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“Over the past few weeks, I’ve been working on several custom Tuscany itineraries, and I’ve noticed they almost all begin with the same wish list.” Almost every itinerary starts with the same wish list: Rome, Florence, and Tuscany. And I completely understand why. If it’s your first trip to Italy, it’s tempting to fit in every place you’ve dreamed about visiting. The challenge isn’t choosing where to go. It’s giving yourself enough time to truly experience each destination. Each deserves time to be experienced, not simply checked off a list. Florence is much more than a stop between cities—it’s one of Italy’s great cultural destinations and the perfect gateway into Tuscany. Spend a few days exploring its Renaissance masterpieces, lively piazzas, markets, and incredible food before heading into the countryside. Then comes Tuscany. And that’s where the pace changes. One of the biggest pieces of advice I give clients is this: You’ll almost always come home wishing you had more time—not fewer destinations. Instead of changing hotels every night, choose a countryside base and spend your days exploring places like Siena, San Gimignano, Montepulciano, Pienza, Montalcino, or the Chianti wine region at a relaxed pace. Tuscany isn’t a destination that rewards rushing. It’s a destination that rewards lingering. Many travelers underestimate how much time transportation adds to a trip. It’s not just the drive between destinations. Every hotel change means checking out, finding parking, navigating unfamiliar roads, walking to and from train stations, waiting for buses, and unpacking all over again. Those hours quietly become part of your vacation. I’d much rather spend them lingering over lunch in a medieval piazza, discovering a family-owned winery, taking the scenic road simply because it looks inviting, or wandering a quiet hill town without looking at the time. Those are the moments people remember long after they return home. The best Tuscany itineraries aren’t the ones that see the most places. They’re the ones that leave enough room to truly experience the places they visit. If you’re beginning to plan your own Tuscany adventure, I’ve put together a free Tuscany Travel Guide filled with routing ideas, favorite towns, and practical planning tips to help you create an itinerary that feels relaxed instead of rushed. “If you’re planning a trip to Tuscany—or anywhere in Italy—and would like help creating an itinerary that’s thoughtful, relaxed, and built around the way you like to travel, I’d love to help.” The best Italy itineraries aren’t measured by how many places you visit. They’re measured by how deeply you experience the ones you do. Buon Viaggio, Dan Eubank Nomad With Dan P.S. If you’re planning a trip to Italy this year, don’t forget to review the practical details before you go. My new Travel Essentials → page includes the latest Italy entry requirements, along with travel insurance information, packing resources, and other planning tools I’ll continue adding to help make your trip even smoother. If you’re planning an Italy trip, you may also enjoy these destination guides: Explore Rome → Explore Florence → Explore Tuscany → Explore Verona → One more Tuscany tip: Leave room for the unexpected. Some of the best days aren’t planned at all—they’re the ones spent lingering over lunch in a hill town, discovering a quiet vineyard, or taking the scenic road simply because it looks inviting. Also confirmed: long lunches in Italy are still undefeated. “Planning Italy becomes a lot easier when you have someone helping you slow things down and experience it more intentionally.” Start Planning with Me → If you ever reply to this email, it comes straight to me.
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