If I sit and quietly reflect on the places I’ve traveled to and think about what makes them so special, they all have one thing in common. No matter what the destination, the most special places to me are the ones that remain seemingly preserved in time. From Luca in Italy, the Cotswold in England, Cuba, Sumba Island in Bali and of course, Nantucket.
Last year was our first time traveling to Nantucket and when we left, I looked at Freddie and told him that this would be our family’s summer tradition year after year. I completely feel in love with this little island off the coast of Massachusetts that so many are lucky enough to have their summer homes on. Ultimate goals!
And getting there isn’t even the hard part, unlike a lot of the destinations we’ve visited, it seems as though the more challenging a place was to get to, the more preserved it would be. It’s true in a sense but that’s the paradox about Nantucket that makes it even more unique. Just a 45 minute flight from New York, we flew in on Tradewind. The island is famous for its unique shape – a graphic widely used on touristy merch – and from the plane, you can actually see the shape of the island! Then as you approach through the clouds, the boats in the harbor begin to peek through. You pass by steps beach and you can even spot brant point lighthouse if weather permits. I’ve never taken the ferry, which is the other way to get in from the mainland, but a Tradewind flight is incredibly easy and very special.
If you’ve not been yet, Nantucket is very walkable. No need for Ubers – just a pair of comfortable flats or sneakers. The cobblestone roads and sidewalks are over 200 years old and this character shows itself in its bumps and holes. There’s one main historic downtown area where all the quaint bars, restaurants and shops reside. The boutique shopping is unreal, and don’t get me started on the antique and estate jewelry stores! Visit Laura at Nantucket Estate Jewelry, it’s her personal collection and where I found that beautiful sapphire tennis bracelet. The hotels, including Greydon House, where we stayed, are converted century year old, clapboard-and-shutters style homes immaculately decorated and cozy beyond belief – often with original fixtures, floors and stories to tell. Greydon House is a 20-room, Greek Revival-style house built in 1850, Americana to its core. We stayed in room 15 – a corner room on the second floor that get flooded with beautiful light, overlooking downtown. I have to say, after peeking at three other rooms, I’d suggest requesting this one or the federal suite. All super quaint but these ones are true gems!
If Nantucket’s been on your bucket list, you must book the trip. Locals tell me that the best time to go is actually September. It’s technically “shoulder season” but it’s less touristy and everything is still open. Be sure to check out my list of spots below and don’t forget to book a sail with Captain Mat on the Blue Peter – it’s a stunning 100 year old sail boat and if you’re staying at Greydon, just ask the front desk to book it for you. While you’re at it, have them book you a massage at Lavender Farms too!
Bar Yoshi – Book a table outside on the wharf, such a romantic spot and the seafood is next level.
Millie’s – Get there for a sunset table. No reservations!
American Seasons – Great wine list, even better service. You’ll also want to make a reservation here.
Sayles Seafood – A bit off the beaten path but well worth the walk through the neighborhood. Get your lobster roll here and here only.
Brotherhood of Thieves – The spicy chicken sandwich is one of the best.
Provisions – Another great sandwich spot on the wharf.
Walters – Everyone’s favorite hole in the wall for lobster rolls and sandwiches.
Born & Bread – Oh god everything is good here. Personally love the breakfast sandwich but their pastries are also next level.
Lemon Press – Great for healthy açaí bowl, coffee and juices.
Sister Ship! – They make a killer signature summer Spritz cocktail.