An NYC Long Weekend Itinerary That’s Actually Fun For First-Timers

Where To Stay

New York City is brimming with all kinds of stays, so where you choose to hang your hat really depends on the kind of vibes you want to surround yourself with. Are you seeking a more-touristy hotel, or a local hostel? There’s no wrong answers here, though I must recommend where we stayed because it was impressive.

When it came to my recent BFF trip, I couldn’t think of a better accommodation than Kimpton Theta New York – Times Square. We were graciously hosted there, and right away, the most evident perk of the property was location, location, location.

Nestled in the heart of Midtown, it's a quick walk (I’m talkin’ 10 minutes, tops) from the hotel to NYC staples like Times Square, Broadway, Central Park, and Rockefeller Plaza, to name a few. This made getting around superbly easy and wonderfully entertaining. Subway stops abound within a two-block radius, staying here also made public transit a no-brainer when walking wasn't an option.

When we weren’t venturing out according to the following itinerary, Kimpton Theta New York – Times Square offered unmatched calm and quiet, both of which are necessities for quality rest and recharge time in NYC. Aside from short (but fulfilling) overnight sleeps, we were able to sneak in power naps during the afternoons, which empowered us to keep all the fun going.

Another redeeming feature of the hotel both my BFF and I clocked upon arriving our first day was that it certainly felt luxurious, but not aggressively fancy. You won’t find decadent chandeliers or overly ornamental furnishings here – it’s more modern, and more than anything, modestly swanky, which helped ground us after exhausting excursions.

With a wide variety of accommodations available (King, Corner King, 2 Queen, and a 1-Bed Suite), an accessible rooftop bar, a lobby marketplace with delicious snacks and drinks, a fitness center, café, complimentary toiletries, loaner bikes for exploring the city, and even a daily social hour for guests, Kimpton Theta New York – Times Square ended up being the perfect landing spot for our action-packed NYC quest.

The Ultimate NYC Itinerary For First-Timers

Knowing it was my bestie’s first time in NYC, we had to lean into our inner tourists, but since we also can’t resist a little hidden gem, this itinerary has a good balance between the two. If you’re enamored by the arts, love to dine, and are prepped for a substantial amount of walking, see the itinerary below for the best long weekend in the charming chaos of the city.

Day 1

Arrive in the city.

This is where the adventure starts, and, really, where the tone of your entire trip is set. Though traveling all day can be draining, pulling up on the New York City skyline will instantly reenergize you – at least, that’s what it did for us.

My best friend, Ivy, and I flew into JFK and ended up Uber-ing to our hotel. If you’ve never been to a big city like NYC before, getting around can be intimidating – but don’t fret! We quickly found that everywhere we went, signs were clear, maps were easy to read, and strangers were generally kind in providing directions. The city's got you. Taking the train into the city is a much cheaper option than Uber, though it can be exhausting after long travel days, especially if you have to lug around larger pieces of luggage. It’s really a ‘choose your own adventure’ vibe everywhere you go.

Visit the Top of the Rock.

Buying the $45 ticket to see the Top of the Rock upon coming into the city was a must for Ivy and I. Offering 360-degree views of the entire city, the Top of the Rock observation deck that lies atop 30 Rockefeller will leave first-timers and NYC veterans alike speechless.

Grab dinner.

By the time we checked into our hotel and hit up Top of the Rock, Ivy and I had worked up quite the appetite. If it’s your first time in the city, hunger will frequently creep up on you, thanks to all the energy spent walking, taking in all the miscellaneous sights (and smells).

So, dinnertime. We enjoyed ours at our hotel’s rooftop restaurant, Bar Sprezzatura, but there really is no shortage of great food in NYC. Whether it's a quick, cheap bite or a sit-down dinner, there’s usually something right around the corner or a quick train ride away from wherever you are.

Venture out for drinks.

Something about the duo of Aperol Spritzes we both enjoyed over dinner convinced us that we needed even more refreshments to recuperate after a 4 a.m. wake-up call. Ivy and I convened with another bestie at Verlaine in the Lower East Side, which had a delightfully convenient $8 lychee martini deal for their happy hour that runs 5-10pm Tuesday to Sunday. Whether out of exhaustion or spirit-induced haze, my full review (diligently jotted down in my notes app the night-of) was a single word: Bangin’.

Day 2

Grab coffee + a bagel for breakfast.

This pairing is a must in NYC. Coffee and bagels await you at practically every corner, so, in my opinion, there’s no excuse not to.

Stop by Grand Central Station.

This is another essential stop for NYC first-timers to take in all the views of historical architecture and the general bustle of people constantly coming and going. Grand Central Station is also outfitted with plenty of places to eat – we ended up bringing our own bagels and chowing down on ‘em as we people-watched.

Visit MoMA.

Of course, I had to work in the arts for our NYC itinerary. I believe it's a must for anyone's first time in the city. Luckily, the city has plenty of famous museums like MoMA, The Museum of Modern Art. Though it’s truly worthy of an all-day walkthrough, we made room for more museums in our plans. So, our MoMA visit was relatively short, but we still got to see all sorts of big names and recognizable works.

Walk through Central Park.

Central Park is conveniently sandwiched between MoMA and The Metropolitan Museum of Art. Thus, the perfect buffer activity between the two famous collections Ivy and I had plans to visit was to grab something fast for lunch and take in all Central Park had to offer. In true NYC fashion, we had to refuel with a street cart cappuccino, too. Highly recommend.

The day we ventured out for art was also moderately rainy, which really amplified our time meandering about Central Park’s paths in the best way possible. From droplet-drenched flowers to weather-resistant runners braving the wet, just existing in the 843-acre park was a testament to how important having a place of green, green respite is to NYC-dwellers and visitors alike.

