- Flights to Nantucket with Tradewind Aviation make arrival seamless, with private terminals and efficient check-ins, making the time spent traveling part of the experience.
- Spring and early summer bring some of Nantucket’s most beloved events—from the flower-filled Daffodil Festival to the prestigious Wine & Food Festival—alongside peak blooms, ideal weather, and a lively social calendar.
- From refined stays like Greydon House and the Wauwinet to standout dining, boutique shopping, biking, and bluff walks, the island offers an effortlessly elegant New England escape.
Nantucket is a captivating kind of escape that feels both timeless and impeccably curated. Signature weathered grey shingles, cobblestone streets, 18th century architecture, and hydrangeas appear on cue each summer, softening every corner in shades of blue and blush.
But first come the golden daffodils, announcing the island’s unofficial start of spring, and the beginning of peak travel season. From there, Nantucket rolls into summer, scented with masses of pink and red roses draped over cottages and fences. The town quiets down in fall, ending the season with resplendent color across the heathlands.
This time of year is when every hour on the island feels well spent, and getting there should feel just as effortless. Tradewind Aviation makes the journey both seamless and convenient with multiple scheduled flights to Nantucket year-round from Westchester County Airport (HPN) in the New York area. All flights depart out of private FBO terminals, allowing for quick pre-departure check-in, meaning you only have to arrive 30-minute before wheels up. Regular commuters can benefit from purchasing ticket books (packages of 10 tickets or more), which offer preferred rates, additional flexibility including mobile app booking, and the option to privatize a scheduled flight. Tradewind also offers private flights to Nantucket from anywhere into Nantucket Memorial Airport (ACK).
The ease of flying personal with Tradewind eliminates the stress of traditional commercial air travel. Private FBO terminals, expedited security, and a comfortably modern Pilatus PC-12 aircraft ensure a smooth trip. For those traveling with pets, Tradewind allows your furry friends to travel in-cabin with you, complimentary for pets under 100 pounds.
Tradewind’s flight experience makes it possible to land in Nantucket, check in at your hotel, and be halfway through a Grand Cru Plateau of towering seafood at Cru before most travelers have even cleared the ferry terminal.
Fly Personal to Nantucket for These Spring Festivals
The Annual Nantucket Daffodil Festival (or The Daffy, as locals call it) in late April is the weekend Nantucket decides winter is over. Millions of yellow, orange, and white daffodils blanket the island, setting the stage for a three-day weekend of family-friendly festivities.
The marquee moment is the antique car parade followed by a tailgate picnic. Vintage cars and motorcycles decorated with flowers line up on Main Street for viewing before parading out to Siasconset. Live music sets the mood as themed picnics are unpacked and judges award ribbons for the most creative spreads. Bring your own picnic of artisanal cheeses, cured meats and a bottle of wine and join in on the fun.
The Nantucket Garden Club’s Daffodil Flower Show, held at Bartlett’s Farm, showcases thousands of entries grouped by individual stems, floral arrangements, and photography. This is the place to see rare varieties and learn about planting, nurturing, and identifying different types of daffodils.
Other activities include the Children’s Beach bandstand and beach bike parade, the dog parade featuring adorable dogs dressed in daffodil-inspired costumes, and the daffodil hat pageant with ribbons awarded for the most creative displays.
This festival is a beloved and popular island tradition (celebrating 50 years this year!) so make plans early, wear something yellow, and don a festive hat.
In late May, Nantucket swaps daffodils for decanters as the Nantucket Wine & Food Festival ushers in the summer season. Renowned winemakers, chefs, sommeliers, and culinary enthusiasts gather for five days of extraordinary tastings, intimate dinners, educational seminars, and immersive culinary experiences. It’s a week of prestigious events and a chance to interact with producers of legendary wines in a social setting.
With more than 50 events attracting a sophisticated, wine-savvy audience, the trick is not trying to do it all but designing a lineup that aligns with your interests: vertical tastings and rare vintages, luncheons with pairings of lobster and champagne, or culinary classes and chef panels are all on offer. Grand Tastings are the soul of the festival, where celebrated wineries from around the world pour hundreds of wines paired with gourmet bites from top chefs.
