What do you get when you pair a weekend in Brooklyn with a fabulous rooftop pool in New York City? You get one helluva good time in one of the most interesting boroughs in NYC — and you get this post to help you plan it.

Despite nearly a dozen visits to The Big Apple during the last couple of decades, I’d never visited Brooklyn nor had I ever stayed at a hotel with a rooftop pool in New York City. I didn’t include our weekend in Brooklyn in my recent Things to do in NYC with Teens post because Brooklyn turned out to be a world of its own; one deserving of its very own list of places to stay and things to do.

First thing’s first, though: one weekend isn’t enough — but it’s doable. And, be warned…you’ll be instantly smitten and curse yourself for not staying longer.

How to do one weekend in Brooklyn with a rooftop pool in New York City

This rooftop pool in New York City can be found at the Hotel Indigo Williamsburg — a fantastic escape from urban noise and city life. (All photos taken with the iPhone 14 Pro)

Even though we only spent three days in Brooklyn, there’s a lot to cover here. So lemme break it down; here’s what you’ll find in this post:

• Where to stay in Brooklyn
• How to enjoy a rooftop pool in New York City — even if your hotel doesn’t have one
• Great Brooklyn restaurants
• Things to do during a weekend in Brooklyn

And, to be clear, we took our teens with us but you could absolutely do everything during your own weekend in Brooklyn without a kid in sight. I’d love to go back on an adult-only adventure because there are places I really wanted to try, like Sauced — a local wine bar — that we just couldn’t fit in this time around. That said, our kids would never forgive us if we didn’t take them back to Brooklyn because they fell as in love with it as much as we did.

Where to stay in Brooklyn: Hotel Indigo Williamsburg (hello, rooftop pool in New York City!)

We’ve stayed in hotels with rooftop pools before, but absolutely nothing like the one at Hotel Indigo Williamsburg. This is a rooftop mecca. And, maybe, when you think about visiting a rooftop pool in New York City this is what your mind conjures up, but for us it was unexpected fabulosity.

This boutique hotel in Brooklyn hosts a party of a rooftop pool called “Tatau” — and you’ll feel instantly transported from funky Williamsburg to the glamorous South Pacific. From its lush greenery and luxe open-air lounge to its absolutely delicious Polynesian-inspired food and drink menu, there isn’t a corner of the space or experience that hasn’t been carefully executed.

I’m not sure if all of the hotel pools in Brooklyn also have a full food and drink menu with poolside service, but the Hotel Indigo in Brooklyn sure does — and it’s amazing.

Tropical oasis? Yes, indeed. And if you’re going to spend even just one weekend in Brooklyn, I implore you: spend it here.

This Williamsburg hotel rooftop bar, lounge and pool features plenty of loungers, a few outdoor tables and some VIP-worthy shaded sectionals. There’s also a covered lounge area that feels like it could be a scene in a James Bond film (you know, before anyone is murdered). The long bar ends where the action begins, and on a beautiful day you can also expect to see all manner of beautiful, bikini-clad people sunning themselves or drinking cocktails perched on the pool’s edge.

Tatau is simultaneously — somehow — enchanting, relaxing, charming, vibrant and downright sophisticated. Oh, and fun. So much fun.

This Williamsburg hotel pool — on the fourth floor of Brooklyn’s Hotel Indigo — welcomes kids of all ages, even though the vibe is mature.

Music pumps out of the speakers, which features an onsite DJ on weekends; bartenders shake, mix and swirl drink after glorious drink; and servers never stop moving, delivering drinks even to those in the middle of this rooftop pool in New York City’s edgy Williamsburg neighbourhood. It’s so cool that you won’t even notice you’re perched above the busy freeway.

And, yes, kids are welcome. It was mostly adults but my kids certainly weren’t out of place. They loved how grownup it felt and they were able to get in on the drink action, too, since the bartenders were happy to virginize any drink on the cocktail menu. Both The K Man and Miss Q agreed that their non-alcoholic pina coladas (made from scratch — not that terrible pre-mixed stuff) were the best they’d ever had.

The Tatau Pool Lounge & Bar has a killer cocktail program — even if all you plan to enjoy are non-alcohol drinks like these shaken pina coladas.

Tatau welcomes hotel guests and ResortPass members (I’ll get to that in a moment), with very limited walk-in availability — so the whole thing feels pretty exclusive.

