Real NYC: A Weekend of Neighborhoods, Food, and Local Discoveries
The best travel experiences happen when you balance planning with flexibility. Here's how three days in New York reminded me why strategic structure and spontaneous exploration make the perfect travel combination.
The Art of Arriving
Day 0 (aka arrival day)
Flying into LaGuardia doesn't have to be a nightmare if you know the right moves. Skip the taxi line chaos and book an Uber shuttle through the app - I scored a clean Sprinter van with AC, power outlets, and comfortable seats that dropped me at Port Authority for a fraction of the stress.
Pro tip: The Uber Shuttle routes gets you to Manhattan efficiently without the premium Manhattan taxi rates.
After checking into Arlo Midtown, I did something most NYC itineraries don't recommend: I rested. Travel doesn't have to be a marathon, and starting strong means acknowledging travel takes a toll on us (especially if it is at the end of a busy work week). The hotel's location was incredibly convenient for getting around the city, though I'll admit being steps from Times Square chaos meant constant tourist energy outside our door. Next time, I'd prioritize neighborhood character over proximity to the main tourist corridor - maybe West Village or Upper West Side for a more authentic New York residential feel.
Once recharged, I hit the hotel's rooftop bar ART at Altair for sunset views and my first proper New York moment of the trip.
Dinner at Zoob Zib Thai proved that sometimes the best meals happen when you simply walk until something looks appealing. No reservations, no stress - just good food and the satisfaction of trusting your instincts in a new city.
When the Subway Wins
Day 1
Here's where my trip took an unexpectedly perfect turn: I got completely lost trying to get to the Metropolitan Museum of Art. Instead of panicking or over-relying on my phone, I embraced it. Getting lost in NYC isn't a failure - it's research.
(Though let's be honest - next time I'll pay more attention to those subway train direction labels. I don’t know if I should blame my eyesight or overall distracted nature to getting on the “E” train instead of the “C” train. Chicago’s single direction, single train line platforms have spoiled me!)
The Met absolutely deserves its reputation - the scale and quality of the collection is breathtaking. But here's what your typical guidebook won't tell you: plan your energy management, not just your time. After soaking in world-class art for hours, we were both mentally stimulated and physically drained.
Pro tip: With over 2 million artifacts, the Met can't be 'done' in one day. Pick 2-3 specific galleries beforehand (Egyptian Art, European Paintings, Arms & Armor, etc.), see those first, then wander. This prevents museum fatigue and ensures you actually remember what you loved instead of everything becoming a blur.
That's when Wrap n Run on 78th and Lexington became our hero with their perfectly portable sandwiches. We took our lunch to Central Park and did something that felt revolutionary in a packed NYC weekend: we sat still. Watching the world go by instead of rushing to the next attraction recharged us completely.
The Frick Collection offered the perfect counterpoint to the Met's grandeur - intimate, manageable, and absolutely stunning. They also don’t allow photographs to be taken, so you walk through the space fully immersed in the moment rather than looking at the art through our screens. The walk back through Central Park with impromptu ice cream was one of those unplanned moments that ended up being trip highlights.
Evening brought baseball at Citi Field with my brother - a reminder that the best NYC experiences often combine iconic activities with personal connections. The subway ride there and back felt like a rite of passage, and ending the night with drinks and meeting fellow travelers at the rooftop bar created spontaneous connections that made the trip feel larger than just tourist activities.
Brooklyn Calls
Day 2
Saturday morning coffee from a corner bodega instead of a trendy café? Sometimes authentic beats Instagram-worthy. Murray's Bagels in the West Village, however, delivered both - exceptional food and prime people-watching real estate.
The progression from Murray’s Bagels to Washington Square Park led us to stops into Goods for the Study and Stumptown Coffee. This perfectly illustrates something I always tell my travelers: let neighborhoods unfold naturally. Each stop built on the last, creating a rhythm that felt organic rather than forced.
After time walking through Washington Square Park, listening to the string bands & browsing the vendor stands, we walked north to the subway. Along the way, we came across Strand Books. Strand Books provided the perfect bathroom break and browsing opportunity (travel tip: bookstores always have the cleanest restrooms), before we ventured into Brooklyn territory.
