The Ultimate 2-Week Itinerary In The USA 

The Ultimate 2-Week Itinerary In The USA 

Chris Singh
Chris Singh


This article is part of a series celebrating Boss Hunting’s 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, you’ll have to practice a bit of restraint. The land of the free is packed with some of the world’s 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 USA’s greatest hits. Boss Hunting’s ultimate US itinerary will take you on an adventure you’ll be talking about for decades.

Best Month To Go

We’d recommend November for this itinerary. You’ll 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 it’s just in time for the holiday buzz.


With this itinerary, you’ll be flying between most cities. There’s a day trip out of Chicago that you’ll need to rent a car for, and you’ll 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 world’s 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.

The Pierre

Day One

The first two days of your trip will be all about art, culture and dining in the Big Apple, so make sure you’ve 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 city’s 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 — or whatever Broadway show catches your eye.

You had a late breakfast; either skip lunch or, if you’re 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 bar’s 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 kitchen’s exceptional duck breast is on the table at some point, and don’t forget to browse the wine list.

If you’ve 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 isn’t far away; start your day here and spend the morning amongst the institution’s 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 you’ve 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 York’s 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, Brooklyn’s finest rooftop bar, sits atop The William Vale Hotel and offers an incredible panorama of Manhattan.

Westlight rooftop

Book a table for dinner at the award-winning cocktail and oyster bar Maison Premiere. The bar focuses on absinthe so make sure you’re pairing some cocktails with the kitchen’s 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 you’ve left the towering skyscrapers of Manhattan behind, it’s 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 Chicago’s most emblematic experience – jumping onboard a river cruise for the world’s most unique architecture tour? Planted along the river, Chicago’s treasured collection of historic buildings is one of the world’s most beautiful man-made sights. Plus, it’s a great way to get your bearings.

When lunch cravings hit, head to Chicago’s most reliable eat street, W Randolph Street, and park yourself up at Au Cheval. This kitschy restaurant and bar serves up some of the country’s best burgers; grab the signature built with two smashed patties, cheese, a fried egg and housemade sauce. 

The Violet Hour

You had a big two days in New York City so take it easy by cruising over to Millenium Park and checking out Anish Kapoor’s 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, you’d need to wake up before sunrise and walk on over; luckily Fairmont Chicago is a stone’s throw from Millennium Park.

The Art Institute of Chicago should take a decent bite of your day and it’ll 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 Capone’s 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 Chicago’s 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.

You’ll want some good food and wine after your day trip. Once you’ve 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 can’t go past a slice of deep dish. Lou Malnati’s, Art Of Pizza and Gino’s East all stake a claim for best in town, and all a walk from the hotel. 

Chicago wouldn’t 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 USA’s most charming small city, Charlotte is proof that some of the country’s 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.

Grand Bohemian Hotel

Day One

If New York City and Chicago felt like big-budget blockbuster movies, Charlotte is that modest indie flick brimming with personality. The city’s 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. You’ve 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 you’ve organised your own sporting tradition: the pre-game tailgate. If it’s 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 hotel’s 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 world’s most prized destinations for fans of the sport. 

Unexpectedly some of the country’s best ramen comes from North Carolina and Futo Buta is only a short walk from the NASCAR Hall of Fame. After you’ve slurped up your lunch, hit the trails of Little Sugar Creek Greenway — a favourite for outdoor enthusiasts and the state’s most impressive linear park — 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.

National Whitewater Centre

Your time in the Queen City wraps with dinner at Bentley’s Restaurant, Charlotte’s 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 country’s most exciting cities. Base yourself in the eclectic Maison De La Luz, right next to the French Quarter and hit the ground running; there’s a lot to cover in NOLA.

Day One

It might be tempting to head to New Orleans’ 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 city’s 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 you’re 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.

Bar Marilou

Now it’s time for that Bourbon Street crawl you’ve always dreamed of. Running through 13 blocks in the heart of the French Quarter, this historic district hosts some of New Orleans’ most kinetic bars and restaurants. Regarded by many as one of the best bar crawls in the country, if not the world, highlights include Lafitte’s Blacksmith Shop, ostensibly the oldest bar in the country dating back to 1772; the rowdy Bourbon Street Honky Tonk; and eclectic Fritzel’s Jazz Bar.

Day Two

Dust off your hangover at Brennan’s with a Cajun Bloody Mary and their famous eggs Sardou.  Once satiated, you’re 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. 

Honey Island Swamp Tours

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. It’s 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 you’re ready to shred because, after the chaos of New Orleans, you’re 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 world’s best terrain for skiers and it’s no surprise that you’ll 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 town’s best buffalo burger before exploring the historic strip and some local talent at Kimball Art Centre. While the Waldorf Astoria is grand, you can’t beat St. Regis’ proximity to the slopes or its reputation as one of the state’s most comprehensive wellness offerings for après 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 – the mountain’s most legendary spot. Alternatively, Deer Valley offers over 100 perfect groomers of skiers-only bliss, across six mountains. 

You’ll 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 Lodge’s Alpenglobes with pristine views over Deer Valley. If you find yourself on the famous 3.5-mile ‘Home Run’ at the end of the day, slide straight into High West Saloon, the world’s only ski-in distillery, before hitting the sauna at St. Regis. 

Stein Eriksen Lodge’s Alpenglobe

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 state’s famously consistent weather. 

Day One

Downtown Phoenix is small, walkable and infinitely charming, framed by the state’s dramatic scenery. Take a stroll through the heart of the city and grab a slice at Chris Bianco’s 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 state’s most important, exclusively showcasing Indigenous art and regularly hosting cultural events so you can get a better sense of the state’s history.

Whether it’s for mountain biking or general hiking, Brown’s Ranch, outside the city near Scottsdale, is an unforgettable yet often overlooked destination for visitors. If you’ve 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 Brown’s 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.

Arizonan Hot Air Balloon

On the way back, you should stop by Scottsdale and grab dinner at Fat Ox. Don’t be put off by the fact that it’s attached to a shopping centre. This upscale Italian restaurant is the city’s 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 don’t 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 world’s most coveted resorts, is something everyone should see at least once in their life. You’ll 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.

Four Seasons Las Vegas

Let’s waste no time here, as there’s 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 Vegas’ history with the underworld and prohibition. Don’t forget to check out the hidden basement bar, where a secret Moonshine distillery produces some of the best you’ll 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 Vegas’ old neon signs, illustrating the city’s illustrious history as an adult playground.

When night hits, it’s 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 Drai’s.

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 you’re 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 you’ve timed everything right, and your accommodation for the evening should reflect the evening you’d like to have. If it’s sundowners overlooking Santa Monica Beach then The Georgian, Los Angeles’ oldest hotel, is a lush bet. 

Ocean view room at The Georgian

If you plan on soaking up movie mania, you can’t go wrong with a night at The Hollywood Roosevelt, where the stars once frolicked during the golden age. And if a night watching Bron’ at the 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; you’ve just ticked off eight of the world’s most incredible cities in 14 days. How good.

This article is sponsored by and is part of a series celebrating Boss Hunting’s favourite corners of the United States. Click here to see more, and thank you for supporting the brands that support Boss Hunting.

Chris Singh
Chris is a freelance Travel, Food, and Technology writer. He has had work published by The AU Review, Junkee Media and Australian Traveller Media and holds tertiary qualifications in Psychology and Sociology.



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