A sample journey · Tuscany & Florence · 8 nights
Thoughtful Tuscany.
Time to settle in.
Hill-town mornings, a long lunch, and a countryside stay you’re happy to return to. Then three nights in Florence, with time for art, neighborhoods, and the pleasure of wandering.
Plan Your Tuscany Trip ↗The shape of your journey
Two bases. Room to enjoy both.
This sample pairs the freedom of the Tuscan countryside with a walkable stay in Florence. It’s a starting point—we’ll shape the days, stays, and experiences around you.
First · 5 nights in the countryside
Settle into southern Tuscany.
Make La Sovana your base for Montepulciano, Pienza, Montalcino, and the Val d’Orcia. Add Cortona, Siena, or an optional stop in Anghiari, with room for winery visits and an afternoon at the agriturismo.
Then · 3 nights in Florence
Trade the car for a good walk.
Return your rental car and settle into Florence. Balance a gallery or food experience with Oltrarno’s artisan streets, Santo Spirito, neighborhood dining, and a view from Piazzale Michelangelo.
The sample route arrives through Rome, with a countryside rental car returned in Florence before the city stay. Flights and transport will be planned around your trip.
Places to settle in
Two stays with a sense of place.
Tuscan countryside · 5 nights
Agriturismo La Sovana
A relaxed countryside base for hill towns and wine country, with time to enjoy the estate, pool, and winery. The sample includes daily breakfast and parking.
Florence · 3 nights
Rivoli Boutique Hotel
A character-filled stay in the historic center, with Florence on your doorstep. Leave the car behind and explore the city’s neighborhoods on foot.
These are example stays, subject to availability. Room choices and any eligible booking benefits are confirmed for your dates and selected rate.
A few moments to make your own
Wine, hill towns, and your Florence.
Beneath Montepulciano.
A guided underground wine-cellar visit and tasting, followed by time in town and an unhurried lunch.
The roads between.
Pienza’s views, Montalcino’s wine traditions, or a morning in Cortona. These are possibilities, with no need to fit them all into each day.
Beyond the checklist.
A thoughtfully chosen art or food experience, then time for Oltrarno, local markets, and aperitivo before dinner.
Dan’s pick: stop for a relaxed lunch at La Vineria di Montepulciano and try the tagliatelle al cinghiale.
What the sample investment includes
Eight nights of accommodations, a rental car for the countryside, selected winery and local experiences, a personalized Tuscany map, itinerary planning, recommendations, and ongoing guidance.
International airfare, travel insurance, personal expenses, and unlisted services are excluded. Meals are excluded unless specified in the itinerary; the sample La Sovana stay includes breakfast.
Starting from $5,000 for two travelers. Final pricing varies with dates, availability, hotel and room selections, and included experiences.
How we can make it yours
We can adjust the number of nights, the countryside base, hotel style, experiences, and pace. Keep more days open, add a special interest, or spend longer in a favorite place. Your final itinerary and pricing will reflect those choices.
Your Tuscany begins with a conversation
Let’s make it your own.
Tell me what you’re imagining, your dates, and how you like to travel. I’ll help bring the right version of Tuscany together.
Plan Your Tuscany Trip ↗I’ll follow up personally.
A glimpse of the planning experience
Your journey, all together.
See how stays, experiences, recommendations, and map links come together in your digital itinerary. The Fora sample offers a more detailed preview of this journey.
Preview the sample digital itinerary ↗For inspiration only. Example flights, reservations, and confirmations shown are illustrative, not bookings for your trip.