It’s strange how far the reach of Nantucket goes. There are times when the island feels criminally small. We all have days when we look like leather face. We’re just trying to chill and be downright gross in our own existence. Eat ice cream in your bed type of day. Try sneaking into Stop & Shop unnoticed with crooked glasses and matted hair to pick up “Half-baked” Ben and Jerry’s in this town. It’s a near impossible task. 

Yet, that small town Nantucket charm is truly awe-inspiring considering its global reach. A Straight Wharf t-shirt hangs from a restaurant’s ceiling in Florence, Italy. A fan sporting a Cisco Brewers hat continuously popped up on FOX during the Cubs-Indians World Series Game 7.  I ran into a summer regular in a club in Barcelona……Barcelona! Nantucket is over a thousand miles from Charleston, South Carolina but it seems all of the best places in the world have a connection to ACK if you reach far enough.


It’s is the ideal recipe for travel inspiration. Maybe it’s the slightly wrongful assumption that frozen tumbleweeds blow through the streets during the winter. The beauty of an off-season allows the perfect time period to improve your cultural savvy and brush the dust off your passport. We simply don’t have time to catch our breath in summer and fall, and as much as I love lounging in my sweatpants in the winter, Nantucket isn’t a breeding ground for the lazy. These people are millennial pioneers, world travelers and professional socializers.  

People don’t find Nantucket on accident. Nantucket seems to find you and never let go.


My father’s reasoning for loving palm trees is obvious… he knows he is on vacation. I’m more of a wash elephants in a sketchy country and get lost in a temple type of guy as opposed to Pina Colada’s and funny tan lines, but I wasn’t ready to let go of summer. Cocktails will always taste better when the heat is on. Considering the only exercise I got in August was sprinting around restaurants because I didn’t stock enough cherries, or walking from bar to bar on the ACK streets, the body wasn’t ready to take on the heavy comfort foods and White Russians I usually pollute it with in the cold winter months. I figured I’d push back the workout regime and take a little Halloween vacation in Charleston before I really let the off-season resonate.


I arrived to sunny Charleston four hours before the rest of the crew. Within thirty minutes of being there I had met another Nantucket fan. I tentatively ventured away from our air bnb to hit the streets to curb my insatiable tuna burger appetite (I literally can’t write a post for blACKbook without mentioning tuna burgers). I landed at the infamous 167 Raw and I don’t remember anything else from the trip…..just kidding. This interaction would change the course of my vacation. After mingling with the staff like any good blogger would, discussing our mutual friends and our affliction for the island, the 167 boys took the ACK crew under their wings and made sure we had just as much fun as they did when they came to our neck of the woods. Proper guidance from the right people is the key to a great vacation. The combination of a deep and fascinating history, unbelievable southern cuisine integrated with world inspirations, and the young vibrant college atmosphere in an up and coming town make this city one of the best. The following are my Charleston musts.


The Ordinary

544 King Street, Charleston 

This place is visually remarkable. A massive ballroom with two large open floors below a breathtaking chandelier makes this restaurant an architectural experience as much as a food one. We were lead up the spacious staircase to one of the eight upstairs tables. The crew has a glutinous approach on a standard summer night off on island, fast forward to those same self-titled foodies and we ordered the menu like it was restaurant Armageddon. Start with a crispy oyster slider and shellfish tower featuring an abundance of condiments including an unreal ginger-citrus mignonette. Honestly, there were growing concerns of King’s disease for your old boy by day three of this trip. The one beautiful lady who had the unlucky punishment of attending this dinner with us got the grouper (don’t look up what this fish looks like alive) and it may have been the best entrée at the table.


76 Queen Street, Charleston 

Husk is the epitome of southern dining. The sheer size of these southern restaurants is a rare find in the compact North. We ate upstairs at a beautiful round table adjacent to a large balcony with obtrusive columns facing the Charlestown streets. Fantastic service and unforgettable food make Husk my number one. The crunchy fried pig ear wraps are a unique southern dish that caused a near fistfight during deliberation for the last lucky piggy. The brussels sprouts prepared with caraway hollandaise are worth mentioning and the strip steak featuring a unique coffee rub was my favorite entrée.

