
lunch
Sandbar
Lunch; no reservation needed, just show up
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

lunch
Lunch; no reservation needed, just show up

dinner
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
dinner
Dinner; sit outside on beach, price-fixed menu, expensive, bring sweater as it gets cold on beach
dinner
Date night option; books far out, good to book in advance and cancel if better options become available
dinner
Dinner; favorite restaurant, best food, small plates, Asian cuisine, reservations 7 days out at 10am on Resy, tiny restaurant, fun drinks, always packed
dinner
Dinner at sunset; lawn chairs in grass where you can order food and drinks, good for sunset viewing
dinner
Early dinner with kids in grass or drink outside; on OpenTable, books pretty far in advance, specify outdoors
dinner
Dinner; good Italian, outdoor vibe; reservations 1 month out
dinner
Dinner; new, trendy, feels like NYC restaurant, reservations 1 month out. Also good for a drink outside before a different dinner res.
dinner
Dinner; good cocktails and small plates, reservations 30 days out, has outdoor seating
dinner
Dinner; good food and fun vibe, reservations same day at 4pm by phone
dinner
Boat ride from Brant Point at 5pm to Toppers, dinner, and boat back; drinks served on boat over, blankets on return; request outdoor table


dessert
Ice cream; described as the best, original shop, worth the long line. Try the dirty grasshopper and cookie butt
Trip highlight

drinks
Afternoon beer, music, food trucks
drinks
Outdoor bar on dock by Cru; chill vibe with TVs, drinks, bring deck of cards while waiting
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Breakfast sandwiches
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Lunch; food truck with lobster rolls and tuna burger

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Mexican food and margaritas at Millies, then beach time in Madaket; long bike ride (about 1 hour)
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Most Hamptons-like beach, favorite for sand and swimming
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Lunch at Sandbar or happy hour with live music some nights


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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

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Cute little town on opposite edge of island; long bike ride or drive; cliff walk goes through houses on cliff by ocean
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Day at beach; most Hamptons-like beach, good for sand and swimming


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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
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