Hey First name / friend,

 

In the dynamic world of travel, we often have to make our best guesses about the future. Sometimes I agree with the masses, other times I have my own, less popular opinions. When it comes to avoiding mass tourism and events that may be more frustrating spectacle than fascinating cultural display, I opt to steer travelers in the other direction.

 

This year, I said Italy might not be the best idea due to the Jubilee. A lot of travelers heeded that advice from the industry, and it seems poor Italy hasn't gotten the abundance of love we all thought it would.

 

So today, let's go to the heart of Italy and consider putting this one back on your radar for fall. Below are a few standout stays in Tuscany and Umbria to get you inspired.

 

Want more? Click the link below for our detailed guide with restaurant picks, experiences, and gorgeous hotels. We've even added some alternative destinations if you're not feeling Italy this year but still crave the slow, endlessly romantic landscapes and historic elegance that this region provides.

 

Tip: if you're last minute, there's still some late summer availability in Tuscany. Read to the end for those.

Borgo Santo Pietro — For those who want to play farm-to-table fantasy without getting their hands dirty (unless they want to). This 13th-century villa turned luxury estate is where hoteliers spent seven years building an organically-cultivated working farm, artisan cheese dairy, and two vineyards, basically creating their own self-contained Tuscan universe. Their sheep's milk becomes the Seed to Skin skincare line in your room, their gardens supply the Michelin-starred restaurant, and you can take cooking classes using ingredients grown steps from your suite. 

 

It's ambitious and beautifully executed, though decidedly more curated experience than authentic discovery. Perfect for special occasions when you want maximum Tuscan luxury with zero effort required. Learn more here.

Borgo Pignano — Ideal for families, creatives, or wellness seekers who want to go off the beaten path. This eco-estate feels like its own enchanted world — 750 acres of wildflower meadows, organic gardens, and olive groves. Stay in a villa or farmhouse, take an art class, explore trails on horseback, or indulge in a Tuscan cooking class.

 

Located near Volterra and San Gimignano, it’s peaceful, inspiring, and totally unique. Learn more here.

Vocabolo Moscatelli — For travelers who want genuine connection over polished perfection. This 12-room property in an 800-year-old monastery feels refreshingly unpretentious. Think spirited hospitality that's "a bit crazy" mixed with mid-century Italian design and hemp linens. The owners describe their approach like welcoming family, and it shows in thoughtful details like handmade colorful tiles and locally crafted furnishings. 

 

Set in a quiet valley near ancient oak forests, it's where you feel the "green heart of Italy beat" rather than just another beautiful backdrop. Located near the Tuscan border, it's intimate, authentic, and wonderfully human. Learn more here.

If Italy is calling sooner, here's your break — these properties in Tuscany still have openings this summer. Each offers something unique, and all come with perks when you book them with me (a complimentary service if you know which hotel you'd like booked):

The challenge? They're all so beautiful!! How do you know which is right for you? This is exactly where a travel advisor makes all the difference — minimizing the risk of you second-guessing your choices. 

 

Whether you're planning a romantic escape, multigenerational family trip, or countryside retreat with friends, I'll do what I do best: match you with the perfect blend of wine, culture, wellness, adventure, or that slow Italian pace you're craving. 

 

👉 P.S. I have a couple of planning slots open later this month. Want to grab one? Book a discovery call below and let's get started.