Travel Guide: Nantucket in the Shoulder Season

Nantucket is a truly majestic place all seasons of the year, but we get most credit for Summer on island. However, as many locals will tell you; the "shoulder seasons" (September, October, May, and June) are a well kept secret. The island is still open and ready to accept visitors of all kinds, but it is not swarmed like it is in the Summer. Here is how I, APJ, would spend a weekend on Nantucket in early October:


10am: Arrive via jetblue direct flight on Friday morning.
1030am: Head straight into town to stay at The Ships Inn (they close after indigenous people's day), Union Street Inn, Blue Iris, or another VRBO. Drop off your bags and freshen up. 
1130am: Walk around town and shop. Some of my favorite stores are Dawn, Nantucket Looms, The Lovely, and Murray's. Definitely be sure to grab a handwoven hand towel from Looms (great gift!) and some Nantucket Reds from Murray's. 
1pm: Go to Cru for lunch. Get a cru-comber on the rocks (they're delicious and so deadly!), some oysters on the half shell, and a warm lobster roll. 
3pm: Head back to your hotel to lounge a bit and maybe nap off the lunch cocktails ;) Change into your dinner outfit.
6pm: Grab an early cocktail at The Pearl. Recently renovated and truly gorgeous inside. Say hi to Christina and Abby for me!
730pm: Go to dinner at Straight Wharf. If it's nice, you can sit outside in the bar area for a more casual bite (no reservations), or make a reservation for a prix-fixe meal inside. Either way, you can't go wrong.
930pm: Head to Gaslight for live music and a good time. Wear comfortable shoes because you will want to dance!


930am: Grab a coffee, green juice, and pastry from the Green Market. Owned by my friend Tessa, she also has amazing snacks to grab for later. Caviar, anyone?!
11am: Putter about town and check out any other shops you may want. Grab a t-shirt or sweatshirt from Annie and the Tee's (say hi to Sophie for me!). 
1130am: Grab the WAVE from the bus stop and head to Millie's for some Mexican food and Margaritas. Watch the waves come in from their top floor. 
130pm: Head back into town, grab a sweatshirt, and catch the shuttle from the town building to the Brewery (AKA Cisco Brewery). Sign up for a brewery tour, eat some food truck food, and listen to some live music. Dogs, kids, everyone is welcome! Great spot to grab some souvenirs :)
430pm: Head back to your hotel and chill.
730pm: Go to Ventuno for dinner. Order the strozzapretti and a bottle of wine. Julia, the sommelier, will expertly guide you to something delicious!
945pm: Grab a taxi and head to the chicken box, our local dive bar. It's walking distance, but I would suggest a taxi. Walk on the way home ;) Vodka soda, close it!


9am: Dry your eyes as it's your last day on island! Walk to Brant Point light house and grab a couple pics of the newly restored beauty! 2 of 3 lighthouses achieved.
10am: Go to Or the Whale for brunch. Order the scotch egg, a coffee, and a mimosa. Rinse and repeat, baby!
Noon: Any last minute buys from town, pack up your hotel, take some advil (ha ha). If time allows, go to the gazebo and get a mudslide and watch a few minutes of Sunday football.
230pm: Head to the airport for your flight back to America. 

Other notable activities to bookmark...

  • Yoga at Supta - all the instructors are SO good. You will have a major yoga buzz after a class here.
  • Walk at Sanford Farms. Nantucket has acres and acres of conserved land (thank you, Nantucket Conservation Foundation!) and Sanford Farms is a beautiful walk with loops ranging from 1 to 7 miles round trip. Spectacular and great if you have a furry friend in tow.
  • Book a sail. Our friends on the Blue Peter or Endeavor will take great care of you. Inquire early as a lot of boats head south for the winter. 
  • Grab a coffee from Pip & Anchor. Make sure you stock up on their dates. They are the BEST dates on island and seriously are so sweet.
  • Bluff walk in 'sconset. Because so many places in 'sconset roll up after labor day, I am not suggesting a trip to 'Sconset on my itinerary above, but it is my favorite place! I originally was going to have Chad and I get married and have our wedding reception at the Sconset Cafe but I digress. Pack a lunch and head east out to Sconset, to do the bluff walk and see the Sankaty lighthouse. It's really beautiful!

Oh, and if it wasn't already obvious; be sure to stop by Anna P. Jay and say hi! And buy yourself a little souvenir :)

Hope this guide helps, xo.