BROTHERHOOD OF THIEVES
An old Nantucket favorite located on Broad Street in the heart of town. We always have the best time at their outdoor beer garden and cozy interior (particularly in the fall and winter!) but the upstairs also underwent a refresh when the restaurant changed hands in 2021. A family-friendly staple with reliable crowd-pleasers like burgers, clam chowder, and lobster rolls.
Ideas for a Nantucket bachelorette weekend?
I would try to do something lowkey the first night like ordering in takeout, food trucks at Cisco Brewers, or dinner at Millie’s and then something a little fancier like Cru on the second night. And even if your night takes you to bars like the Chicken Box, Slip 14, or Straight Wharf, I’d splurge on sunset cocktails at Galley Beach one night if you can score group seating on the sand. During the day, I’d head to the beach or book an activity like chartering a sailboat, doing stand-up paddle boarding with Paddle Nantucket, or taking a Forme barre bus class on the beach.
Ideas for a Nantucket honeymoon, minimoon, or anniversary?
I would recommend staying at a nice hotel in town like Greydon House or the White Elephant and renting bikes as your primary form of transportation. I would definitely make dinner reservations at Cru, Galley Beach, or Ventuno, all of which would be walking or biking distance. And a sailboat ride on the Endeavor is always a special treat if you’re willing to spend more than you would at a restaurant to bring your own bottle of wine and picnic fare! And whether you decide to bike the six miles out to ‘Sconset or take an Uber, I highly recommend spending an afternoon on the ‘Sconset Bluff Walk taking in the island’s most beautiful homes before a romantic dinner at the Chanticleer.
Best kid-friendly spots on Nantucket?
I would definitely recommend renting a house if you’re coming with little ones! If you can, make a reservation to bring your car across on the Steamship Authority ferry and do a big Costco run ahead of time. Looking for the best beaches with little kids? Children’s Beach and Jetties Beach in town and Steps Beach nearby have very calm water that’s great for young kids, as does Sesachacha Pond out in Quidnet if you’re willing to make the drive for a little more peace and quiet. We spend a lot of time at Codfish Park in ‘Sconset and the playground on Old South Road, but it’s fun to do a 90-minute sailboat charter on the Endeavor for a special occasion! Millie’s is an easy pick for our favorite kid-friendly dinner and we love Island Kitchen for a group breakfast or lunch. And ice cream cones at the Juice Bar are a must for kids of all ages, yours truly included!
Ideas for bringing my dog to Nantucket?
We loved bringing our pup to Nantucket! Cisco Brewers is always filled with dogs but they can also run around at Sankaty or at Madaket or Surfside Beach (on a leash, unless it’s the off-season). We also brought our pups along for a sailboat ride on the Endeavor and they were obsessed!
Thoughts on visiting Nantucket in the off-season?
Definitely look up which restaurants are open depending on the time of year you’ll be visiting. Some places close in October and don’t reopen until April or May, while others remain open for off-season weekends like Christmas Stroll. It’s nice to have a car on island in the off-season if you’re willing to bring yours across on the ferry or rent one from Affordable Rentals or Hertz, but you can definitely get by using Uber or the Wave shuttle if need be, particularly if you’re staying in town. We love taking off-season walks on the beach (even when it means bundling up in sweaters and jackets), plus visiting in the off-season means you’ll have any of the three lighthouses to yourself!
Thoughts on visiting Martha’s Vineyard from Nantucket?
We’ve only done one day trip to see friends on Martha’s Vineyard and found it tricky with limited ferry and flight times! It’s definitely doable to move from one to the other if you have overnight stays booked on both islands, but we found it hard to explore much of Martha’s Vineyard going there and back in one day.
What should I pack for a week on Nantucket?
