A Weekend Itinerary | Booklyn & Manhattan

New York City has been one of my favorite places to visit these last few years and every time I visit, I grow to love it more and more. Everything is so accessible in this city; from the best restaurants and street food vendors, theater, art, landmarks, parks, and people, it’s no wonder New Yorkers are proud of their city and rarely want to leave. 

The island itself is 23 square miles, boasts 1.6 million population, 24,000 restaurants, and 83 museums. With all these options at your disposal, it can be overwhelming to figure out how to spend a weekend in the City!


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I found myself with a ticket to NYC booked (thanks DELTA!) to meet up with some of my closest friends from a 2009 Semester at Sea study abroad program. One of our gals from our trip was tying the knot to a handsome Green Beret on the shores of Williamsburg, Brooklyn, with the entire NYC skyline as the backdrop (and us cheering tearfully in the background, hearts pouring with joy, all the feels!!) Check out the venue HERE!

After the wedding, my boyfriend and I took to the streets of Brooklyn and Manhattan for 3 full days of sightseeing, Broadway shows and the best eats the city had to offer.  Here is the highlight reel of our favorite places and must-dos in Brooklyn and Manhattan;

Brooklyn: Dumbo Neighborhood

·        Stroll Brooklyn Flea Market @bkflea  open Sundays 11-5 for vintage records, jewelry, bags, and other treasures. I found a vintage Chanel bracelet and hair bow

·        Have lunch at Cecconi's Dumbo: a lovely eatery overlooking the Manhattan skyline. Be sure to stroll next door to see Janes Carousel (100-year-old carnival ride) for a unique photo op! Rides are $2

·        Save room for dessert because across the street from Cecconi's is the famous Jacques Torres chocolate shop where you can build your own ice cream sandwich for $6- I went with chocolate chip cookie with chocolate-chip-hazelnut ice cream. If cheesecake is more your vibe, then you have to go get a Junior's Cheesecake.

·        If you’re a gossip girl fan, be sure to spot Lonely Boy Dan Humphrey at his loft at 455 Water Street, Apartment #6, Brooklyn, directly under the Manhattan Bridge: one of the most photographed places in Brooklyn. Get a FULL Gossip Girl location guide HERE (for those ULTIMATE GG fans!) 

·        Kings County distillery; is New York City’s oldest, largest, and premier whiskey distillery,  the first since prohibition

·        Take the Ferry (2.50/ticket) across the river to Manhattan

·        Walk the Brooklyn Bridge from Dumbo to the Lower East side to China town (2 miles)


·        China Town

o   Brassanova: best ramen in town. Cash Only. Awarded by The New York Times and Food Network

o   Uniqulee: a darling antique shop run by the most fabulous woman, boasting antique chandeliers, camera equipment, glassware, jewelry, candles, vintage photos, and other treasures!

·        Lower Manhattan

o   Stroll through the Wall Street neighborhood and walk past the NYC Stock Exchange, Courthouse, take a pic by the famous Bull and end at the 9/11 Memorial.

§  The Reflecting Pools are a humbling experience. Spend time reading the names. Say a prayer for the families who lost their loved ones on that September day in 2001. Touch the water.

§  Buy Skip the Line tickets to the Freedom Tower and journey 102 floors up to the highest building in the western hemisphere. Soak in the 360-degree views of the entire city of Manhattan, Brooklyn, Staten Island, Jersey, Ellis and Governor Island.

·        West Village (my personal favorite neighborhood!)

o   Feast on some famous NYC thin crust pizza at Bleeker Street Pizza and chat with Greg, the Owner, who will make you feel right at home and feed you the best pie on the west side. You may get lucky and get a funny story of one of his kids. Slices are about $6 each and are bigger than your face- you’ll be in-and-out in 20 minutes or less!

o   If you’re a FRIENDS fan, the FRIENDS apartment is 1 block west of Bleeker Street Pizza, so is Carrie Bradshaw’s place for those SATC fans!

o   Grab a cocktail of While We Were Young; a super chic Bahamas inspired wine house.

·        Theater Experiences

o   If you want to experience something unique and out of the ordinary, we highly recommend buying tickets to Sleep No More at the famous McKittrick Hotel. Based on the play Macbeth where you, the audience, is part of the story. You arrive at the hotel, “Check-In” and are instantly transported to roaring 20’s were the cocktails are strong, the dresses are sequined and the bar is filled with fog and a live blues band. You can even have your Tarot read, too. You are then escorted into a dark lobby and provided with a mask you are required to wear on your journey into the hotel, there is no talking allowed and you are encouraged to explore all 5 floors of the hotel to view the different plot lines unfolding throughout the evening. I won’t tell you much because I want you to experience this for yourself, but we saw scenes of a bar fight, lovers bath, creepy hospital, dancing on a bookshelf, a ballroom dancing party and a séance. We left with our minds blown and took in a drink to recap our experience at the Gallow Green Rooftop Garden; which boasts a view of the Empire State Building and lush gardens.

o   Splurge on a Broadway play. We picked The Book of Mormon. We couldn’t stop laughing. The writers of South Park created a timeless story filled with politically incorrect jokes that will have you roaring the entire play


Midtown: Scarpetta; great for late night Italian food and high-quality service

               The Seville- underneath Scarpetta and connected to The James Hotel. Great cocktail and club spot

Hells Kitchen: Hell’s Kitchen Mexican Cantina; incredible guac bar options and habanero margaritas

West Village: While We Were Young; great for a pre-dinner glass of wine

                          Bleeker Street Pizza; awesome for  quick, authentic New York Minute Lunch

China Town: Brassanova; best Ramen in China Town

Central Park: You can’t go wrong with a street cart gyro or hotdog

Pop Up Events: We didn’t make it to The Rosé Mansion, but our friend did! Stop by for a quick around-the-world tour of the different rosé . Each room is themed from flowers, swings and ball pits! @rosewinemansion

If city life isn’t your jam and you want to escape for some quiet time with ocean views (more my speed these days), you’re only 2 hours and a $26 jitney ride up to the beautiful coastal Hamptons. Catch our guide on How To East Hampton next week on the blog!

Stephanie Zillmer