The “Great Wines in Grand Homes” series are some of the most coveted and intimate events of the festival, held in private residences on the island. Winemakers lead in-depth tastings of iconic wines; others feature visiting chefs who pair the wines with multi-course meals. There are also entertaining sessions like “James Bond’s Bordeaux” that explore the wines of Bordeaux through the lens of James Bond films. And afterwards, there are parties under the stars at Nantucket Harbor.
Plan on booking three to five events a day. Or, attend one grand tasting event and a ticketed dinner if you want to allow for beach time and shopping during the day. With 4,000 attendees each year, events sell out quickly, so plan well in advance.
Looking ahead to summertime is the highly anticipated Nantucket Film Festival. Join the throng of enthusiastic festivalgoers hopping between historic theaters and waterfront venues, where premiers, panel discussions, and comedy roundtables spill into garden parties and post-screening cocktails.
Where To Stay
Faraway Nantucket, in the middle of Town, is a collection of six charming houses clustered around a chic courtyard. Sister Ship is the hotel’s restaurant and bar, which offers a lovely cocktail terrace outfitted with rattan sofas and fringed umbrellas. Complimentary bicycles are offered for guests to get you around town and to the beach.
Greydon House, just off the wharf in Town, is a stylish hotel set within a former sea captain’s Greek Revival home, where historic charm meets modern sophistication. Interiors designed by Roman & Williams reference the island’s seafaring past.
The Wauwinet, about 10 miles from Town on the waterfront, is refined, old Nantucket elegance. The inn has 32 elegantly appointed guest rooms and freestanding cottages with beach access, complimentary bicycles and kayaks. A complimentary Jitney service shuttles guests to and from Town.
Where To Eat and Drink
Visitors are spoiled for choice on this little island, with local, line-caught seafood, oysters, and plenty of culinary talent. Restaurants fill up quickly in peak season so be sure to book well in advance.
Cru Oyster Bar located on Straight Wharf is the place to go for fresh oysters and champagne, and the tastiest lobster rolls for lunch or dinner.
Straight Wharf Restaurant is where the locals go for seafood like a deconstructed clambake with lobsters, clams, and mussels with roasted potatoes. After dinner, it’s a bustling late-night scene.
If you want to get away from the crowd, go to Millie’s in Madaket, which serves lobster rolls, fish tacos, seafood salads, and the famous rum punch called Madaket Mystery.
Cisco Brewers, known for craft beer, wine, and spirits, is a fun place to stop in after the beach for a beer flight and a snack from one of their food trucks.
The Chanticleer, located in a rose-covered cottage surrounded by lush gardens in Sconset, is a romantic choice for elegant, French-influenced fare.
Company of the Cauldron, owned by Joseph Keller (brother to Thomas Keller of French Laundry fame) serves a single three-course menu that changes nightly. It’s American cuisine with French nuances, served in a cozy candlelit dining room.
For great bread, pastries and sandwiches to-go, stop in at Born & Bread, an artisanal bread bakery and mercantile space in Town.
What To Do
Nantucket is small enough to feel manageable, which is part of its charm. Start in Town, the island’s historic center, where cobblestone streets thread past shingled cottages and preserved sea captains’ homes into an easy loop of shops, galleries, and restaurants.
Stop in at Mitchell’s Book Corner for beach reads and local history and Nantucket Looms for handwoven throws and textiles. If you want the island’s most famous wardrobe staple, Murray’s Toggery Shop is home to Nantucket Reds, the red canvas pants that are “guaranteed to fade.”
For a quick hit of history, duck into the Whaling Museum, the flagship of the Nantucket Historical Association, which is the fastest route to understanding how this small island became so influential.
Rent or borrow bikes from your hotel and explore the bike paths. It’s the easiest way to get around. Head toward the north shore beaches, where the water is generally calmer and warmer than the surfier south shore. On the way, stock up at Bartlett’s Farm, a family-run farm and market with sandwiches, soups, salads, and picnic-ready takeaway.
To really appreciate Nantucket’s natural beauty, follow the public footpath called ’Sconset Bluff Walk along the east-shore bluffs behind oceanfront homes. Enjoy gorgeous ocean views, sea air, and that windswept, end-of-the-world feeling that is quintessential Nantucket.
Whether you come for the daffodils, the wine, or just want to breathe the sea air, Nantucket in peak season is well worth the trip, especially when getting there is as effortless as the stay.
To learn more about Tradewind’s private charter and scheduled flights to Nantucket, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1.