From Skyscrapers to Redwoods: A 17-Day USA Journey
Discover how a carefully planned 17‑day USA itinerary turned iconic cities like Washington DC, Chicago and San Francisco into a relaxed, joy‑filled adventure. From Amtrak trains and river cruises to redwood forests, wine country and even driverless cars, this story is packed with practical tips to help you see more of America without feeling rushed.
Planes, Trains, Boats and Driverless Cars: A 17‑Day USA Journey
If you have ever dreamt of “doing it all” in the USA without feeling as if you are in a race, this 17‑day journey is a perfect example. I helped my clients design a route that linked major cities, mixed planes, trains and boats, and still left room to slow down and savour the moments in between.
Across 47,696 kilometres, eight flights, an Amtrak train and multiple boat trips, the focus was on variety, clever logistics and just enough breathing space.
Major cities were linked by air, but one of the most memorable stretches was the Amtrak journey from New York’s Penn Station through Philadelphia to Washington DC, rolling into the grand Union Station. Travel became part of the experience, not just a transfer.
In Washington, a funky, modern hotel just a 15‑minute walk from Union Station made arrival simple. Self check‑in, relaxed social spaces and a late lunch set a fun, contemporary tone.
Tip: Mix transport types where you can. A train leg breaks up flights and lets you watch America unfold outside the window.
Tech that quietly does the hard work
A few apps can be very handy in getting around. MyTC App, a personalised travel companion, where itineraries, documents and booking details are kept in one secure place. All is well organised and up to date, and helps to stay in touch with me, your dedicated Travel Counsllor easily before, during and after a trip. Citymapper solved the “how do we get there?” puzzle, comparing walking, buses, trains and rideshares with times and costs. Lyft proved a safe, and reliable option, especially for late‑night tours when nobody wanted to be navigating unfamiliar streets.
Tip: Let navigation and ride‑hailing apps do the thinking so you can enjoy the journey, not the junctions.
Walking into history in Washington DC
A day of “walking into history” at the Library of Congress’ Thomas Jefferson Building. Marble, murals, the iconic dome and the Gutenberg Bible brought the story of America’s ideas to life. Knowing that Jefferson’s books helped rebuild the Library after the 1814 fire, and standing there during the 250th anniversary year of Independence, gave the visit extra emotional weight.
Tip: For headline attractions like this, free timed‑entry passes often need booking about a month ahead.
Chicago: skyline, river light and open‑air art
Chicago didn't dissapoint with its mix of architecture, water and food. An architecture boat tour revealed the skyline from the river, followed by Grant Park, Buckingham Fountain and the Taste of Chicago food and music festival.
From there it was on to Millennium Park and Cloud Gate (“The Bean”), a stroll past the Tribune Tower’s “vertical museum” of stones from around the world, and a cruise through the Chicago Harbour Lock to Lake Michigan, ending with fireworks over Navy Pier. An open‑top bus on the final day tied it all together: skyscrapers from new angles, the start of Route 66 and Chicago’s rich public art, including sculptures by Picasso, Calder and Abakanowicz.
Tip: In big cities, pair one water‑based view with one open‑top bus tour. You see more, walk less and still have energy for evenings.
San Francisco: hills, cables, redwoods and wine
San Francisco brought another change of pace. This is not a city to conquer on foot in a single day, thanks to those famous hills, so buses and the classic cable cars took centre stage, including a ride past Lombard Street, the “crookedest street in the world”. Overhead, electric transit wires and fully autonomous Waymo cars felt almost futuristic.
A day trip over the Golden Gate Bridge swapped city streets for misty hillsides, sparkling wines at Korbel, towering redwoods in Armstrong Redwoods State Natural Reserve and a relaxed tasting at Russian River Vineyards.
Tip: Balance clusters of urban days with at least one day in nature or wine country for a complete reset.
What this itinerary was all about
On average, there were 15,000 to 18,000 steps per day and a mix of flights, trains, boats and road transfers. Yet the overall feeling was not of ticking boxes, but of collecting stories: fireworks over Lake Michigan, mirrored skylines in polished steel, centuries of history in marble halls and the hush of a redwood grove.
With thoughtful planning and a tailor‑made itinerary, the USA does not have to be overwhelming. It can be a beautifully paced journey that lets you travel far and wide, then come home with thousands of photos and a sense that you experienced the country entirely on your terms. If you would like a USA holiday crafted around your own pace and interests, I would be delighted to help you design it.
