Nantucket Island

Born and raised in New York and finally had the chance to experience the charm of Nantucket Island.

One of our bucket list trips: Visiting all of the “Outer Islands”. Nantucket, Block Island, Martha’s Vineyard, Cape Cod and the Elisabeth Islands (Cuttyhunk,  Naushon) and Long Island? First stop, Nantucket. I think the reason it took us so long to visit this quaint charming summer island is that is not so easy to get to. Sure, you can fly from NY to Nantucket but on top of the flight cost, you still need to drive/park or book car service and deal with traffic. After weighing all the options, we felt it was best to just get in the car and drive for a Nantucket weekend. What trip is on your bucket list?

  • 21 Broad Hotel (Modern Boutique Hotel)
  • Check-in: Thursday Check-out: Sunday
  • Room: Deluxe King Bedroom with Harbor views
nantucket street charm

Street Charm

sailing on nantucket island blue sky

Island Sailing

Brant Point grill at white elephant nantucket lobster mac and cheese

Brant Point

Day 1
  • Late June, departed from New Bedford, MA on a high speed ferry to Nantucket. Highly recommend since you can avoid leaving from Hyannis which is a traffic jam guaranteed.
  • A short walk from the dock to our hotel. Dropped our luggage and headed out to explore.
  • Dinner: Fabulous meal at Dune, currently closed and sold to a Florida restaurateur.
Day 2
  • Morning walk to Brant Point Lighthouse. Nothing better than burning some calories so you can eat and drink at lunch with no remorse!
  • Lunch: Brant Point Grill at White Elephant. BPG’s Signature Lobster Mac & Cheese. Yum! Just order it.
  • Afternoon sail around the island aboard Endeavor Sailing.
  • Dinner: A relaxed meal at the end of the south wharf, Slip14. with dessert from Aunt Leah’s Fudge.
  • Ended the night with a casual stroll in and out of the shops.
Day 3
  • Island Biking: Rented e-bikes and off we went. 1st stop, Sconset. Of course a bike that doesn’t lose its pedal half way during the ride would be ideal.🤣. The one desolate part of the small island and we breakdown. Thankfully, we had cell connection. Found a mechanic on a quiet dirt road. A vacation curveball that ended up being a memory that we will never forget.
  • Lunch: Claudette’s. A hidden gem. Outdoor seating at this cottage sandwich stop located right in the roundabout circle of the village was the perfect stop for some body fuel before venturing off.
  • Off we go to our 2nd stop, Sankaty Lighthouse, riding through the street lined waterfront cottages blanketed with hydrangeas & roses.
  • Back on the bike to ride along the south shore. Riding an electric bike is work! Oh look, Cisco Brewers, our 3rd stop and its happy hour, isn’t that convenient? Or maybe planned? lol. Live music and a few much needed cold ones before heading back to the hotel.
  • Dinner: Sunset picnic on the beach, anyone? A quick bus ride to grab delicious takeout from Millies Nantucket and after a 5 minute walk to Madaket Beach, we were having an unforgettable sunset picnic in the sand with our cozy sweatshirts.
Day 4
  • Breakfast: Black-Eyed Susan’s, the perfect vibe to wrap up our weekend on Nantucket island before heading back to our reality.