Kaitlyn Rosati

New York: it’s a frantic experience. That’s why, when you’ve only got a handful of days to dine, sight-see, museum hop and shop, that oh-so-precious shut-eye becomes all the more important. But, despite its famous moniker as the “city that never sleeps”, the Big Apple is brimming with stylish, innovative, and world-renowned hotels. So, here’s Time Out’s gleaming collection of our absolute favorite places to stay, all tried and tested by local writers.  New for spring 2026 are reviews of Nine Orchard, Ace Hotel Brooklyn, The Ned NoMad, and our brand-new number one, The Fifth Avenue Hotel. Scroll on. Which area is best to stay in New York? Well, we’ve compiled an entire neighborhood guide to help you find the best fit for your trip, but first-timers should consider Midtown (particularly on and around Fifth Avenue), frequent visitors who want to feel like a local should opt for hotels in Williamsburg, and for particularly stylish boutique stays, you’ll find plenty of those in Tribeca, NoMad, the Lower East Side, and the Meatpacking District.  New York’s very best hotels at a glance: 💎 Most luxurious: The Plaza 👛 Best budget: The FiDi Hotel 🌃 Best view: The Ritz-Carlton New York NoMad 👙 Best pool: Equinox Hotel New York 🍸 Best boutique: Nine Orchard 🪩 Coolest: The William Vale 🤩 Most iconic: The Hotel Chelsea 📍 Discover our ultimate guide to the best hotels in New York How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—

No matter your age, New York is one magnetic city, and from the brilliant museums to kid-friendly Broadway shows, it’s primed for a family vacation—in fact, we’ve compiled a list of all the best things to do with kids in New York. As for where to stay, everything you need to know is right here: our revamped list of the Big Apple’s most family-friendly hotels includes everything from affordable Midtown stays to luxury resorts with tons of amenities. Scroll on to find your ideal hotel.  Which area is best to stay in New York? With the whole family in tow, opting to stay somewhere well-connected which is a step back from the busy NYC streets is a must—that’s why this list is peppered with stays in neighborhoods like Midtown West, Murray Hill, the Upper West Side and Hell’s Kitchen. Check out our guides to all NYC’s neighborhoods, to help you decide.  New York’s best family-friendly hotels, at a glance: 👙 Best pool: The Peninsula New York  👛 Best budget: TRYP by Wyndham New York Times Square 🤩 Most iconic: The Lucerne Hotel 📍 Discover our ultimate guide to the best hotels in New York City How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in between—to bring you fresh, honest recommendations, all year round. We have reviewed many of the hotels featured below, but we may not have stayed at every single one. Any we haven’t stayed in have been selected by experts based on their ameniti

Whether it’s your first or your one-hundredth time in New York, you could do a lot worse than booking a hotel right in the middle of the concrete jungle. Manhattan’s Midtown neighborhood is perfectly placed for sightseeing and exploring all of the shops, bars and world-class restaurants right at your fingertips. You’ll find everything from luxury landmarks  plus more affordable boutiques, and to keep you up to date with all the very best places to stay, we’ve added brand-new reviews of Andaz 5th Avenue and Sofitel New York. Enjoy. Which area is best to stay in New York? Well, we’re obviously gonna make a strong case for Midtown, which is home to a shedload of any first-time visitors’ bucket list attractions. It’s also well connected to both the Upper West and East, Lower Manhattan, Brooklyn, and pretty much anywhere else you’d want to go. Have a read of all our guides to all NYC’s neighborhoods, to help you decide.  New York’s best Midtown hotels at a glance: 🌃 Best view: The Shelburne Sonesta  👙 Best pool: The Peninsula New York 👛 Best budget: voco Times Square South New York 💎 Most luxurious: Ritz-Carlton Central Park 🤩 Most iconic: The Knickerbocker 📍 Discover our ultimate guide to the best hotels in New York How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in between—to bring you fresh, honest recommendations, all year round. We have reviewed many of the hotels featured