The pool deck is seasonally open (usually from Memorial Day weekend in May through September) daily from 10 a.m. to 6 p.m., while the lounge and bar is open Monday to Thursday from 3 p.m. to 10 p.m., Friday and Saturday from 11 a.m. to 11 p.m. and Sunday from 11 a.m. to 10 p.m. That 3 p.m. to 6 p.m. time slot is the sweet spot for your weekend in Brooklyn; the pool is vibing, the music shifts from a house playlist to a guest DJ and drinks are flowing. It’s a beautiful thing. We actually cancelled an entire afternoon to spend more time at Tatau, and I am an absolute stickler for my pre-planned itineraries, if that tells you anything.

The Hotel Indigo in Brooklyn — a stunning rooftop pool in New York City

But wait…there’s also a whole hotel here, too. Williamsburg’s Hotel Indigo is so much more than just the site of a must-visit rooftop pool in New York City! With just seven floors, this pet-friendly boutique hotel in Brooklyn is located mere steps from the Metropolitan Avenue subway station and is a short walk from the neighbourhood’s best shopping and restaurants.

Hotel Indigo in Brooklyn has huge rooms compared to most New York City hotel standards! Our adjoining room had two queen beds in the same space and it still felt very roomy.

It was so easy to get to Brooklyn from Manhattan using the subway that it was actually faster than hopping into an UBER, which was clocking in at an estimated five minutes longer mid-morning on a Friday. Plus, it only cost us $2.75 each instead of the $65 plus tip that UBER wanted.

Before you enter, there’s a colourful, cheery fence lining the hotel’s northwest wall and a huge garden with seating among foliage that will make you forget you’re in one of the world’s most bustling cities. There’s a gorgeous lobby bar that greets you and a sleek lounge nearby that becomes much more of a focal point than the front desk, which is cleverly tucked out of the way on the main floor.

Hotel Indigo Williamsburg is a boutique hotel in Brooklyn with a rooftop pool and lounge.

We had two adjoining rooms — one with a king bed and the other with two queens. Rooms at Hotel Indigo Williamsburg are exceptionally spacious for New York City, and since it’s part of the IHG family of hotels, you can rest assured that the bedding will be top-notch.

When we return to Brooklyn during a future summer vacation, there’s no question that we’ll book rooms here again; the rooftop pool in New York City scene is totally our jam.

Considerations:

• The hotel elevator will not take you to the rooftop pool area; you need to walk through the lobby and across to a different elevator shaft. To avoid waiting for robes to be delivered to your room, pack coverups
• The hotel doesn’t offer slippers, so be sure to bring along some slides or flip flops to wear to this rooftop pool in New York City
• There are two hotel entrances; use the one with the roundabout on Keap St. if you’re going to or coming from the subway lest you walk unnecessarily around an entire block to the front entrance
• Skip the in-room coffee (just trust me) in favour of a local cafe, like the West coffeehouse & bar

Hotel Indigo Williamsburg, which opened in 2022, feels inviting despite its minimalist aesthetic.

No hotel rooftop pool in New York City?

No problem. Let me introduce you to the ResortPass. Though I haven’t used it myself yet, it was something I discovered while I was looking for a rooftop pool in New York City during the Manhattan leg of our trip. I ordinarily wouldn’t post about something I haven’t personally experienced but we met a few people who were enjoying the Tatau Pool Lounge & Bar at Hotel Indigo Williamsburg thanks to the pass, so I’m confident recommending it. Because it works.

A ResortPass allows you to experience the rooftop pool life in many different cities — NYC included — without being a hotel guest. You can even book loungers and cabanas as part of your pass at some properties. At Tatau, for example, it’s USD$75 per person for a day pass or $185 for a day pass that includes a guaranteed lounge chair. (Keep in mind, though, if you’re a family of four like we are, that’s $75 x 4, which is $300 — and an entire room for the night won’t cost much more.)

Didn’t have Brooklyn on your NYC bucket list? My 4-day New York itinerary will take you to Manhattan instead.

Brooklyn restaurants & eateries you’ll want to shortlist

After just one weekend in Brooklyn, this section won’t be quite as robust as the one in my “Things to do in NYC with Teens” post that features 14 of our favourite Manhattan restaurants, or my “Restaurants – NYC” post that lists more than 80 eateries, but it’ll help steer you in the right direction. Please note this is alphabetical to make it easy to add new restaurants down the road.

