There’s something special about finally living out a long-held dream. For me, that dream was driving oversand on Nantucket in a classic 4x4—something I had imagined ever since getting into cars as a kid. It wasn’t just about the adventure; it was about the journey to get there, the history behind classic 4x4s, and the thrill of experiencing it all firsthand.
The Dream of Driving Oversand
Growing up, I was always fascinated by the idea of oversand driving on Nantucket. The thought of exploring remote beaches with a 4x4, finding the perfect spot with friends, and spending the day surrounded by nothing but sand, surf, and sea breeze felt like the ultimate summer experience. It was a dream that stuck with me for years. So when I started looking for a classic 4x4 of my own, I knew that one day it had to make the trek to Great Point.
Delivery and Planning
By June of 2021, Nigel, my 1995 Land Rover Defender was registered and ready to go, so I started investigating the Steamship Authority website for ferry openings. Little did I know that booking a ferry in the summer was nearly impossible, especially at the last minute. With limited options and no solid plan, I finally secured a 6 AM boat for a weekend in late September. It was happening—Nigel was going oversand.
Getting 30 Miles Out
With no place to stay and only a vague itinerary, I left my childhood home north of Boston at 4 AM, running on Red Bull and sheer excitement. The drive to the Cape was smooth, and before I knew it, I was rolling onto the ferry for my first-ever car trip to Nantucket. Watching the waves pass from the upper deck, I could feel the anticipation building.
As we rounded Brant Point and the steam horn blasted, I realized this was different from any trip before. This time, I was bringing something special—Nigel, a vehicle that had traveled across continents to make it here. From England to Spain, then across the Atlantic to the U.S., and now onto another boat to Nantucket—it was surreal.
Rolling off the ferry, I took in the feeling of driving on the island for the first time. Nigel rumbled over the cobblestones of Main Street as I made a quick pit stop in town for supplies before heading straight to the Wauwinet Gatehouse. It was time to get my first-ever oversand sticker.
The Sticker
For some, Nantucket’s oversand stickers are just another status symbol, but to me, they’re trophies—symbols of resilience, adventure, and commitment. Getting one isn’t just about slapping a decal on your car. You have to get to the island, navigate the ferry, pass the sticker inspection, and ensure your vehicle is properly equipped. None of which are a given for a 30 year old Landy.
As I walked the gatehouse attendant through my recovery gear and aired down my tires, I could feel the excitement building. Finally, I was handed my first Great Point Oversand Sticker. I proudly placed it on Nigel’s bumper—it was official.
The First Drive on Sand
After everything it took to get here, I was finally on the sand. I cautiously made my way past the firm whoops and onto the soft stretches of Great Point, adjusting to the unfamiliar, vague steering at 15 PSI.
The vastness of Great Point and Coskata-Coatue was staggering. As I passed other beachgoers and fishermen, I got approving nods from drivers in newer Jeeps and trucks—Nigel was earning his respect.
I took a moment to soak it all in. I snapped a few photos of Nigel’s first time on the beach, realizing I had just checked off a real lifelong goal. There’s something powerful about setting your mind to something, no matter how niche or trivial it may seem to others, and making it happen. I wish I could go back and experience those first moments again—it was a feeling of pure accomplishment.
Friends, Memories, and More Stickers
Since that first trip, Nigel has collected seven more oversand stickers—on Nantucket, Martha’s Vineyard, and Race Point—each one attached to a new adventure. I’ve gone "night fishing" on Chappaquiddick, camped in the interior of Nantucket, and driven countless miles next to the waves.
But the best part? Getting to relive that first-time magic through the eyes of my friends. Watching them fall in love with Great Point, Chappaquiddick, and the thrill of driving oversand in Nigel is just as rewarding as experiencing it myself.
If you’ve ever thought about picking up an old 4x4 to chase those unforgettable summer days, do it. The effort is more than worth it. There’s nothing quite like the feeling of airing down, hitting the sand, and knowing you’re exactly where you’re meant to be.