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What is the best month for visiting Nantucket?
June, July and August are high season. Weather temperatures peak at the 70s or 80s, and the fog mostly burns off as the sun's rays beam through any clouds. However, you'll still be met with the occasional cold front or sprinkles, so bring layers. "Sweater seasons" May and September may be my favorite time of year to visit as crowds thin, making it easier to get ferry seats, restaurant reservations, and a spot on the beach. Even at the start of September, the weather stays sunny and in the 70s.
1. Get a good spot on the ferry
If you're traveling with kids or dogs or both, you may want to try to line up early to secure either a spot inside at tables, or up on the first-floor deck (if you so choose.) While it's windy, many prefer the deck for the ocean breezes and first-rate views of Cape Cod, the Atlantic, and the first views of Nantucket. If you're on the 7:05 p.m. ferry, the "golden hour" sunsets can't be beat.
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2. Decide where to stay
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3. Stroll downtown
Quaint cobblestone streets greet you upon disembarking at the wharf. The walk to Main Street features jewelry shops, fudge (Aunt Leah's award-winning penuche is a must-try), and plenty of Nantucket gear (even for your pup!) Further down, you'll find preppy boho-inspired boutiques such as Milly & Grace, Nantucket classics Lily Pulitzer and Vineyard Vines and For Now. For exquisite home finds see Nomad.
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5. Check out an art gallery
What's a beach vacation without a juicy beach read? When in Nantucket, you must start with one from Queen of the Beach Read herself and famous islander Elin Hilderbrand. She's been known to make stop-ins to sign her latest novels at Nantucket institution Mitchell's Book Corner. You'll also find her own Nantucket guide, The Blue Book, the ultimate island guidebook, which contains the best recommendations (including references from her novels!)
7. Hit the beach—and the beach bar
8. Bike around the island
Biking is one of the most fun ways to explore the island. You can rent a bike or scooter at Nantucket Bike Shop (you can just walk up and rent a bike for about $50 a day). The 1 to 2-hour trip to Cisco Brewery and Bartlett's Farm is a popular one, but if you've got half a day, you can take Polpis Road to Siasconset ('Sconset) for views of the climbing rose-covered cottages and beach bluffs, and take photos at Sankaty Head Lighthouse.
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Cisco Brewery is notorious for its afternoon party scene—enjoy live music while sipping a large selection of craft brews, including its famous Whale's Tale Pale Ale. If crowds are already lining up, you can also head to Nantucket Vineyard and Triple Eight Distillery, also on Bartlett Farm Road. Don't forget to try a "Figawi Wowie" — a blueberry vodka lemonade named after the famous Memorial Day sailing race.
10. Visit a lighthouse—or three
For that classic coastal New England Instagram shot, you're going to want to visit one of the lighthouses on the island. Brant Point Light House, closest to downtown and visible by ferry, is stunning, especially at sunset, as is Sankaty Head Lighthouse. The most hard to reach, Great Point Lighthouse is only accessible by Jeep or foot over seven miles of sand (and you've got to know what you're doing since you can quickly sink!)
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12. Walk the Bluff
If you've got time on the island, the 'Sconset Bluff Walk is def worth some space on your camera roll. Starting at Front Street, you can meander down the narrow footpath past gray-shingled cottages with flowering shrubs—it's especially pretty during hydrangea-peeping season! It's about two miles long, so grab a canned beverage or two, a sandwich from Claudette's, and have a picnic at Sankety Head Beach.
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14. Have a cone
Lola 41 is notoriously the best sushi spot on the island (and also my favorite.)Cru, right on the wharf, is "iconic" says Dwyer, and the place to see or be seen. (If you can get a reservation, champagne and oysters are divine.) Another relative newcomer and sister to bar Yoshi, O bar, located at 7-8 Old South Wharf, has an all-day raw bar menu, seasonal cocktails and a 10-seat bar with incredible views of the north side of the marina and Straight Wharf.
16. Or some upscale coastal eats
17. Sing at a piano bar or to a live band
The Chicken Boxwill sound familiar if you're a fan of Hilderbrand's beach reads. "Nantucket isn't necessarily known for its nightlife but this one spot is the go-to on the island!" says Dwyer. "They often have the best cover bands (i.e., the Joshua Tree)—I swear I thought U2 was really playing, but they also get big acts too, like The Revivalists." Piano sing-a-long bar The Club Car is also iconic for Hilderbrand fans.
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