This obviously depends on the time of year, but my summer uniform involves a lot of striped shirts, white jeans, and Jack Rogers or espadrilles. Don’t forget a cable-knit sweater or comfy sweatshirt for chilly evenings in line at the Juice Bar (cold weather has never stood in the way of me needing to get my fix!) and a raincoat or windbreaker for gray days (and it’s likely you’ll have one or two if you’re staying for a week). For daytime you’ll want swimsuits, cover-ups, and sneakers if you’re renting bikes; for evenings you’ll probably want a dress or two depending on where you’re dining (but nothing fancy — you’ll see Lilly dresses at even the ritziest of Nantucket restaurants). I tend to avoid heels (besides the aforementioned wedges espadrilles) on the island, particularly if I’m anywhere near the cobblestone streets in town. I’ve watched too many tourists roll their ankles on Main Street to take the risk!
What’s the easiest way to get to Nantucket?
Let me start by saying Nantucket can be notoriously difficult to get to and it’s best to go in with the mindset that the juice will be worth the squeeze. Your two options are to arrive by plane or by ferry. Direct flights are available from Boston, New York, and Washington, D.C. Ferry options are available from Hyannis on Hy-Line (one hour) or Steamship Authority (one hour or two hours and 15 minutes, depending on whether you want to bring your car) as well as New Bedford on Seastreak (two hours, but you’ll stop short of all the traffic on Cape Cod). Traveling from Connecticut, we typically take the Seastreak ferry from New Bedford, but if it’s the off-season or we’re bringing a car, we do the slow ferry on Steamship Authority. When my husband and I lived in Dallas for two years, getting to Nantucket meant a flight to Boston or New York and then a connection to fly to Nantucket.
What’s the easiest way to get around Nantucket?
My strong preference is to have a car on the island, but it’s around $500 round-trip to bring yours across and often more expensive to rent one for the weekend, so it depends on with whom we’re traveling and how long we’ll be staying. If we don’t bring our car (or have a sibling or friend’s already on the island), we rely on Uber, bikes, and the WAVE shuttle, which is clean and reliable but not always super convenient if you’re staying outside of town. If you’re staying in town, you can absolutely get by without a car — you’ll only need to rent bikes or call an Uber if you want to see ‘Sconset or dine at Millie’s in Madaket.
What would your 36 hour guide to Nantucket look like?
If you only have 36 hours on the island, I would recommend staying at a hotel in town. If you can arrive on Friday evening, I would make reservations at Cru to enjoy a lobster roll and glass of rosé on the water and then walk to Juice Bar for a homemade waffle cone.
On Saturday morning, I’d recommend renting bikes and biking the seven miles out to ‘Sconset (or taking an Uber if that sounds too rigorous!) to treat yourself to iced coffee and blueberry muffins from the ‘Sconset Market. Spend an hour or two on the ‘Sconset bluff walk enjoying the beautiful homes and ocean views as you head toward Sankaty lighthouse. Once you’ve worked up an appetite for lunch, head back on Baxter Road then walk across the foot bridge to the Summer House Beachside Bistro where you can compare lobster rolls with the one you had last night.
If you’d rather relax than get your 10,000 steps in, stop and pick up beach fare from Bartlett’s Farm before making your way to Ladies Beach, a spot with manageable waves that’s not nearly as crowded as nearby Surfside. When you’ve had your fill of sun and sand, head to Cisco Brewers for sangria or a Whale’s Tale pale ale at a picnic table near the live music.
Saturday night is all about the sunset. If you’re willing to splurge, make dinner reservations at Galley Beach (or go there for cocktails and Ventuno in town for dinner). If you want something a little less pricey, enjoy the sunset on Madaket Beach before margaritas and tacos at Millie’s.
On Sunday morning, have your hotel hold on to your luggage so you can enjoy your final day in town. Grab an outdoor table for breakfast at Lemon Press or enjoy a leisurely brunch at Brant Point Grill. Then spend your remaining hours doing a little shopping (28 Centre Pointe and Milly & Grace are two of my favorites!). If you have time, you could walk or bike to Brant Point lighthouse, but no one would blame you if you skipped the field trip in favor of one last Juice Bar run before your boat!
21 Broad
A reasonably-priced hotel in a great location two blocks from the Steamship Authority and right up the street from the Juice Bar. Expect colorful decor, modern amenities, and an outdoor deck for happy hour.
