Main destination
Tuscany
Florence, Tuscany, Umbria, and Assisi / 9 days
Tuscany & Umbria
Renaissance art, hill towns, wine, and spiritual history
A nine-day Tuscany and Umbria itinerary through Florence, Siena, Chianti, Perugia, Assisi, Montepulciano, and Pienza, balancing Renaissance art, medieval towns, wine country, and Umbrian charm.
Florence art and culture
Siena and Chianti
Perugia and Assisi
Montepulciano and Pienza
Trip snapshot
A sample framework, refined through InJoy's personal edit.
Renaissance art, hill towns, wine, and spiritual history
Length
9 days
Travel style
Cultural exchange
Core route
Florence, Siena, Perugia, Assisi
The route begins in Florence, moves through Siena and Chianti, continues into Umbria for Perugia and Assisi, then returns through Tuscan hill towns before ending in Florence.
The live InJoy page gives this itinerary a strong day-by-day structure. Mona and Team can make it more personal with boutique lodging, private touring, carefully chosen wineries, and a slower countryside cadence.
Best for
Art and architecture loversWine country travelersSpiritual and historic sitesCouples and small groups
Source signals
TuscanyUmbriaItalyAssisiCulture
InJoy edit
Make it yours
A layered central Italy route for travelers who want art, wine, hill towns, and a more soulful Umbrian note. Mona and Team can tune the hotel bases, private guides, winery stops, Assisi timing, and driving rhythm so the route feels graceful.
Hotel style
Private touring
Travel rhythm
Hotels / timing / guides / pace
Sample itinerary
A considered rhythm, day by day.
Edited pacing
Personal details
Private proposal ready
Day1
Florence, Tuscany, Umbria, and Assisi
Arrival in Florence
Arrival day
Arrive at Florence airport or Santa Maria Novella station, check into a central hotel, and spend the evening exploring historic streets before a Tuscan dinner.
Day2
Florence, Tuscany, Umbria, and Assisi
Florence art and culture
InJoy the day
Visit the Uffizi Gallery, Florence Cathedral, the Baptistery, and the Accademia Gallery for Michelangelo's David, with Tuscan meals woven into the day.
Day3
Florence, Tuscany, Umbria, and Assisi
Siena
InJoy the day
Depart for Siena to explore Piazza del Campo, the cathedral, the Torre del Mangia, and a medieval city center rich with Tuscan character.
Day4
Florence, Tuscany, Umbria, and Assisi
Chianti wine country
InJoy the day
Spend the day in Chianti with vineyard landscapes, local wineries, tastings, and a relaxed Tuscan lunch before returning to Florence.
Day5
Florence, Tuscany, Umbria, and Assisi
Perugia
InJoy the day
Travel into Umbria for Perugia, visit the Palazzo dei Priori, enjoy Umbrian cuisine, and settle into the town's evening atmosphere.
Day6
Florence, Tuscany, Umbria, and Assisi
Assisi
InJoy the day
Take a day trip to Assisi, birthplace of St. Francis, for the Basilica of St. Francis and a deeper spiritual and historic layer of Umbria.
Day7
Florence, Tuscany, Umbria, and Assisi
Montepulciano and Pienza
InJoy the day
Explore Tuscan hill towns known for beauty, wine, and village charm, with wine tasting and a traditional lunch in Montepulciano.
Day8
Florence, Tuscany, Umbria, and Assisi
Return to Florence
InJoy the day
Return to Florence for remaining sights, last shopping, and a farewell dinner in a Florentine restaurant.
Day9
Florence, Tuscany, Umbria, and Assisi
Departure from Florence
Until next time
Enjoy final time in Florence if the schedule allows, then transfer to the airport or train station for departure.
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Are you ready?
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