1. Tucany Villa Vacation

There are tours where you’re a number on a roster. And then there’s this.
 
Our Tuscany Villa Vacation takes a maximum of 12 travelers — small enough that you’ll know everyone’s name by dinner the first night. No rushing to keep up with a crowd. No waiting for stragglers. Just a handful of like-minded people exploring Siena, Volterra, and Lucca together at a pace that lets you actually breathe.
 
Seven nights at a hilltop vineyard villa. A private pool. Sweeping views you’ll want to sit with for a while.
 
September 3–12, 2026 · From $3,959 + air
TTTD readers- $100 discount until June 20, 2026

2. Volterra – Deep Dive into this destination

Volterra is my favorite Tuscan hill town and the perfect place for a visit. Not too big, not too crowded, and certainly not loaded with tacky tourist shops; it is authentic in every way. It is a beautiful town surrounded by ancient fortifications, guarded by an impressive fortress, and perched high on a hill overlooking the fertile fields of western Tuscany. Visiting here tends to make you forget about touring and focus on settling into the laid-back lifestyle of the local folks.

It’s hard not to “go local” with a visit to the market or a stop at the neighborhood bar to knock down an espresso. Engage in conversation with the shopkeepers and get lost wandering the narrow, cobbled streets. On the town square, enjoy a crisp glass of wine at a café and then hang out for the late afternoon passeggiata where everyone gets out to visit.

Read more and get my exclusive Destination Guide

3. The COVID-19 Pandemic recovery- Volterra

#TravelTalkTuesday tonight features Volterra, Italy, and the surrounding countryside. We’ll set up for a few days at Podere Marcampo, my favorite villa-agriturismo in the area. Volterra itself is a treasure, with not much tourist traffic, old cobbled streets, good dining, and fine wine!

Tuscany – September 3-12, 2026

$100 discount for TTTD patrons!

More info here

Please note the travel details, promotions, and offers mentioned in this TTT Dispatch are timed and dated and subject to change.