Wednesday, December 6, 2017

Nantucket Christmas Stroll | First Timer Tips

If you follow me on instagram you very likely saw (30+ posts!!) that I went to the annual Nantucket Christmas Stroll with a couple girlfriends.  The Stroll is held the first weekend of December every year.  I have dreamed of going for the last 5 years and I'm so grateful we finally made it happen. It lived up to every expectation I had, making it the perfect girls trip to kick of the Christmas season!

I will do my best to answer some of the questions you all have had as well as give you a glimpse of how we spent our time and what we would do differently next time.  Here we go...

Where did we stay?
We rented a home in town, pictured left.  Yes, it was big!  We booked a home last summer.  VRBO and Airbnb are your best bets if you want to go this route.  There are lots of amazing hotels in town too, especially if you are traveling as a couple.  We were only there to sleep, with a little morning and evening lounging around so having a house was nice but not essential, it will save you a little money over a hotel though.  You will want a place in walking distance of the shops since you don't want to pay to bring a car over on the ferry and the buses no longer run in winter.  Cabs are also available, of course.

A lot of people asked if I preferred staying in town over staying in Sconset.  You can't really compare the two because staying in Sconset in the summer is a completely difference experience.  If just going for the Stroll, town is the way to go!  See my other Nantucket posts to read all about why we love Sconset so much in the summer.

How did we get to Nantucket from Cincinnati?
Getting to Nantucket isn't easy but it's always worth it.  We chose to fly into Boston on an early flight.  We arrived before 9:00 AM then we rented a car and drove to the Cape.  We parked in the long term ferry parking and took the ferry.  We learned the hard way that ferry tickets on the high speed boat sell out more than a month in advance.  So we took the slow ferry there and fast back.  Some other options that we will explore next time are taking the bus from Logan to Hyannis or booking two flights, one to Boston and then a Cape Air flight to Nantucket.  There are no direct flights from Cincinnati and those with a connection are unreliable and very expensive.  I also think we might come in on a Thursday and leave late Sunday next time.  

What were some fun things to do that are unique to the Stroll?
In typical Nantucket fashion, you have to do a bit of discovery work to find all that the island has to offer.  I found ideas here and here to be really helpful. We took an evening home tour of some gorgeous old homes on Orange Street on Friday when we arrived, which was such a highlight for all of us.  This tour wasn't mentioned on the Stroll Events website and we noticed that many of the people on the tour were local residents.  We pre-purchased tickets online and picked them up at the Whaling Museum when we arrived.  
There was an indoor craft show at the Preservation Institute on Centre Street that was easy to miss unless you knew it was there.  I'm so glad we found it because my favorite artist had a booth and I was able to pick up a couple new pieces for our home.
I did the early morning guided walking tour of the mansions of Cliff and Brant Point. My friends opted to sleep in, so I re-created the walk for them the next day which was even more fun.   
There are so many other unique activities from book signings to wreath making at Bartlett Farm to eating fresh shucked oysters on the warf to special brunches and champagne tastings, that you just have to do a little research and see what floats your boat and know that you can't do it all.
The main attractions are shopping and eating and drinking!  Oh and there is a lot of pomp and circumstance over the arrival of Santa on the boat and everyone gets very festive with their attire, including the dogs.  Think light up necklaces and crazy hats.  

Where to eat?
Here are the places that were recommended to us, some we ate at, others we'll save for next time...
Ventuno, Italian, make reservation far in advance.  No walk-ins.
Straight Warf, no reservations, long wait, seafood
Greydon House, the prettiest restaurant on Nantucket in my opinion, but very pricey.  We made reservations, then found out they switched to a prix fixe menu but at $150 a person, it was more than we wanted to spend for a girls night out. Better for a date night! We did have drinks in the cozy bar though and that was perfect.
Pi Pizzeria, you'll need to take a cab, it's super cozy and delicious for a casual dinner.
Brotherhood of Thieves - pub food, no reservation needed
Queequeg's -  Came highly recommended from a local. Was closed the day we wanted to eat there but sounds really good!
Wicked Island Bakery - worth the walk, go early in the morning.  It's still my favorite bakery on the island.  
The Hub - Their breakfast croissants are amazing! 

^^ The most iconic tree for the Stroll, you'll find it hidden in the water right behind the movie theater! ^^

We lingered in unique stores and chatted with owners and artists, we took evening walks along cobblestone streets among Christmas lights, and we ate most of our meals next to roaring fires in charming old buildings.  I loved the quiet mornings walking through town and on the beach and I loved the happy holiday bustle in the stores during the day. It was such a joy to be able to see Nantucket through my friend's eyes and watch them fall in love with my favorite place!  We brought home wonderful treasures and lots of happy memories.  And we all vowed to make this a new holiday tradition!  I can't wait till next year!!  Thanks for letting me share it all with you!



  1. I enjoyed the Instagram posts as well as this post. I need to add this trip to my bucket list!

  2. Yes, I loved seeing all your Instagram posts! It looks like you had a fabulous time. Thanks for all the tips. I did a girls weekend in Martha's Vineyard this past May and it was wonderful. Nantucket has been on my list forever so it was so much fun to follow along with you!

  3. Lovely, lovely, lovely! You have captured Nantucket beautifully!