Nantucket, Massachusetts is a tiny island off the coast of Cape Cod and happens to be the perfect destination for a long weekend away. With its cedar-sided buildings, cobblestoned streets, and quaint boutiques, Nantucket is one of the most charming places I’ve ever visited.
My first (and only) trip to the island was this past weekend for a close friend's bachelorette party. Getting there was very simple, but there are a couple different modes of transportation, depending on your preferences and schedule. Many of my friends chose to fly from Boston, while others hopped on a ferry from Hyannis. I opted for the ferry and the faster one at that - arriving in only an hour. I bought my ticket online ahead of time and parked my car right across the street for $15 a day - not too shabby! Try to remember to bring cash, as parking is cash only. But don't worry if you forget because there is an ATM directly inside the ticket office. When planning your arrival, give yourself around 20 minutes before departure. The ferry's website recommends an hour, but I had no issues.
Once we arrived in Nantucket, there was no need to call an uber because taxis were all lined up waiting for passengers. We hopped in the taxi and headed over to Cisco Brewery, where all the other girls were expecting us. Cisco Brewery is very popular on the island, as it contains a vineyard and distillery as well! During peak season there is usually a queue line all the way down the street. We were lucky to be on the island a couple weekends before the high season tourists, so we walked right in! The brewery is unlike any I've ever been to - food trucks lined the outside, while live music flowed from within. If you venture through the brewery and into its "outside area", you will find fresh air, a fire pit, and picnic tables set up for groups to lounge together and enjoy a flight...or two ;).
For places to stay, there are many different hotels and B&B's, but I'd recommend a house rental. We snagged a great deal for a beautiful home right on Surfside road. This was a convenient location, with an adorable breakfast place, Handlebar Café, right across the street and a pizza joint next door (in case you're one of those people who enjoy a late night slice – I know I'm guilty!) Also, just steps down the road was a bike rental business. My girlfriends and I rented bikes for $27 for the full day (I can't think of a more pleasurable way to navigate the island). The owners of the rental shop were very friendly and accommodating. We rode around the island exploring for a few hours while the other partygoers tried to rejuvenate from the previous night’s activities. Seeing the island was amazing - the streets were almost empty so we had plenty of room to make wrong turns as newcomers to the area. It was probably my favorite experience during the trip!
Another Nantucket highlight is Jetties beach bar. Jetties is an open air restaurant, where you can admire the dune-backed beach right from the bar. The oysters are a fan favorite and they have a few different fun drinks to try - Frosé anyone? Probably a little more enjoyable to drink frozen rosé in the warm summer months, but nonetheless everyone seemed to love them!
For dinner we headed to a charming restaurant called Proprietors. The dishes were delicious! A couple of my friends and I split four different plates and each one was mouthwatering. We would have ordered more if we weren’t already stuffed (the empty bottles of wine along the table may have added to the gorged feeling). The meal was very reasonably priced for a high end restaurant, and I will absolutely visit again next time we’re there.
The final stop of the trip was a place that had been raved about by everyone we met on the island. It was named the Chicken Box or as the locals call it "the box"...either way, let’s just say the box didn't disappoint. The live band was playing a diverse music selection that had all the girls dancing their tail feathers off (get it, ha). Not big on dancing, but enjoy live music? No problem. There are high top tables around the dance floor as well as pool tables in the back if you're looking for a more chill atmosphere. It's a "see for yourself" type of place, but if you are in Nantucket, do yourself a favor and visit the box.
I can't believe it has taken me this long to find this endearing, isolated island. I will definitely be bringing Kyle on the next trip! Please make sure to keep in mind that I visited during the "off-season", so the island was much quieter than it is during the summer months. However, locals encouraged us to visit again during high season, so that I could enjoy the beaches, and the hustle and bustle the island has when it is filled to the brim with tourists. I may do just that because it sounds like a blast no matter what season we choose.