Luxury Travel Companies Are Building Custom U.S. Road Trips
AFAR reports that operators from Black Tomato to All Roads North are selling curated domestic road trips with five-star hotels, private guides, and fly-and-drive logistics starting in the five figures.
What happened
AFAR reported on September 29, 2025 that luxury travelers are increasingly booking customized U.S. road trips through high-touch travel companies, not just DIY van routes or budget motel runs.
Operators including Black Tomato, All Roads North, Untamed Travelling, and HunterMoss are designing itineraries with five-star hotels, private guided tours, and reserved dining in place of traditional roadside stops. All Roads North specializes in custom road trips starting around $15,000 and has recently routed clients to Yellowstone with private naturalist guides.
Black Tomato's Mary Cropper told AFAR that luxury domestic road trips in New England and the Southwest often average around $40,000 but can go higher, with clients choosing vehicle type based on terrain, from larger SUVs in the Southwest to convertibles on coastal New England routes.
HunterMoss, debuting U.S. road trip itineraries in early 2026, offers shorter curated trips such as a four-day Napa Wine Country package from $11,490 per person based on double occupancy and a Santa Ynez Valley weekend from $10,490 per person.
EXP Journeys offers a classic-car Highway 1 drive toward Big Sur from about $1,500 per person per day. AFAR tied the trend to rising domestic travel interest and travelers seeking independence on the road without sacrificing logistics, lodging, or insider access.
The Eastward Take
This is road-trip culture split into two Americas that rarely talk to each other.
One version is the family SUV, the Costco stop, and the argument about whether to leave at 5 a.m.
The other is a Black Tomato itinerary with a private Yellowstone naturalist and a hotel that remembers your name.
For Asian North American travelers who already spend real money on multi-generational trips, the interesting part is not the $40,000 average.
It is that domestic driving is being sold as a luxury product at all.
That validates something a lot of our readers already feel: the right car on the right route is not just transport.
It is the trip.
You do not need a concierge to apply the lesson.
Pick the vehicle that survives hour four, map one great stop, and book one meal worth detouring for.
The curated operators are selling planning and access.
Eastward Drive is selling the part you still own even on a budget: which car makes the miles feel intentional instead of endured.
Source
This note summarizes reporting from AFAR. Read the original for full details.