A well-preserved whaling town 30 miles off the coast of New England.

1. Take the Tour at Cisco Brewers

More of a block party than a traditional Brewery, this outdoor collection of 3 separate tasting stations (Nantucket Vineyards, Cisco Brewers, and 888 Distillery) offers a great drinking tour, food trucks, and live music! I highly recommend the boozy tour, it comes with drinks at each station (wine, beer and hard liquors). It is a laid-back party scene after a day at Cisco beach. Fun fact, it is too windy to grow grapes in Nantucket, so the grapes come from Washington State but the wine is made on-site. Try their most popular beer, Whale's Tale Pale Ale. 

2. Stroll The Bluff Walk

"Are we allowed to be here?" I ask as we walk unscrupulously through people's backyards. Short answer, yes! This gorgeous walk along the Sconset shore is public property and part of the Nantucket historical association. Well worth the hike, you'll see some stunning views as well as beautiful houses up close. Paths from The Bluff Walk to the beach have some epic waves. 

3. Bike Somewhere

This small island is easy to navigate by bike, and the ferries and busses have bike racks. Cisco beach is an easy bike ride from downtown, the lighthouse is a quick ride from Sconset. Consider putting your bike on a bus and then biking around a section of the island. 

4. Belt It Out at the Club Car Bar

A vestige of the old railroad, this little car has been transformed to a lively bar with sing-along piano nights after 8:30 on weekends! Small and intimate, The Club Car is a good place to grab a drink and sing your heart out with total strangers. Get there before 8:30 if you want a table, naturally this little spot gets crowded!

5. Dine at a BYOB Restaurant

I was surprised how many restaurants are BYOB on the island. Two musts that allow this are Centre Street Bistro and Black Eyed Susan's (smiling brunch pictured here).
While not a BYOB restaurant, some of the best clam chowder ("quahog"chowder) in Nantucket is at The Brotherhood of Thieves Restaurant. 

6. Enjoy Sunset at The Galley

A fancier, trendy evening... but worth it to put your feet in the sand, listen to house music, drink a cocktail. Galley Beach is a great spot to grab a drink before dinner and watch the sunset. 

7. Nerd Out at The Whaling Museum

I know... I know... Lectures? On a beach vacation? The Whaling Museum is simply worth it... and the stories volunteers from the Nantucket historical society tell (especially about the ill-fated Essex) are fascinating. While you're at it, take a walking tour (they depart from the museum) where you'll get to visit inside some of the restored colonial houses.

8. Stay in a Historic Home

A lot of rentals on the island are historic homes. We stayed in a little house downtown owned by the Macy family. Yes, the family that founded the department store! It is a quaint experience that gives you the feeling of going back in time. These book up fast, so be sure to grab one in advance!

Lessons Learned

1. Parking at the Steamship Authority is $15 per day, this can add up quickly so be sure to consider these costs when you debate flying or driving. When there is weather, flights are also less likely to get cancelled than ferries. 

2. It gets cold at night and the island is windy. Even over Labor Day, it's still New England! Bring a sweater.

3. It is a very seasonal island, after Labor Day many bars, cab companies, and restaurants (like Millie's for example) close their doors. Your best bet is to visit in the summer and book in advance, it's already an expensive island, so the good deals on airbnbs and hotels go quick.