Summer in Nantucket feels like stepping into a postcard, where white picket fences, lush flower window boxes, and flag-lined streets capture the essence of classic Americana. This spectacular island blends rich history with timeless coastal beauty, offering a serene escape that’s as elegant as it is enchanting.
From its pristinely manicured gardens to its stylish harbor town energy, it exudes the epitome of summer perfection and understated luxury. It’s so picturesque that it looks like it’s straight out of a page of Town & Country.
Given the immaculately-kept town’s extreme popularity amongst elite travelers, notable people, and celebrities, it stands to reason that the businesses and homeowners make a concerted effort to ensure it looks impeccable year-round.
Everyone from Martha Stewart and Ben Stiller to Drew Barrymore and Beyoncé has been known to vacation on this exclusive East Coast island. Even during our recent visit, we spotted a well-known Nantucket resident, Greta Van Susteren (internationally recognized journalist and television news anchor), dining at one of the iconic local eateries known as Black-Eyed Susan’s.
Located 30 miles from the mainland, it’s easy to see why this New England town is recognized as one of the most prestigious vacation destinations on the East Coast. Aside from its renowned reputation as a delightful travel hotspot, especially during the peak summer season, Nantucket is revered for its deep roots in American history.
A Brief History of Nantucket Island
Once known as the whaling capital of the world, Nantucket, Massachusetts, played a pivotal role in 18th and 19th-century maritime history, with its ships and sailors traversing the globe in pursuit of whale oil (which was used for lighting, candles, and more). By the mid-1800s, Nantucket began a remarkable transformation, from a whaling powerhouse into a sought-after summer retreat. As the whaling industry declined (due to various factors, including the Civil War), the island’s focus shifted toward hospitality, laying the foundation for its future as an elite retreat known for its natural beauty, tranquility, and everlasting appeal.
Today, the island stands as a beautifully preserved tribute to that storied past. Designated as a National Historic Landmark, the entire 47.8 square-mile island exudes undeniable charm, from its cobblestone streets, brick walking paths, and gas-lit lamps to the centuries-old homes adorned with blooming hydrangeas and colorful window boxes overflowing with vibrant flowers.
How to Get to Nantucket
Getting to Nantucket takes a bit of planning, but the journey is part of the adventure. While private planes and commercial carriers like Cape Air and JetBlue do service ACK Airport, frequent flyers know that Nantucket’s famously foggy weather (earning it the nickname “The Grey Lady”) can lead to flight delays, diversions, or even cancellations.
For a more reliable and scenic arrival, many seasoned travelers and locals alike recommend the high-speed Hy-Line Cruises ferry, which departs daily from the port of Hyannis (a short 2-hour drive from Boston) and brings you to the island in about an hour.
When you arrive on the island, since it’s so small, you can easily get by without a car rental, especially if you plan to stay in downtown (which makes everything virtually walkable). Plus, there are convenient rideshare services such as Uber and even the eco-friendly NanTukTuk (which is a pedal-powered island transit service). Beyond that, most of the hotels will arrange to pick you up and drop you off at the ferry, making it an effortless experience.
Where to Stay in Nantucket
Just a couple of blocks from Main Street, in the heart of downtown Nantucket, you’ll find 21 Broad – an enchanting inn that effortlessly blends old world beauty with contemporary style. Originally built in the 1800s as a private residence (which used to be the home of Captain Swain’s children), the stately Victorian structure has been thoughtfully reimagined into one of Nantucket’s most design-forward boutique hotels. While it retains the architectural elegance of its past, it was renovated in recent years by a local designer, offering a refreshingly modern space that feels both elevated and inviting.
Inside, the hotel surprises and delights with bold, clean-lined interiors that nod to coastal minimalism (inspired by beachy elements like sea glass) while embracing a playful, youthful spirit. Pops of cheery color, sleek furnishings, and curated abstract art pieces give each room a fresh and stylish aesthetic. Guest rooms feature spa-like bathrooms, plush linens, and tasteful designs, creating a cozy, comforting space that beckons you to relax. It’s a refreshing contrast to the island’s more traditional lodgings, perfect for travelers who appreciate heritage wrapped in modern sensibility.
Beyond the visual appeal, 21 Broad offers thoughtful luxuries that enhance your stay. Mornings begin with a curated breakfast spread featuring delectable bites (such as delicious pastries, muffins, and granola), while afternoons invite you to indulge in a cocktail during happy hour or unwind by the fire pit in the colorful courtyard. One of my favorite aspects of the property is its unbeatable downtown location, which means you’re steps away from upscale boutiques, acclaimed restaurants, and harbor views.
What truly sets the hotel apart, beyond its design and amenities, is the exceptional hospitality that defines each guest experience. Hotel Manager (Amanda Jardin), who brings decades of experience from luxury properties in Carmel-by-the-Sea and Lake Tahoe, leads the team with a warm, personalized approach. Whether offering insider recommendations, helping with tech in the room, or answering questions with a sense of enthusiasm, the hotel’s entire staff is genuinely attentive and thoughtful, ensuring you feel cared for and attended to.
