May 2026 Adventures in North America
Time your adventure perfectly with 500 tours departing in May 2026 in North America. Seasonal highlights and optimal conditions await, backed by 2,600 verified experiences.
Route 66 From Chicago to LA - 12 days - May 2026
Hit the open road on a westbound adventure along Route 66, from the skyscrapers of Chicago to the sun-soaked shores of Santa Monica. This 12 day tour isn’t just about the miles - it’s about the stories behind every roadside diner, neon sign, and quirky small town. Walk in Lincoln’s footsteps in Springfield, explore the depths of Meramec Caverns, stand beneath the Gateway Arch, and snap a photo at the Cadillac Ranch. From blue whales in Oklahoma to wild burros in Oatman, this is classic Americana at its most vivid. With iconic sights, local eats, and a deep dive into the soul of the Mother Road, it’s a one-of-a-kind road trip through the heart of the USA.
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