A station wagon filled with coolers, road maps gathered from your local AAA office, and energetic children snacking excessively is how my family used to travel when I was a kid. The Great American Road Trip has always had a unique spot in domestic travel, but things have evolved significantly over time, and taking a DIY vacation in your own car is no longer the only option.
Exciting road trips are now highly desired by affluent travelers, just as they are by those living in vans and carrying backpacks. Several companies are enhancing the journey significantly beyond what most travelers could manage independently, providing personalized itineraries that replace roadside motels and quick meals with top-tier lodging, private tours, and gourmet dining options. Travel agencies are focusing on sophisticated travelers who seek the freedom of the open road combined with some luxurious elements throughout their trip.
In addition, the increase in local travel is contributing to this trend, partly because ofreducing international air travel demand due to global instability, and a worry for certain travelers aboutanti-American sentiment abroad, road trips are gaining new popularity. Although clients of such companies as Black Tomato, All Roads North, Untamed Travelling, and HunterMoss(the latter of which will unveil its U.S. tour schedules in early 2026 following years of preparation) are not likely to be discouraged by the increasing expenses of international travel, Sam Highley, CEO of All Roads North, stated that the company has observed a shift in travel trends—fewer international tourists visiting the USA, and a rise in local travelers drawn to the Wild West.
These days, “everyone wants to be a cowboy,” remarked Highley.All Roads North, which focuses on personalized road trips beginning at $15,000, has recently been creating travel plans that bring visitors to Yellowstone National Park, where “they could be picked up from their hotel by a private naturalist and driven into the park,” for a unique experience. The tours involve driving on your own, but are enriched by experts who guide guests further into the destination.
“The goal is to preserve the best method of traveling in the U.S., the freedom and unexpected discoveries that make it exceptional,” stated Highley, who started exploring the country’s marvels over 15 years ago when he relocated to California from the United Kingdom.
Untamed Travelling, which began in 2001 as a safari expert and has now grown to offer trips to over 150 locations, has also witnessed the United States becoming a top choice for its travelers. From 2022 to 2024, the USA was consistently within the operator’s top five global destinations, with almost all trips to the country planned as road journeys.
Travel expert Mary Cropper inBlack Tomato, who has been organizing domestic trips for nine years, has recently been arranging many high-end road journeys in New England (the fall leaf season is a major attraction for road travelers) and in the Southwest.
The journeys, which typically cost about $40,000 but can increase significantly, are completely tailored. A lot of Black Tomato’s customers value staying in five-star hotels with excellent facilities, although “there might be one or two nights at a hotel in a national park, which is usually more basic,” Cropper said, noting that she always goes over these details with clients to grasp their “priorities and plan the right itinerary.”
Regarding the type of vehicle (many of these are fly-and-drive trips where customers fly to a nearby airport and then rent a car for the road journey), it really comes down to your preferences. “If you’re in the Southwest, that’s more desert terrain with some rocky areas, so a bigger car might be better. If you’re traveling along the coast of New England, a convertible could be really enjoyable,” explained Cropper.
Customers of All Roads North, according to Highley, are typically not car enthusiasts looking for the ideal Lamborghini to drive for a week. Instead, they are travelers seeking authentic experiences that come from interacting with locals who have a deep understanding of the area. Every aspect of the trip—duration, daily driving limits, type of lodging, dining reservations for each meal, or even recommendations for food and drinks along the way—is planned and arranged ahead of time.
“My very first question is: How much time are you prepared to spend in the car? Do you have a few days where you can handle a journey of five or six hours?” Cropper asked. The responses to these questions determine the entire trip.
For individuals seeking the essence of a road trip experience with reduced driving time, there’sHunterMoss, who focus on luxury vehicles and in-depth travel experiences.
The company offers U.S. road trips, including a four-day escape to the Santa Ynez Valley ($10,490 per car/couple) and a four-day experience in Napa Wine Country ($11,490 per car/couple), where “every detail from the moment guests arrive to when they leave is carefully handled,” according to co-founder Julie Hunter. These trips cover less distance than those of other companies but focus on deeply immersing travelers in the location. Traveling with elegance is essential.
Unlike the tailored journeys designed by Black Tomato, All Roads North, and the inclusive travel options that welcome all budgetsCrush Global, HunterMoss’s new supercar adventures occur on specific dates and include a small group of approximately 12 people. Each group drives the fleet—Aston Martins, Lamborghinis, Ferraris—on their own, but no previous experience with high-end cars valued at a quarter of a million dollars is necessary.
It’s not only about the vehicles, said Hunter. “It’s truly about integrating the distinctive features of the selected location, whether it’s the major emphasis on food and wine in Napa Valley or the powerful art focus in Santa Fe, and striving to create a pleasant and well-rounded experience that isn’t solely for drivers.”
“It’s somewhat like elevating the road trip to a higher degree,” said co-founder Anthony Moss. “Everything is carefully selected. Everything is organized—lunches, coffee breaks… people can arrive and have a good time without worrying too much about the specifics,” Moss added.
Other companies offer a unique approach to the road trip vacation. That’s true ofEXP Journeysa travel company that focuses on national parks and exclusive, engaging luxury vacations.
Kevin Jackson, one of the founders of EXP Journeys, mentioned that they have been observing an increase in structured and organized road trip options. This includes a particular experience where participants take the wheel of vintage vehicles such as Porsches, Thunderbirds, and Corvettes, and travel along the coastline via Highway 1 to Big Sur, at a cost of $1,500 per person each day.
Today, as more local travelers seek to discover remote parts of the country, they are flying into the area (sometimes through)private aviation) and taking the driver’s seat in a vehicle of their preference (or entrusting themselves to a private driver and knowledgeable guides), to start a well-organized travel journey with unique benefits (and pre-arranged car snacks, naturally).
