Tuscany — Itinerary

itinerary guide for Tuscany luxury travel.

The perfect Tuscany itinerary balances iconic highlights with unexpected discoveries, structured enough to maximize your time yet flexible enough to follow inspiration. Here's a recommended approach.

Your Day-by-Day Journey

A carefully paced itinerary that balances must-see moments with personal discovery.

Tuscany is not a destination — it's a philosophy. Rolling cypress-lined hills, Renaissance art in every piazza, Brunello in every cellar, and a pace of life that reminds you why you work hard in the first place. The Rosewood Castiglion del Bosco and Castello di Casole define villa luxury here.

Tuscany practical detail

• Region: Central Italy
• Typical spend in Tuscany: $5,000–$30,000+ per couple per week
• Best time to visit: May–June and September–October for ideal temperatures and harvest season
• Climate: Mediterranean continental, 15–35°C
• Currency: Euro

What sets Tuscany apart

• Rosewood Castiglion del Bosco — a Brunello di Montalcino estate with private suites in a restored borgo
• Castello di Casole — a 10th-century estate in 4,200 acres of unspoiled Tuscan countryside
• Brunello di Montalcino and Super Tuscan wines — private tastings at legendary estates
• Renaissance art and architecture accessible through private, after-hours museum tours

Sample Itinerary highlights in Tuscany

Private Uffizi Tour

After-hours access to Florence's Uffizi Gallery with an art historian guide.

Brunello Wine Journey

Helicopter tour of Montalcino's finest estates with private cellar tastings.

Truffle Hunting

Dawn truffle hunt with trained dogs followed by a truffle-focused lunch.

Vespa Tour of Chianti

Classic Vespa ride through Chianti villages with stops at family-run estates.

Villa Cooking School

Multi-day cooking immersion at a private estate with a Nonna's guidance.

How a Tuscany trip is usually structured

• Day 1: Arrive Florence, private Uffizi tour, dinner at Enoteca Pinchiorri
• Day 2: Transfer to Montalcino, Brunello cellar tour, estate check-in
• Day 3: Truffle hunting, cooking class, afternoon in Siena
• Day 4: Vespa Chianti tour, sunset at San Gimignano, estate dinner
• Day 5: Morning at thermal baths, departure via Florence

Published by Peters Signature Travel.