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This article is part of a series celebrating Boss Huntingโs favourite corners of the United States. Click here to see more.
If you only have two weeks to carve your ideal trip to the USA, youโll have to practice a bit of restraint. The land of the free is packed with some of the worldโs greatest places, from the typical hotspots of Los Angeles, California and New York City, New York to unforgettable small cities like Charlotte, North Carolina, and pristine ski resorts like Park City, Utah.
There is almost too much choice in a land celebrated for its diversity, however, 14 days is still a decent amount of time for those seeking to tick off the USAโs greatest hits. Boss Huntingโs ultimate US itinerary will take you on an adventure youโll be talking about for decades.
Best Month To Go
Weโd recommend November for this itinerary. Youโll be stopping by Park City, Utah on your second week, when ski season starts. November is also the perfect time to visit Arizona, the crowds are thinning for New York City, and Chicago, Illinois may be getting chilly, but itโs just in time for the holiday buzz.
Transit
With this itinerary, youโll be flying between most cities. Thereโs a day trip out of Chicago that youโll need to rent a car for, and youโll obviously need some wheels if you want to hit the road between Las Vegas, Nevada and LA. Aside from that, flights will be the easiest way to maximise your two weeks.
New York, New York (1-2 Days)
Your ultimate USA itinerary kicks off in the worldโs most recognised concrete jungle. Try and touch down in New York City as early as possible on a Saturday and head straight to the Upper East Side to check in to The Pierre, your accommodation for the next two days.
Day One
The first two days of your trip will be all about art, culture and dining in the Big Apple, so make sure youโve packed a healthy appetite, and have your reservations sorted well in advance.
After checking in to The Pierre, walk through Central Park and make your way to Veselka in NoHo. This Ukrainian restaurant illustrates the cityโs famously multicultural dining scene, best experienced at breakfast where the signature fried egg sandwich with grilled ham and Swiss cheese will hit all kinds of spots.
Head back uptown to check out the Museum of Modern Art and spend a few hours there before catching a matinee performance of Hamilton โ or whatever Broadway show catches your eye.
You had a late breakfast; either skip lunch or, if youโre feeling peckish, grab a bite nearby at the Viennese-style Cafe Sabarsky.
Freshen up at The Pierre and take a train to the Lower East Side for a drink at the award-winning Double Chicken Please. This highly-rated cocktail bar is considered the best in the country, so try a few of the barโs signatures before heading to dinner at the swanky Gramercy Tavern. The Michelin-starred institution is classic New York and there is a dress code. Just make sure the kitchenโs exceptional duck breast is on the table at some point, and donโt forget to browse the wine list.
If youโve still got the energy after dinner, check out the schedule at Nublu. This glitzy bandroom is where well-known musicians come to jam, and there are few better ways to end the night in NYC than with live music. Alternatively, end the night with a drink at JIMMY, the breezy rooftop bar with a mini pool on top of ModernHaus Soho.
Day Two
Your second day in New York is all about Brooklyn. Wake up nice and early at The Pierre and have breakfast at the hotel; ask to dine in The Rotunda room if available. The Metropolitan Museum of Art isnโt far away; start your day here and spend the morning amongst the institutionโs many collections and exhibitions.
Before you head to Brooklyn, pop on over to Hudson Yards and hit up The Edge, the highest outdoor sky deck in the Western Hemisphere where brave souls lean out over Manhattan while suspended mid-air.
If youโve timed this for a Sunday, then head out to Nowadays in Bushwick. This indoor-outdoor venue welcomes DJs Eamon Harkin and Justin Carter every week for Mister Sunday, New Yorkโs coolest day party and a great place to dance and mingle for a few hours.
You can catch a gig at Brooklyn Bowl, a unique concert venue with a bowling alley, or finish the day at Westlight. The latter, Brooklynโs finest rooftop bar, sits atop The William Vale Hotel and offers an incredible panorama of Manhattan.
Book a table for dinner at the award-winning cocktail and oyster bar Maison Premiere. The bar focuses on absinthe so make sure youโre pairing some cocktails with the kitchenโs glorious New England lobster roll. Alternatively, jump a cab to Hometown Bar-B-Que in Red Hook for casual pit-smoked meats and live jams.
Chicago, Illinois (1-2 Days)
After youโve left the towering skyscrapers of Manhattan behind, itโs time to hop on a flight and make your way over to The Windy City. Often voted as the best big city in the USA, Chicago has plenty to offer. Check into The Fairmont and get ready for a big two days of dining, live music, and day trips.
