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Nantucket continues to be a family favorite and checks all the boxes for New England charm and beauty. Year after year, we vacation every summer on the island and even find ourselves returning in different seasons for another taste of this special destination. Every season on The Grey Lady offers up a bit of magic. From the spring Daffodil Festival, to the arrival of peak summer travel season, to the peaceful shoulder season, to the wondrous spectacle that is the Nantucket Christmas Stroll, there is so much this island has to offer. Here are five ways to make the most out of your next Nantucket visit.

Great Point
*Photo Credit : Kristy Cadwallader*

Rent a Jeep and Explore Great Point Beach and Lighthouse

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Lower that tire pressure and spend a day driving out on the beach on this long stretch of peninsula that is a wildlife refuge and home to Great Point Lighthouse. We booked with Nantucket Rentals, which meant that their on-island concierge service had our Jeep rental reserved and ready for our island adventures.

Great Point Lighthouse is only accessible by Jeep, and you will want to make sure to carve out extra time to explore this special part of the island. Seals and an array of wildlife are abundant at this refuge. Shorebirds including osprey, seagulls, arctic terns, jaegers, and shearwaters inhabit these sandy shores. There is a large seal population and sharks do rove these waters frequently, so swimming is prohibited. It is such a peaceful place to enjoy. As the breeze dances among the beach grass and the waves crash onto the shore, you will see why this is a favorite way to spend a day on the island.

Our tip: Pick up a lobster dinner to go from Sayle’s Seafood and pack a blanket and chairs to have a picnic on the beach.

Endeavor Sailing
*Photo Credit : Kristy Cadwallader*

Enjoy a Sail Aboard Nantucket’s Oldest Sailing Charter

Head out onto the pristine waters of Nantucket for a sail with Captain Jim and his crew aboard his classic wooden Friendship sloop with EndeavorSailing. Captain Jim sails May through October and offers day sails, afternoon sails, sunset sails, and private charters. Nantucket Rentals’ concierge service can reserve your sail for you, so all you have to do is sit back and enjoy a day on the water.

Our tip: Pack a cooler of rosé and acrylic wine glasses to enjoy an afternoon sail. Plan ahead and book a table at CRU for dinner after your sail; it’s located right on Straight Wharf, just a stroll from the Endeavor dock.

Walk the Sconset Bluff Walk

Siasonset, or “Sconset” for short, will give you a whole other island experience. In June and July, the rose-covered cottages make it truly like stepping into a fairy tale. No matter the season, this side of the island has a quaint New England charm that will win your heart. The Sconset Bluff Walk starts right in town, where you step foot on a seashell-laden path that meanders past little cottages overlooking the ocean. As you traverse this path it takes you through grassy lawns of some magnificent beach homes to little dirt paths that overlook that amazing sea view. Be sure to end your walk by heading out to the Sankaty Lighthouse. This iconic red and white painted light is seated on such a picturesque perch. Having a Jeep on-island for your stay makes getting out here a breeze. If you want to up your activity, you can bike out to Sconset on the bike path too.

Sconset Bluff Walk
*Photo Credit : Kristy Cadwallader*

Our tip: Start your day with breakfast at Claudette’s. When you head back to town after your bluff walk, enjoy a scoop from the walk-up window at Sconset Market. If you want to make a day and night of it, be sure to reserve a table under the roses at The Chanticleer for a top-notch dinner experience.

Spend an Afternoon at Steps Beach

There are so many beautiful beaches to explore on Nantucket, but one of my favorites is Steps Beach. Tucked away off Lincoln Circle, it’s an easy walk or bike if you are staying in town. As you enter the little beach path, it leads you to a giant staircase overlooking quite an amazing view. Walk down the staircase and the powdery sand awaits your feet. The sand is so soft here and I love all the views. You can catch a really lovely sunset here too. Just note, there are no lifeguards or facilities at this beach.

Steps Beach
*Photo Credit : Kristy Cadwallader*

Our tip: Bike down to Something Natural for a late lunch and then ride over to Steps for an afternoon on the beach.

Explore Madaket

For our most recent trip, we extended our time and booked a vacation home in Madaket through Nantucket Rentals. Booking with them is a breeze and they offer so many great properties and work directly with home owners and brokerages. Their on-island concierge service can assist you with stocking your fridge upon arrival, booking your on-island activities, and reserving your vehicle or bike rentals.

Nantucket Rentals
*Photo Credit : Kristy Cadwallader*

Madaket is another part of the island that is on the quieter side and a great place to stay. There are bike paths everywhere and it’s an easy drive to get back into town. Madaket Beach is another beautiful one to add to your list. The sunsets here are some of the prettiest on the island.

Our tip: Have dinner at Millie’s. After dinner, stop in Millie’s Market to grab cocktails and enjoy a sunset on the beach.

Kristy Cadwallader

5 Ways to Make the Most Out of Your Next Nantucket Visit