lunch
Sandbar
Lunch; no reservation needed, just show up
Trip highlight
Places from the trip
Restaurants
15 placesLunch
Dinner
dinner
Cru
Dinner; favorite lobster roll, outdoor seating preferred by the yachts at end of dock; indoor reservations open 1st of month prior for full month ahead
Trip highlight
dinner
Galley Beach
Dinner; sit outside on beach, price-fixed menu, expensive, bring sweater as it gets cold on beach
dinner
American Seasons
Date night option; books far out, good to book in advance and cancel if better options become available
dinner
Nautilus
Dinner; favorite restaurant, best food, small plates, Asian cuisine, reservations 7 days out at 10am on Resy, tiny restaurant, fun drinks, always packed
Trip highlight
dinner
Toppers at the Wauwinet
Dinner at sunset; lawn chairs in grass where you can order food and drinks, good for sunset viewing
dinner
Brant Point
Early dinner with kids in grass or drink outside; on OpenTable, books pretty far in advance, specify outdoors
dinner
Ventuno
Dinner; good Italian, outdoor vibe; reservations 1 month out
Trip highlight
dinner
Sister Ship
Dinner; new, trendy, feels like NYC restaurant, reservations 1 month out. Also good for a drink outside before a different dinner res.
dinner
Proprietors
Dinner; good cocktails and small plates, reservations 30 days out, has outdoor seating
Trip highlight
dinner
Lola 41
Dinner; good food and fun vibe, reservations same day at 4pm by phone
dinner
Toppers dinner boat from White Elephant
Boat ride from Brant Point at 5pm to Toppers, dinner, and boat back; drinks served on boat over, blankets on return; request outdoor table
Drinks
drinks
Cisco
Afternoon beer, music, food trucks
Trip highlight
drinks
The Gazebo
Outdoor bar on dock by Cru; chill vibe with TVs, drinks, bring deck of cards while waiting
Dessert
dessert
Juice Bar
Ice cream; described as the best, original shop, worth the long line. Try the dirty grasshopper and cookie butt
Trip highlight
Activities
10 placesExplore
Morning walk around town
Explore
Bike to Bartlett Farms
Breakfast sandwiches
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Bike to 167 Raw
Lunch; food truck with lobster rolls and tuna burger
Explore
Bike to Millies for lunch and Madaket beach
Mexican food and margaritas at Millies, then beach time in Madaket; long bike ride (about 1 hour)
Trip highlight
Explore
Bike to Surfside for day on beach
Most Hamptons-like beach, favorite for sand and swimming
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Day at Jetties beach with Sandbar lunch
Lunch at Sandbar or happy hour with live music some nights
Trip highlight
Explore
Rent a boat for day
Next Level Watersports - highly recommend. We do a day of tubing / skiing / wakeboarding / knee boarding with kids (3 hours), and a day of e-foiling as adults (2 hours). They drive you and bring all of the equipment. Meet at pocono beach and boat in the harbor. We used to use Island Boat Rentals when the kids were younger. You can rent a speedboat to drive yourself, watch kite surfers, check out the sound; usually half-day rental followed by lunch at Cru or wharf restaurants.
Trip highlight
Explore
Sconset town visit and cliff walk
Cute little town on opposite edge of island; long bike ride or drive; cliff walk goes through houses on cliff by ocean
Explore
Surfside beach
Day at beach; most Hamptons-like beach, good for sand and swimming
Trip highlight
Explore
Great Point
Get beach pass for car and spend the day out at great point. Can drive onto beach and set up chairs etc. Bring food. Can spend a whole day
Trip highlight
Notes & Tips
Rent bikes for whole trip; recommend renting a burley for kids seat to carry towels, umbrellas, and beach gear. We love staying in surfside by the beach. Used to stay in Brant point closer to town when kids were little. Nantucket is casual. Flats, no heels. Double check restaurant reservation notes. They change their policies every year
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