New York Summer Weekend Itinerary: A Breezy 3-Day Guide

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New York Summer Weekend Itinerary

There is nothing quite like a summer weekend in New York City.

I kept saying on this trip, I forget how amazing New York is in the summer. It’s so lively and vibrant, everyone is outside, and there is this energy that makes you want to walk everywhere and stay out just a little bit longer.

I think when you picture New York in the middle of summer, it’s easy to imagine hot sidewalks, huge crowds, and that sticky city heat. But this trip felt like the complete opposite.

We spent so much of our weekend outside—strolling through Central Park, walking along the Hudson, sitting by the water with drinks and good food, and wandering around DUMBO with the East River and the bridges in front of us. We took a boat out to see the Statue of Liberty, had drinks and appetizers aboard a sailboat, and loved Drift In so much that we ended up back along the Hudson for dinner the very next night.

The funny thing is, we didn’t plan the weekend around the water at all.

Somehow, we just kept drifting toward it.

At Pier i, I remember seeing two girls sitting together with books and drinks, completely settled into the evening. No rushing. No big plan. Just enjoying the city, the river, and each other’s company.

And that really became the feeling of the weekend.

Even Central Park had its own version of it. The park was so green and beautiful and full of life. People were picnicking and reading in the grass, couples were out on the lake, music was playing, people were running and playing sports—and we just strolled. It felt like this little enchanted escape right in the middle of Manhattan, while still having all of that New York energy around you.

Looking back, that’s really what this weekend was: breezy summer days, lots of walking, really good food, sweet treats, time by the water, and nowhere we were in too much of a hurry to get to.

I am so used to visiting during Christmastime that I forget how lovely and breezy New York is during the summer. My suitcase wasn’t packed down with heavy coats, scarves, and sweaters and I didn’t feel like a marshmellow walking down the streets of Manhattan. Everything just felt lighter, breezier, and New York just felt a bit more alive. However, do not get me wrong, New York during the holiday season is the best–but it was refreshing experiencing the city a little bit brighter and breezier.

Just New York in the summer.

And I think I fell in love with the city all over again.

If you’re planning your own summer weekend in New York City, here’s our New York summer weekend itinerary so you too can enjoy three lovely days of eating, strolling, exploring, and soaking up one of my favorite versions of New York.


New York Summer Weekend Itinerary

Our New York Summer Weekend Itinerary at a Glance

New York Summer Weekend Itinerary

Thursday — Central Park & the Hudson

  • Arrive in New York at Moynihan Train Hall
  • Grab tacos from Birria-Landia
  • Picnic and stroll through Central Park
  • Watch the sunset over the Hudson at Pier i Cafe
  • Wine, Culture Espresso cookies & catching up with the girls

Friday — Bagels, Lady Liberty & the West Village

  • Morning coffee at Söte
  • Smoothies and ginger shots at Hawa Smoothies
  • New York bagels from Broad Nosh
  • Take a one-hour Statue of Liberty cruise
  • Lunch and spritzes along the Hudson at Drift In
  • Vintage shop through the West Village
  • Happy hour and dinner at Fumo
  • Conduct a very important NYC frozen-yogurt taste test
  • Evening stroll through Central Park

Saturday — Brooklyn & Cocktails on the Hudson

  • Brunch at Vinegar Hill House
  • Explore DUMBO
  • Shop Brooklyn Flea
  • Take in one of my favorite free NYC views from the Time Out Market rooftop
  • Walk along the waterfront through Brooklyn Bridge Park
  • Happy hour at Dante
  • Drinks and crab dip aboard Grand Banks
  • Head back to Drift In for dinner
  • Ice cream from Salt & Straw
  • One last stroll through the West Village

If You’re Staying Through Sunday

  • Grab coffee and take a slow morning stroll
  • Attend Church of the City
  • Wander through the Sunday outdoor markets
  • Grab lunch before heading home

Thursday: Tacos, Central Park & Sunset Along the Hudson

New York Summer Weekend Itinerary

One of my favorite ways to arrive in New York is by train.

Stepping off Amtrak into Moynihan Train Hall feels like such an easy beginning to a weekend in the city. No long ride in from the airport, no complicated transition—just dropped our bags and pretty much headed straight back out.

First Stop: Birria-Landia

My friend recommended Birria-Landia, which my friend who lives in New York recommended as an easy first meal—and some of her favorite tacos in the city. 

