A Weekend on Nantucket

28th July 2009

Nantucket is hands-down my most favorite place on earth. I lived on island after college and love going back.

A few weeks ago I went with some of my friends and I’ve been working on this post ever since. Honestly, there is just so much I love about the island, it’s impossible to know when to stop writing!!

Great Point


If you have some money to spend I would suggest the Wharf Cottages in town. It’s a fabulous location on the water with lovely accommodations (recently updated). I also love the Veranda House and the White Elephant – both just remodeled, both right in town.

If you’re looking for more affordable lodging, I love the Cobble Stone Inn and the Center Board Guest House. If you have a family or large group, the boat house room at the Center Board is really fun. I’ve also stayed at the Safe Harbor Guest House, which is a lovely inn just down the street from Children’s Beach. Ask for the South Wind room – it has a great deck with views of the harbor.


American Seasons – amazing food, fabulous service and atmosphere. A little on the pricey side, but well worth it.

Black Eyed Susan’s – expect a line outside outside at all times! Black Eyed Susan’s serves breakfast and dinner seven days a week, and it’s a favorite with the locals and tourists alike. The breakfast is amazing – I highly recommend the Dutch pancakes (pancakes with Jarlsberg cheese on top), french toast or an omelette with pesto. For dinner you need to arrive at 6pm (or before) to get a reservation for the evening. Everything on the menu is amazing, but my personal fave’s are the caesar salad and tuna tartar. Also, it’s BYOB, so bring your favorite beer or wine!

The Boarding House – one of my favorite spots in town! Personally, I love sitting downstairs because it feels like you’re sitting in a wine cellar. The food is amazing, as is the wine list. I’ve never been disappointed. If lobster is on the specials list, get it!

The Juice Bar – just off the Steamship Dock is a part of town we like to call “the strip”. Basically, it’s a strip of “fast” food restaurants that serve take out. If you’ve got a sweet-tooth, there is nothing better than a scoop of ice cream from the Juice Bar.


No trip to Nantucket would be complete without a mudslide at the Gazebo! Here are some of my other favorite spots: The Straight Wharf, Slip 14, Cambridge Street and the back bar at 21 Federal. Late night you can’t miss the Chicken Box – it’s the best time ever!

See and Do

I’m not even sure where to start. First and foremost, you must go to the beach (hopefully the sun is shining while you’re there!). My personal favorites are Madequecham, Starbuck in Madaket, Steps and Great Point (first photo above). Great Point is particularly special because you have to drive a four-wheel drive vehicle out on the sand to get there. It feels totally secluded – always the highlight of our trip! 


I also love the charm of town – just walk around for a few hours and take it all in. Have a drink at the Gazebo, stop in the shops on Main Street, take a stroll on the docks and check out the boats. If you’re a history lover, check out the newly restored Whaling Museum just off Steamboat Wharf.

If you’d like to enjoy the water, I would suggest a sail on the Endeavor. And, if you’re up for a lot of fun, spend a day fishing with Captain Tom. Nantucket is known for its fishing – sure to be a great time!

If you’re a beer-lover, a trip to Cisco Brewery is always a blast. You can taste the local beer, wine and alcohol. Stop by Barlett Farm on your way and pick up lunch; when you’re finished with the tastings you can sit outside and enjoy the scenery.

Most importantly, spend some time exploring. Nantucket is full of hidden treasures – every year I find something new to love.

2 thoughts on “A Weekend on Nantucket

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