Long Weekend in Nantucket
One of the things that makes Nantucket feel special and like a real vacation is that it's simply not that easy to get to. A trip to Nantucket usually involves a combination of transportation vessels including but not limited to trains, planes, automobiles, and of course ferries. And there are many options. I prefer to balance efficiency with cost effectiveness. My typical journey to Nantucket involves driving from the NY area to New Bedford, MA and getting on the Seastreak Ferry to Nantucket. Cost is $70 for a round trip ferry ticket and $15/day for parking. Multiple ferry options exist from Hyannis but I prefer New Bedford because it involves less driving if coming from the NY, CT, RI area. Other options include direct ferries from NYC (5hr ferry and $260 for RT ticket feels long and pricey!). Sometimes you can luck out with an inexpensive flight especially if you are coming during the off season or mid-week. Always check because flying onto the Island can feel very luxurious.
Where to Stay
There are many great AirBnB, hotel, and Inn options on the Island. But for five star luxury, nothing beats The Wauwinet Inn. It's a gorgeous compound all the way out on the east end of the island (and close to my favorite Squam Beach - see below). Service is impeccable and accommodations chic albeit small. Delicious fare can be had in the dining room or lounging on the lawn in the two dozen lounge chairs.
Another great option are the Summer House Cottages in Siasconset (pronounced 'Sconset). Nice pool, great views, and delicious dining experience can be had. You're also close to the quaint town and the bluffs walks (see below).
My favorite beaches are Squam, Cisco, and Surfside. Squam is located all the way out east by the top Wauwinet Inn. While all the beaches are public, this one lacks parking and is difficult to access, but worth making the trip out there for the dreamy beach walk and chances are you may be the only one out there. Other fun beaches include Cisco and Surfside on the north side of the island for waves and liveliness.
Once you're done at the beach head to Cisco Brewers for live music starting at 3pm along with cocktails, food trucks, and of course, the raw bar.
The town of 'Sconset is worth a trip for the quaint shops and grocery store. Score yourself a coffee and fresh blueberry muffin or cookie and walk off the extra calories with a long walk along the water. A hidden footpath leading to the 'Sconset Bluff Walk can be found by walking down Front Street. Go for the amazing views and real estate envy as well as some public access points down to the beach.
If you're not into crowds, come to Nantucket during scallop season (October-March) to enjoy a tourist free vacation and dive into the chilly waters for some scallops.
All About Town
I love walking around town, peaking into the shops, or just passing by the windows. For fun Nantucket gear along with a candy store and "zero gravity room" downstairs and a mini golf upstairs, head on over to Town Pool. Afterwards cool off with a juice or acai bowl from Lemon Press (now moved next door). Make your way up Main Street and over to Centre Street for jewelry at Patina and athleisure gear from Crane and Lion. Before you leave, make sure to check out the shops that line the docks by Straight Wharf for that cozy sweatshirt or Nantucket souvenir.
Where to Eat
For a leisurely brunch, make your way to Topper's at The Wauwinet, reasonable prices and great service, plus explore the grounds afterwards and hang out on the dock or beach for a relaxing morning. I love Sayle's Seafood for a super casual lunch of chowder and fresh or fried stuff from the sea. Shop for provisions at Bartlett's Farm and get your chef on at home. If that's not in the cards, fine dining spots are abundant. Some of my favorites include Dune, Proprieters Bar & Table, Cru, and The Nautilus. Before you catch the ferry, pick up some sandwiches at Provisions and don't sleep on the "turkey terrific" a Thanksgiving inspired sandwich served year round and featured on The Food Network "Best Thing I Ever Ate."
A Brief Spotlight on Nightlife
If I'm being honest, I don't make it out to party on the town very much as I find the scene a bit funny, but I've had good times at Straight Wharf, The Gazebo, and B-ACK Yard BBQ all within a few steps from each other. And people swear by The Chicken Box for its live music and sticky floors (if you're into that sort of thing).