We grabbed them to-go and headed toward Central Park. for a little picnic.

A Summer Afternoon in Central Park

Central Park was so beautiful and lively that afternoon.

We found a spot to eat our tacos and then spent some time strolling through the park with nowhere in particular to be. People were picnicking and reading in the grass, music was playing, friends were gathered together, and couples were rowing across the lake.

It felt like everyone was outside simply enjoying summer in New York.

That’s one of my favorite things about Central Park. It’s green and serene and almost feels like an enchanted forest tucked into the middle of Manhattan, but at the same time, it’s full of life. There is always something happening around you.

We wandered, people-watched, and took our time before eventually making our way west toward the Hudson.

New York Summer Weekend Itinerary

Golden Hour at Pier i Cafe

Pier i Cafe sits right along the Hudson River, and on a summer evening, it is such a fun place to be. People were running and biking along the waterfront, friends were meeting for drinks, boats were passing by, and everyone just seemed happy to be outside.

We grabbed a table, ordered drinks—I had the Fresh Fruit Sangria—and settled in for sunset.

I remember looking around and thinking, this is such a nice way to experience New York.

There were two girls nearby with books and drinks who looked like they had been there for hours, completely content to spend their evening by the river. And I got it.

We stayed for a while too, enjoying the breeze, people-watching, and watching the sun go down over the Hudson.

We didn’t know it yet, but we would spend a lot of this weekend finding our way back to the water.

A Cozy Night In

Eventually, we headed home for a relaxed night with the girls.

My friend had picked up cookies from Culture Espresso  earlier in the week and saved some for us to try, so we divided those up, opened a bottle of wine, and spent the rest of the night catching up.

Nothing elaborate. Just a really good first summer day in New York.

Friday: Bagels, Lady Liberty & an Afternoon on the Hudson

Friday started exactly how I like to start a morning in New York: with a walk, coffee, and a really good bagel.

New York Summer Weekend  Itinerary
New York Summer Weekend  Itinerary

Our first stop was SOTTE Coffee Roasters for coffee before making a quick detour to Hawa for our non-coffee drinkers in our group. We also tried their fresh ginger shots, which came with a pineapple chaser—and yum! The pineapple completely cuts the burn of the ginger.

Then it was time for New York bagels.

Breakfast at Broad Nosh Bagels

New York Summer Weekend Itinerary

We stopped at Broad Nosh Bagels, where I ordered the Broad Nosh Special with a fried egg, jalapeño cream cheese, avocado, cheese, and microgreens.

I ordered mine on an everything bagel, but it came out on a jalapeño cheddar bagel instead.

I was not complaining.

It was warm, cheesy, a little spicy, and so good. I will also forever stand by the fact that a fresh New York bagel does not need to be toasted. There’s just something about them that you can’t quite replicate anywhere else.

After breakfast, we headed back to the apartment to get a few hours of work done before heading back out for the afternoon.

See Lady Liberty from the Water

For as many times as I’ve visited New York City, I had somehow never seen the Statue of Liberty up close.

My mom had done it before and always told me it was something everyone should experience at least once. Now that I’ve finally done it, I completely agree.

We booked a one-hour sightseeing cruise along the Hudson River with Liberty Cruise. Our tickets were around $49 each after tax when we visited, and we didn’t even have to purchase them in advance.

The entire process was surprisingly easy. There were people outside helping travelers find the right cruise, and the Liberty Cruise representative who helped us walked us directly to the shuttle that took us to Pier 40.

Once aboard, there was plenty of room to spread out with both indoor and outdoor seating, plus snacks and alcoholic and nonalcoholic drinks available for purchase.

Then we were off!

One thing I loved about the cruise was seeing how different New York feels from the water.

We cruised along the Hudson with Manhattan on one side and New Jersey on the other, passing Jersey City and Ellis Island before making our way toward Lady Liberty.

And then there she was.

New York Summer Weekend Itinerary

Seeing the Statue of Liberty from Manhattan is one thing, but cruising directly in front of her is completely different.

The boat gets close enough for an incredible unobstructed view, with plenty of time to take photos and simply admire her. Our guide also shared some history along the way, including how approximately 12 million immigrants passed through Ellis Island and how the Statue of Liberty’s famous green color comes from the oxidation of her copper exterior.

If you’ve never seen the Statue of Liberty up close, I really do think it’s one of those quintessential New York experiences worth doing at least once.