Day One
Why not start with Chicagoโs most emblematic experience โ jumping onboard a river cruise for the worldโs most unique architecture tour? Planted along the river, Chicagoโs treasured collection of historic buildings is one of the worldโs most beautiful man-made sights. Plus, itโs a great way to get your bearings.
When lunch cravings hit, head to Chicagoโs most reliable eat street, W Randolph Street, and park yourself up at Au Cheval. This kitschy restaurant and bar serves up some of the countryโs best burgers; grab the signature built with two smashed patties, cheese, a fried egg and housemade sauce.
You had a big two days in New York City so take it easy by cruising over to Millenium Park and checking out Anish Kapoorโs Cloud Gate. Since 2006, this bean-like mirror has served as a symbol of Chicago. Pro tip: if you want a good photo without the tourists in it, youโd need to wake up before sunrise and walk on over; luckily Fairmont Chicago is a stoneโs throw from Millennium Park.
The Art Institute of Chicago should take a decent bite of your day and itโll likely be time for an early dinner by the time you finish. Walk on back to W Randolph and take your seat at Girl & The Goat. This award-winning restaurant is focused on healthy, minimal dishes with fresh local produce so nothing will weigh you down for your post-dinner show at The Green Mill.
The Green Mill was most noted as Al Caponeโs favourite jazz club and its reputation guarantees a gold-standard live music programme each week. Drive on down to trendy Bucktown later to end the night with a bar crawl, starting at one of Chicagoโs classiest establishments, The Violet Hour.
Day Two
Wake up early, grab breakfast at the hotel, and make the short drive to Indiana Dunes National Park for a picturesque day trip. The 61st National Park in the USA has some excellent hiking trails like the 157-acre Coffee Creek Watershed Preserve so work up a sweat while you thread through beautifully preserved wetlands, woodlands, and prairie.
Youโll want some good food and wine after your day trip. Once youโve returned to the city The Oakville Grill & Cellar back on Randolph Street is dedicated entirely to the Napa Valley so good wine, even better cheese, and simple, produce-forward dishes are all on the cards. If you want to eat like the locals, you canโt go past a slice of deep dish. Lou Malnatiโs, Art Of Pizza and Ginoโs East all stake a claim for best in town, and all a walk from the hotel.
Chicago wouldnโt be the same without its world-class cocktail bars so head on over to The Milk Room to get started early. Located in the Chicago Athletic Association, this 8-seat whiskey bar is mixing up some of the best signatures in the state; spend a bit of time here before heading off to your next bar, Three Dots and a Dash. Equally as reliable, this blend of Chicago speakeasy and Pacific Island Tropicana is held together with excellent service and creative twists on classics. Finally, end your bar crawl at Kumiko, where tasty Japanese food is matched with minimalist signature cocktails.
Charlotte, North Carolina (1-2 Days)
Consistently voted as the USAโs most charming small city, Charlotte is proof that some of the countryโs best moments are found outside of the hotspots. Check into the boutique Grand Bohemian Hotel Charlotte and bunker down for the next two days of arts, sports, and food.
Day One
If New York City and Chicago felt like big-budget blockbuster movies, Charlotte is that modest indie flick brimming with personality. The cityโs romantic old-world architecture is one of its defining features, and the best way to see it is via a walking tour around the heart of town. Youโve earned some rest and relaxation over the past few days, so take a long lunch at the Peruvian-flavoured Yunta.
If the Charlotte Knights have a game that evening, head on down to the immaculate Truist Field to get behind some hometown heroes, right after youโve organised your own sporting tradition: the pre-game tailgate. If itโs the NBA you seek, head to the Spectrum Centre to see LaMelo Ball in action for the Hornets.
Ready for a nightcap? Pop by your hotelโs stylish, South American-inspired Buho Bar for a post-game tipple.
Day Two
Charlotte has plenty of classic American diners, with some of the most popular being the 24/7 Midnight Diner and RedEye Diner. Take your pick for breakfast before heading on over to the NASCAR Hall of Fame. More than 50 interactive experiences mean this shrine to stock car racing is one of the worldโs most prized destinations for fans of the sport.
Unexpectedly some of the countryโs best ramen comes from North Carolina and Futo Buta is only a short walk from the NASCAR Hall of Fame. After youโve slurped up your lunch, hit the trails of Little Sugar Creek Greenway โ a favourite for outdoor enthusiasts and the stateโs most impressive linear park โ or opt for something a bit more intense at the US National Whitewater Centre. As the largest man-made whitewater river in the world, and an Olympic training site, this 1,300-acre complex is built on adrenaline, with rock climbing, zip-lining, and mountain biking on offer as well.
