Ultimate Guide to a Weekend in Nantucket
Nantucket
Nantucket is the perfect destination for a summer weekend getaway. The well-known, warm, New England island is located just 30 miles off of the coast of Massachusetts.
Easily accessible by a short flight from the Northeast, Nantucket is filled with beautiful beaches, an enchanting town, and many activities for all ages and lifestyles. Nantucket is so popular in the summer that the population during peak season (July and August) increases from 10,000 to 50,000. But don’t worry, there’s still plenty of room to enjoy!
When planning your trip to Nantucket, look no further. Fly Louie’s Ultimate Nantucket Weekend Guide is a true insider’s perspective on the best spots to eat, drink, and moments to experience on the island.
Get to Nantucket (Friday)
To spend a full weekend out on Nantucket, there’s no need to head out of work early. And, if you do sneak out of the office early, well, we won’t tell. Flying time from the greater New York area (White Plains, Teterboro, Danbury, for example) is about 60 minutes. The best way to get to the island is by private charter. No need to arrive hours before your flight only to wait around and stand in long lines at TSA. Instead, arrive just 15 minutes before takeoff. And if you’re based out of the New York City metro area, you can leave work by 5 pm and arrive at ACK in time for dinner in Nantucket.
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Breakfast and Boogie Boarding (Saturday)
There are two ways to go about a weekend getaway: Sleep in or get going bright and early. If you’re ready to get ‘up and at ‘em,’ we recommend an early morning bike ride, a Nantucket favorite, to start your day with the sun warming up the island. You’ll find solo cyclists and entire families riding all over the island thanks to the protected bike paths that cover it. Many hotels, such as the White Elephant, offer bikes to their guests at no additional fee. Or head over to one of Nantucket’s bike rental shops in town, although it’s best to reserve your ride in advance.
After your morning ride, reward yourself with a delicious breakfast. Black-Eyed Susan’s makes the best blueberry pancakes on the island. Downyflake Donuts offers both sit-down breakfast as well as takeout. No matter what you order, make sure to order a side of sugar donuts. Bartlett’s, Millies, and Provisions all offer delicious grab-and-go breakfast sandwiches/burritos and baked goods. If you like to sleep in, you have our full support. It’s important to note that Black-Eyed Susan’s closes at 1 pm and Downyflake closes at 2 pm.
After breakfast or brunch, there are so many options with which to fill up your day.
If you love shopping, head to town and walk around on the cobblestone streets, which are lined with locally owned shops offering everything from clothing to homegoods. You’ll notice that there are almost no chain stores (Ralph Lauren and Vineyard Vines are the rare exceptions). While you’re out shopping be sure to pick up a few items in “Nantucket Red.” This iconic color was introduced in the 1960’s by Philip C. Murray. The red canvas fabric was meant to fade over time, resembling the color of the sails that dotted the coast of Brittany, France.
The beaches are a big draw for vacationers in Nantucket. This small island has 82 miles of pristine shoreline which boasts a wide variety of gorgeous beaches. Each beach offers something a little different. The Nantucket Sound in the north features smaller, rolling waves and warmer temperatures which is a great option for families. In addition to calm, warm water, Children’s Beach offers a grassy area with a playground -- hence the name! Surfers prefer the southern beaches, which serve up bigger swells and cooler water. The east shore is another Atlantic option, perfect for those who crave larger surf and the sunrise. The west shore offers more tranquil beach options with fewer people and fewer amenities, but the waves on the west shore, such as at Madaket beach, are perfect for boogie boarding! And Madaket is also one of the best spots to watch the sunset in Nantucket (more on this later). There’s also opportunities for off-road adventures. Please note special permits may be required to drive on the beach or access certain areas.
Other suggested activities:
Sign up for a fishing charter from the harbor in town or the marina out in Madaket.
Hike at Ram’s Pasture which takes you along green, rolling hills, through a historic farmhouse, out to the ocean.
Spend your day playing golf or tennis at any of the public courses or courts. You can play 18 holes at Miacomet or 9 holes at Siasconset or hit some serves at the public courts at Jetties.
