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Nantucket as a Cruising Destination

Soul Mates

After twenty-two years, Nantucket continues her perpetual seduction of the author. That’s just fine with him.

The author’s restored 1968 Boston Whaler Nauset is the ideal beachcomber.
Nantucket beach

Eat + Drink

My wife Lindsay and I make getting away from crowds an art form. This is darn tough to do on Nantucket during the summer. After boating on the Whaler on July 12, we headed out to Millie’s in Madaket for a little happy hour (508-228-5435).This is down the street from my old house and the current owners finally figured out that this end of the island needed a casual, beach café.

WHEN TO GO: Go around sunset. Some of the best on the island happen here.

For dinner, Topper’s (508-228-8768) is just as special to me now as it was in 1993. For those of us in the restaurant business, a group dinner at this special restaurant within The Wauwinet was the highlight of our summer. It still is for Lindsay and me.

WHEN TO GO: Whenever you want to remind yourself of how hard you work and deserve to be pampered.

OTHER CHOICES: There are loads of good restaurants on the island. Many however, are trying to replicate their version of New York sophistication. In my opinion, leave the Upper East Side in New York and look for the true island establishments.

OFF THE BOAT: Lindsay and I make a point of catching a production of anything that The Theatre Workshop of Nantucket ( is putting on when we’re on the island. The quality of every show we’ve seen is beyond expectations.

WHEN TO GO: We’re fans of spending Thanksgiving on the island and catching a production like The Christmas Carol the weekend after is a wonderful way to jumpstart your holiday spirit. Cisco Brewers (508-325-5929) is worth the side trip down Bartlett Farm Road. There’s a casual beer garden and often really good local live music. The beer ain’t bad either.

Perhaps it’s nostalgia that makes Nantucket so alluring to me. I admit I was smitten by the island’s charm the day I walked down the gangway from the Steamship Authority ferry to the wharf. It was 1993 and I had graduated from college the day before. I had 100 bucks to my name and needed to jumpstart the next chapter of my life before the student loans came due.

So when a classmate mentioned he was heading to Nantucket and offered me a ride to Hyannis to catch the ferry, I jumped into his big Chevy station wagon without a second thought. Heck, I like boats and islands.

I arrived on a Friday with all of my belongings squeezed into a grungy sail bag, and with my dog Jezebel tugging at my arm. Her rear was flying from side to side with excitement over the pre-weekend activity around the ferry terminal. We made our way up the cobblestones of Main Street to the bulletin board at the Hub—the nexus of all job and living opportunities on the island. The next day my friends and I secured a cottage—held together by duct tape, Styrofoam, and chicken wire—in Madaket, on the western end of the island. It was perfect.

Escape the summer crowds in the serenity of Madaket.

And by Monday, I was gainfully employed as a pantry cook at Cioppinos Restaurant on Broad Street. Owners Tracy and Suzy Root took me under their wing from the moment I walked through the door. They taught me about the art of fine dining, good wine, hard work, and poker. More importantly, they showed me the charm and color of Nantucket. They were hosts to a slew of characters who occupied their restaurant, telling tall tales at the little black bar tucked in a corner off the lobby. There were politicians, writers, Fortune 100 CEOs, famous entertainers, gangsters, lobstermen, drunks, heirs, drunken heirs, bartenders, and even an opera singer. After I closed the kitchen, I’d just sat at the bar and listened to the discussions.

When I wasn’t making Caesar salads or pecan pies, I was busy discovering the island. I whiled away my limited free time by fishing for stripers, diving for lobster, scalloping with a mask and inner tube during season, and windsurfing in Polpis Harbor. Life is intertwined with the ocean on an island and well, so was I. Jezebel would let herself out in the morning before her breakfast for a walk and a morning dip in Hither Creek. (She was a very civilized lady.) I didn’t leave the island once for more than 12 months, which was all right by me.

I eventually turned in my chef’s whites for a suit and today my time on Nantucket is only counted in weeklong spells at the most, versus years. Yet the moment I hear the seagulls and smell the salt air after a long week at work, the reset button is automatically hit. I’ve changed a lot in those 20-plus years, and so has Nantucket. (Not completely for the better, I might add.) However, out on the water and around the waterfront, it’s pretty darn close to the utopia that I’ve retained in my memories.

So, it was only natural that my wife, friends, and I spent our Mid-Summer Boating Fest exploring the Gray Lady by boat. We keep our 1968 Boston Whaler Nauset on a mooring in Polpis and made a point this past summer to get out as much as we could. There is still no other place on this planet that comes close—except maybe an empty backcountry ski trail—to soothing my soul like Nantucket. At right are some tips on how we enjoyed our day like the local I still am, at heart.

Iconic Great Point Light marks the island’s northernmost point.

Island Time

After planning a day on the water for six months, mistakes still happen.

10:30: Departed town and headed out to Polpis Harbor.

10:50: Launched dinghy filled with gear and food, rowed out to boat with friend Derek.

10:55: Duh! Put key into ignition and realized the yard changed the switch, yet I never picked up the new key. 

10:57:Derek rowed back into the beach to pick up his wife, two-year-old son Bergen, and my wife Lindsay. Sweat began dripping off my forehead. We’d had this day on the boat planned for about six months. Here I was just bobbing at the mooring.

11:09: Derek is back with everyone and I haven’t been able to reach my friend Jack who may have the new key. Son of a… when are they going to get better cell phone service on this island?

11:11:Everyone is remarkably calm. Derek’s wife Kristy observes we have cold wine, some good food, and are moored in a remarkable spot. Maybe a little swim from the non-operational boat?

11:27: Jack calls, saying he has the key but is stuck near the airport. I will need to go to him. I jump in dinghy and row to the beach.

11:35: My truck is blocked in by a boat and trailer on the ramp that got stuck on the corner. 

11:40: We unhitch guy’s truck from trailer and the whole thing makes a beeline for the water. Nearly get crushed on the fence. Back on road.

12:20: Return with key and back at boat. Everyone is happy. Bergen is sound asleep. We depart for a day of swimming, eating, touring, and just good times.

4:45: On way to Madaket, get another key made.

This article originally appeared in the December 2015 issue of Power & Motoryacht magazine.