Nantucket, MA

Nicknamed Billionaire’s Island

Should I rent a car?

No, but you should rent a bike. Nantucket is mostly flat so walking, taking the (clean!) shuttle, or bike riding are the best and cheapest forms of transportation. Try Easy Riders as they are the most affordable and deliver to you for free!

Where should I go to eat?

For breakfast: 45 Surfside, Wicked Island Bakery, Lemon Press, Black Eyed Susans, Downyflake and Island Kitchen. For lunch: 45 Surfside, Provisions, Claudette’s, Something Natural, 167 Raw. For dinner: Via Mare or Ventuno, Bar Yoshi, Millie’s, and Gemelle. For late night eats + treats: Stubby’s, Juice Bar, Island Kitchen, and Cisco Brewery for local beer!

What activities should I do?

You must go do the Sconset Bluff Walk. It’s a mile-ish long walking path through perfectly landscaped backyards that overlook the ocean. Speaking of beaches, visit Steps and Surfside. While you’re at Millie’s, head on down to Madaket Beach to watch the sunset. The walk to Brant Point Lighthouse will have your head on a swivel as you marvel at the homes on the way. For shopping: Bon Ton was my number one favorite. Blink and you’ll miss it and it’s nearly impossible to find on Google Maps, but it’s across from Current Vintage. The Hospital Thrift Shop is worth stopping into, along with For Now, The Skinny Dip, Ralph Lauren, Nantucket House Antiques, Island Treasures, Four Winds, and the Nantucket Crisps pop-up shop. Don’t miss going into Mitchell’s Bookstore! The Farmer’s Market is every Saturday from 8:30 a.m. - 12:30 p.m. Check out the Whaling Museum on a rainy day.