Many travelers assume summer is the ideal time for a cycling vacation. But across Europe and North America, the weeks before peak summer can offer some of the most rewarding riding conditions of the year.
Whether you are dreaming of tropical islands, coastal trails, ancient landmarks, or dramatic alpine landscapes, a winter cycling vacation lets you keep riding while discovering somewhere new. From the turquoise waters of the Florida Keys to summer scenery on New Zealand’s South Island, these destinations offer memorable ways to escape the cold and stay active.
Discover five extraordinary U.S. bike tours showcasing Glacier National Park, an iconic rail trail, welcoming mountain towns, Pacific Northwest islands, and the sparkling shores of the Great Lakes.
May and June bike tours come with some of the best rewards of the season, comfortable temperatures, fresh spring landscapes, and more room to enjoy the ride before summer crowds roll in. If you’ve been thinking about a cycling vacation, late spring is a wonderful time to go, especially on these five Discovery Bicycle Tours that pair scenic riding with charm, history, and easygoing adventure.
Our guides spend their days out on the road — leading rides, spotting wildlife, and watching guests fall in love with new places. They know which moments take your breath away, which trails deliver the best views, and where to find the perfect post-ride treat. Here are their top picks for 2026.
While your neighbors back north are shoveling driveways and scraping windshields, you're pedaling through Florida sunshine on one of America's most remarkable cycling adventures.
