Marking 100 years of Route 66, this three week self drive journey crosses eight states and traces the original “Mother Road” from Chicago to Santa Monica, mixing big cities, small towns, desert landscapes and classic Americana along the way. With handpicked stops, city hotels and time in Santa Monica at the end, it’s a nostalgic and varied way to experience the full length of the historic highway.
Route 66 traditionally begins at Jackson Boulevard in Chicago, where downtown streets and art deco buildings set the tone for the start of the journey. Spend a night here to get your bearings before collecting the car, with time to walk along the lakefront, visit Millennium Park or enjoy the skyline views. Leaving the city marks the symbolic beginning of Route 66 as you head south towards St. Louis.
Spend two nights in St. Louis, staying downtown within easy reach of the Gateway Arch, riverfront and local neighbourhoods. This stop helps ease into the pace of the road trip, with plenty to explore on foot, from museums and historic streets to barbecue joints and jazz bars. Crossing the Mississippi River the following day reconnects you with the historic route as you continue into the Midwest.
A one night stop in Springfield brings you into small town America and the heart of Route 66 country. Classic diners, museums and roadside signs tell the story of the early years of the highway, while the compact centre makes for an easy evening after a day on the road.
Arrive into Tulsa for one night, with time to settle into the downtown area and enjoy its mix of art deco buildings and music heritage. It’s an easy city to navigate, with neighbourhood restaurants and bars close by, before continuing deeper into Oklahoma the next day.
Spend two nights in Oklahoma City, where the Bricktown area centres life around canal paths, ballparks and an open, walkable district. This is a good place to take a break from long driving days, with time to visit museums, urban parks or simply enjoy the easier pace of the Midwestern stretch of the route.
Crossing into Texas brings you to Amarillo for one night, a natural stop known for its roadside attractions, western culture and wide open landscapes. This marks the transition into more arid scenery and the beginning of the Southwest portion of the route.
Two nights in Santa Fe offer a clear change in atmosphere, with adobe buildings, galleries and mountain scenery replacing the plains. The historic centre is walkable, and the high desert backdrop gives this part of the journey a distinct regional character, making it a highlight for many travellers.
Continue along Route 66 to Albuquerque for a two night stay downtown. Old neon signs, diners and motels nod to the road’s heyday, while the city offers viewpoints, local markets and desert scenery on its doorstep. Evenings are relaxed, with plenty of places to eat nearby.
A one night stop in Gallup places you close to the state line and the iconic mesas of western New Mexico. The town has long served as a base for artists, traders and travellers, giving it a layered cultural history that ties neatly into Route 66’s past.
Spend two nights in Flagstaff, a mountain town surrounded by pine forests and wide desert views. Its position makes it useful for side trips to national parks or simply enjoying the high elevation scenery and local craft breweries. Cooler temperatures and clear skies make it a refreshing change after the low desert.
One night in Kingman brings you back into long-distance driving territory, where roadside diners, motels and wide roads recall the classic imagery of 1950s Route 66. It’s a relaxed stop with enough local history to keep things interesting without complicating the day.
Continue into California for a one night stay in Barstow, a railway and highway town that marks the final stretch towards the Pacific. It’s a functional and atmospheric stop on the original corridor, surrounded by desert landscapes and historic rail lines.
Finish with three nights in Santa Monica, where the Route 66 “End of the Trail” sign sits by the pier overlooking the Pacific Ocean. Here, the journey slows down, with time for beach walks, shopping, relaxed dining and visits into nearby Venice or Beverly Hills. After three weeks of varied landscapes and towns, the oceanfront setting provides a fitting finish before flying home from Los Angeles.
Return flights from Dublin to Chicago and home from Los Angeles with Aer Lingus, 3 week Route 66 self drive itinerary with pre booked accommodation throughout, daily car hire for the full duration with inclusive insurance, and all necessary documentation and route notes. Based on 2 passengers sharing. Flights depart Dublin 07 April 2026. Price correct at time of posting 13 January 2026. Offers subject to change.
Price from €3,650 per person
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