If there’s one thing—just one thing—you’re coming to New York City for, it’s got to be the views. There are few spectacles more iconic than the twinkly Manhattan skyline, after all, but housed inside many of those towering skyscrapers are hotels with magnificent views. With brand-new coverage from our local writers on Equinox Hotel, The Shelburne Sonesta and the Park Terrace Hotel, as well as many, many more.  Which area is best to stay in New York? Manhattan’s dense concentration of high-up, high-end hotels means you’re blessed with options for up close and personal views of The Big Apple, but heading over to Brooklyn is also a great option for more sweeping city vistas. Have a read of all our guides to all NYC’s neighborhoods, to help you decide.  New York’s best hotels with a view, at a glance: 🌃 Best view: Ritz-Carlton Central Park 👙 Best pool: Equinox Hotel 👛 Best budget: The Shelburne Sonesta 💎 Most luxurious: Mandarin Oriental 🤩 Most iconic: The Plaza 📍 Discover our ultimate guide to the best hotels in New York How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in between—to bring you fresh, honest recommendations, all year round. We have reviewed many of the hotels featured below, but we may not have stayed at every single one. Any we haven’t stayed in have been selected by experts based on their amenities, features, pricing and more. By the way, this article includes

Nowhere in the world does luxury quite like New York City, and from sleek, glassy, towering stays which overlook Columbus Circle and Central Park to tiny little boutique hotels which feel more like ridiculously fancy private homes, luxury comes in all grandiose shapes and glitzy sizes here.  But we aren’t just talking about cloud-like bedding and pretty decor—luxury also means gorging on dishes crafted by world-class chefs, being in prime New York locations, and enjoying polished, attentive service. So, looking to splash out on an ultra-luxe stay in NYC? Here’s where we would recommend, with new reviews of The Fifth Avenue Hotel, The Knickerbocker, and obviously, The Plaza.  Which area is best to stay in New York? For proper, over-the-top luxury, blockbuster New York hotels live on Fifth Avenue, in FiDi, or on the Upper East and West sides. You can browse our comprehensive guide to all of New York City’s best neighborhoods—it will help you figure out which is the best for your trip.  New York’s most luxurious hotels at a glance: 🤩 Most iconic: The Plaza 💎 Most luxurious: The Lowell Hotel 👛 Best budget: The Wallace Hotel 🌃 Best view: Mandarin Oriental 👙 Best pool: The Peninsula New York 📍 Discover our ultimate guide to the best hotels in New York How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in between—to bring you fresh, honest recommendations, all year round. We have re

Take a stroll down a New York street and from the glint of the skyscrapers and trundle of yellow cabs to the dollar slices and food trucks, iconic details about this city are in every which way. It’s only appropriate then that the city has a roster of hotels which are just as legendary, from The Plaza’s glitzy quarters to the unmatched artistic legacy of the Hotel Chelsea. That’s why we’ve compiled a list of New York’s most celebrated hotels, which includes brand-new reviews of The Knickerbocker, The Standard, High Line and, of course, The Plaza for spring 2026.  Which area is best to stay in New York? Midtown is busy and full of visitor hotspots, but it’s also the site of some of the city’s most legendary hotels, as well as undoubtedly being the most convenient neighborhood to stay for first-timers. However, if you’re a fan of stylish restaurants and lively nightlife like us, stay in the Meatpacking District, or opt for something over the Bridge like Williamsburg for a spot with all the New York charm without quite so much bustle.  New York’s most iconic hotels at a glance: 💎 Most luxurious: St. Regis New York 👛 Best budget: Hotel Edison Times Square 🌃 Best view: The Standard, High Line 👙 Best pool: The Greenwich Hotel 📍 Discover our ultimate guide to the best hotels in New York City How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in between—to bring you fresh, honest recom

The most wonderful time of the year is finally approaching. As someone who grew up in a small town in upstate New York, I have an affinity for small towns during the holidays. While we all know major hubs like New York City and Chicago go full out during Christmastime, there’s something particularly dazzling about that quintessential small town charm. Whether it’s a cup of comforting hot cocoa from a local coffee shop or bakery, jolly music to enjoy while shopping for friends and family, Christmas light displays, horse-drawn carriage rides, holiday markets, carolers and everything else that makes the holidays particularly magical, there are some hidden gems around the country to add to your radar. So, embrace the holidays in one of these Christmas towns in the U.S. that are perfect for experiencing a little (or a lot) of yuletide joy.