I’m also including two honourable mentions here — one for the random guy in downtown Williamsburg with a huge orange juicer on a portable table who was selling freshly squeezed OJ for $5/cup and the other for Oneg Heimishe Bakery (188 Lee Ave, Brooklyn, NY 11211) where I’d planned an entire morning around buying its double-chocolate babka, which is so popular they will ship it to you anywhere in the USA; sadly, they were closed for summer vacation, which had not been updated in the Google listing that I double-checked immediately before hauling my family there on foot.

Martha’s Country Bakery | Williamsburg | website

Martha’s Country Bakery has several locations across NYC, with two in Williamsburg alone.

There are two locations in Williamsburg, and as one of New York City’s most-beloved bakery chains since 1972, I doubt it matters which one you visit. FWIW, we had breakfast one morning at the Bedford Avenue outpost. Though I wasn’t particularly impressed with the coffee or the cinnamon bun, everything else we ordered was drool-inducing: the frappuccino, the muffins and the almond-covered cheese danish get top foodie marks.

Milk Bar | Williamsburg | website

I was so happy to hit up Milk Bar in Brooklyn — but not as happy finding out that Tosi’s famous Crack Pie has been given a much more boring name.

Fans of Chef’s Table (a Netflix docu-series) will already know Milk Bar as the brainchild of James Beard award-winning pastry chef Christina Tosi. We used to have the tiniest little Milk Bar offshoot in Toronto at the Shangri-La, attached to the once-popular Momofuku, but you could only get a few of Tosi’s iconic offerings in pre-packaged format. It was nothing to write home about.

Standalone Milk Bar locations, however, at home on their NYC soil, open the door to her well-known cereal-milk-flavoured soft-serve ice cream and the dessert hated by dentists everywhere — Crack Pie. Which, I learned during our Milk Bar Williamsburg visit, is no longer called Crack Pie and is now simply called — very boringly, I might add — the Milk Bar Pie. At $53 per pie, you’ll be glad to know you can buy it by the slice. It’s for hardcore sweet-tooths only, so it wasn’t my thing but the fam loved it. I, however, was devastated that the ice cream machine was broken during our visit on a particularly humid summer night.

Smorgasburg | Williamsburg & Prospect Park | website

Smorgasburg New York spends its weekends in Brooklyn. We visited the Williamsburg location and I drank way too much watermelon juice.

This weekly foodie affair — held in Williamsburg on Saturdays and Prospect Park on Sundays from May through October — is the largest weekly open-air food market in the United States. Featuring dozens and dozens of local vendors, you can eat, drink and be merry all day long if you wish. The New York Times calls it “The Woodstock of Eating” and I have to agree because there’s something for every palate, whether you come with $5 or $50.

Tacombi | Williamsburg | website

The Tacombi Brooklyn location was every bit as yummy as the Nolita location I’ve been frequenting for years.

I’m a big, BIG fan of Tacombi and eat at its Nolita location just about every time I go to Manhattan. So when we walked by one in Williamsburg, we changed our dinner plans to eat there instead. Everything on the menu is fresh and full of authentic Mexican flavours. You can’t go wrong with any of it, but if you’re looking for my personal faves, they include the corn esquites, beef birria tostadas, gringa quesadilla, the spicy margs and yummy palomas.

the West coffeehouse & bar | Williamsburg | website

If you’re staying at the Hotel Indigo Williamsburg, the nearby West coffeehouse & bar is a great spot to grab a coffee before you embark on your weekend in Brooklyn.

Coffee shop by day, bar by night — the West was a great find during our weekend in Brooklyn. We stumbled upon it walking from Hotel Indigo to South Williamsburg in search of double-chocolate babka, and all of our bevvies were noteworthy enough to land this place a spot here.

Time Out Market New York | DUMBO | website

The Time Out Market New York in Brooklyn’s DUMBO area is open for breakfast, lunch and dinner and offers so much more than just food and drinks.

Even though Time Out magazines only exist online now, back in the day — when I was a frugal 24 year old living in the UK — the London edition of Time Out was my cultural bible, providing me with the what, where and when of London life. Time Out also produced a NYC magazine (among others) and, like its current online iteration, it features the latest and greatest restaurants; now, all of that knowledge is also housed under Time Out Market roofs. And one of those is in Brooklyn’s DUMBO neighbourhood. Think of them as a dining-and-culture experience — curated by editors.

A 24,000-square-foot, multi-floor destination, Time Out Market NY has some of the city’s most-popular eateries, scaled down with communal seating areas. We loved breakfast from Clinton St. Baking Company and there’s even a Jacob’s Pickles outpost here, which is one of the best restaurants we visited in Manhattan. There are also three bars and a 5th-floor rooftop terrace where you can take in spectacular views of both the Brooklyn and Manhattan Bridges — not to mention the art installations you’ll have to check out while you’re here. 