Ideal for discerning travelers who value substance, style, and an idyllic location, this adorable luxury inn is where Nantucket’s history meets a new era of refined hospitality.
Where to Eat in Nantucket
Lemon Press
To start your day, head to Lemon Press, a bustling organic eatery and cafe on Main Street. Featuring a wide variety of enticing dishes from a hearty avocado toast (topped with avocado, fennel, pickled onions, confit tomatoes, sun-dried tomato tahini, and quinoa crumble) and a decadent french toast (with saffron-cardamom-rosewater custard, cardamom syrup, and pistachios) to outrageously-good fresh-baked pastries, refreshing juices, and flavorful smoothies, there’s no wrong way to get your morning going here.
With cozy booths, charming rustic decor, and an inviting ambiance, since launching in 2015, it’s quickly become the go-to spot for breakfast and brunch, especially during the peak summer season. Be sure to arrive early, as the stylish restaurant fills up quickly, given its adorable setting and delightful menu. Starting in June 2025, the restaurant will begin offering dinner service with reservations available via Resy.
Cru
If you talk to anyone “in the know” in Nantucket, they’ll tell you to dine at Cru at least once during your trip. This popular restaurant is an iconic harbor-side lunch spot that perfectly blends laid-back coastal charm with upscale indulgence. Known for its raw bar offerings (such as freshly shucked oysters, lavish seafood towers, and crisp glasses of rosé), Cru delivers a quintessential Nantucket experience with a side of glamor.
The sleek, nautical-chic interior opens onto sweeping views of the marina, making it an ideal place to watch boats drift by and spot a well-dressed crowd of socialites. Whether you’re savoring lobster rolls, indulging in the Summer Pappardelle (my personal favorite), or toasting over chilled shellfish, Cru is the place to see and be seen on a Nantucket afternoon.
Breeze at The Nantucket Hotel
Breeze at The Nantucket Hotel offers a serene coastal dining experience with an elegant indoor‑outdoor atmosphere that feels effortlessly refined. Nestled within this historic hotel, the restaurant pays tribute to its past while feeling freshly modern. The ahi poke bowl is a standout masterpiece, with hearty chunks of marinated tuna nestled atop crisp vegetables and dressed in bright, clean flavors, making it a go‑to for anyone seeking a nourishing yet satisfying lunch. With its cozy, vintage decor and elevated, health‑focused fare, Breeze strikes the perfect balance between polished and laid‑back on the island.
The Proprietors Bar & Table
The Proprietors Bar & Table delivers a stylish, bohemian‑coastal dining experience that’s both cozy and romantic. Picture fresh flowers on candlelit tables, artfully weathered wood finishes, and an intimate, warm ambiance.
The restaurant’s seasonal small plates draw on global inspiration, and several standouts are absolute must-tries: the brown‑butter roasted carrots (served with fermented carrot muhummara, soaked dates, and walnuts) bring rich, nutty sweetness; the grilled asparagus and dandelion greens (topped with black olive breadcrumbs, ricotta salata, and a soft‑poached egg), strike a perfect balance of earthy and bright; and the lumache (with rock shrimp in a spicy tomato passata and topped with chili‑infused breadcrumbs), delivers a playful kick.
Save room for their legendary Lemon Meringue Ice Cream dessert, a rare combination of visual artistry and deliciousness. We’re still raving about how scrumptious that dessert was. Truly unforgettable, to say the least.
Black-Eyed Susan’s
Last but certainly not least, is one of the most iconic restaurants on the island – Black-Eyed Susan’s.
Beloved by residents and tourists alike, I quickly learned that this local gem has a cult following. Housed in a 1930s-era building, the restaurant blends rustic charm with a cozy, eclectic atmosphere that feels nostalgic yet elevated. In 2023, the original owners passed the torch to the team behind The Proprietors, bringing new creative energy while honoring its 30-year history.
The interior channels a rustic-chic diner style, complete with wood-clad walls, antique chandeliers, and an open kitchen where Chef Todd can be seen crafting dishes nightly. Quaint floral-printed tablecloths, fresh flowers, and candlelight in vintage glasses add to the intimate, welcoming ambiance that keeps locals and visitors returning year after year.
What to Wear in Nantucket
When packing for Nantucket, think preppy-chic with a nautical twist; effortless style that blends coastal charm, an homage to Americana, and a classic polished finish.
The island’s signature look leans into crisp stripes, soft pastels, dainty florals, and elevated staples like white denim, lightweight knits, and breezy maxi dresses. Preppy fashion brands with boutiques on the island, such as Ralph Lauren, Vineyard Vines, and J.McLaughlin, embody the traditional style that defines Nantucket.
For example, a striped boatneck top paired with jeans, sneakers, and a hat feels at home here, whether you’re exploring town, diving into an exciting novel, or heading to lunch by the harbor. For evening, a comfortable floral maxi dress, paired with a denim jacket and espadrilles, is perfectly appropriate for dinner on the town.
Because Nantucket’s weather can shift throughout the day, layering is essential. Foggy mornings and cool sea breezes often give way to warm, sunny afternoons, so pack smart pieces like a cardigan sweater or denim jacket to throw over your shoulders.
