I had known about the Nantucket Christmas Stroll for years. When I finally decided to go this year,  I could find little information to assist with my planning.  I provided my general impressions of the event in a previous post, The Nantucket Christmas Stroll: A Festive Weekend in New England, but the information below is meant to provide the practical tips to make your travel successful.

What is the Nantucket Christmas Stroll?  Nantucket is an island off the coast of Massachusetts.  The Christmas Stroll was created as a way to help local businesses attract Christmas shoppers over 40 years ago. It has become a popular annual tradition involving shopping, decorations, activities, eating, and fun.

Nantucket Lighthouse at Christmas

When is it? The Nantucket Christmas Stroll takes place the first weekend of December.  It begins on Friday and ends on Sunday.  Many people come over to the island just for Saturday and do not spend the night.  I stayed the entire weekend in Nantucket and had a wonderful time.

Where is it and how do I get there?  The Christmas Stroll takes place on Nantucket Island, which is a 1-hour ferry ride away.  Ferries leave from Hyannis, Massachusetts.  The two companies providing ferry service are The Steamship Authority and Hy-Line. The ferries sell out for the Christmas Stroll Weekend, so you must reserve your tickets as far in advance as soon possible.  Hy-Line also provides an option to reserve your parking, which is a good idea for Christmas Stroll weekend.

Another Cute Nantucket Lighthouse

Where should I stay?  There are lovely hotels and inns on Nantucket Island, but space is limited.  I reserved my hotel rooms in August, but few rooms remained even at that time.  So, again, reserve a room as far in advance as possible.  I was lucky to find a room at the Jared Coffin House.  It is a beautiful and historic hotel, and it was full of Christmas charm for the weekend.

What should I wear?  Knowing that Nantucket Island is a upscale destination, I didn’t want to get too crazy with Christmas cheer. I need not have worried.  Some “strollers” did not dress with any outward signs of Christmas, but many visitors went all out and wore fun Christmas sweaters, reindeer hats, and blinking Christmas light necklaces.  I found that by dinner, though, patrons had changed into more appropriate attire to dine at nice restaurants.  Also, it is winter in New England.  So, dress warmly.  However, as I note in, It’s Winter: Start Traveling! , don’t let the cold scare you away.

Nantucket is filled with adorable, cobblestone streets.  I love looking at cobblestone, but it hurts my feet.  My husband came up with the brilliant idea of using hiking boots for cobblestone, because these boots are made for rough terrain.  I wore them during the day, and changed into more fashionable footwear at night. My feet were perfect all weekend, and my sister, who was bootless, limped around in pain.   I am guessing she will pick up a pair of hiking boots for her next cobblestone-filled vacation.

Two Girls and Their Christmas Hats

Where should we eat?  The food in Nantucket is excellent.  Expensive, but delicious.  We had an elegant meal at Nantucket Prime in the Jared Coffin House and indulged in a prix fixe menu at Company of the Cauldron on Saturday night.  I had to call for reservations on a specific date and battle busy signals for 20-30 minutes to secure my reservation for Company of the Cauldron. It was worth it.

You should make reservations for lunches and dinners, especially on Saturday.  This is a small island, and many people are attending the Stroll.  I had not made a lunch reservation on Saturday, and my group was getting a bit sulky when we could not find any option with less than a two-hour wait.  Thankfully, we found an adorable “pop-up” restaurant that hadn’t officially opened.  It didn’t even have a name yet!

Nantucket Christmas Stroll Decor

What is there to do?  The Nantucket Chamber of Commerce publishes an entire booklet full of Christmas Stroll events.  Oddly, they did not release it online this year until a few weeks before the Stroll.  Many people come for the shopping opportunities, of course, but my favorites memories included:

• Greeting Santa at the Wharf:  I love a good community celebration.  I really enjoyed gathering on Main Street to hear the town crier announce the stroll on Saturday morning.  Then, he led the crowd to the wharf to greet Santa, who was arriving by Coast Guard boat.  There were thousands of people in the crowd, including men, women, and children, but everyone was in a good mood.  Santa rode an old-fashioned fire truck up Main Street to the Jared Coffin House, where he sat for pictures with the kids.  And, might I add, he was a great-looking Santa with a vintage costume.  There was a long line for pictures with Santa at 1:00 PM, but my adult sisters and I were able to walk right up for a photo at 2:40 PM.  Several other adults were joining in the fun at that point.

Waiting for Santa at the Wharf

• Holiday House Tour: We participated in the Annual Holiday House Tour, in which homes decorated for Christmas are open to the public for charity.  One tip is to not tour the homes in the published order, because this cuts down on the crowds quite a bit.  Also, the self-guided tour starts at 4:30 PM, and you may want to wait until 6:00 PM to let the initial rush go through the tour first.

• The Festival of Trees: This event at the Whaling Museum was fantastic.  There were approximately 80 trees decorated throughout the museum, and they were gorgeous.  The combined ticket for the home tour and the Festival of Trees was $45.  I bought our tickets the day of the event at the Whaling Museum with no problem.  The price originally seemed a bit high to me, but I left thinking it was very reasonable for the experience we had.

• Tour the Island: We wanted to see more of the island, but we did not have a car or a tour booked.  Visitor Information staff  told us that taxis are not allowed to give tours of the island.  Instead, we specifically asked to be taken first to the Sankaty lighthouse in Siasconset, and then to another spot on the opposite side of the island.  Our taxi driver was wonderful and chatted with us about the island as we drove.  Our taxi “non-tour” was a highlight of our weekend.

Who goes to the Stroll?  Everyone!  We saw families with children; couples who attended with friends; girlfriends who traveled together, etc.  In other words, it was a great event for men, women, and children.

Nantucket Island