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If you’d like the space and privacy of a vacation apartment but still want the service and amenities of a hotel, the Cottages & Lofts at the Nantucket Boat Basin are ideal. You’ll be whisked away from the Hy-Line ferry and taken to the wharves of Nantucket’s harbor, about as close you can get to the water without staying on a boat. Cottages and loft rooms range from studio-size to three bedrooms, all with full kitchens and private patios. A complimentary shuttle bus can take you to the beach, and bicycles can take you wherever you can’t walk from the cottages. There’s no restaurant on-site, but plenty of options are at the marina, and guests get a discount at the White Elephant’s Brant Point Grill. Children and pets are VIP guests as well: Kids get fishing and beach gear to use during their Nantucket stay, and a pet concierge will assist with stays at the “Woof Cottages.”

White Elephant has been a Nantucket landmark for nearly a century, with more rooms than a typical inn but without sacrificing the intimacy and personal service of a small property. Located on the waterfront a short walk from Brant Point Light, the inn has a sprawling lawn with chaises for relaxing, as well as shuttle service to the area’s beaches. Accommodations range from king-bedded guest rooms (each with a private balcony or patio) in the main inn building to spacious garden cottages (some with kitchens and fireplaces) and penthouse-like lofts in downtown Nantucket. A small spa offers therapeutic massages, facials, and body treatments. A luxury resort that is truly family-friendly, kids and babies can get fully kitted out for bath time, mealtime, or beach time with a wealth of amenities and toys. The Brant Point Grill is a local favorite for an al fresco lunch, lobster dinner, or Sunday brunch (complete with Bloody Mary bar). The White Elephant also provides regular transfers on the 21-passenger boat, Lady Wauwinet, to the Wauwinet Inn’s restaurant TOPPER’S, which cultivates its own oysters.

The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.

A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

The water is usually calm and a bit warmer on the Nantucket Sound side of the island. Steps Beach is off Cliff Road about four miles from town, sandwiched between Dionis and Jetties, and is not on most people’s radar. Before you take on the massive set of stairs leading down, enjoy the view of Great Point Light off to the right. Steps Beach offers protected shores with gentle waves washing onto the sandy beach, and gray-shingled mansions dotting the surrounding sand dunes. Come prepared, as there are no lifeguards or facilities, and make sure to save some energy to make the climb back up the steps.

One of the most popular spots on the island, Cisco Brewers began as a winery 25 years ago and has now grown into a destination that showcases offerings from the Nantucket Vineyard, Triple Eight Vodka, and the Cisco Brewers beer label. Summer weekends there is a lively crowd listening to music and taking advantage of the food carts and raw bar. For a tour and a more intimate view of the production, visit during the week. There is a seasonal shuttle available and the new bike path makes Cisco all the more accessible.

Galley Beach has one of the best locations on Nantucket. With views out over the ocean from the dining room and tables spilling onto the beach, there’s not a bad seat in the house. It’s a popular spot with a stylish crowd, and the martinis flow freely. Come early to snag a seat for sunset, one of the best shows in town, and as the evening gets underway enjoy the breeze on your face and scrunching your toes in the sand while tiki torches light up the night.

It’s easy to stay health-focused, even on vacation, if you stop by the Lemon Press. This adorable space in the middle of town has fresh cold-pressed juices and super smoothies. Liquid Sunshine is a winning combination of mango, peach, and organic apple juice. And if you are looking for damage control from the previous evening, try the Scenic Root or Georgia Green. Both will help you get back on track. Also on the menu are delicious sandwiches and photo-worthy toasts.

For an especially scenic drink, try the umbrella-shaded Beachside Bistro at the Summer House. Down a flight of stairs into the gentle dunes, you can’t get much further east unless you want to go swimming. A full bar is available and you can snack on the likes of lobster salad or crab cake. Come at sunset, and even though you won’t see the sun itself, the entire sky glows pink and dreamy as the waves roll in.

Cru is a spectacular location for a drink, with the harbor and Billionaires Row as its backdrop. The outdoor patio is great for people-watching, as is the silky-smooth stone-topped bar. The tart and refreshing Crucomber is the signature cocktail: a mix of bison grass vodka, lemon, cucumber, and toasted sesame. If you want to snack, the cocktail pairs well with any of the delightfully fresh crudos and oysters on the menu. After a few, take a walk along the pier and fantasize about life aboard a luxury yacht.

Award-winning Nautilus offers seasonal cocktails, over 20 wines sold by the glass, and an extensive list of mezcal, beer, and sake. Warm and friendly, this is the kind of place where you’ll no doubt meet the folks sitting next to you at the bar. Owned by a threesome who know their way around the industry, the lively, hip scene almost feels like you’re at a cool friend’s cocktail party.