For shoes, leave the stilettos at home. Instead, opt for espadrille wedges, ballet flats, or block-heeled sandals, which are easier for navigating cobblestone streets comfortably without sacrificing style. Nantucket fashion is all about relaxed sophistication, channeling the timeless appeal of East Coast summer.
Things to do in Nantucket – Activities & Places To Visit
Stroll and Shop Downtown
Shopping in downtown Nantucket is perfect for those who appreciate thoughtful design and elevated style. Stroll along the brick-lined walking paths and discover a mix of high-end fashion boutiques, coastal-inspired home décor shops, and curated art galleries featuring local and contemporary artists. Whether you’re on the hunt for a designer woven straw clutch or are browsing for a feminine floral dress, you’re guaranteed to find whatever your heart desires. Quite frankly, there were so many adorable stores, I could easily spend hours shopping in Nantucket.
While you’re there, make sure to pick up a cozy Nantucket sweater, which will come in handy when the weather unexpectedly gets chilly (which happens more often than you’d think).
Don’t miss a stop at the iconic Murray’s Toggery Shop, a multi-generational family-owned business which has been an island staple since the mid-20th century and the birthplace of the famous “Nantucket Reds,” a signature faded red pant that has become a hallmark of coastal preppy style. Whether you’re browsing for statement pieces or timeless classics, downtown Nantucket offers a shopping experience as memorable as the island itself.
Visit the Whaling Museum
Perfect for a rainy or foggy day, a visit to The Whaling Museum in Nantucket is an enriching stop that offers an in-depth look at the island’s maritime roots and cultural evolution. Inside, you’ll find impressive exhibitions that delve into the rise of the whaling industry and explain its massive impact on the island’s economy, global connections, and way of life. Personal stories and family histories are woven throughout, giving insight into the people who helped shape Nantucket’s past (many of whom still have descendants living on the island today).
One of the most fascinating aspects is the collection of historical clothing and textiles, showcasing how Nantucket apparel influenced what we now recognize as classic preppy style (it was even referenced in The Original Preppy Handbook, which was published in the 1980s). The three-story museum paints a vivid picture of life in old Nantucket, making it a must-visit for history lovers and design enthusiasts alike. Atop the museum, you’ll discover a rooftop observatory, which makes it easy to take in views of the surrounding town.
Bike or Walk the Island
Bicycling or walking around Nantucket is a wonderful way to soak in the island’s scenic charm, especially when the sun decides to come out. With easy-to-navigate paths that weave through quaint neighborhoods and along sun-drenched beaches, it’s a great place to rent a bike or lace up your sneakers for a brisk walk. Coastal trails like the South Shore and Cisco make for a leisurely ride, offering ocean breezes and the chance to pause at quiet sandy stretches. Meanwhile, wandering through residential streets reveals lush gardens, charming storefronts, and a sense of small-town discovery.
Relax at Jetties Beach
Jetties Beach is one of the most convenient and family-friendly stretches of sand on Nantucket, just a quick walk or bike ride from town. With calm waters, a wide shoreline, and stunning views, it’s ideal for swimming, sunbathing, and beach games. Steps from the sand, you’ll find Sandbar, which is a lively beachside restaurant and bar that draws a crowd on sunny days. It’s the perfect spot to enjoy a casual lunch or a cocktail with your toes in the sand, making Jetties a go-to destination for both relaxation and a bit of seaside buzz.
Explore Hand-made Crafts at The Farmers & Artisans Market
Each Saturday (late May to mid-October) in downtown Nantucket, you’ll find the Farmers & Artisans Market buzzing with local creativity, offering an inviting space to explore and shop for locally-made handcrafted treasures.
Wander between stalls overflowing with hand-knit scarves and cozy throws, artisanal jewelry pieces (crafted in silver, sea glass, and natural stones), and unique Nantucket artwork that captures seaside scenes and island life. You’ll also encounter makers showcasing small-batch textiles, pottery, and woodwork, all reflecting the island’s rich artistry and homemade ethos. The sustainable market is the perfect place to discover one-of-a-kind souvenirs and support local artisans doing inspired, heartfelt work.
As you can see, Nantucket’s enduring appeal as a vacation destination lies in its serene pace, refined beauty, and effortless sophistication. Whether you’re wandering through character-rich streets lined with hydrangea-covered cottages, savoring fresh seafood by the harbor, or watching the fog roll in over the sea, Nantucket invites you to slow down and soak in its quiet elegance. It’s this delicate balance of relaxed luxury and historic charm that continues to captivate both longtime visitors and first-time travelers.
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[Disclosure: Hosted accommodations, meals, and media access provided by 21 Broad, Lemon Press, Black-Eyed Susan’s, and The Whaling Museum. Image credits: Christina-Lauren Pollack for Inspirations & Celebrations. Disclosure: Affiliate links included. Inspirations & Celebrations partners with several affiliate programs, meaning that this author may earn a commission from purchases/clicks by those who visit this site at no additional cost to you. All opinions are my own.]
