The Lowdown

This is a 5-day adventure, running from April to October 2025, when Tuscany’s weather is basically perfection—think warm days and cool evenings. You’ll cover about 30-50 km a day, with enough rolling hills to keep things spicy but not so tough you’re cursing your life choices. The guided tour costs $2,000, which gets you a local guide who’s basically a walking encyclopedia of Tuscan history, plus a support van for snacks and gear. Want to channel your inner lone wolf? The self-guided option is $1,400, with detailed maps, GPS routes, and tips to keep you on track. Either way, you’re in for a treat.

The Landscape

Tuscany’s like a dream you don’t wanna wake up from. The rolling hills are gentle enough for most riders but still give you a decent workout, with smooth, cypress-lined paths winding through endless vineyards and olive groves. You’ll pass golden fields, ancient stone farmhouses, and those iconic Tuscan hills that look like they were sculpted just for Instagram. The roads are mostly paved, with some gravelly bits thrown in for character, and every turn feels like it’s begging you to stop and snap a pic. Towns like Siena and San Gimignano, with their medieval towers and cobblestone streets, are the cherry on top.

What’s It Like to Ride?

This tour’s rated moderate, so it’s great for folks who cycle regularly but aren’t out here training for the Olympics. Expect some uphill grinds—nothing too brutal, maybe 300-500 meters of elevation gain per day—but the descents are pure bliss, letting you coast through scenery that’ll make your heart sing. You’ll pedal through quiet countryside, past locals tending their vines, and into historic towns where time seems to have stopped in the 14th century. Guided tours come with a support crew who’ll handle your luggage and keep you fed with local treats. Self-guided riders get a slick itinerary with all the routes and recommendations, so you can explore at your own pace.

Local Tips to Make It Epic

Trattoria time: Stop at small, family-run trattorias for fresh pasta dishes like pappardelle al cinghiale (wild boar ragù). They’re usually tucked away in villages, and the food’s so good you’ll wanna move to Italy.

Lock it up: Bring a small bike lock for when you’re chilling in towns like San Gimignano. Parking your bike outside a café is fine, but a lock keeps it safe while you sip an espresso.

Wine o’clock: Tuscany’s Chianti and Brunello wines are next-level. Most vineyards offer tastings, so plan your stops—your guide or itinerary will point you to the best spots.

Sun protection: The Tuscan sun doesn’t mess around. Slap on sunscreen and wear a breathable hat for those midday rides.

A Quick Look at the Itinerary

You’ll start in Florence, the cradle of the Renaissance, with a short ride out to the countryside to get your legs warmed up. Day 2 takes you through the Chianti region, where you’ll pedal past vineyards and stop for a wine tasting (or two). Day 3 is all about San Gimignano, with its famous towers and gelato that’ll ruin you for all other ice cream. Day 4 brings you to Siena, where you can explore the Piazza del Campo and refuel with a massive plate of ribollita (Tuscan soup). The final day loops you back toward Florence, with a leisurely ride through olive groves and a farewell dinner featuring—you guessed it—more wine and pasta. Guided tours include luggage transfers and daily briefings; self-guided folks get a detailed packet to keep you rolling smoothly.