Chicago: The Perfect City Break

I started in Chicago, a city that blends culture, architecture and big-city energy perfectly.

From ticking off “The Bean” in Millennium Park to gliding along the Chicago River on an architecture cruise, every moment felt iconic. A highlight was cheering on the White Sox at a baseball game and soaking up the local passion for sport.

Evenings meant skyline views and cocktails at 360 Chicago’s CloudBar, high above the city lights.

Chicago is ideal for a vibrant, experience-packed city break, whether you are travelling as a couple, with friends or building it into a wider USA itinerary.

Springfield, Illinois: History and Route 66 Charm

Next came Springfield, Illinois, where Route 66 nostalgia meets key chapters of American history.

The day began at the Ace Sign Company, a fascinating look behind the scenes of neon signage and classic roadside Americana. I then delved into the life and legacy of Abraham Lincoln at the Presidential Museum, which brings history to life in a very engaging way.

Dinner was a classic Route 66-style experience at Motorheads, surrounded by vintage memorabilia that really captured the spirit of the road. I finished the day at the famous Route 66 sign, a fitting moment on this legendary highway.

St. Louis: Iconic Landmarks and Memorable Moments

Arriving in St. Louis on a Cardinals game day was the perfect introduction, with the city buzzing.

We kicked off with excellent BBQ at Salt + Smoke before visiting the Cardinals Hall of Fame for a great insight into the city’s sporting heritage. Then it was time for the city’s most famous landmark: the Gateway Arch. Standing beneath it, you really appreciate its scale, and travelling to the top for panoramic views over the Mississippi was a standout moment of the trip.

The day continued with a private tour of the St. Louis Art Museum before ending at The Gin Room, a stylish spot to unwind.

Day two began at Spencer’s Grill in Kirkwood, a classic Route 66 diner, followed by a tour of the Budweiser Brewery. A tornado alert briefly paused our visit, making it an experience I certainly will not forget. Once the skies cleared, we carried on with lunch at the popular Balkan Treat Box and rounded things off with Ted Drewes’ famous frozen custard.

Route 66: Classic Americana All the Way

Continuing along Route 66, I crossed back into Illinois for the final stretch.

Highlights included the beautifully restored Ambler’s Texaco Gas Station in Dwight, the towering Gemini Giant in Wilmington and the Joliet Area Historical Museum and Route 66 Welcome Center. It was the ideal place to reflect on just how special this route is.

Route 66 offers something truly unique. Whether you drive it end to end or weave shorter sections into a wider itinerary, it adds nostalgia, character and that unmistakable Americana road-trip feel.

Seattle: A Fitting Finale

The final stop on my Brand USA journey was Seattle, a cool and creative contrast to the Midwest.

We started with big views from the Seattle Great Wheel and an immersive FlyOver experience that showcased the landscapes of the Pacific Northwest. At Pike Place Market, I joined a hosted experience at Atrium Kitchen, sampled local flavours and watched the famous fish throwing in full swing.

Other highlights included visiting the original Starbucks, a scenic boat trip and the stunning Chihuly Garden and Glass, which is a must for anyone who loves art and design.

We rounded things off with two of Seattle’s most iconic experiences: riding the Monorail and taking in the sweeping city views from the top of the Space Needle. It was the perfect finale to an unforgettable journey.

Why This Trip Matters for My Clients

This journey really underlined how diverse the USA is, with something for every style of traveller: big-city thrills, historic routes, foodie finds and coastal culture.

Because I have now experienced these places first-hand, I can offer:

Honest, personal recommendations based on what I have actually seen and done
Insights into the best areas, neighbourhoods and experiences, not just the obvious highlights
Tailor-made itineraries that match your pace, interests and travel style
Access to trusted partners and special experiences that help make your trip feel unique

Ready to Plan Your Own USA Adventure?

I have travelled to the States more than 15 times and still find something completely different on every visit. Whether you are drawn to Chicago’s buzz, the nostalgia of Route 66 or the culture and scenery of Seattle, I would love to help you create a trip that reflects what you love to see and do.

From short city breaks to multi-centre road trips, I can design a personalised USA itinerary that fits your wish list, budget and timings, and support you every step of the way.

If this has sparked some ideas, get in touch and let us start planning your own unforgettable USA journey.