Nantucket Island Surf School: If the waves are good, give it a try! The instructors are young, many of them current or former Nantucket High School students who grew up surfing right there at Cisco Beach. Website: Nantucketsurfing.com; Instagram: @nantucketsurfing.
Endeavor Sailing: The Endeavor runs three sailing cruises per day plus a sunset cruise （weather permitting） on a thirty-one-foot Friendship Sloop that was built by Captain Jim Genthner. You can reserve spots on the boat with others or rent the entire thing for yourself. Perfect for groups—large families, bachelorette parties, girls’ weekends, and so forth. You can bring your own food and drink. In Winter Storms, someone gets engaged aboard the Endeavor! Website: Endeavorsailing.com; Instagram: @endeavorsailing.
Miacomet Golf Course: As Blond Sharon points out in this book, it can be tricky getting a tee time at Miacomet Golf Course, because it’s the only public eighteen-hole course on the island. Miacomet also has a very good and popular restaurant and bar, a driving range, and a putting green. Website: Miacometgolf.com; Instagram: @miacometgolfcourse.
Absolute Sports Fishing ACK and Bill Fisher Outfitters: For all my Angler Cupcakes out there! I know the captains involved in these two charter fishing businesses and you’ll be in good hands. Charming and professional. Websites: Absolutesportsfishing.com, Billfishertackle.com; Instagrams: @absolutesportsfishingack, @billfishertackle.
Holidays and Festivals
Daffodil Weekend （the last weekend in April）： Daffodil Weekend （aka “Daffy,” as in “Are you coming for Daffy?”） kicks off the unofficial season on Nantucket. The stores in town reopen, the ferries fill up with people wearing yellow and green, and you start seeing a lot of classic cars around. Daffodil Weekend began in the mid-1970s when the Nantucket Garden Club sponsored a flower show. Two years later, garden-club member Jean MacAusland started an initiative to plant one million daffodil bulbs across Nantucket. Today, there are over two million daffodils on Nantucket, and the island celebrates their blooming with not only a flower show but also an antique car parade that starts in town and travels out the Milestone Road to Sconset. The cars often have themes—“Renoir’s Boating Party,” for example—and once in Sconset, the cars park along Main Street and set up tailgate picnics. I have scenes set at Daffy in my novels The Matchmaker and 28 Summers.
Figawi （Memorial Day weekend）： Are you older than thirty? Skip Figawi. Figawi （the name reportedly comes from sailors who were lost in the fog and shouted, “Where the f*ck are we?”） is technically a sailing race between Hyannis and Nantucket, but over the years it has devolved into a weekend where people in their twenties come bearing thirty-packs of Bud Light with the intent of drinking as much as they can for as long as they can. （I describe Figawi in my novel The Rumor.） Figawi is such a blight on the island that every Memorial Day weekend, I hope for rain…and I am not alone in this.
Nantucket Book Festival （mid-June）： I’m obviously not impartial, but as a person who has done many, many book festivals, I can say that the Nantucket Book Festival is the best. （It often falls when I’m on tour, so I don’t always participate.） Website: Nantucketbookfestival.org; Instagram: @nantucketbookfestival.
Nantucket Film Festival （mid-June, but after the book festival）： The NFF was founded in 1997 and from the beginning has been focused on screenwriting. It is very low-key as far as film festivals go, though celebrities do come to Nantucket during this week. The films are screened at both the Dreamland and the Sconset Casino, and there are plenty of talks as well, some at glorious private homes around the island. Website: Nantucketfilmfestival.org; Instagram: @nantucketfilmfestival.
Fourth of July: The Fourth of July is undergoing something of a transformation after COVID. Traditionally, this included a bike parade up Main Street, pie-eating contests, and then an infamous water fight with the Nantucket Fire Department. On the evening of July 5, Visitor Services sponsors fireworks, and people crowd onto Jetties Beach. This was canceled in 2020 and 2021. Nobadeer is the beach of choice for revelry on the Fourth—again, if you’re over twenty-five, you might want to check out one of the other beaches I’ve suggested in this guide!
The Pops （second Saturday in August）： My personal favorite “holiday” on Nantucket. The Boston Pops at Jetties Beach began in the late nineties to benefit the Nantucket Cottage Hospital and usually raises upwards of two million dollars. People pack picnics （like Mallory in 28 Summers） and sit in the sand while the Boston Pops perform. In recent years, they’ve included various special guests—we’ve had Carly Simon, Kenny Loggins, the Spinners. The show ends with a magnificent fireworks show. It’s the best night of the summer.