If you’re looking for things to do in DUMBO during your weekend in Brooklyn, the Time Out Market is a must.

7 awesome things to do during a weekend in Brooklyn

Sure, your weekend in Brooklyn would be complete with just a party at a rooftop pool in New York City. But if you visit in the off-season or it’s not exactly pool-friendly weather during your stay, let’s be sure you go armed with plenty of ideas to keep you busy.

One of the best things to do in Brooklyn is see both of its main bridges — the Brooklyn Bridge and Manhattan Bridge — from one awesome vantage point. The fifth-floor rooftop of the Time Out Market in DUMBO offers excellent views of each.

1. Visit the best neighbourhoods in Brooklyn — by ferry!

You can easily walk through a number of the best neighbourhoods in Brooklyn, but getting to them is going to take a little more effort. The transit system in Brooklyn just isn’t as efficient as Manhattan so if you’re a dedicated subway rider, don’t expect it to be as easy to get around once you arrive in Brooklyn. We found there were more bus routes here and far more transfers required. It got so time-consuming that we frequently splurged on UBER rides to make the most of our single weekend in Brooklyn.

One of the best ways to get to all of the best neighbourhoods in Brooklyn is by ferry. The NYC ferry has loads of stops in this borough, from Greenpoint at the north end of Brooklyn to Bay Ridge in the south. It also connects to Manhattan and some of the other boroughs if you’re hoping to hop around even more. For USD$4 one way or a pack of 10 rides for $27.50, it’s the most scenic transit system in New York City.

On a clear day, you can’t beat the changing view of the Manhattan skyline you’ll get aboard the NYC ferry.

Both North and South Williamsburg have dedicated ferry stops. The one in North Williamsburg is a quick walk from where Smorgasburg sets up on Saturdays and the South Williamsburg Ferry terminal is just 20 minutes on foot from one of the most interesting places you can wander on a Saturday morning — the Hasidic Jewish neighbourhood. During Sabbath (Shabbat), you’ll see men and their sons and groups of women walking to and from temple in their traditional garb. The buildings all have Hebrew writing on them and it’s a very peaceful place to walk since there are almost no cars on the road, no one is talking on cellphones and families are simply heading to worship on their most holy day of the week.

DUMBO — which has nothing to do with a baby elephant; it stands for “Down Under the Manhattan Bridge Overpass” — has the Fulton Ferry stop, which is also a transfer point to Manhattan. There’s so much to do in DUMBO that it occupies two of the things on this list alone. While you’re here, go see Jane’s Carousel; built in 1922, this Brooklyn Bridge Park carousel is unique because it’s housed inside of a huge glass pavilion. You can still go for a spin on it, too, for $2.

Jane’s Carousel near the Brooklyn Bridge can be seen from the rooftop of the Time Out Market, but you should definitely walk over to take it in up close.

If you’re a big walker, you could also get within an hour’s walk of Industry City (noted below) using the ferry. It sits almost right in between the Red Hook and Sunset Park/Brooklyn Army Terminal ferry stops. It’s not one of the best neighbourhoods in Brooklyn, though, nor the most enjoyable place to walk around, so we chose to UBER from DUMBO to Industry City instead. But if you’re determined to use only the ferry and your feet, you certainly can.

2. Go shopping in Brooklyn.

You’ll find some of Brooklyn’s best shopping all around Bedford Avenue. From big names like Le Labo, Glossier, Malin + Goetz and Urban Outfitters; to smaller one-offs like Awoke Vintage, NORBU Bijoux, Spoonbill & Sugartown Books and Soap Cherie; and New York favourites like Dyptique and Gorjana — there’s truly something for every shopper on every budget.

Over in DUMBO, look for Canada’s own John Fleuvog store, New Zealand’s Rodd & Gunn and the biggest Scotch & Soda store I’ve ever been to, among others.

If you’re looking for that quintessential NY Yankees baseball cap, the cheapest place to buy one — believe it or not — is up on the Brooklyn Bridge. The vendors up there sell them for as little as $4 a pop. They’re cheaper than bottled water, for crying out loud!

Miss Q and I made sure we visited the original Glossier store in Brooklyn, where your purchases are delivered in a really unique way (no spoiler alerts here!) as you wait near this “You look good!” mirror.

