How to Enjoy a Perfect Weekend on Nantucket


Nantucket is my happy place.

Over the years, I’ve enjoyed so many special weekends on the island that as soon as I step off the ferry, I am instantly excited (…and probably in a better mood, ha!). While Nantucket is only about 30 miles south of Cape Cod, when you are there, you truly feel like you’re in some distant destination. Everything from the architecture to the landscape is picturesque, and despite visiting a few times a year, I always find new places and areas to explore. Whether you’re on foot or opt to rent a bike or jeep, there’s so much to see and do — not to mention eat and buy!

September is an ideal time to visit Nantucket because the crowds are lighter and the weather is still gorgeous! While my list could literally go on and on, I wanted to share a few of my favorite places and activities.

Enjoy exploring the Grey Lady…she’s a beauty!





The A-Lyst for How to Enjoy a Weekend on Nantucket

alyssamainstGo on a Lighthouse Tour

Nantucket has three lighthouses – Brant Point Lighthouse, Sankaty Head Lighthouse, and Great Point Lighthouse, and the latter two can provide for a fun daytime excursion. Brant Point is the closest to town and is one of my favorites, as it’s the first and last landmark you see when arriving or leaving Nantucket. It is always decorated for the season (think holiday wreath, daffodils, or a beautiful American flag) and the nearby beach provides a great vantage point to see boats and yachts coming and going. Sankaty Head is close to Siasconset, and during Daffodil Weekend in April, the fields surrounding it are blanketed with hundreds of the happy yellow flower. It’s a beautiful site to see! Great Point is a hidden gem because it can only be reached by a 7-mile shoreline walk or by renting a jeep and traveling off-road. This lighthouse sits at the northernmost tip of the island and the area is home to hundreds of seals. It’s absolutely worth the trek or drive to watch the seals frolic from afar!

“House-hunt” in the Downtown Historic District

The houses in Nantucket’s Downtown Historic District are stunning. Think quintessential New England complemented by perfectly manicured yards, white picketed or wrought iron fences, and an American flag proudly dancing in the wind. We love strolling down Main Street as well as all of the other little side streets “house-hunting” a.k.a dreaming! Each antique charmer is nicer than the next and it’s fun to spot historical details like hitching posts and the 19th century “built” dates on the exteriors.

Imbibe Sunset Cocktails at Galley Beach

This activity deserves its own category because it is literally an event! Make sure to dress in your favorite summer outfit and be ready to move quickly to grab a highly coveted fireside lounge seat. Once the sun begins to set, everyone moves to the beach to take the perfect sunset photos, and when the sun finally goes down, there’s always a round of applause. While a martini will set you back $20, the scenery and, for that matter, the scene, is worth it!

Stimulate the Economy and Shop Local

It’s almost overwhelming how many fantastic small businesses and shopping destinations the island offers its visitors. Beyond the boutiques on Main Street, I love exploring the stores on Old South Wharf, Centre Street, and Federal Street, and over the years, have developed a method on how to navigate them. I typically “scout” the merchandise on the first day and then revisit my potential purchases right before we catch the ferry. Call me crazy, but you could drop a lot of dough if you don’t show self-restraint! My favorites are MonelleMilly and GraceBlue Beetle, and SHIFT for clothing, Isabel HarveyCJ Laing, Peter Beaton Hats, and Vis-a-Vis for accessories, and Lion’s PawBest of the Beach, and Freedman’s for home decor.

Explore Siasconset (‘Sconset)sconsethouse

Jump on”The Wave” (local bus transit) and pay $2.00 to head to the charming village of ‘Sconset. We usually grab sandwiches at Claudette’s (one of the only spots to eat there and cash only), stroll the Bluff Walk to eye the gorgeous rose-covered homes, and round out the trip by grabbing a cocktail at The Summer House’s beachside bistro. ‘Sconset, which was actually settled as a fishing village, is incredibly quaint and absolutely worth a visit.

Spend an Afternoon at Cisco Brewery

Although the brewery is not withing walking distance of the town, you can take advantage of Cisco’s free shuttle that leaves hourly from the Visitor’s Center on Federal Street. The brewery is essentially three different entities in one – from Cisco Brewers’ well-regarded beers, like the Grey Lady and Whale’s Tale, to Triple Eight Distillery’s vodka and liqueurs, and the Nantucket Vineyard’s wines, there is literally something for everyone plus food trucks, live music, and lawn games. My go-to libation is always the Figawi Wowie (888 Blueberry Mint Liqueur, lemonade and club soda) and a few oysters!

Enjoy a Ridiculously Delicious Brunch and Dinner. REPEAT.

There are so many amazing restaurants on Nantucket that it’s hard to narrow down my favorites. For a relatively small island, I am always so impressed with the amount of culinary talent, and whether you are a total foodie or very picky eater, you won’t be disappointed! A few of my go-to spots include Nautilus (the whole roast peking duck for the table is amazing), The Proprietors Bar & Table (three words…pig ear fries!), Cru (amazing location on the water and chic outdoor lounge area), The Pearl (the Salt & Pepper Wok Fried Lobster is their signature dish), Ventuno (order a few half orders of different house-made pasta to try them all), Lola 41 (amazing music selection and sushi!), Brant Point Grill (they have a great Sunday brunch buffet), and Black-Eyed Susans (THE best breakfast spot on the island — the only downside is the long wait!). The list could go on and on…!

Bike to the Beach

Biking is by far the easiest way to see Nantucket, and unlike riding your bike in Boston, it’s relatively safe, as the island has numerous paved (and very scenic!) bike paths. A few of my favorite routes include heading out to Madaket Beach and stopping for lunch at Milie’s, biking towards Cisco Beach and picking up sandwiches and picnic supplies at Bartlett’s Farm, and if you’re up for pedaling 8 miles and some hills, biking to ‘Sconset via Milestone Road. You can either rent bikes once you’re on Nantucket or bring yours on the ferry for a small fee.

Indulge in an Ice Cream Cone at The Juice Bar

As you already know, I am a huge fan of ice cream (you can browse my list of top Boston spots for ice cream here), and The Juice Bar is on my all-time favorite ice cream list. On a beautiful summer night, the line to get ice cream here goes around the block, and I’ll be honest, it does not move very fast. However, the smell of freshly made waffle cones wafts through the air beckoning you to wait for 10…err…30 minutes to get one. My favorite flavor is the Crantucket (vanilla base with chocolate covered cranberries) and I love how they not only have waffle cones, but also waffle cups, which are SO much easier to manage. My advice is to go at an off-time and don’t forget your cash, as they don’t take credit cards!

Outfit Details:

Brant Point Photos

Dress: Transatlantic Voyage Blue and Ivory Striped Midi Dress

Shoes: Sam Edelman Greta Thong Sandal in Jute

Downtown Historic District Photos

Dress: Shoshanna Leia Midi Dress

Handbag: YSL Camera Bag (similar YSL style here)

Shoes: Sam Edelman Gigi Sandal in Bright White Leather

Photos by @TheLyleStevens