Travel in Tuscany: Lessons from a Week in Montepulciano
Affogato - Italian for "drowned" - or, the best of both worlds and why I think the Italians have it figured out: a scoop of a gelato flavor of your choice, drowned in a shot of espresso.
Need I say more?
During a recent family trip to Tuscany to celebrate my daughter Claire and her new hubby's marriage, our group ranging from young adults to my 85-year-old parents experienced Italy for a week. Here are our highlights, local recommendations, and why Montepulciano might just be the secret to your next unforgettable European vacation.
3 Highlights in and around Montepulciano
1. Living Like a Local
For a full week, the hilltop town of Montepulciano became our home base. Staying right in town allowed us to skip the rushed tour buses and truly soak in the atmosphere—dodging local delivery vans on narrow cobblestone alleys, finding our early opening coffee shop, and enjoying endless views of the Tuscan countryside right from our apartment.
2. Authentic Farm-to-Table Dining
One drive led us to Podere il Casale, an organic farm and restaurant in the Tuscan hills. Dining on fresh, local ingredients while taking in sweeping valley views is an absolute must-do for anyone visiting the Val d'Orcia region. These are easy to find!
Photo credit @podereilcasale
3. Day Trips from our Italian "Home"
Siena: We caught the town buzzing with excitement as local neighborhoods prepared for the famous Palio di Siena horse race. After exploring the stunning Cathedral of Santa Maria Assunta, we beat the midday heat with the required local gelato.
Monteverde & Etruscan History: Exploring ancient 2nd-century B.C. Etruscan ruins and enjoying local wine and lunch at Zita at Monteverde offered a peaceful, crowd-free peak into Italy’s rich history.
Photo credit @monteverdituscany.com
Taking the time to stay in one place allowed us to slow down and truly absorb the local culture, which became my biggest takeaway from this trip. Another Italian city that won my heart, what will be next?
Concepts in the Types of Travel
Garešnica, Croatia, photo by Vladimir Srajber
Advocating for a type of travel that allows time to absorb, I thought about calling it SID travel:
S–Slow: Taking time to settle into a destination
I –Immersive: Connecting with local culture, food, & people.
D–De-tourism: Step off the beaten path to explore
While SID works as an acronym for a type of travel I enjoy, I rather like how foreign words describe the concept beautifully:
-In French, there’s the concept of the Flâneur—someone who wanders the streets aimlessly just to observe and experience the city
-In Spanish, Vacilando describes enjoying the journey and the wandering just as much as (or more than) the destination itself.
-In German, Fernweh is a longing for distant places.
Planning a trip around these concepts, travel becomes less about sight-seeing and more about life-changing experiences. I think I'll call it Vacilando Travel.
Tips for Planning a Multi-Generational Tuscan Getaway
Planning a trip with family members ranging in age from 20 to 85 requires thoughtful strategy:
1. Pick a Single Home Base: Renting an apartment or villa in a walkable town like Montepulciano gives everyone freedom to explore at their own pace without packing and unpacking.
2. Embrace Unscheduled Downtime: Leave open blocks of time for spontaneous gelato breaks, people-watching, or relaxing by the pool.
3. Master the Logistics: If you're renting a car in Italy, keep in mind that historic hill towns have narrow streets and tight parking. (Pro tip: Always back into your hotel parking spot—it will save you precious time during early morning departures!)
Ready to Experience Italy at Your Own Pace?
Whether you're dreaming of a romantic Tuscan escape, a multi-generational family milestone, or a slow-travel itinerary through Europe, Two Herons Travel is here to design a custom journey tailored to how you love to travel. Somewhere else on your mind? Let's talk about it!
steph@twoheronstravel.com 303-775-7128