‘Tis the season for tinsel, ornaments and towering glistening Christmas trees. In true New York fashion, some hotels go bigger than others when it comes to decking out for the holidays. Even if you feel more like Scrooge or the Grinch this holiday season, we have a feeling these hotels and their over-the-top Christmas decor will manage to make you feel merry and bright. RECOMMENDED: The best hotels in New York City

With an uprise in uneasy airline news as of late, it’s no surprise that road trips are as popular as ever. But what exactly are road trippers seeking when they plan their next great adventure? While some road trip patterns are here to stay, there’s been a recent uptick in trends like micro-tripping, passion-tripping and gig-tripping. Regardless of the reason behind hitting the open roads, it all points to one consistent factor: having control over the wheel means travelers have more control over their itinerary and plans. So, for those worried about flight cancellations and lost luggage, road trips are a pretty stellar way to nip those fears in the butt while still getting the ultimate travel experience. Whether you’re seeking inspiration for your next road trip or are curious as to what’s driving travelers, no pun intended, here are the top 10 USA road trip trends in 2025.    

There’s no time quite like the festive season to visit New York—the already twinkly city will be draped in endless lights, red ribbons will be wrapped around banisters and the parks will be glazed over with ice rinks. Hell, you might even get some snow. But, it’d be a shame to find yourself in a hotel which isn’t giving it’s all to the Christmas spirit, and that’s why we’ve done some digging to compile this ‘nice’ list of top places to stay in the month of December. New additions ahead of winter 2025 include The Plaza, The Knickerbocker, Park Terrace Hotel, Loews Regency New York and voco The Franklin, but there’ll be merriment spreading all over the city, so check out the full list below. Which area is best to stay in New York? Midtown is chaotic, but on your first visit to the city it’s arguably the best central spot to be at the forefront of the action. However, we’re also fans of staying in the Meatpacking District to have stylish restaurants and a lively nightlife to hand, or Williamsburg for a cool spot slightly farther from the Manhattan bustle.  New York’s best Christmas hotels at a glance: 💎 Most luxurious: Mandarin Oriental New York 👛 Best budget: voco The Franklin New York by IHG 🤩 Most iconic: St Regis New York 🎄 Best Christmas Tree: The Plaza 📍 Discover our ultimate guide to the best hotels in New York City How we curate our hotel lists Our team of writers and travel experts review hotels all over the world—new openings, old classics and everything in betw

A three-day weekend is the perfect opportunity to bid farewell to summer. While we’re sad for summer to end, Labor Day gives us a chance to celebrate with one last hurrah. It’s never too soon to start planning an amazing Labor Day getaway from NYC, so check out these options, from relaxing to adventurous. While there are plenty of day trips from NYC that can scratch the itch, the long weekend is enough time to squeeze in a weekend getaway. Looking for some culture? Head to the Hamptons. Partial to the outdoors? The Adirondacks are for you. If you’re more of a shorebird, consider Wildwood or Fire Island or a lakeside adventure. Sure, you could hit up the best beaches in NYC or salute the summer at an outdoor bar or beer garden, but to squeeze every last drop out of summer, start planning one of these Labor Day getaways from NYC today. RECOMMENDED: Full guide to Labor Day in NYC

Pizza is one of the most popular dishes on the planet, so when you’re in New York, it’s understandable if that craving hits tenfold. While the city is well-renowned for those classic, foldable New York-style slices and charred, Neapolitan-inspired rounds, the pizza capital of the country (no matter what Connecticut claims) is also home to a plethora of chewy, thick deep-dish pies. Deep dish in New York terms expands far beyond “Chicago deep-dish,” including specialty Sicilian and Detroit-style pies. Since cheap eats cravings are meant to be satisfied, we flung ourselves headfirst into field research and happily deviated from the thin-crust norm (and sub-par slices from 24-hour pizza spots, which, post-pandemic, are fewer and farther between). From spongy Sicilian squares paired with live music to nostalgic ‘90s Detroit-style cheesy and spicy pies, we’ve rounded up standout eateries slinging delicious NYC deep-dish options. So, follow our lead: if you’re craving something outside of the traditional New York slice, add these deep dish pies to your New York bucket list.  July 2025: We’ve included some old-school “if it ain’t broke, don’t fix it” classics, along with some newer openings, featuring toppings like whole burrata and Calabrian chili pesto that would make pizza purists squeamish. RECOMMENDED: Find more of the best pizza in NYC How we curate and review at Time Out