DUMBO's waterfront views of the Manhattan and Brooklyn Bridges are mandatory, but here's the insider move: catch the ferry from Brooklyn Bridge Park to North Williamsburg for even better views (& a quicker commute!). The artist flea market and plant shops there showcase Brooklyn's creative heart without the tourist crowds.
Pro Tip: Many cities that are bordered or split across bodies of water have public ferry options. New York City has some of the best options to seamlessly let you explore the many neighborhoods of Manhattan & Brooklyn in a way that a bus or taxi can’t quite replicate.
During our neighborhood walk, we stopped for lunch at Teddy's. Stopping into Teddy’s felt like discovering a neighborhood secret, and the afternoon college football viewing back at the hotel reminded me that sometimes the best travel pace includes downtime.
Dinner at Capizzi wrapped up the food exploration perfectly - a meal that felt both special and unpretentious.
& On Day 3…
We were up & out of the hotel for our early morning flight back to Chicago! I always recommend giving yourself some breather time before you go back into “normal” life, so early Sunday flights are usually my go to option. Also, always remember to schedule your ride the night before! The last thing you want is to be panicking at 4:30am trying to find a ride to the airport.
What This Trip Reinforced About NYC (And Travel)
This wasn't my first New York rodeo, but it reinforced some key truths about both NYC and travel in general:
Embrace the detours. Getting lost led to better neighborhood exploration than any guidebook route.
Mix planned and spontaneous. Having loose anchor points (the Met, baseball game) left room for discovery without feeling aimless.
Transportation is part of the experience. The subway, ferry, and even that Uber shuttle became integral parts of the trip story.
Local interactions matter. From hotel bar conversations to bodega coffee runs, the human connections made NYC feel welcoming rather than overwhelming.
Pace yourself. Rest periods and college football viewing weren't wasted time - they were essential recharge moments that made the active exploration more enjoyable.
Travel Advisor Debrief: What I'd Do Differently
Every trip teaches something new, and this NYC weekend was no exception. Here's my honest professional assessment of what I'd adjust for next time:
Hotel Location Strategy: While Arlo Midtown was fantastic in terms of amenities and subway access, being in the heart of the Times Square tourist zone meant constant crowds and inflated prices for everything nearby. Next time, I'd prioritize neighborhood authenticity over transportation convenience - areas like the West Village, Upper West Side, or even Brooklyn Heights offer better local vibes while still maintaining good subway connections.
Pre-Trip Research: I definitely should have spent more time considering what we might want to do that required advance tickets. While we filled our time perfectly, I was reminded that places like the Comedy Cellar or popular Broadway shows require planning ahead. As a travel advisor, I usually build this into client itineraries - apparently I need to follow my own advice on personal trips!
Subway Navigation: Okay, this one's obvious (and slightly embarrassing for a travel professional), but pay close attention to the train lines & their schedules. Certain lines will skip specific stops during off hours or change completely at a different time of day. You might have the options of trains A, C or E one direction but not the other direction. I learned this when the E train started going east instead of continuing north!
Spontaneous Entertainment Budget: I underestimated how many last-minute opportunities would arise - from show tickets to extended bar conversations to interesting market finds. Building in a more flexible "serendipity budget" would have eliminated any hesitation about saying yes to unexpected experiences.
The beautiful thing about travel mistakes is they become the foundation for better future trips - both for myself and for the travelers I advise. Sometimes the best professional development happens when your own plans go sideways.
Planning Your Own Authentic NYC Weekend
If this resonates with your travel style, here's how to recreate the approach:
Create a flexible research map. Spend time before your trip building a custom Google Map with restaurants, shops, bars, and attractions that interest you. This isn't a rigid schedule - it's your downtime decision-making tool for when you have extra energy or time.
Build in strategic flex time. Schedule 2-3 anchor activities per day, but leave gaps for wandering and discovery. This pacing prevents burnout while ensuring you hit your must-sees.
Research transportation shortcuts. That LaGuardia Uber shuttle saved both money and stress - sometimes the less obvious option is the smartest choice.
Plan strategic fuel stops. Knowing where to grab good, portable food keeps energy high and budgets reasonable.
Mix neighborhoods. Manhattan and Brooklyn offer completely different energies - experience both.
Say yes to local interactions. Whether it's hotel bar conversations or asking for recommendations, people make places memorable.
New York rewards the curious traveler willing to balance planning with spontaneity. Sometimes the best itinerary is knowing when to abandon your itinerary.