167 RAW

289 East Bay Street, Charleston 

We managed to fit in three meals at 167 Raw during five days and as any restaurant connoisseur will tell you, ambiance and vibe are almost as integral to any restaurant as the food itself. Identity is everything. I’d come back to this place if they served Ramen Noodles just to hang with the staff. 167 keeps it simple, but it keeps it so damn fresh. The Tuna Burger is a beautiful patty mixed with various seasonings and topped with a delectable house-made guacamole. The scallop roll was the most pleasant surprise, and the daily fish taco (the swordfish with fresh pico de gallo was number one) is a must for the table. Wash it down with a side of their unique Orange wine and you may need a restraining order to stay away from this place. A word for the wise, 167 serves the same menu from 11am until 10pm. This gem is no secret though, make sure to come at opening or between 4:30-5ish to ensure a seat at this tiny popular restaurant.


Stars Restaurant Rooftop & Grill Room

495 Kings Street, Charleston 

This place is a straight up dance party on the weekends. If you want to do some funny dance moves then look no further. Classic sing-a-longs pump from the downstairs speakers and the massive wrap around bar makes grabbing your next cocktail a relatively easy task. Despite the first floor tango going down, the upstairs sports a roof deck that takes home the top spot on my list. With an amazing view of the city, and a much quieter bar scene, this is the perfect spot to soak in that warm South Carolina air.

The Cocktail Club Charleston

479 King Street, Charleston 

What a spot. This quickly became the rendezvous and clubhouse of choice. Featuring a fantastic wooden bar and high ceilings, live music plays in the background while you supply the juice for your engine. A rooftop deck with spacious couches and ample lounging space provides a place to get some oxygen if you’re suffering from extensive stanky leg or just need to take 5 and talk about how great Charleston is.

Home Team BBQ

126 Williman Street

Best nachos I’ve ever had. This massive, open, barbeque spot boasts countless flat screen televisions, long picnic table type dining and a plethora of BBQ sauces that made my head spin. Imagine Cisco Brewery’s atmosphere merged with a sports bar and you have Home Team. You’d have to be a descendant of the Grinch to not have fun here.

Charleston Beer Works

480 King Street, Charleston 

Charleston Beer Works makes the list for the men who can’t miss the pigskin on Sundays. The place was a blast to watch football. The chicken tenders were strangely satisfying and there is a contingency of fans from teams all over the country. With a large group of Bills fans that dwell at beer works on Sundays, this is the perfect spot to chirp random people for rooting for strangers that we’ve most likely never met and getting upset over past football results we simply have no control over.



10001 Back Bay Drive, Isle of Palms 

It’s about forty minutes from central Charleston, but it is well worth the drive. South Carolina is the golf capital of the country for good reason. This is one of the best public courses I’ve ever stepped foot on. A beautiful clubhouse, a cart girl who seems to get an alert every time your drink slips below the half way point, incredible landscaping, smooth greens, as well as a little southern nature including alligators and flying fish and you’re in for a memorable golf experience. The post card picture of this course comes on holes 17 and 18. It’s your first direct view of the ocean and these two beautiful holes are simply breathtaking. Pretty enough to make me forget about how terrible I am at golf.


3550 Ashley River Road, Charleston 

I couldn’t make a trip to the low country without diving into its rich history. Selecting the tram tour to view the amazing garden and hand dug trails throughout this fascinating plantation decorated with weeping willows and vegetation not seen in the North was a truly eye-opening experience. Charleston was an integral figure in the Revolutionary war as the Americans fought bravely in defending its precious port. Charleston also figured prominently in the country’s painfully slow abolition of slavery. In addition to the ubiquitous history, this trip was a sneaky haven for nature. The swamps and ponds are dotted with catfish and turtles, and of course, alligators. They were everywhere. Moms, dads, babies and of course, the 19-foot female Betty roamed one pond all to her self.


32 Ann Street, Charleston 

We make most of our final decisions on where we want to go based on our enumeration of Nantucket’s favorite band: The Revivalists. Once again they stole the show as we bounced around in our banana costumes. The Music Farm venue was electric and I strongly recommend seeing a show here.

This city is awesome. Great restaurants, warm sun, live music, a small town feel, and some of the best golf in the country makes Charleston one of the best cities around. Until next time my southern friends.  
PS. Don’t drink all day on a golf course in the sun before attending dinners at beautiful restaurants.
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Keep the energy up and make sure to follow as continue with the travel posts this winter. See MANtucket’s adventures on Instagram @swoops44