Your time in the Queen City wraps with dinner at Bentleyโs Restaurant, Charlotteโs finest French diner, before you call it a night and make haste for The Big Easy.
New Orleans, Louisiana (1-2 Days)
The crunch of crawfish and the smell of deep, soulful gumbo waft around the historic streets of New Orleans, one of the countryโs most exciting cities. Base yourself in the eclectic Maison De La Luz, right next to the French Quarter and hit the ground running; thereโs a lot to cover in NOLA.
Day One
It might be tempting to head to New Orleansโ most renowned area straight away, but you might want to save your Bourbon Street debut for when the sun goes down. Instead, get familiar with one of the cityโs most defining traits at the New Orleans Jazz Museum to kick off your visit with a bit of culture. After all, New Orleans is the birthplace of jazz.
Your stomach will be grumbling by the time youโre done, so hop on over to Creole-based brasserie Luke for comfort classics like silver queen corn bisque and shrimp with grits before a drink at Bar Marilou. The incredibly eclectic architecture that threads through the city is a constant source of inspiration so take your time when walking between venues and soak up the atmosphere.
Now itโs time for that Bourbon Street crawl youโve always dreamed of. Running through 13 blocks in the heart of the French Quarter, this historic district hosts some of New Orleansโ most kinetic bars and restaurants. Regarded by many as one of the best bar crawls in the country, if not the world, highlights include Lafitteโs Blacksmith Shop, ostensibly the oldest bar in the country dating back to 1772; the rowdy Bourbon Street Honky Tonk; and eclectic Fritzelโs Jazz Bar.
Day Two
Dust off your hangover at Brennanโs with a Cajun Bloody Mary and their famous eggs Sardou. Once satiated, youโre ready for a quintessential Louisiana experience with Honey Island Swamp Tours exploring the wildest swamp in the state, just a short drive from the city.
Back in town, grab a late lunch at Josephine Estelle, noted as the best Italian restaurant in New Orleans. What happens next depends entirely on your energy levels. Itโs a Saturday night after all, so the French Quarter will be at its peak. Head on back to Bourbon Street for some unfinished business or take a leisurely ghost tour around one of the most haunted cities in the world.
Park City, Utah (1-2 Days)
We hope youโre ready to shred because, after the chaos of New Orleans, youโre wrapping yourself in the luxury of Park City, Utah. Get amongst the skiing-only action and check in at the St. Regis Deer Valley.
Day One
This part of the USA has some of the worldโs best terrain for skiers and itโs no surprise that youโll bump into plenty of Aussies when in Park City. Spend the first day in the heart of town by taking a stroll down the charming Main Street. Listed on the National Register of Historic Places, this atmospheric street maintains much of its late 20th-century silver mining town character, flecked with old west-style saloons and colourful art galleries.
Head on into No Name Saloon for lunch and order up the townโs best buffalo burger before exploring the historic strip and some local talent at Kimball Art Centre. While the Waldorf Astoria is grand, you canโt beat St. Regisโ proximity to the slopes or its reputation as one of the stateโs most comprehensive wellness offerings for aprรจs R&R.
Day Two
Due to its high elevation and low humidity, Park City is renowned for its deep powder and incredible selection of terrain with the mammoth Park City Mountain Resort (which merged with Canyons Resort in 2015), famed Deer Valley and the state-of-the-art Woodward Park City all minutes apart. Locals suggest picking a side and staying there to maximise your time on-piste rather than wasting it traversing.
For seasoned pros, head over to McConkey Express to reach the famed McConkey Bowl, named after professional skier and base jumper Shane McConkey โ the mountainโs most legendary spot. Alternatively, Deer Valley offers over 100 perfect groomers of skiers-only bliss, across six mountains.
Youโll want to spend most of your day on the slopes, but make sure you have time for lunch at Tombstone BBQ for epic on-mountain dining, or take it even higher by dining in Stein Eriksen Lodgeโs Alpenglobes with pristine views over Deer Valley. If you find yourself on the famous 3.5-mile โHome Runโ at the end of the day, slide straight into High West Saloon, the worldโs only ski-in distillery, before hitting the sauna at St. Regis.
Phoenix, Arizona (1-2 days)
Phoenix, Arizona is often ranked as the best city in the USA for hiking enthusiasts given its proximity to incredibly scenic and rugged trails. Check into the boutique Rise Uptown Hotel when you land, swapping snow for sun and the stateโs famously consistent weather.
