The New England coastline is one of the most beautiful parts of the world in the summertime. From Bar Harbor to Newport there are so many great places to visit where nature, the ocean, and American history all come together. In Northern Maine the forest meets the ocean. In Rhode Island you can tour Gilded Age mansions and glimpse into the lives of American royalty during the Industrial Revolution. Each little town has its own unique characteristics based on geographical location dictating local traditions and commerce for nearly two-hundred years.

We all live in a world that is constantly evolving, but they’re still some pockets where it seems like nothing ever changes and the feeling you had when you first visited is somehow recreated each time you go back. The one place just off the East Coast that embodies this spirit for me is Nantucket. I’ve been visiting this island off the coast of Massachusetts for the past fifteen years and was lucky enough to get back there again last week. Here is my guide to having a great time on the island.


Getting There

There are direct flights from New York to Nantucket (ACK), but Jen and I always drive to Hyannis and take the one-hour high-speed ferry over. The drive takes around five hours from NYC which goes by pretty quickly with a mid-way lunch break at a clam shack. Although cars are permitted on Nantucket, they’re expensive to bring over and a pain in the ass to park unless you’re staying in a house. You can leave your car parked across from the ferry terminal in Hyannis for $15 a day. If you like to ride your bicycle you should definitely bring it with you. There are magnificent bike paths everywhere and a great way to explore the island.


Where To Stay

I’ve always felt the best way to experience a new destination is to live among the locals. On Nantucket there are two ways to try to achieve this. Your first option is to rent a house near the beach…if you can afford it. As much as Nantucket is mellow and rustic, it is not cheap. The next best option for your first trip is a Bed & Breakfast in town.


We stayed at the Centerboard Inn which was just a short walk from the ferry terminal and Main Street. The Innkeeper Barbara has been a year-rounder on the island for twenty five years and a Nantucket food and lifestyle writer. If you need to know anything about a restaurant, current event or happening, she knows what’s going on. The Inn is clean, freshly decorated, centrally located and reasonably priced.


The Innkeeper is also a cookbook author who arranged a beautiful breakfast spread of homemade croissants, almond milk yogurt, fresh fruit and granola. The Centerboard Inn is right across the street from a great restaurant called American Seasons. You can smell them smoking their own meats during the afternoon and the menu is deliciously out of control. The ambiance also makes it a great spot for a late-night desert or nightcap before retiring back to your room.


There are also a few resorts on the island, but they’re very expensive and generally not the way I suggest experiencing Nantucket. If you want to lay poolside all day and order bottle service you might as well just go to The Hamptons instead.


What To Do

We’ll start right in town because that’s where you’re staying and there’s plenty going on just outside your door and within walking distance. Main Street is the center of this traditional seaside New England town. If you want to buy a whale belt, sapphire ring or locally woven basket, you’ll find it here. The majority of shops, bars and restaurants on the island are centrally located in this area. Enjoy an afternoon stroll on the cobblestone streets and finish your day with a drink at one of the local bars in town or Slip 14 on Old South Wharf.


If you walk a couple blocks out of town in either direction you find yourself in a maze of back alleys and streets lined with historic homes and beautiful gardens. There are strict guidelines on the island regarding house renovations and even paint colors so it doesn’t seem like much has changed from when it was the whaling capital of the world two hundred years ago. During the day you’ll be able to spend a couple hours just looking at houses and flowers. Sometimes when you’re half drunk at night it feels like the wind is blowing old spirits in from the sea. That’s a little extreme but probably not far off. When you’re walking around this little maritime village that hasn’t changed in two centuries, it’s easy to imagine what it might have been like during the days of hunting Moby Dick.


Walking around town you’ll probably notice a number of vintage trucks and jeeps parked on the streets. Nantucket is filled with cobblestone and dirt roads so you aren’t going to see any fancy sports cars speeding around. The ultimate vehicle to drive on the island is a vintage Land Rover Defender. It’s the truck to have. We also spotted a few old Jeep Wagoneers, a 1960’s Chevy Greenbrier Van, and a mint green Geo Tracker from the 1980’s. The coolest beach vehicles of the past 70 years have been preserved here.


I also suggest taking a boat ride around the harbor. The row boats pictured above won’t cut it, but I’ve cruised around on a Boston Whaler which is perfect for gliding past the lighthouse at Brant Point, yacht-sighting at the Boat Basin and pulling up on little beaches and checking out some of the shoals which used to house oyster farms and can still be used for clamming. If you don’t have your own boat or dingy check down at the wharf for assorted sightseeing, fishing and whale watching tours.


After spending one full day in town you’ll want to venture out and explore the rest of the island. Even if you’re not the most athletic person in the world, consider renting a bicycle. Any beach on the island is accessible from town via a flat and smoothly paved bike path separated from the roads and surrounded by nature. The beach doesn’t necessarily have to be your final destination, but that’s the direction all the paths lead.


