Family Adventure to Nantucket, Massachusetts

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Advisor - Jill Albino
Curated By

Jill Albino

  • USA

  • Massachusetts

  • Domestic Travel

  • Family Travel

  • Nature Escapes

  • Coastal

  • Fields

Nantucket Massachusetts Travel Itinerary
Curator’s statement

Nantucket is one of those places that remain engraved in your heart from visiting as a child to eventually returning with one’s own family. It is a happy place with so much to do, see and shop. Plus, all the food is fantastic! Today Nantucket is growing like never before with many new hotels and restaurants popping up. But the landscape remains the same – sublime and perfect for a summer getaway with the family. Don’t forget to top each day with a creamy ice cream cone at one of Nantucket’s many shops!

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Day 1: Town and beach exploring

Acai bowl in Boston, Massachusetts

Start the day off with breakfast at The Lemon Press. Think: açai bowls, wraps and juices. Then, head to Jetties Beach, where you can take a sailing or tennis lesson and spend the afternoon on the beach or steps nearby. There is an excellent sandbar you can walk out to – a fun time for the kids as well! Finally, head to the snack bar at Jetties for drinks and food with tables on the sand for small bites or lunch.

In the afternoon, walk into town and do some light shopping. Town Pool is every kid’s favorite for the duck scavenger hunt. Also, stop by The Bookstore, Gift and Box Nantucket to support local artisans, Murrays just because it's a Nantucket original, Breezin Up for Nantucket sweatshirts,  and Sunken Ship for fun kid toys. Take a stroll, and maybe you'll catch the moon or sunset at Children's Beach. Have dinner at Straight Wharf, the eggplant is something out of this world! Skip out on dessert and head out for ice cream at Jack and Charlies.

Advisor - Jill Albino

A note from Jill

Reservations for dinners are super important and made way ahead of time, so are sailing, tennis and surf lessons unless you get lucky.

Day 2: Biking, surfing and shopping

Boat in Nantucket, Massachusetts

You should start your second day with breakfast at Black-Eyed Susan’s – I always order the spicy Thai tofu scramble and a side of the Dutch cakes. Bike to Nobadeer for a booked in advance surf lesson. After your class, ride your bike to Stones Beach then Surfside, where you can grab lunch at the beach shack or, if available, a food truck – my favorite is the Crunchy Vietnamese. After lunch, get back on your bike and head through town to check out Bodega home store, The Lovely for beautiful cotton dresses, Milly and Grace, Erica Wilson for beautiful apparel and Salt for bathing suits and sunnies. Have a drink at Galley Beach and watch the sunset. Dinner at Oran Mor is a lovely choice. Stay at Oran for dessert or grab a cone from The Juice Bar. Expect a long line that can more recently span to Federal St.

Day 3: Food trucks and relaxing

Martha's Vineyard local cafe.

Take out breakfast from Wicked Island Bakery – get there early or you may miss those cinnamon buns! From there, head out to spend the afternoon at Ladies Beach and don't forget your book. Then, grab lunch or snacks at Bartlett Farms. After lunch, head to Cisco Brewery, where kids are welcome and there are food trucks and music on some days. 

Catch a sunset at Cisco Beach (my favorite night activity) and head out to dinner at Proprietors Bar. Stroll downtown after dinner. You'll probably be too late for ice cream at The Pharmacy, but Town Pool is just a few doors down and is open late. They have excellent ice cream sandwiches made by The Lemon Press. Sit on a bench watching the stars and enjoy your ice cream! Cheers to another perfect day in Nantucket. 

Day 4: Sconset and aquatic activities

Beach town in Nantucket, Massachusetts

When in Nantucket, you must catch the sunrise at Altar Rock. It is stunning and worth getting up for. After the morning sun salutations, pick up a hot donut at The Downyflake – you won’t regret it! An alternative option is a breakfast at Surfside Cafe

Post breakfast, drive to Sconset and walk the small town and streets. There is a pathway between all the tiny homes down to the beach. Seeing Sconset is a must if you are a first-timer, especially the lighthouse. Pick up lunch at Provisions

Rent a kayak or paddleboard at Sea Nantucket Paddle on Washington Street and paddle to Monomoy and then through Nantucket Harbor throughout the afternoon. Not into aquatic activity? Shop the stores on The Wharf and check out the Whaling Museum. Try to catch a sunset at Steps Beach after, maybe bring a blanket and some rosé for the occasion. Tonight's dinner is served at Lola 41 or The Nautilus if you can get reservations. Lola opens at 5 pm to make reservations by phone only. By 5:01 pm, they are pretty much all gone.

Day 5: Day at the beach at Great Point

Lighthouse in Nantucket, Massachusetts

Start the day off with breakfast at Island Kitchen. Next, head to Yummy or Something Natural and grab everything you need for lunch at the beach. Stop at the Hatch's Package store to grab drinks. Pack a change of clothes, bathing suit, day outfit and dinner outfit and anything fun you may want for the beach – including chairs, tables, inflatables, beach games, kites and so on. Buy a day pass at the gate of Great Point – it's not cheap, but it's worth it. You'll have to inflate your tires but that's part of the fun! Spend the day and drive or walk to the lighthouse. It depends on the day, but sometimes you won't be able to drive out to the lighthouse. In that case, it's worth the walk. Bring water and bug spray – it gets hot and buggy! Change for dinner at The Wauwinet for the most beautiful sunset and superb dinner. 

Advisor - Jill Albino

A note from Jill

It's helpful to have a car to get to Great Point Beach unless you want to walk it, but it can get very buggy if it's too hot. You can explore the island on the bike (my favorite way), bus or uber. You can walk around the entire island because all the beaches are open to the public.  The bike paths take you all around the island – you will want to download the app ACK Trails.  

Day 6: Take the ferry back to mainland

Ferry in Nantucket, Massachusetts

When you are leaving, grab food and coffee at The Corner Table. They have indoor and outdoor seating and a culinary institute above it that offers classes. Stop into another favorite, Gypsy, for designer apparel if you have time. Then, head to your ferry. Don't be late because it is quite a punctual mode of transport! 

Advisor - Jill Albino

Travel Advisor

Jill Albino

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