Despite its famous moniker as a concrete jungle, New York actually brags a fair bit of green space, and Bryant Park is one of the best examples. So, if you’re keen to be in the center of Midtown action but still have a little nature nearby, Park Terrace Hotel is a tough one to beat.  It sits just opposite the park, but also has an onsite sauna, a lovely restaurant, views over New York Public Library and some seriously top-notch service, which is more than enough to make you want to stay awhile.  Why stay at Park Terrace Hotel? While crammed hotel rooms are common in Midtown (the area is known both for tight rooms and super cramped apartments) my Deluxe Studio King Room was larger than anywhere I’ve ever lived in the city. My room would have been ideal for two people, but as a solo traveler I revelled in having a little extra space, including a couch to lounge on while I soaked in the views of the library and Bryant Park each morning.  It’s also pretty hard to find a Midtown hotel which has a good – and I mean really good – wellness element, but the sauna in the hotel’s ‘basement’ was an unexpectedly luxe touch.  What are the rooms like at Park Terrace Hotel? With a total of 225 rooms and studios across 15 floors, many of which offer unparalleled views of Bryant Park and the New York Public Library, Park Terrace Hotel sure has variety. There’s the Classic Room, a cozy yet contemporary space that can accommodate up to two guests. The Deluxe is also best for two, but with an upg

Being a full-time traveler means I’ve slept in my fair share of hotel rooms, but I seldom find a stay which hits every mark: spacious rooms, niche and well-preserved history, a good location, incredible dining, and top-notch service. But the Shelburne Sonesta New York is as well-rounded a hotel as you can get.  Located just steps from Grand Central Terminal and the Chrysler Building, this hotel is close enough to be a visitor’s playground, but has dining options where you’ll be sat side-by-side with locals. The 1929-built building has plenty of apartment-style rooms, giving you the chance to step back in time and live in old New York, and these are especially ideal for families seeking more space. But what I learned staying here is that they can cater to every type of traveler. Why stay at The Shelburne Sonesta New York? It’s rare that I’d encourage you to book a hotel specifically with the incentive to not leave it, but the Shelburne Sonesta New York has everything you need for a one or two night stay. Their onsite restaurant, Take Care Bistro, opens early and has a full barista bar, and as the hours throughout the day pass, their veggie-forward menu makes for one of the best lunch and dinner options in the area.  There’s a traditional USPS mailbox located in the lobby, which, despite being nearly a century old, is still functioning. You’ll find plenty of comfortable space to catch up on work, and if you forgot your laptop, there are two computers available to use with print

Times Square is one of the flashiest neighborhoods in New York. Some would argue it’s the epicenter of the city. It’s loud, chaotic, and busy all the time, but the draw to be based in Times Square is understandably enticing.  But The Knickerbocker Hotel proves that even the busiest parts of the city can offer not only some peace and quiet, but luxurious respite, too. It’s full of rich history (the dry martini was born here, guys), and has one of the most comfortable beds I’ve ever laid my head on in this city. All that with its soundproof rooms and minimalist decor, you’ll enjoy the convenience of the most chaotic parts of Manhattan while feeling light years away. Why stay at the Knickerbocker Hotel? Location and comfort are two important factors to consider when booking any hotel, and The Knickerbocker has nailed both. Because of its prime midtown location, you not only have easy access to New York’s top attractions, but also to just about every major subway line. Getting out to more local-populated hangouts like Jackson Heights, Queens (just jump on the 7 train) and Williamsburg, Brooklyn (jump on the M) are easy jaunts. Aside from its prime real estate, the Knickerbocker is a flavour of proper, old-school New York suave without feeling dated, and that’s thanks to the modern tech touches incorporated throughout. It even gives a little Hollywood glamour–my first thought on arrival was that Marilyn Monroe would have blended in perfectly here.  What are the rooms like at the K

