Vacation or staycation? Twenty four hours on Nantucket

An aerial view of Nantucket from the tower of the First Congregational Church.

I’ve lived on Martha’s Vineyard for almost four years, and recently returned from my second trip to Nantucket in all that time. Chances are, most of you reading this don’t get there too often either. When the subject of visiting the “other island” comes up, I often hear from friends and colleagues that they’ve never been, or visited years ago and don’t really remember their experience. There’re usually complaints about the hassle of the travel, and misconceptions that there’s little payoff, or this: “Isn’t it just one big Edgartown?”

Let’s set the record straight. First of all, it’s only a 70-minute passenger ferry ride from Oak Bluffs Harbor, available via Hy-Line Cruises seasonally from May to October. For comparison’s sake, 70 minutes is less time than it takes you to wait in line at the Steamship and get to Woods Hole. Not to mention the Hy-Line offers a significant Islander discount ( that provides you with a serious price reduction ($49 round trip versus $65 for full price). They offer it on the Vineyard-Hyannis service as well, so make sure you’re signed up.

Second, Nantucket is technically one town, but it’s not one big Edgartown. (Every island doesn’t need six individual towns, after all … but I digress.) If you’re a relatively recent wash-ashore like me, you might actually remember the first time you stepped off the boat and saw Martha’s Vineyard in all its beauty. If you don’t remember it, if you’ve always lived here, or if your perception of this place is jaded (we all get there), then it’s definitely time for some island hopping. It’s like being out and about on Martha’s Vineyard, only you can discover new things and not run into everyone you know, everywhere you go. Yes, there’s a similar landscape of boats, and cute shops, and great restaurants, but the novelty is still there.

To make it really easy to get there, the Winnetu and its sister property, the Nantucket Hotel and Resort, recently teamed up to offer Island residents an inter-island getaway package. The deal is you agree to purchase dinner at the Breeze restaurant at the Nantucket Hotel and Resort, and purchase your ferry tickets through the hotel, and you get a free night’s stay — a savings of hundreds. My husband and I were quick to take them up on it (full disclosure: Our dinner was complimentary, so we received an extra good deal, but I’ll happily return on my own accord and pay full price). Look for the offer on Winnetu’s Facebook page in the future; they run it occasionally for our Island community.

If you’ve been to the Winnetu in Katama, you feel a world away, but you’re still on Martha’s Vineyard. The Nantucket Hotel and Resort was similar but different, in that it was new to me, but still comfortable and reminiscent of home. Our experience began as soon as we stepped off the boat and were greeted at the ferry dock by Andre, the driver of the hotel’s iconic antique green bus — an upgrade from the Palmer Ave. shuttle, that’s for sure. One of the first things I noticed was the narrow cobblestone streets of Town (that’s how the locals refer to downtown Nantucket), which Andre navigated effortlessly. A short ride brought us to the steps of the Nantucket Hotel, an in-town, year-round resort that was built in 1891, and completely renovated and “lovingly restored” in 2012 by Winnetu owners Mark and Gwenn Snider, who also spearheaded the restoration of the Capawock and Strand Theaters on the Vineyard.

Cozy chairs and firepits lined the front porch, and a violin player serenaded guests nearby. Once inside, we were immediately drawn to the mechanical steampunk whale sculpture behind the front desk, a kinetic and interactive piece that was specially created for the lobby as part of the renovation. Downstairs we stumbled upon a kids’ room, with crafts and games, a family-friendly amenity similar to the children’s evening program at the Winnetu, which offers free babysitting while you enjoy dinner.

We eventually made our way to the Breeze restaurant for dinner, and were surprised to see an option for the Nantucket Restaurant Week menu, which happened to coincide with our stay. (Can we please get that going on Martha’s Vineyard?) The food was delicious, and Michael, the food and beverage director, stopped to talk to us about island life. We shared tales of tourists and housing crises — all the comforts of home.

After dinner we walked the cobblestone streets, peering into dark storefronts and comparing them to the versions we have on Martha’s Vineyard — complete with a Black Dog and a Vineyard Vines, of course. We stumbled upon Charlie Noble, a casual bar downtown that was blasting live music. It drew a diverse crowd, and there were definitely a lot of locals, so we ponied up to the bar to enjoy the band, which included the violinist from the hotel (I thought, “Of course he has more than one job”).

The next day we started out with a continental breakfast at the hotel, then ventured outside to take in the sights by day. On a historic walking tour we passed the First Congregational Church and noticed the tower atop the church, which was open for tours. We climbed the 94 steps, past exhibits of historic church photos, to the top of the 120-foot bell tower. While we took in breathtaking, panoramic views, I was reminded of my visits atop the Edgartown and Aquinnah lighthouses (other must-dos if you haven’t), and looked out across the Sound in search of my Island home. After an informative chat with the volunteer about local history, we made our way back to town and up to the Jethro Coffin House. Built in 1686, it’s still in its original location, and is the only surviving structure from the island’s 17th-century English settlement; it’s another landmark worth exploring.

As our time on Nantucket came to a close, we decided to do the only thing that seemed right to a couple of tourists — order an overpriced lobster roll at a restaurant on the water. We chose Cru, a hot spot at the harbor known for its seafood and its scene. I won’t even admit what we paid for the lobster rolls, but they were really good, and after all, we were on vacation, so they just tasted better. All in all, it was a worthwhile time and a good reminder of the reasons people flock to our own Island home — we surely can’t blame them.


This article by Angela Proud originally appeared on