Scouting: Nantucket

"In the midst of waters," or "far away island" are the two suggested translations for Nantucket offered by Wikipedia, font of all random facts. It’s an Algonquin word - and now I want to quote Wayne’s World all day long, so there’s that, but really my point is that they were pretty spot-on with their description. As I mentioned before, Nantucket takes a little effort to get to, but once you’re there it feel like the rest of the world falls away.

Nantucket  | Image:  Laura Messersmith

Nantucket | Image: Laura Messersmith

In a continuing trend of all our spring travels (see also Croatia and Santa Barbara) we arrived about a week before everyone else just as the shops and restaurants were waking up from a long winter’s nap. If you’re not a fan of crowds mid-May is the perfect time to go – town was relatively quiet, the sun was warm, but not hot, the apple trees were in bloom, and the sea air mingled with the scent fresh mulch in the flowerbeds.

Nantucket Wine Festival  | Image:  Laura Messersmith

Nantucket Wine Festival | Image: Laura Messersmith

Our visit was timed with the Nantucket Wine Festival, so much of our time was spent near the White Elephant Hotel, site of the festival, but I did have a chance to do a little scouting and a lot of “shutterbugging.” Of course I have recommendations for you – a mix of a few old favorites and some new discoveries. Here’s what we did:


Nantucket Town is incredibly charming with whaling era cobblestone streets (wear flats!), a multitude of nautical themed weathervanes to take pictures of, and lots of little antique shops to snoop through. One of my favorites is an antique shop/gallery called Four Winds Craft Guild & Sylvia Antiques where I learned about (and actually got to meet!) David Lazarus, a really talented scrimshaw artist and oil painter.

Nantucket   | Image:  Laura Messersmith

Nantucket  | Image: Laura Messersmith

The Beach! There are lots of options for beach-going (Surfside, Brant Point, etc.) but my favorite is Madaket. It’s a long-ish, but not overly challenging bike ride from town and despite the island bus service I’ve never seen it crowded. The sand is wide and the view is gorgeous even on a chilly late spring day.

Cisco Brewery has a great patio, live music in the afternoons and is just a stone’s throw from Bartlett Farm. So, when you’re done sipping a locally brewed beer you can make a quick stop and pick up dinner.

‘Sconset Cliff Walk is utterly charming and gorgeous. Definitely plan a drive over to the east end of the island to see village and take a stroll up to the Sankaty Head Lighthouse.

Madaket Beach, Nantucket  | Image:  Laura Messersmith

Madaket Beach, Nantucket | Image: Laura Messersmith


Cottage all the way! since we were traveling with a group it made sense to find a place with a little more space. This cottage on Crooked Lane was perfect. Quiet and peaceful but only a 10 minute bike to town. 

Nantucket Cottage  | Image:  Laura Messersmith

Nantucket Cottage | Image: Laura Messersmith


Dune was the location for our anniversary dinner and the one ‘fancy’ place on our itinerary, so standards were extra high. (No pressure.) Thankfully, the food was delicious – I loved the Pan Seared Halibut and Mike was really happy with the Grilled Steak with bok choy. I also have to give a shout out to my Bill Burr cocktail (if you like Dark N Stormys…) and to the Apple Cinnamon Donut  - so good. The setting is what I’d call ‘modern coastal,’ like being in a sleek beach house, and we were delighted with the service. We had a great time.

Nantucket Pasty Co. I followed my nose to this little shop and found a great, quick, hot breakfast. Read “pasty,” think “turnover” in both sweet and savory versions. We shared one ham, cheddar & rutabaga and one apple. Yum. The fillings were delicious and the pastry was buttery and flaky. An excellent option, especially when you don’t have a lot of time.

Nantucket   | Image:  Laura Messersmith

Nantucket  | Image: Laura Messersmith

Something Natural Nantucket is home to several excellent sandwich shops, but Something Natural - just outside of ‘town’ on Cliff Road - is my favorite. I love to stop here on the way to the beach (I always get turkey and cheddar on multigrain and a chocolate chip cookie) or set up camp at one of their picnic tables for lunch. Delicious!

Straight Wharf Fish Store is my new source for take-out, prepared seafood. We were hosting a dinner at our rental cottage, so I picked up New England clam chowder, crab cakes, and the biggest lobster rolls I’ve ever seen here. The SWFS staff were really helpful and our guests were really impressed with the food. Note: they are cash or check only! 

Nantucket  | Image:  Laura Messersmith

Nantucket | Image: Laura Messersmith