And I loved that the cruise was only an hour. We got beautiful views, a little New York history, and time out on the Hudson without sacrificing half of our day.

New York Summer Weekend Itinerary

Lunch & Spritzes at Drift In

After the cruise, we were within an easy walk of our next stop: Drift In.

And this ended up being one of our favorite spots of the entire weekend.

Drift In sits right along the water, with outdoor tables overlooking the Hudson. It was sunny and breezy, boats were passing by, and after spending the afternoon out on the river, we were more than happy to stay right there.

I ordered the Skipper Key Spritz with rosé, lemon, strawberry, and seltzer, and we shared the watermelon salad before ordering lunch. The fish and chips were so fresh, and everything coming out around us looked good—the Caesar with shrimp was huge!

It was casual, summery, and exactly the kind of place that makes you want to stay for another drink.

We loved it so much that we would end up back here the very next day.

Wander Through the West Village

After lunch, we spent some time wandering and vintage shopping through the West Village.

This is one of my favorite ways to experience New York. Pick a neighborhood and just walk.

The West Village is filled with beautiful brownstones, sidewalk cafés, little restaurants, boutiques, and vintage stores, so you really don’t need much of a plan. We popped into whatever caught our eye and took our time exploring.

After a day spent mostly outside and along the water, it was nice to simply wander for a while before heading back to get ready for dinner.

Dinner at Fumo

That evening, we headed to Fumo in the East Village.

We made it in time for happy hour, which included some surprisingly good deals when we visited—including an entire Margherita pizza for around $7.

In New York!

Obviously, we ordered one.

The pasta vodka was another favorite, and overall, Fumo was such an easy, fun dinner for a girls’ night. Pizza, pasta, drinks, and plenty to share.

Then it was time for dessert.

Or, technically, desserts.

Our Very Important NYC Fro-Yo Taste Test

Apparently, some people go to New York determined to find the best slice of pizza.

We went determined to find the best frozen yogurt.

Our first stop was Butterfield Market.

I had seen their famous Dot Cakes all over social media and was hoping to finally try one, only to learn that the location we visited offered them on Wednesdays and Sundays.

Next time!

Obviously, we weren’t leaving empty-handed.

We ordered the peanut butter frozen yogurt with chocolate chips and chocolate fudge. Simple, creamy, delicious.

My rating: 8/10.

Then we headed to Madison Fare, which was completely different. The frozen yogurt was much tangier and tasted more like actual Greek yogurt. At first, we weren’t sure what we thought.

Then we tried it with the pistachio and it was incredible. By the end of our investigation, we had a winner: Madison Fare.

One Last Summer Walk

Full from bagels, spritzes, pasta, pizza, and entirely too much frozen yogurt, we ended the night the best way we knew how—with another walk.

We wandered through Central Park, grabbed a bottle of wine on the way home, and settled in for a movie night.

New York Summer Weekend Itinerary

It had been a full day, but it never felt like we were rushing around trying to fit everything in.

A boat ride, lunch by the Hudson, vintage shopping, really good food, frozen yogurt, and a summer walk through the park.

Pretty perfect Friday in New York.

Tomorrow, we’re heading to Brooklyn.

New York Summer Weekend Itinerary

Saturday: Brooklyn Brunch, Vintage Finds & Cocktails on the Hudson

Saturday morning, we hopped on the subway and headed to Brooklyn for brunch.

We had a full day ahead of us, but this ended up being another one of those days where we mostly just wandered from one good thing to the next.

Brunch at Vinegar Hill House

Our first stop was Vinegar Hill House, a cozy neighborhood restaurant tucked away on a quiet street in Vinegar Hill.

We ordered a few things for the table and shared everything family-style, which is always my favorite way to do brunch with a group.

Whatever you do, order the pancakes.

They were easily one of our favorites and absolutely worth sharing with the table.

After brunch, we started walking toward DUMBO, popping into shops and taking our time along the way.

Vintage Shopping at Brooklyn Flea

New York Summer Weekend  Itinerary

We eventually made our way to Brooklyn Flea which is such a fun stop if you love vintage shopping.

There was a little bit of everything—clothing, art, jewelry, home finds—and my friend Caitlin scored the cutest red-striped Ralph Lauren jacket.

New York Summer Weekend Itinerary

From there, we grabbed Mister Softee and kept wandering through DUMBO—short for Down Under the Manhattan Bridge Overpass.

