and loaded up on entrées. A favorite is the classic Fishbones Burger ($13), which is served with curly fries and topped with all your burger essentials. The Jerk Chicken Salad ($20) is made with dry rubbed fresh jerk chicken breast, black bean roasted corn salsa, avocado, and mango, with a pomegranate vinaigrette. The Blackened Mahi Sandwich ($15) is another solid choice. It’s a fresh mahi filet topped with a mango sauce on a bulkie roll. For an extra $4, you can swap out french fries for sweet potato fries — which are profoundly tasty as far as sweet potato fries go. We recommend dipping a couple in honey mustard dressing.

So there you have it — five bars along the harbor, and five reasons to embrace the Island tourist within, next time you’re in Oak Bluffs.