No matter how you choose to spend your day, you will surely work up an appetite. A favorite lunch option is a sandwich from Something Natural on Portuguese Bread, a white bread that is unique to Nantucket. The bread is crusty on the outside and soft on the inside and justifies Something Natural’s motto, “If you bake it, they will come.” And what’s a weekend in Nantucket without a lobster roll? For an iconic lobster roll, head over to Sayle’s Seafood. For a sit-down lunch, Millie’s and their tacos, poboys, and poke is a top choice!
Even though we just covered lunch, it’s never too soon to plan for dinner. There are many options on Nantucket. Brant Point Grill at the White Elephant Hotel offers some of the finest dining to be found on Nantucket. Indulge in exceptional seafood, steak, and choice selections from an award-winning wine cellar. Request a table looking over the harbor for a perfect backdrop for a romantic dinner or celebration.
Or pick up fish tacos at Millie’s and head over Madaket for a beach picnic and the best of sunset on the island. (With this third mention, it’s quite clear that Millie’s is a Team Fly Louie favorite!) Bring chairs or a blanket and don’t forget a sweater -- it can get chilly at night.
After dinner, if you’re in the mood for dancing and drinks, bring yourself to the Chicken Box. This Nantucket institution, originally founded by a purveyor of Southern Fried Chicken, is a popular restaurant and watering-place with live band entertainment. More on the Chicken Box’s unique history.
If you have a sweet tooth, ice cream at the Juice Bar cannot be missed! Order two scoops of cookies and cream or coffee ice cream in a homemade waffle cone with hot fudge. Don’t get discouraged by the line. Trust us, it’s worth it!
Lighthouse and Lobster (Sunday)
Take Sunday to relax.
If you went to Black-Eyed Susan’s on Saturday go to Downyflake on Sunday for breakfast. We also recommend traveling to the east of the island, known as Siasconset (also spelled “Sconset”), for the Sconset Market’s tasty baked goods.
Take a stroll around Siasconset’s town (located at the roundabout) and then spend time at Quidnet, a stunning hamlet that overlooks Sesachacha Pond, the ocean, and Sankaty Lighthouse. It is quite a unique view to see a beach with the ocean on one side and a huge pond on the other.
Throughout your visit, there’s no doubt that you’ll notice that the Jeep is a popular vehicle on the island. Notice the many permits on the Jeeps you pass by. The unofficial record is 36 permits on one Jeep (try and beat it!).
Jeeps and other types of four wheel drive vehicles are necessary to drive on the dirt roads as well as to off-road on the beach. Great Point, for example, is a real treasure, but it takes real effort to get out there. A jeep is required to handle deep, soft sand. There are options to rent a Jeep with a permit (there is a fee entrance to the road if you are using a rental). If you’re not an experienced off-roader, it might be best to kick back, relax and leave the driving to the experts. The Trustees of Reservations offers tours.
If you’re still looking for more adventure on Nantucket, the Brant Point Lighthouse and Cisco Brewers are must-visits. Brant Point Lighthouse is located on a piece of land jutting out into Nantucket Harbor. It’s a great view of the entire Harbor and you can watch local fishermen pull up Scup from the seafloor. Cisco Brewers, with locations throughout New England, was first established in Nantucket, and the venue remains a great place for drinks, street food, and live music, throughout the day. They also bring in food trucks from some of the great spots on the island, including 167 Raw, who have the best fresh seafood. Be sure to check their monthly calendar for happenings when planning your trip
As the weekend comes to a close, take an afternoon or evening return flight. Nantucket airport is only 15 minutes from the center of town and if you fly by private charter, there’s no rush to get to the airport more than 15 minutes ahead of time. Although returning flights to the mainland take a bit longer due to the headwinds, it’s still a short flight–only about an hour flying time to the greater New York City metro area.
When you’re ready to check out Nantucket, one of America’s true gems, Fly Louie would love to get you there!
If you’d like to learn more about on-demand charter with Fly Louie, the Fly Louie team is standing by and ready to help!