Day One
Downtown Phoenix is small, walkable and infinitely charming, framed by the stateโs dramatic scenery. Take a stroll through the heart of the city and grab a slice at Chris Biancoโs Pizzeria Bianco. After that, take a walk up to the picturesque Tovera Castle at Carraro Heights for commanding views back over town. Alternatively, the Heard Museum is one of the stateโs most important, exclusively showcasing Indigenous art and regularly hosting cultural events so you can get a better sense of the stateโs history.
Whether itโs for mountain biking or general hiking, Brownโs Ranch, outside the city near Scottsdale, is an unforgettable yet often overlooked destination for visitors. If youโve had enough excitement on the slopes, however, hit the pubs of Phoenix and mix it up with the friendly locals. The charming, English-style George & Dragon is a great place to start.
When hunger sets in Steak 44 is considered the best steakhouse in the area, which will hit particularly well if you exhausted yourself at Brownโs Ranch earlier. Take it easy by walking through the city after dinner; you might want to check out the award-winning Bitter & Twisted for a nightcap before heading back to Rise Uptown.
Day Two
For something romantic and unique, a sunset hot air balloon ride over the Sonoran desert is perhaps the best way to appreciate this beautiful state. Otherwise, your second day should be focused on getting an early start to hike one of the greatest natural wonders in the world. Take the 3.5-hour drive out to Grand Canyon National Park and explore the productive South Rim with its seemingly endless bounty of trails. Pack your own lunch and have a picnic in a designated area of the park before heading back into town.
On the way back, you should stop by Scottsdale and grab dinner at Fat Ox. Donโt be put off by the fact that itโs attached to a shopping centre. This upscale Italian restaurant is the cityโs most popular, typically heaving with locals any night of the week which makes it a great place to mingle at the bar post dinner.
Tomorrow you depart for Las Vegas so we suggest taking it easy.
Las Vegas, Nevada (1 day)
They donโt call Vegas the Entertainment Capital of the World for nothing. There are few better ways to cap an epic trip in the USA than partying on the world-famous Strip. The glitzy neon row, lined with some of the worldโs most coveted resorts, is something everyone should see at least once in their life. Youโll have one night to drink in the energy, but first base yourself out of Four Seasons Hotel Las Vegas, which is one of the smaller properties on the Strip with a private entrance away from the action.
Letโs waste no time here, as thereโs plenty to do in Vegas. But save the Strip for sundown and head over to Downtown Las Vegas. The pedestrian-only mega-strip that is the Fremont Street Live Experience is perfect for day drinking and checking out all the kitschy old-school resorts like Golden Nugget and The El Cortez Hotel. Start by gliding over the crowds with the SlotZilla Zip Line before having lunch at Downtown Container Park and visiting the fascinating Mob Museum to learn about Vegasโ history with the underworld and prohibition. Donโt forget to check out the hidden basement bar, where a secret Moonshine distillery produces some of the best youโll taste anywhere in the country.
Stick to Downtown and take a ride over to The Neon Museum. This incredibly unique space is a boneyard for Vegasโ old neon signs, illustrating the cityโs illustrious history as an adult playground.
When night hits, itโs time to head back to the hotel and freshen up before conquering the famous Las Vegas Strip. Either start your night with a show at Encore Theatre or skip everything and launch yourself straight at the nightclubs, with two of the best being Omnia and Draiโs.
After spending the night in the supreme comfort of the Four Seasons, see why Vegas has a reputation for some of the best spas in the world by recovering at Sahra Spa at The Cosmopolitan. Now youโre ready for your final destination; hire a car and start the easy four-hour drive to Los Angeles.
Los Angeles, California (1 day)
You should arrive in L.A. in the late afternoon if youโve timed everything right, and your accommodation for the evening should reflect the evening youโd like to have. If itโs sundowners overlooking Santa Monica Beach then The Georgian, Los Angelesโ oldest hotel, is a lush bet.
If you plan on soaking up movie mania, you canโt go wrong with a night at The Hollywood Roosevelt, where the stars once frolicked during the golden age. And if a night watching Bronโ at the Crypto.com Arena AKA Staples Centre is beckoning, Hotel Indigo in Downtown L.A. is a short walk. If you are catching a game, grab a late-night feed at L.A. Cafe to finish your trip with some classic American fare.
Give yourself a moment; youโve just ticked off eight of the worldโs most incredible cities in 14 days. How good.
This article is sponsored by VisitTheUSA.com.au and is part of a series celebrating Boss Huntingโs favourite corners of the United States. Click here to see more, and thank you for supporting the brands that support Boss Hunting.
