A trip to the countryside completes your Tuscan itinerary. Overflowing with culture and history, Florence is the iconic urban gateway to Tuscany. Though many tourists will opt for two or three nights in the city of Michelangelo’s original David, the impressive Duomo, and the prominent Uffizi gallery, others may simply use it as a home base to branch out to the various towns throughout the Tuscan countryside; Pisa, Montepulciano, and Siena being among the most popular. You can buy Twitter likes right now! 

Undeniably, Pisa’s UNESCO World Heritage site tops a visitor’s Italian bucket list, but all too often, it’s a rushed visit—part of the experience is actually climbing the tower, and wandering around the square—but tours, and individual tourists, typically prefer to stop by for a quick photo for proof of visit before they carry on to another photoworthy town.

But there’s so much more to Tuscany than these quick pit stops! Though many tourists may not realize it in advance, it becomes obvious on the Walks Pisa and Lucca day trip from Florence. In one day, I was able to visit three different regions of the Tuscan countryside; a vineyard, a small religious town, and of course, the renowned Pisa.

The variation in landscapes and atmospheres of these cities and towns offer a compelling day trip, packed with history and experiences, rather than hopping from one overcrowded tourist trap to another. Here are four reasons to check out the itinerary:

Take a break from Florence

Less hectic than Rome, the capital city of Tuscany definitely swells during peak tourist season (June through August). Even in the off-peak months and shoulder season, Florence attracts tourists to experience its rich history and splurge on leather goods. Don’t get me wrong, I don’t dislike Florence, but if you go to Tuscany and only see this city, you’re missing out.

Tuscany is comprised of towns steeped in religion, culture, history and natural beauty that would be a shame not to explore while you’re in Italy. You’ll realize this as soon as you hop in your private transfer for the day, scooping you out of the bustling streets and into the rolling hills of vivid vines in the distance; the drive is an experience in itself.

Appreciate all of Pisa

With social media infiltrating the way we travel, a simple photo of the Leaning Tower of Pisa isn’t enough. It’s become an unspoken competition to snap the best shot, no longer just a smile with the leaning monument. During our tour, I noticed that people were spending their entire time snapping photos, trying to get the best shot possible, therefore, missing out on the entirety of the world heritage site.

That’s right, what many visitors don’t realize is the entire Pisa square, the Piazza del Duomo, is a UNESCO site. This includes the cathedral (the Duomo), the baptistry, the campanile (now known as the Leaning Tower of Pisa) and the cemetery. The four monuments were bestowed the UNESCO title in recognition of their symbolism of 11th- to 14th-century architecture.

So sure, the tower steals the show, but on this Walks Tour, you can actually appreciate the history as well as delve into the symbolism of this piazza.

Unwind at an intimate winery

When you’re in Italy, you can get quality wine practically anywhere; from the inexpensive house wine at a hole-in-the wall off Campo di Fiori in Rome, to exclusive labels in a Michelin starred restaurant on Capri. But it’s the wine experience that truly elevates a trip to Italy; and there’s no better place to garner that experience than in the Tuscan countryside.

After a couple hours of walking around Pisa, the tour moves to an intimate winery in Montecarlo (Italy, not France!). Draped in wisteria amidst rows of vines, the team at the winery welcomes you to their family-run, small production vineyard with an introductory tour to their unique blends.

The property is most renowned for their Vin Santo, which is aged in the winery’s old kegs for five years. Over lunch, you’ll have the chance to try the Vin Santo, along with three of the winery’s other varietals.

Again, it’s all about the experience so your wine is paired to your courses; from antipasti and unsalted bread (in old times, Tuscany didn’t have access to salt, so they weren’t able to make bread with salt—today most places haven’t re-added it to their recipes) to the pasta and meat course. It’s like discovering a lost Italian relative as the team at the winery makes you feel at home.

Visit a less tourist-run town

The last stop on this day tour is Lucca. En route back to Florence, it provides the perfect opportunity to sit back and daydream at the picturesque Tuscan hillside—especially after indulging in wine and pasta.

Upon arrival, take in the city and its renaissance buildings from the ancient city walls (16th- to 17th-century) then enter into the heart of it all. Wander under the intricate, original facades of Church San Michele in Foro and the Basilica of San Frediano.

As you stroll through the quiet cobblestoned streets, you’re transported back in time, walking in gladiator’s footsteps to end at the town’s center, and former colosseum. Today, compact, pastel apartments occupy the former seating plan, looking down onto the al fresco seating, perfect for an espresso or Aperol Spritz.

You’ll have free time to enjoy this flow of life, so put down your camera and live like a local would. As you anticipate heading back to Florence, Lucca may just spellbind you to stay behind, or at least return if not for a second trip to its tranquil town, then to explore even more of the Tuscany region


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