Looking for ideas for what to do in Manhattan? You’re in luck, because I have what you need! I like to get my dose of New York every 2 years or so. I typically plan around staying for long weekends. It’s such an easy flight from Chicago and I love that you really don’t have to plan too much in advance. Get a flight and hotel room or AirBNB and you’re done. Public transportation is so easy and abundant that once you’re there, it’s super simple to get around.

I’ve explored the island of Manhattan through and through from the Upper West Side to the Upper East Side, Central Park, Midtown, Chelsea, Hell’s Kitchen, Greenwich Village, Wall Street, Battery Park, Soho, Tribeca and the LES. There is SO much to see and do in Manhattan that it’s overwhelming at times. I think there is something for everyone in New York and depending on what you’re looking for, the neighborhood to target will change.

What you need to do if you’re planning a long weekend is pick a cluster of neighborhoods and immerse. Don’t try to cover the whole island. You’ll just get wiped out and may feel like you’re getting a watered down version of something. Look up the best restaurants (those are always changing) and plan to become a New Yorker for a weekend. Make it your city.

My personal favorite parts of Manhattan include the Lower East Side, the Village, and Soho/Tribeca. I’m definitely a lower Manhattan kind of girl. I’m glad I have seen Rockefeller Center, Central Park, Times Square and all the other famous sites, but I really like the New York that feels like a neighborhood and home.

Greenwich Village

On a Crisp Fall day, there is literally nothing better than walking around the winding and charming streets of the Village. Unlike much of the grid-like structure of Manhattan’s streets, the streets in the Village lose the organization and it becomes less expected and rigid than some of the city’s other areas. There is something really cozy about this neighborhood to me. Maybe it’s the fact that it was essentially evolved by an artist community or the fact that NYU’s campus is nearby and filled with energy, but I think it’s fantastic. I’ve never actually stayed in the Village, but I think it’s good for a brunch stop and a walk or to have drinks on Bleecker before turning in for the night. This could be a great area for an AirBNB.

Tip: For an amazing lunch (if you’re a meat eater) check out The Meatball Shop in the Village. There are a few locations, but this one is good.

Buildings in Soho Manhattan New York


Soho to me is a mish-mash of architecture and different vibes within a pretty small area. While some of the streets feel more like Midtown to me and are way too crowded for my taste (like the main shopping drag on Broadway) I love the charm of some of the tree-lined streets like Prince and Spring. Pro tip: Because of New York tax law, you can make clothes and shoes purchases under $110 without paying sales tax so even though I don’t love the Broadway crowds, I’ll usually hit up H&M, Zara, Topshop, etc. while I’m in Soho to see if I can get any deals and not pay the high sales tax I have the pleasure of paying in Chicago.

Soho also has a good share of cool boutique hotels, upscale restaurants and places to grab cocktails. Some of my favorite dining experiences have been in Soho, which is why it made it on the list of fave neighborhoods.

Standout Soho dinner joint:

Blue Ribbon Sushi some of the best sushi I’ve had in a very cool environment with interesting lighting and modern wood paneling. They even made a replica of this New York gem in Las Vegas. We had a really cozy and private booth for 4 of us, which made the experience really nice. I imagine it is a good date place, but I was there with a group of girls. If you want to check it out and are using Google Maps or another online service to find it, make sure you find the right restaurant. It is at 119 Sullivan near Prince. There are a lot of Blue Ribbon restaurants and the first time I went I was led to the wrong restaurant, so pay attention on the map providers.


Tribeca sits just below Soho and has charming cobblestone streets, some shopping and cafes and a lot of converted warehouse residences and lofts. It’s actually now a really pricey place to live as the real estate in this area has boomed and it’s gained credibility for being a safe neighborhood with good schools. Maybe it’s because a lot of people actually live here and you see families walking around and less tourists crowding up the streets, but I really like the vibe and feel of this neighborhood for a daytime stroll after a hectic weekend. It has a relaxing feel to it. I’ve spent a whole Sunday morning just walking around after breakfast watching the families play at the park and it was really peaceful.

The Lower East Side (LES)

I saved the best for last. I love the area that is known as the LES and Nolita just kitty corner. Let me be clear, there are grittier parts to this area and it’s not necessarily the most glamorous part of Manhattan, but it is a revitalized area and is steeped in history as this was often the first place immigrants lived when they came to America. I’ve read enough books that I have a romanticism and appreciation for this part of New York. If you are a reader, check out Rules of Civility about 1920’s New York. I read it right before my last trip over and although it was fiction, I had a deeper appreciation for history of the Lower East Side of New York City and could imagine how it must have been nearly a century ago.