One of the biggest hurdles visitors to New York can face is which area to stay in, but as a long-time resident of the city I always advise first-timers to choose somewhere that’s within walking distance to some of Manhattan’s top attractions.  Enter the Hotel Park Ave. Formerly the Mondrian Park Avenue hotel, this place is practically on the doorstep of tried and trusted local hangouts and must-sees like Madison Square Garden, the Empire State Building, and Herald Square. The Lore Group (who took over in November 2024) have given this place a modern refresh, and plenty of the rooms, including my 18th floor suite, have balconies to show off that iconic Manhattan skyline.  Why stay at Hotel Park Ave? Manhattan is the kind of place where you want to soak in the skyline at every possible opportunity, and if you opt for one of the 23 rooms which have balconies, Hotel Park Ave’s are pretty solid. You don’t even need to worry about feeling too crammed, as each one has alfresco seating so you can properly kick back, but splash out on the Nomad Penthouse (a gleaming 1,275 square foot space on the twentieth floor) and you’ll be treated to two.  The Lore Group’s ultra-modern refresh of the place also isn’t just about its look, though you will be greeted by a chic lobby with Jan Hendzel Studio’s monumental ‘Pebble Jumble’ sculpture featured. However, there’s also contactless check-ins and check-outs. As for the rooms, my most important must-have is a bed which feels like a cloud, and all

Many associate New York ‘za with grabbing a quick slice on the go, whether for a quick mid-day snack or a late-night booze soaker-upper. At Ace’s Pizza in Williamsburg, however, their Detroit-style pizza is an entire dining experience. Detroit-style pizza has seen an uptick in popularity in recent years, and Ace’s is partially to thank. Opened in February 2021, Ace’s is serving up the fluffiest, cheesiest pizza that could easily convert the highest of pizza purists. The dough is pillowy, but the cheese takes it over the top: they use a mix of low-moisture mozz and brick cheese (the signature Midwest touch), and put the sauce directly on top before finishing the bake. They offer three sizes: personal pie (two pieces), medium (six pieces), or large (10 pieces). You can’t go wrong with any of their toppings, but their pepperoni pie is completely coated in crispy little cups of pepperoni that are oozing with spicy oil, taking the umami factor to a whole new level. But it’s not just pizza you’ll want to head here for. Their wings are crisped to perfection, coated in sauces like Nashville hot or Carolina gold, and their “double-stuffed cheesy bread” is pretty much cheese with a hint of bread. Ace’s also offers a great natural wine list and some draft beers, including “Ace’s Perfect Pilsner” made by Flagship Brewing Company out in Staten Island. The vibe of Ace’s can best be described as nostalgic. It feels like a time machine back into the '90s, with Nintendo consoles, red and yell

The New York restaurant scene can transport you anywhere from Malaysia to Brazil, but if you crave something a little closer to home, Chicago-style Emmett’s will certainly do the trick. Opened in 2013 by Chicago native Emmett Burke, and not to be confused with their sister restaurant, Emmett’s on Grove, Emmett’s is ideal for a nice night out, offering stellar food and a warm, chill atmosphere. The vibe: Offering both seasonal outdoor and year-round indoor seating, Emmett’s is a prime option regardless of season. Inside is dimly lit and moody, with a small bar and just a few tables. The outdoor seating area consists of one table right out front, along with a covered patio area featuring a bench and two additional tables. The staff is efficient yet friendly, frequently checking in on guests while also handling takeout orders and bussing tables. Emmett’s has that quintessential neighborhood feel. The food: I specifically came to Emmett’s for their deep-dish pie, but the super crispy, thin Chicago-style tavern pie is an equal standout. Emmett’s does not skimp on the toppings, and a knife and fork is served with the deep dish for good reason. The deep dish takes 30-40 minutes to cook from the time it’s ordered, but if you’re in a New York hurry, the tavern-style pizza arrives faster. The menu has several nods to Chicago, like a Chicago-style hot dog and an Italian beef sandwich, but other standouts are a bleu cheese-stuffed burger and an arugula salad with sliced apple for some ta

I’m sitting at lunch at Lattanzi Cucina Italiana in Manhattan, inspired by Lady Gaga and fiancé Michael Polansky’s dinner date there during the week she hosted SNL. My mom and I are reliving the night before, where we attended the first Mayhem Ball at Madison Square Garden, reeling from her piano rendition of “Hair” over glasses of Pinot Grigio and plates of pollo con peperoni. My friend Julie texts me. “How was it?” she asks, referencing the show from the previous night. “Incredible,” I respond. “Want to come to Florida and go to the Miami show next weekend?”I laugh, and hypothetically say, “Um yes.” But despite my light take at her suggestion, the conversation quickly turns serious, and before the bill even arrives at Lattanzi, I’m on the Delta app booking a flight to Fort Lauderdale. While Gaga was the driving factor, there was another incentive in it for me, too. Despite having traveled to over 90 countries across all seven continents, I had still never been to Miami. Truth be told, Miami was never at the top of my list. I imagined the city to be the Las Vegas of Florida: a kitschy, overpriced theme park for adults with ridiculously good looks and workout routines that consumed half their day to keep up with said good looks. Someone like me, a gritty, tough-as-nails New Yorker with a loud Italian-American accent and the attitude to match, would never fit in in a place like Miami. But for Gaga and Julie, I was finally willing to find out firsthand. Less than a week later,