3. Enjoy a rooftop pool in New York City.

Hotel Indigo Williamsburg isn’t the only rooftop pool in Brooklyn! The William Vale has one as does Arlo Williamsburg and CODA Williamsburg — though they’re all pricier with ResortPass than the Hotel Indigo in Brooklyn. If the weather is stellar and you’re spending the weekend in Brooklyn during pool season, please please please carve out time and budget for this. You won’t regret it.

The Williamsburg hotel rooftop at Hotel Indigo is where the party’s at when you’re looking for a rooftop pool in New York City.

4. Take a classic Manhattan Bridge photo.

No, there won’t be a single drop of originality in your photo, but this viewpoint is so recognizable that you’ll even find it noted on Google Maps. It’s the bridge viewpoint, located at Plymouth & Washington Streets (or use 39-21 Washington St, Brooklyn, NY 11201 if you’re taking an UBER) and it’s where you’ll find the midsection of the Manhattan Bridge flanked by two buildings. 

Unless you really enjoy editing out throngs of people from your photos, I suggest you arrive no later than 9 a.m. The crowds really start to fill in by 10 a.m.

One of the best neighbourhoods in Brooklyn to explore is DUMBO. Start here, with this must-have shot of the Manhattan Bridge.

5. Walk across the Brooklyn Bridge (and then cool off in a rooftop pool in New York City!).

…and take the ferry back to Williamsburg, if you like. Everyone needs to walk on NYC’s most well-known bridge at least once. It’s big and epic and offers killer views of the Manhattan skyline. But whatever you do, no matter how thirsty you are, do NOT buy bottled water on or anywhere near the bridge — unless you absolutely love paying $5-8 for a lukewarm 375mL bottle. Instead, head to nearby Peas & Pickles, a supermarket at the corner of Washington and Front Streets, where you can get a cold one-litre bottle for $1.50.

You know your weekend in Brooklyn isn’t complete if you don’t even step one foot on the iconic Brooklyn Bridge, so make it happen already! (Pro tip: on a warm day, this walk is going to make you sweat! Plan it so you can head immediately back to a rooftop pool in New York City to cool off.)

6. Go to Industry City.

Is it really far from basically everything else in Brooklyn? Yes. But this former warehouse and manufacturing complex along the Upper New York Bay waterfront in Brooklyn’s Sunset Park neighbourhood has been totally revitalized (thanks to an injection of $450 million) and is so massive you could spend an entire day wandering through its 16 campus buildings. Industry City has, well, everything — and then some. Boutique grocery stores and chocolate shops; artisans like jewellers, potters and papermakers; restaurants galore plus distilleries, bars and breweries; a games room; art installations and beyond. There are some 550 companies and more than 50 eateries and retailers that call Industry City’s 35 acres of repurposed industrial space home.

Industry City in Brooklyn is a trek, but worth the effort. You could stay all day and still not come close to peeling back all of its layers!

Called an “intermodal city,” there’s Innovation Alley and a bunch of courtyards that act as community gathering spaces, outdoor takeout seating, event spaces — or whatever you imagine them to be. Each building is a short walk to the next and there are several floors in every building to explore. My kids’ favourite was Japan Village, where we spent more than two hours. Sunrise Mart, a marketplace featuring imported Japanese goods (like unique KitKat flavours, for example) was super cool, and those looking for Japanese beauty brands can find them upstairs at Japan Village.

Spend a day at Industry City and your evening at a rooftop pool in New York City and you’ll have created a full-circle Brooklyn experience!

Japan Village at Industry City is a must for your Japanese-obsessed kids or that Manga-loving cousin you brought along for your weekend in Brooklyn.

7. Look for street art.

This is just one example of the street art in Brooklyn that we passed — without even looking for it. Now if only a rooftop pool in New York City thought to decorate it with local street art, you’d have a winning combination!

Anywhere. Everywhere. This New York City borough is full of bright, thought-provoking, silly, beautiful art — from huge murals to small patches of graffiti. You won’t have to look too hard to find it as you unearth everything Brooklyn has to offer.

Oh, snap…it’s raining?! I’m sure there are lots of things to do on a rainy day in Brooklyn but since I’ve only got experience over in Manhattan, let me take you there instead with my New York City in the rain post.

DISCLAIMER: We paid for all of our own food, drinks, activities and transportation throughout Brooklyn. Hotel Indigo Williamsburg hosted our stay to facilitate a review of its rooftop pool in New York City; neither the hotel nor IHG influenced or reviewed this post and all opinions and suggestions throughout are my own.