Nantucket and I are currently going through a bad break up. Every night, my heart aches with separation. I’ve tried cartons of Ben & Jerry’s Chunky Monkey, but I just end up longing for Juice Bar. Nantucket cheated on me with a younger, seasonal crew. Now I spend night after night losing sleep, stalking it on social media, watching from afar. I’ll never be over the pain, but I’m ready for my next Nantucket fling.



For many of us, including myself nowadays, summers can no longer be dedicated to Nantucket. Heck, not even every weekend can be a Nantucket weekend. Apparently, there are only so many vacation days you can ask for. I’d be lying if I said I haven’t considered becoming a teacher just for the summer off.

Until I can happily retire, nestled in a sizable ‘Sconset cottage with my two labs named Salt and Pepper, I have learned to divide and compromise my weekend visits. Check out my Lucky 7 Tips for Summerers turned Visitors – see you Friday old friend.



1. Gotta Get There First

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When you only have a few cherished weekends, you’ll want to come squad deep. Bringing friends on your visit can make for an incredible time, but don’t sugar coat the travel. You may be used to it, but they certainly are not. Traveling to Nantucket is a marathon, not a sprint. I made the mistake of making it sound like it was a hop, skip and a jump. Travel can put a damper on a short weekend, but don’t let it. Warn everyone ahead of time that if its not all smooth sailing, its worth it – and there’s a beer waiting for you on the ferry.


2. Make Your NanBUCKET List

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Definitely have a loose plan or at least a NanBUCKET List. When I had a group of friends for MDW, I went in blind and found myself not seeing everyone I wanted to. If you don’t have a plan at all, whether you’re with family or friends, you’ll leave island feeling like you didn’t get everything done. Make your Spark Notes edition of a Nantucket summer. During previous summers, my nights were consumed with nightlife. When you only have two or three nights to play, make sure you have some variation. Friday night at the BOX, Saturday night in town having drinks at the Tree Bar, and Sunday winding down, sipping Whales Tales on the beach.


3. Don’t Leave out Town Time

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You would think I had enough shopping to choose from in NYC. Even so, Nantucket has some truly amazing boutiques, so don’t leave it out on vacation! In New York, the sidewalks are your runways and instead of being the fourth person in the same Urban Outfitters off the shoulder sundress within a 5-block radius, add some Nantucket chic to your wardrobe. It will make you feel connected to island even when you’re not. Next trip, I’ll be stopping by Eye of The Needle and The Lovely for some one of a kind pieces.


4. Take it in ACKtively 

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You might see your vacation as a one way ticket to booze town, but give yourself a little alone time with Nantucket. Clearly Nantucket and I have some talking to do after this break up. Try to designate Saturday morning for a little ACKtivity. MANtucket recently showed us that anyone can rent surfboards, and its wicked fun. Another great way to take in island is by bike. Get your wheels turning with a Nantucket Bike Tour from our good friends over at the Handlebar. For me, I’ll be running from my house to Brant Point lighthouse. Running through the streets of town is my favorite way to take in all the beautiful homes and lush landscapes.


5. Do Something Different 

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We all have our tried and true beach spots. Trust me, It’s a rare day that I don’t instagram from Ladies Beach. There’s simply no time for routines when you’re just visiting, so make each weekend its own by testing out a new beach with friends! Last September, I spent the quieter months exploring island. I won’t give a way my secrets without a Figawie Wowie first, but there are some incredible spots out there that you won’t need to be toed out of. I’ll give you a hint, when you feel lost on a dirt road, you’re probably close.


6. Don’t Pick, Picnic 

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I have so many favorite dishes at so many places. So why just pick one per night? Make the most of your stay with a tapas style restaurant crawl in the evenings. Have cocktails + apps at CRU, split entrées at Ventuno, followed by dessert at The Pearl. As for the earlier part of the day, pack a diverse picnic. Provisions sandwiches, Nativ Made pasties, Lemon Press acai bowls and a charcuterie spread from Current Vintage all make for a well packed cooler. The rose and beer will go in its own cooler.


7. Bring Something bACK 

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Going to island is spoils you with nature, beauty, fresh air and sunshine. And then you get back to your minimally light filled apartment, in a concrete jungle, with the sounds of a neighbor singing opera coming through your air vents. Its a painful slap from reality. I do my best to ease the pain by bringing a little something back. Whats that mean for little miss blACKbook…a loaf of Something Natural Portuguese bread. Even though I’m gluten-free, I make an exception – plus it travels well. Trust me, Monday morning when you’re missing ACK, dreading going back to work, it’ll  be the perfect breakfast (cue avocado toast) to make you smile. You’re welcome.


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Little Miss blACKbook… follow our gal Courtney on Instagram @courto19