Agents on the Open Road: RoadTrips USA Edition – Iconic Cities and Beyond

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Welcome to Brand USA’s Agents on the Open Road: RoadTrips USA Edition, in partnership with Travel Gossip and Gold Medal.

U.S. road trips are on many people’s bucket lists, and helping a client plan a trip needn’t be daunting if you use the expertise of Brand USA. Between now and October, on the first Friday of each month, we’ll be bringing you a new itinerary from the RoadTrips USA collection on the Brand USA website.

Each month, we’ll also speak to an agent who has done a similar itinerary, to get their insight, hints and tips.

And, at the end of each monthly feature, there will be a question. Agents who answer the questions correctly will enter a grand prize draw to win a £5000 Gold Medal voucher that can be redeemed against any 2025 Gold Medal package holiday, as well as a £50 One4All voucher being up for grabs each month.

There are more chances to win prizes, through a fun online game called RoadTrips USA Rally Challenge, which launches on 4 July – to coincide with Independence Day in the United States. During the six weeks the game runs for, agents will have to drive through the changing landscapes of the USA, avoiding obstacles, and collect coins during the journey. The three agents that hold their place at the top of the leaderboard at the end of the six weeks will win a first prize of £150, second prize of £100 and third prize of £50.

Here’s the first itinerary: Iconic Cities and Beyond, covering Massachusetts, New York, Pennsylvania and Washington, D.C.

Boston, day 1 and 2

The best place to start is on The Freedom Trail’s 16 historic steps, including the famous Old North Church, Paul Revere House and Faneuil Hall Marketplace. Then, spend a day at the Museum of Science, the Isabella Stewart Gardner Museum or the Nichols House Museum.

Walk across the Charles River on the Longfellow Bridge or take the ‘T’ (subway) to charming Cambridge, known locally known as ‘the City of Squares’, and ivy-trimmed campus of Harvard University and Massachusetts Institute of Technology.

For shopping, Newbury Street in the affluent Back Bay, has high-end boutiques; Copley Place is a two-level mall with top brand-name stores. South Boston, known as Southie, is a newly emerging Seaport District, with restaurants and cruise tours.

Sports fans can watch a Boston Red Sox baseball game (April-October), or take a tour of Fenway Park, the oldest Major League baseball park in the country.

New York City, day 3-5

See a Broadway show, visit museums and view the city from on high – from the  Empire State Building’s open-air observatory; Top of the Rock at Rockefeller Center or the One World Observatory’s 100th floor.

Then explore the ethnic and cultural diversity of New York City’s five boroughs, such as Greek food from Astoria in Queens; dim sum in Manhattan’s Chinatown; Russian dinner in Brighton Beach, Brooklyn; pizza in Staten Island and Little Italy in the Bronx.

Sports fans can catch a New York Yankees baseball game in the Bronx or a Mets game in Queens; see U.S. Open Tennis matches at the Billy Jean King National Tennis Center; or a New York Rangers or New York Islanders hockey match.

Philadelphia, day 6 and 7

Take a selfie at the famous LOVE statue, the ‘Rocky Steps’ at the Museum of Art or try a Philly cheesesteak sandwich. Visit Independence Hall National Historical Park, home to the Liberty Bell and Independence Hall, where the U.S. Constitution and Declaration of Independence were signed.   

Philadelphia is home to an astounding collection of museums, artistic venues and historical attractions, including the Ben Franklin Museum. Here you can learn about one of the Founding Fathers of the USA. View classical works by Renoir, Cézanne and Picasso at the Barnes Foundation or at the Philadelphia Museum of Art; dine al fresco at Rittenhouse Square; browse more than 400 shops and restaurants at the King of Prussia Mall.

The Reading Terminal Market, the USA’s oldest farmers market, is one of the city’s most popular attractions.

Washington, D.C., day 8-10

A trip to the National Mall, which encompasses the Washington Monument, Lincoln Memorial, the U.S. Capitol and more, is highly recommended, as is the National Harbor with its lively waterfront.

Take a water taxi from Georgetown to Virginia by crossing the Potomac River to Old Town Alexandria’s charming historic district that dates to the 18th and 19th centuries; and visit the Arlington House, once the home of Confederate Gen. Robert E. Lee, as well as Arlington National Cemetery for a moving experience.

Head back to Washington, D.C. to the revitalised Southwest Waterfront, which is the home of the Washington Nationals baseball team, and check out the buzzy restaurant and bar scene.

Agents’ views

While it’s possible to do this trip by road, Brand USA suggests an alternative way is via the Amtrak rail route, as West Lothian-based Personal Travel Expert Greig Ewins did.

“Our boys were 13 and nine – a good age to do this trip. We had travelled to New York before as a family but definitely prefer it as a destination in the summer for just wandering around parks, sightseeing and visiting rooftop bars. We also had a rooftop pool. We went to a Liverpool pre-season game at Yankee Stadium which was great.

In D.C., Washington Zoo was fantastic and our youngest loves pandas, so it was great to see them. It is free to enter, as were quite a few of the museums that we visited. The Holocaust Memorial Museum and National Museum of African American History and Culture were really educational. 

Philadelphia was great to learn about American independence and there was a big Marvel exhibition on, which the boys loved. We did a bus tour round the main sights, which I’d highly recommend, along with racing your kids up the Rocky steps. We also liked the shopping in Philly as it is tax free and has big stores, like Macy’s, too.

We took the Amtrak and booked in advance, so fares were very reasonable. We wanted the experience of travelling by land so we could see what the scenery was like going city to city, which was mixed between very industrial and nice countryside and it was great going over some of the rail bridges too.

Travelling downtown to downtown is so convenient; everyone gets a seat, although if you travel coach/economy seats aren’t reserved, so it’s best to be at the departure gate early.  We loved the big grand stations of Philly and DC. We would definitely do Amtrak again.”

Gavin Morton, Managing Director at Usher Travel Service, Wallasey

“From NYC, we travelled up to Boston – it just happened to be over St Patrick’s weekend, so we enjoyed the ‘hospitality of the city’ extremely well in between visiting the historic tourist sites.

We also managed to get last-minute tickets to watch the Boston Bruins playing ice hockey at the Boston Garden, a loss, but everyone seemed in high spirits, regardless. Boston was a great experience. I really enjoyed the almost European feel to the place, especially around the Faneuil Hall and Quincy Market area.

In D.C., I was surprised at how many of the major museums and art galleries were free of charge to enter and a trip to view the White House was a must. Georgetown, with its ‘olde world’ atmosphere was lovely to wander around, the Lincoln Memorial was extremely impressive and a trip out to see the grave of JFK in Arlington ended my trip there. Being an embassy city, the choice of different world cuisines on offer is astounding.

I’ve used my experience to book plenty of clients on similar holidays and have always had positive feedback. For me, visiting the East Coast between April to June and also September and October bring out the best in the region and steers clear of the stifling heat that can descend in the height of summer.”

There are plenty more road trip suggestions on the USA Itineraries section of the Brand USA website.
Also check out the newly refreshed Brand USA training platform.

From £2,399pp on 14 March 2025, including direct return flights, nine nights’ accommodation and Amtrak Coach Class.
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To book this or any USA RoadTrip itinerary, call 0800 014 7777 or visit

Answer this month’s question to enter the draw

Please read the itinerary here to find the correct answer.

The closing date to enter this month’s draw is 6 June 2024. View the competition Terms & Conditions.

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