If you want to keep it casual you can ride just a couple miles to Millie’s in Madaket for lunch. The restaurant is two hundred yards from the beach where you can sit outside at picnic tables or upstairs near the bar with panoramic views of the water. They have a dozen different fish tacos on the menu along with a bunch of seafood po’ boys. There’s also a take-out window with salads and sandwiches and Millie’s Market rents beach chairs and umbrellas. Consider this when planning a nice afternoon on the beach.


For those of you who want to elevate your heart rate, I recommend getting out early and riding the Polpis bike route to Sankaty Lighthouse, it’s a fifteen mile ride from town.


From the lighthouse make your way towards the rose-covered cottages in Sconset for more photo opportunities. It’s best to park your bike near the Sconset General Store and walk around from there to really soak it in.


By this time you have probably worked up an appetite so here are two options for lunch. There is a little sandwich spot where you parked your bike or you can step it up at the Summer House where you can pop some Veuve and suck down a colossal seafood tower. They want you to ball out here and feel like you’re in the Hamptons but there’s no full-blown party going on or anyone worth showing off for. There are no hot chicks in bikinis dancing around the pool.


On your way back, keep cruising along the water for more scenic vistas and then you can go back to town the same way you came or take the Sconset bike route. The Polpis route has the Shipwreck and Lifesaving Museum which is pretty cool and Sconset path has this one section that reminded me of Morocco as I rode past…in the rain, and it was still awesome. In New York City I worry about shit-water splashing in my mouth as I ride down Second Avenue. On Nantucket you can forget about it and smile.


Let me also mention that you can rent Vespa scooters on the island, which are another great way to get around. Not as treacherous as Norman Manley Boulevard in Negril and just as scenic. You can also rent a Jeep and drive on the beaches. You want a four wheel drive vehicle so you can really get into the rustic nooks and crannies of the island. You’ll see some cool houses with vintage trucks and little wooden boats out front, salt ponds and hidden beaches, and all types of cool shit.


The destination you must visit (by taxi or bicycle) when you’re on Nantucket is Cisco Brewers. This place has grown enormously since I first visited in 1998 and has become the hottest spot on the island and best place to spend an afternoon. You have three barns set up here with tasting rooms for beer, wine, vodka and whiskey. You can order samples or full glasses of anything. When I was here years ago it seemed like a $5 sampler lasted for hours and sent me home in shambles, but today things are a little more family oriented for the wine and cheese crowd.


Outside of the sheds is a large open courtyard with picnic tables, food trucks, raw bar and live music every afternoon. You can throw drinks back and suck down oysters or have a picnic with your family and golden retriever. If you are going to pack a basket ask the cabbie to drive you to Bartlett’s Farm first. It’s just down the road and has everything you could possibly want for a great spread. The nicest vibes on the island are at the brewery every single day. Just sit in the sun with a smile on your face and be thankful you’re on Nantucket.


Where To Eat + More Drinking

This is where you get banged out on Nantucket. If you’re lucky to have a house or friends with one you can barbecue every night and kick it old school. When you’re staying in town you have to go to restaurants. There are some great places to eat, but you’re going to average at least $100 per person every night on dinner.

I already mentioned American Seasons which you should definitely check out. The Club Car is really fancy with dramatic white-gloved waiters. My octopus appetizer was excellent and they knew how to hook a steak up. Pazzo just outside of town had very good Mediterranean food and drinks. There was some cool old black and white sailing movie on the television and I forgot to ask what it was. The Lobster Trap is the place to go if you want to get down and dirty with a three pound lobster and some local littleneck clams. The outdoor bar usually has a decent crowd and there’s some local live music a few nights a week. There are some other tablecloth restaurants in town promoting well known chefs but most seem overrated to me coming in from New York City. If you stay at the Centerboard Inn just talk to Barbara. She’s a food and lifestyle writer for a Nantucket magazine and knows what’s going on and will help pick out the right place for you.


You should be worn out by now but if you’re still looking for action in the 11pm – 1am range, check for live music at The Chicken Box. Robert Randolph was in town while I was there so I linked up with my buddy and long time island guide Jon Green and we got down old school like we were back in college. The place was packed and the band was rocking. They invited some girls on stage to dance and one of them almost tore down the rafters when she decided to try to hang from them. I’ve never seen those dudes play before and they really brought it that night with a mix of rock, funk and blues. This place gets packed with the rowdiest crowd on the island when a good band is in town, so make sure you get your tickets early.


Hopefully you’ve been inspired enough by my enthusiasm and photographs to begin planning your trip. It may be hard to find a room, but if you can make it there for the first week of August you can see Bruce Hornsby and Steel Pulse headline the Nantucket Music Festival. If that’s too soon you can always consider September when it still feels like summer but is less crowded, or start planning for Summer 2015. Whatever you have to do to get here is worth the trip.

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