If you’ve ever come back from a vacation in Italy or Japan, you’ve probably been left wondering why on earth the U.S. has not developed better and faster trains. Well, it’s been a long time coming, but we’re finally onboard, no pun intended, with the launch of Amtrak’s NextGen Acela.  With a speed of up to 160 mph, the NextGen Acela is the first of its kind when it comes to high-speed trains in the U.S. I got to experience it firsthand as one of the first to ride the NextGen Acela on its launch route along the Northeast Corridor, ahead of its public launch on August 28 (specifically, I was whisked from New York City to New Haven). My immediate impression was that it is very similar in style to Italy’s sleek and modern Frecciarossa trains, and the speed certainly added to that effect. That said, we never hit top speed on my journey, and NextGen Acela won’t be hitting top speed until there are infrastructure improvements to the tracks—but it’s still noticeably faster than a standard Amtrak ride when you look out the window and watch everything flash by. There were moments we slowed down quite drastically, but as someone who frequently takes Amtrak trains between upstate New York and New York City, I can confirm the NextGen Acela is a massive step above all of my Amtrak experiences in both speed and comfort. Photograph: Kaitlyn Rosati for Time Out How big is the train and where does it go? There are eight cars on the NextGen Acela, including a first-class car and designated qu

I’ve been a fan of Lady Gaga since the first time I heard “Just Dance” while driving down La Brea Avenue in Los Angeles in 2008. I was a 17-year old starving artist, and it was refreshing to hear a New Yorker on the radio during a time I was really missing the East Coast. That feeling would be validated even more when I heard her lyrics in “Marry The Night” throwing subtle shade at Hollywood: New York is not just a tan that you’ll never lose. One of the reasons I respect Lady Gaga so much is that she brilliantly encapsulates in her music what it means to be a New Yorker. She wears her love of her hometown like a badge of honor in her lyrics, her stage performances and her interviews—frequently referencing how much being a ground-up artist in the city has contributed to her success. This weekend, fans from all over the world will flock to the Big Apple to catch the Mayhem Ball at Madison Square Garden, where Gaga will play six shows in total (August 22, 23, 26 and 27, and September 6 and 7). If you want to go beyond just seeing the show and explore New York through the lens of Gaga, here are a few places in the city with ties to the pop megastar. View this post on Instagram A post shared by Lady Gaga (@ladygaga) The Bitter End Prior to adapting her stage name, Lady Gaga performed around the city without an alias as Stefani Germanotta. One of the most prominent places she performed before she made it big was the Bitter End. Located in Greenwich Village

Prior to the pandemic, traveling frequently to far-flung destinations was not out of the ordinary for me. I was a bartender in New York and would arrange my schedule to take long weekends to go swim with nurse sharks in Caye Caulker, Belize, or eat late-night arepas on the streets of Cartagena, Colombia. I once even booked a flight to Rovaniemi, Finland, that left later that day because I got a good flight deal during prime northern lights season. RECOMMENDED: The best pet-friendly hotels in the U.S. So, when travel as I knew it had changed in March 2020, I watched as my passport collected dust, wondering if I’d ever hear the sweet sound of being stamped into a new country again. With a serious travel itch that felt impossible to scratch, one day in February 2021, I looked at my dog, Bowie, who would soon be undergoing intensive surgery to remove a cyst in his neck, and thought, what if I give us both the gift of getting out of this house? He was about to spend an unknown amount of time in a hospital, and I had reached textbook levels of stir-crazy. So, with very little planning and the same wing-it approach that I’d always taken, Bowie and I got in the car and began driving on Valentine’s Day. Photograph: Kaitlyn Rosati for Time OutBowie in Virginia Beach, Virginia Our first stop was Louisville, Kentucky. I had never been to Kentucky before, and had seriously underestimated what a far drive it is from New York City (roughly 12-13 hours). We shared Tupperware takeout briske