The LES is the spot for cutting-edge fashion, boutiques, indie restaurants, cocktail clubs and boutique hotels. A good concentration of this scene can be found on Orchard St., particularly between Stanton and Rivington. I like this area because it is such a historic area, which you see in the old architecture that is now bustling with new energy, new opportunity and modern art + design.

For me, if I want to walk around and enjoy a relaxing day, I’ll go to the Village or Tribeca for that, but when it comes to dinner and cocktails, I want to be in the LES. Here are a couple of ideas:

Freemans Restaurant – Freemans (literally in Freeman Alley) is a really cool spot that you might never find without knowing about it. Or you would totally stumble upon it un-expectantly. It’s literally at the end of an old alley that is invitingly decorated with lighting and a welcoming entrance. The décor inside is cozy and warm with a “cabiny” type of feel. There is wood, taxidermy and whiskey cocktails. The cuisine is comfort American food with some game fare such as quail. I went here with three other girls and we had an amazing dinner with a double order of mac and cheese to share. I will warn: You will wait to get seated at this restaurant nearly without a doubt. We had to wait about an hour, but we gave them our cell phone number when we checked in and went to a bar nearby and they called us when they were ready for us so it was no big deal. Just don’t go starving and expect to sit right away.

Freeman’s Urban Cul-de-sac by Jon Gilbert Leavitt

The Stanton Social The Stanton Social was another spot my boyfriend and I hit up for dinner and really enjoyed. I have some friends who don’t love this place because they think it’s too sceney, but I like it. The ambiance is really cool with some soft elements inspired by the 1940’s mixed with industrial materials like metal and concrete. It’s a place you may want to put on your new cute outfit and get apps and cocktails or dinner. The dinner is mainly served as small plates tapas-style (although it is a multi-ethnic cuisine) so you really get a taste of a lot of different tasty treats. My favorite dishes were the Old School Meatballs, the French Onion Soup Dumplings and the Potato and Goat Cheese Pierogies.

Beauty & Essex –This place late at night is definitely clubby but it is also a restaurant with small plates and brunch. When you first walk in, it looks and feels like you are walking into a pawn shop rather than a bar or restaurant. But, it is just a front like a speakeasy. Try to book a table on OpenTable before you go. Then, once you tell them you have a reservation, they escort you into the main part of the club/restaurant. It’s actually really big with several rooms of varying décor. It’s got a very glamorous and 1930’s feel to it with tufted banquettes, chandeliers and winding staircases that are reminiscent of an old mansion. The drinks were great and the people-watching was even better. People really brought their fashion game for the night out with killer heels, and runway hair and makeup. I will say that the conversation became strained as the night went on because the music was loud and it was hard to hear each other sitting across the table, but overall it was still a great time if you’re ready for a nightclub vibe. They actually have opened up a Las Vegas version of this place now, which I have not checked out so I can’t compare.

Lower Manhattan Hotel Tip

The Nolitan If you are looking for a boutique hotel near Soho, the Village and LES, I would recommend The Nolitan. I stayed here for a long weekend last year and I thought the service was great and the location was perfect for me. It is situated just above Little Itally (Nolita = NOrth of LIttle ITAly) and a close walk to all my favorite neighborhoods. I personally loved the décor, warm yet slightly minimal with a Scandinavian feel. The staff was super attentive and really welcoming. There is a really nice rooftop with gorgeous views of the New York skyline (especially at night) and they offered wine and cheese happy hours in the lobby. The rooms were a more industrial, loft-like feel with concrete walls and vibrant colors. The rooms are small, but most are in NYC. There is also French-American bistro, Cantine Parisienne, that offers breakfast, lunch, dinner and drinks.

If you need help deciding between an AirBNB or a hotel for your New York trip, check out my article that helps break this dilemma down. If you decide to go with an AirBNB, check out my tips for choosing a good host.

Nolitan Hotel New York Manhattan Interior

Nolitan Hotel Room New York Manhattan

Adventure awaits!


Marissa is a travel consultant and digital marketing professional from Chicago, USA. Her business, Sips & Sojourn, specializes in helping busy people with full-time jobs travel more and travel better. Travel is Marissa's absolute passion but she believes you can hold down a successful career AND travel the globe. Marissa enjoys unique destinations, design hotels, sampling a culture's food and drink and meeting local guides focused on small, immersive experiences.

Write A Comment

Join the tribe :: Get travel tips and exclusive giveaways sent right to your inbox!