CITY GUIDE: Nantucket

Today’s City Guide is brought to you by Rachael of Boston, MA! I’m especially excited for this guide because I spent a few days in Nantucket last year and it’s one of my most favorite places in the world! Enjoy!

Before I moved from Indiana to Boston, I don’t think I’d ever heard of Nantucket. But after my husband and I ran a business on this little island off the coast of Massachusetts for three summers, I fell completely in love. Though it is an elite destination spot for the wealthy, and everything on island is expensive (due to the need to ferry everything over on boats) it’s still one of the most delightful places you can visit. Try to carve out at least three days for your trip, just to make the travel time worthwhile. Once there, you can rent bikes or use the easy shuttle system to get around island. Unfortunately I don’t feel comfortable recommending any particular place to stay, just try to find the best deal, and use avid reviewers on tripadvisor.com to assist you.

The Beaches

Visitors to Nantucket spend a lot of time asking what beach they should go to. “What’s your favorite beach?” is a question we heard all the time at the market. Almost the entire edge of the island is a beach, and all of it is beautiful. Try them all, pick the closest one to your hotel, bike to the furthest one possible…they’re all clean, beautiful, and never overly crowded.

Straight Wharf Restaurant, Bar & Provisions

It’s dangerous to even begin talking about restaurants for dinner on Nantucket. Suffice to say majority of them are expensive but totally worth it. You may have some of the best meals of your life while on island. This restaurant, which has a fine dining half, a casual bar side with delicious bar food, and a sandwich shop for breakfast and lunch, is one of our favorites. I think they do everything well, in a wonderful island-stye way.

The take-it or leave-it, along Madaket Road, halfway between Madaket and Town

It may sound funny to visit a public dump on your vacation, but really this one of my favorite spots on island. Not only because you get to observe one of the most innovative trash sorting and recycling spots in the country but mostly because of the Take It or Leave It. Instead of throwing perfectly good things away, or having a garage sale, Nantucket residents and visitors drop things here. It makes for the most exciting thrift store of all time. The amount of true-keeper stuff my friends and I have found here is the stuff of myths. Cozy sweaters, classic books in the best editions, leather shoes, vintage kids’ clothes, pretty bedsheets….be sure to go before 12pm on the weekends!

Black Eyed Susan’s

The line outside this place on any summer morning can attest: they mix magic into their eggs. Try to go early if you can, but if that sounds like heresy on vacation, just put your name in and amble around the shops while you wait. Truly everything here is delicious (I dream about their pile of crispy bacon) but you’ll see lots of regulars ordering the paper thin pancakes with jarlsberg cheese cheese crisped on top.

The Nantucket Athenaeum

The free public library right downtown, stop by here for the lovely architecture, a cool spot to page through magazines, or quick lounge in their lovely contained yard.

Surfside Burger shack, at Surfside beach

Regularly voted the best burger on island, to me this place is quintessential Nantucket: affordable, friendly, simple, and classy. I love seeing the kids run up from the beach with their dollars in hand, lining up for slush puppies, burgers, bags of Ruffle potato chips, or frozen candy bars. But seriously, watch out for the seagulls here! They are dive bombers with a keen eye for an unwatched burger. Bonus: surfside beach is the easiest beach to bike to and it has the cleanest bathrooms and showers.

A big thanks to Rachael for giving us a virtual tour of the island. Be sure to visit her blog and follow her on Twitter! Click here to see more photos and to read about my visit last September!