No real agenda. Just shopping, ice cream, and a beautiful summer day in Brooklyn.

One of the Best Free Views in NYC

If you’re spending a day in DUMBO, make your way toward Time Out Market. and head straight to the rooftop.

Even if you’re not hungry, it’s worth going up for the view alone.

From the rooftop, you can see the Brooklyn Bridge, Manhattan Bridge, and the Manhattan skyline stretching across the East River—and the best part is that you don’t need a ticket or reservation to enjoy it.

Since we’d just eaten brunch, we skipped the food downstairs and went up purely for the view.

After paying for plenty of beautiful views in New York over the years, finding one this good for free felt like such a hidden gem.

Definitely don’t miss it.

New York Summer Weekend  Itinerary

Enjoy the Views from Brooklyn Bridge Park

New York Summer Weekend  Itinerary

From there, we made our way down toward Brooklyn Bridge Park.

This entire stretch is beautiful and gives you the iconic New York views of the Brooklyn Bridge with Lower Manhattan rising behind it. There are plenty of places to sit, take photos, and enjoy the view before heading back into the city.

You’ll also pass Jane’s Carousel, a beautiful glass-enclosed carousel right along the waterfront.

By this point, I think we’d fully accepted that if there was water nearby, we were probably going to end up next to it.

Cocktails at Dante

We had a 3:45 reservation at Dante in the West Village, which ended up being the perfect time for an afternoon cocktail before continuing with our evening.

I ordered the Limoncello Spritz and also tried the 20th Century Martini, and both were delicious.

Dante is known for its cocktails—especially its Negronis—and it was the perfect afternoon stop before continuing our little cocktail crawl.

Because, naturally, our next stop put us right back on the Hudson.

Drinks Aboard Grand Banks

New York Summer Weekend Itinerary

Grand Banks s a seasonal oyster bar aboard a beautiful wooden schooner docked at Pier 25.

This was another one of those places that just felt made for a summer weekend in New York.

We ordered drinks and crab dip and sat aboard the boat with the skyline behind us and the Hudson all around us.

There is something about having a cocktail on a sailboat in the middle of New York City that just feels special.

And somehow, despite having absolutely no intention of planning a weekend around the water, here we were again.

Back to Drift In for Dinner

For dinner, we ended up somewhere very familiar….

We had loved sitting along the Hudson so much the day before that when we were deciding where to eat, we all wanted to go back to Drift In. 

This time, we ordered the burger, Caesar salad, and chicken sandwich and settled in for another evening by the water.

I think the fact that we returned says more than any restaurant review could.

Sometimes you find a place on a trip that just fits the mood perfectly, and for us, Drift In was that place.

One Last West Village Stroll

We finished the night with Salt & Straw and one last walk through the West Village.

Looking back, this really was such a perfect Saturday in New York. We had brunch in Brooklyn, shopped the flea market, walked along the waterfront, had cocktails at Dante and Grand Banks, and somehow ended up back at Drift In because we loved it that much.

It was a full day, but we never felt like we were rushing from one thing to the next. We just took our time, wandered, ate really good food, and enjoyed being together.

Exactly how a girls’ weekend in New York should be.

If You’re Staying Through Sunday

If you’re staying through Sunday, keep the morning slow.

We started ours with coffee at Frame Coffee before heading to church, then grabbed lunch and spent the rest of the morning walking through the city.

Sundays are such a good time to wander in New York. We stumbled across outdoor markets lining the streets, stopped to browse, and just took our time walking with nowhere we really needed to be.

After three full days, it was the perfect way to spend our last few hours in the city.

Coffee, church, lunch, a little shopping, and one last stroll through New York before heading home.

Sometimes the simplest days are the best ones.

More New York City Travel Guides

Planning your own trip to New York? Here are a few more of my NYC guides to help you plan your weekend:

All in All

There’s just something about New York in the summer.

The city feels a little softer and more relaxed. Strolling through green parks during the longer evenings, pastel painted skies, dinner outside, something cold and sweet after dinner, and the summer breeze rolling off of the water.

We walked everywhere, ate so well, stayed out late, and somehow kept finding our way back to the river.

I left already missing it.

New York, I think I fell in love with you all over again. ♡

Also, shoutout ADPI and finding sisters everywhere you go! <> 💎

Love Always Ava
Love Always Ava

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