Over the years, I’ve spent my fair share of time exploring Nantucket overland and oversand. I’ve been lucky enough to venture into some of the island’s most scenic and remote locations with my trusty 1995 Land Rover Defender 110—Nigel, aka 'The White Rover.' If you’re looking to experience Nantucket beyond the cobblestone streets and boat-filled harbors, here’s how to do it right.
Meet Nigel
Nigel is a 1995 three-door Land Rover Defender 110, powered by a small but mighty 300TDI 4 cylinder diesel. I imported this truck from Spain during the winter of 2021, and over the last four years, it has become my adventure companion. From surf trips up to Maine to ski trips in Vermont, Nigel has seen it all—but most importantly, he has tackled the oversand trails of Cape Cod and the Islands like a champ.
Booking Ferries
If you’re bringing your 4x4 to Nantucket, you’ll need a ferry reservation—and they’re notoriously tough to get. Steamship Authority’s summer ferry reservations open to the public on an early February morning at 8 AM sharp. It’s like registering for college classes: be online early and ready to go! If you miss out, keep an eye out for cancellations, but don’t bank on it.
First Stop: Fuel Up
Once you roll off the ferry, especially if you’re on a morning boat, make your way to Lemon Press on Main Street for the best coffee on the island—or in my case, the best lavender lemonade (highly recommended). If you go down Main Street, make sure to loop around the right side of the fountain at the bottom of the street...
After that, head over to Hatch’s to stock up on liquid provisions for the day ahead.
Hitting the Sand
Your first stop for overland adventures is the Wauwinet Gatehouse, where you’ll need to get your Great Point Oversand Sticker. To qualify, you’ll need basic recovery gear—tow straps, a shovel, and a jack, at minimum. Once you’ve got your sticker, it’s time to air down your tires and hit the sand.
Great Point & Coskata-Coatue
This area offers some of the most breathtaking scenery on the island. The drive to Great Point Lighthouse is nothing short of magical. The lighthouse itself, standing tall at the northern tip of Nantucket, has guided sailors through these treacherous waters for generations.
From there, head back down through the woods toward Coskata-Coatue, an incredibly remote stretch of sand. If you’re driving a classic Rover like me, go with a friend—it’s a long way from help! You’ll have the option of following the outer beach or taking the inner road along the lagoon. Either way, there are plenty of quiet spots to park, set up a beach day, and enjoy the isolation of this stunning part of the island.
For the best experience, find a spot between Trail Markers 1 and 4, where the beach is most protected from the wind, the waters are calm, and the views are endless. Break out the cooler, the grill, the chairs, and a football—it doesn’t get much better than this.
When it’s time to leave, remember the unspoken rule: vehicles coming off the beach have the right of way. The gatehouse has an on-site air station for reinflating your tires before heading back into town.
Where to Stay
Faraway – A favorite downtown spot within walking distance of the best restaurants, bars, and the ferry. Their in-house restaurant, Sister Ship, serves up some of the best cocktails on the island.
Airbnb – If you’re traveling with a group, there are plenty of great rentals within walking distance of town. Just book early!
The Beachside – A more affordable option, just outside of town, with onsite parking (a rarity on Nantucket). Located near Jetties Beach, it’s perfect for those looking to balance convenience and affordability.
Where to Eat & Drink
Slip 14 – Right on the wharf, this is the perfect spot for a pre-dinner drink and people-watching.
Bar Yoshi – If sushi’s your thing, this is the spot. Their fresh fish and outdoor seating make for a perfect summer night.
Or, The Whale – Located on Main Street, their steak frites is a personal favorite. Try to snag a table outside.
LoLa 41 – A Nantucket staple that books up fast—so make reservations early!
Cru – Iconic waterfront dining with unbeatable harbor views. Oysters and a Crucumber cocktail here are a Nantucket must.
Straight Wharf – A classic island spot known for incredible seafood and a lively atmosphere after dinner.
The Gaslight – Live music every night all summer. If Buckle & Shake or Foggy Roots are playing, you’re in for a great time.
The Chicken Box – If you’re up for a rowdy, live-music-filled night, the world-famous Chicken Box never disappoints.
Final Thoughts
Nantucket is often associated with its exclusive summer scene, but there’s so much more to love about this island than just the yachts and high-end dining. The real magic of Nantucket lies beyond the cobblestone streets and historic whaling cottages—out where the sand stretches for miles, the waves crash against remote shorelines, and adventure is always just a turn down an unmarked path.
From the thrill of airing down your tires and cruising Great Point at sunrise to winding through the moors toward the endless dunes of Coatue, Nantucket is a paradise for those who love to explore. Whether you’re tackling the sandy trails of Smith’s Point or setting up a campfire on the edge of the Atlantic with nothing but the stars above, the island’s oversand opportunities are second to none.
And when the day winds down, Nantucket delivers just as much off the sand as it does on. A world-class food scene—ranging from dockside lobster rolls to fine dining with harbor views—keeps you fueled for whatever comes next. When the sun dips below the horizon, the nightlife picks up, offering everything from casual drinks in a lively beer garden to unforgettable nights dancing under the stars.
So, air down your tires, pack up the Rover, and set out to experience it all. The best way to do Nantucket is overland and oversand—where the road ends, the real adventure begins. See you out there!