Marvel at The Met.

Even if you're not a huge art aficionado, The Met will feel like magic. Spanning thousands of years and endless art styles (and not to mention the beautiful venue), their collection is massive in scale. We simply couldn’t see it all, but some of my favorite exhibits included: Arms and Armor, Greek and Roman art, Medieval art, and Photography. If it’s your first time visiting NYC museums of this caliber, I’d recommend not pressuring yourself to see all of it in favor of reserving some energy for the rest of your trip – and giving yourself an excuse to come back!

Time for dinner.

By the time we’d perused both MoMA and The Met’s vast offerings of art and passed through Central Park, it was most certainly time for dinner. Creeping hunger, I tell you. Ivy and I declared a mutual craving for Thai food, and thus, we walked to a small spot that was only several blocks away from The Met. In fact, when it came to dining in NYC, we had the most success with a quick Google search of whatever it was we wanted. The city always delivers.

Get ready for a night out.

Ivy and I both knew we’d want a night out during time in NYC, one packed with yummy drinks and, of course, dancing. In the wake of walking nearly 10 miles that Saturday, our getting-ready ritual was not complete without a power nap. Like I mentioned before, our hotel provided the perfect nest of calm for us to recharge – so much so that our hour and a half shut-eye properly prepped us for the long evening ahead.

Venture to Brooklyn.

New York City was a total culture shock to Ivy and I when it came to the nightlife. But again, it was in the best way. Our home base of Denver simply isn’t designed for late-night lovers like us; Lots of youngsters in the Mile High city would rather tuck themselves in by 9 p.m. in order to make it to the slopes or catch a sunrise hike. While we can be those outdoorsy people from time to time, there’s no denying the rush of getting giddy on drinks and dance-worthy music in a larger-than-life city like NYC.

A few trains later, and we ended up in Bushwick at a groovy bar called Carousel. True to its name in the way it was built in a circular shape that guided us ‘round and ‘round, it was the perfect not-too-flashy place to get a little rowdy. Featuring cozy lighting, conversation pits, and the number one night out essential, a photo booth, it was, undeniably, what the kids call “the move.”

The night evaporated before our very eyes, and after multiple bevs and a much-needed New York slice, it was time to venture back on the L train to our hotel in Midtown. The train was so nice in this way – well, it wasn’t always nice, per se, but it was always convenient. Even during our hazy post-4 a.m. night, we were able to weasel our way back to our comfy hotel beds with ease. Case in point: take the train.

Day 3

Have a lazy morning.

After hours worth of shenanigans, we had truly earned a sleeping-in sesh on Sunday morning. I can’t stress enough how important quality recharge time is for maintaining morale in busy NYC, and I’m endlessly thankful we were able to kick up our feet at Kimpton Theta New York – Times Square. Morning bagel and coffee in-hand, Ivy and I woke up slowly to the sounds of the city.

Spend time at the Guggenheim.

Our only plan for this rainy Sunday was visiting the Guggenheim Museum – an absolute must for architecture nerds like me. We had waddled our way through Central Park again to the cylindrical structure, gawking at horse-drawn carriages, street vendors, and historic bridges along the way.

The Guggenheim Museum itself was stunning. As my second Frank Lloyd Wright landmark visit within a year (the first being Fallingwater in Pennsylvania), I felt simultaneously closely connected and distantly awe-struck at the spiraling floor plan. The art itself was masterfully curated, too, always leaving us with something to look at. It's a must for first-timers or anyone enamored with architecture.

Hot dog for lunch.

One thing about New York City is there will always be street vendors at every turn. Conveniently, there was a hot dog cart parked outside of the Guggenheim Museum. Hot dog for lunch? Duh.

Walk the Brooklyn Bridge.

Clocking in at just over one mile long, the Brooklyn Bridge is easily walkable and offers tons of fun sights, from moving traffic and boats on the East River to the iconic NYC skyline. My only note here is make sure you have some good walking shoes (the same goes for all of your trip) and watch the weather. Walking into Brooklyn from Manhattan was one of our favorite parts of the long weekend. It'll be yours, too.

Dinner in Brooklyn.

Thanks to yet another rapid-fire Google search, Ivy and I ended up at Oregano in Williamsburg – and I’m so glad we did. What could’ve been just a random Sunday night dinner actually resulted in me eating perhaps the best pasta I’ve had in my life. Once a shared Caesar salad, Aperol Spritz, and fettuccine Alfredo was put away, we trained back to our hotel near Times Square and simply chilled out, recapping our weekend thus far with pure elation.

Day 4

Sneak in some shopping.

Ivy and I’s long weekend would eventually end Monday night, when our departure back to Denver was scheduled for the late evening. We simply had to sneak in some shopping before we left. After a morning coffee, we hit up Buffalo Exchange near Washington Square Park and stopped in several generic souvenir shops (as one does in NYC) as we ventured closer to Little Italy.

Be spontaneous.

Our moment of spontaneity landed us at Tiny Zaps, a flash tattoo-focused studio in Nolita with thousands of tiny tattoo designs to choose from. With booked appointments and a readiness for more permanent ink on our bodies, Ivy and I both got ‘zapped’ within an hour, making it such an easy in and out.

Soak in the city before heading out.

We eventually moseyed back to our hotel before packing up our bags – souvenirs and all – and stopping for a quick lunch in Times Square.

Unlike on our way in, we took the train back to JFK instead of Uber-ing. This venture was flat-out tiring – it could have been worse (more people), it could have been better (more sitting room). It could have also been the compounding physical and mental exhaustion from the entire weekend.

No matter what it was, we had an undeniably fabulous time as first-timers in New York City.