New York, Chicago & L.A.: City Hopping Across the USA


All Year Round


From $10,077pp excl. flights
(based on 2 ppl sharing)

How long

12 nights ideal length

For years, popular culture has celebrated the cities of the US as some of the most iconic and magical subwaypolises in the world, and for good reason. From the soaring skyscrapers of New York, to the gourmet greats of Chicago, to the Hollywood sign blazoned across the rolling LA hills, this itinerary will leave you floating in the clouds of the American Dream, and lapping up the luxury of some of the world’s finest hotels – and we have a feeling you won’t ever want to come back down to earth…


After being met by your driver, enjoy the ride through the streets of Manhattan to the iconic 5th Avenue where The Peninsula New York awaits. Your luxury abode for the next few nights, this red carpeted palace lies in the heart of the city’s most prestigious shopping, entertainment, and cultural district. Home to a stunning glass-enclosed pool, a world-class spa and the revered Salon de Ning rooftop bar and terrace, the temptation to stay enclosed in your Peninsula paradise will be very real. But, you’re in NYC, and the bright lights are calling. Hop into your chauffeured Peninsula MINI Clubman (a complimentary service for those of you that opt for a suite) and get to know this wonderful city. If you’re an NYC first-timer, we’ll ensure you tick off the must-sees like the nearby Central Park, the Rockefeller Center in Manhattan and Midtown’s Times Square. If you’ve seen it all before, we’ll skip these sights and head straight to your appointment with your personal shopper, who will help you fill the trunk of your car with the latest trends. Back at the hotel, The Peninsula Academy will have lots of bespoke excursions to offer you too. From a day searching for the perfect bridal gown with bridal stylist Julie Sabatino to sea-plane excursions to Long Island for a private lesson in sea oystering, fishing and clamming; The Peninsula Academy will ensure your time in NYC is completely unique.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

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It’s always important to view things through a new set of eyes, so take it to new heights on your next day in a thrilling helicopter tour that will see you soaring above the magnificent New York skyline. This evening will change your perspective once again in a one-of-a-kind interactive experience that will see you taking to the streets in a theatrical bus ride that uses the city sidewalks as its stage. Intrigued? We promise this won’t disappoint.

No trip to NYC would be complete without a visit to Broadway, the musical center of the world. So take your pick from the popular all-time greats. Then, enjoy a toast to your time in NYC with a drink at Peninsula’s atmospheric Salon de Ning as the lights of the city twinkle below you.

Windy City wandering

Next stop, Chicago – a cultural US hub that’s home to improv comedy, jazz, blues and soul music. The Peninsula Chicago is where you’ll rest up for the next few nights, the discerning first choice in a city renowned for its imaginative art and design. Situated a stone’s throw from the city’s celebrated Magnificent Mile, if shopping is what you’re after, you couldn’t be better placed. What’s more, you’ll be staying in a luxurious and spacious room, with a fleet of chauffeured vehicles at your beck and call throughout your stay. Having undergone a recent renovation, you’ll find that the 331 suites and guest-rooms at the hotel are adorned in rich Macassar wood and feature hand-crafted pieces by renowned artist David Qian. So freshen up in your restyled abode before heading out for a guided tour through several of Chicago’s distinct neighborhoods and explore the famed architectural treasures of downtown, including some of the world’s first skyscrapers.

Take a light breakfast on your next morning and maybe squeeze in a swim in the Peninsula pool – you’ll want to work up an appetite for the day ahead. Today will see you exploring and enjoying the culinary greats that originated from this cultural melting pot, from deep-dish pizzas to Chicago-style hot-dogs and pastrami sandwiches – overindulgence at its finest.

It’s time to immerse yourself in that iconic Chicago skyline, and thanks to The Peninsula Chicago’s Keys to the City programme, you’ll be enjoying a variety of exclusive experiences. Think fast-pass access to The Art Institute of Chicago, culinary experiences and sunset views from 360 Chicago. And to finish up your time in the Windy City, head to The Willis Tower for a trip up to their stunning Skydeck on the 103rd floor. Be sure to step out onto the The Ledge, consisting of four all-glass boxes that you can step out onto for the ultimate viewing experience. Not for the faint-hearted, you’ll feel as if you’re floating over the sidewalk hundreds of meters below.

LA living

The home of Hollywood calls, so head to Los Angeles to discover a trend-setting global subwaypolis with a fascinating history and rich cultural heritage. Stay with the stars in The Peninsula Beverly Hills, one of Southern California’s best addresses. Recuperate from your journey by relaxing in one of the hotel’s poolside cabanas as you sip a signature cocktail. Equipped with flat-screen TV’s, i-pod docks and telephones, you’ll be amazed at how quickly time flies when you’re in the lap of luxury. Before you know it, the sun will be setting and it’ll be time to dine on the finest cuisine at the hotel’s Roof Garden.

Having woken feeling refreshed, meet your private chauffeur and allow yourself to be transported to the hottest spots in LA. Shop till you drop on Rodeo Drive and take a look around the Getty Center before working up an appetite with a hike in Franklin Canyon. Back at the hotel, treat yourself to a spa treatment and allow the staff to take care of your every wish before moving on to dine at the newly renovated Belvedere restaurant. With a Mediterranean-inspired menu (think locally sourced ingredients and the freshest seafood) and beautiful interiors, your evening will be both delicious and relaxed.

Your final few days will see you living the active LA lifestyle, with a horseback riding tour through the rolling Hollywood hills and a surf lesson from surfing world veteran John Philbin. Be sure to soak up your surroundings as you master those LA waves – this will be the magical memory that marks the end of your bi-coastal US tour.

Where to rest your head

The Peninsula New York

Located on the address of dreams, Fifth Avenue’s Peninsula hotel is a 1905 landmark building that exudes New York's opulent chic. Think grand lobby staircases,…
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The Peninsula Beverly Hills

If you’re looking for luscious gardens, spacious balconies, and palm trees swaying in the breeze, The Peninsula Beverly Hills is the place for you. The…
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The Peninsula Chicago

The fresh, bright feel of The Peninsula’s Chicago hotel makes it the discerning first choice in a city renowned for its imaginative architecture and design.…
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