Florence & the Tuscan Hills
Why Tuscany
Most trips to Italy give Tuscany two rushed days between Rome and Venice. I built this gay Tuscany tour the other way around, with a rhythm I believe in: Florence first, for four nights, while you’re still full of energy and want to see everything; then four nights in the countryside, when you’d rather see less and stay longer. In between are the towns most itineraries rush through or skip: Pistoia, the Tuscan town I love most; Lucca, still inside its Renaissance walls; Pisa, done properly in half a day.
Florence has the most documented queer history of any city in pre-modern Europe, and Italy has recognized same-sex civil unions since 2016: here, two men at a table are simply two men at a table. It sits beside the other Italian journeys I design.
When to go
April–June · September–early November
Length
9 days, 8 nights
Florence 4 · Borgo Pignano 4
Price
From $9,500 pp
8 nights · two sharing · flights not included
Includes every stay, train tickets for the long legs, a private driver for everything in the hills, private guides where it matters, and all the experiences listed. International flights excluded. How it works
The trip in a nutshell
Two bases, one change of hotel, the long legs by train and a private driver for everything in the hills. You fly into Rome and are in Florence an hour and a half later, at Palazzo Castri, a nineteenth-century palace a few minutes from the Duomo. Four nights there: the Oltrarno workshops, the Uffizi or the Accademia with a private guide, and two days out by train to Pistoia and Lucca.
Then a private driver takes you west to Pisa and on into the hills between Volterra and San Gimignano, to Borgo Pignano, a medieval hamlet restored as a small hotel. From there: San Gimignano early in the morning, a family wine estate for dinner, Siena, Volterra at sunset, and a last day with nothing on it at all.
Who this is for
This route is for the couple who wants Tuscany without the rush, and who doesn’t want to change hotels every other night. For the two of you who would rather walk Lucca’s walls at an unhurried pace than tick off five towns in a day, who will cross a city for a carved pulpit most visitors never see, and who think a slow last day by the pool is part of the trip, not time lost.
It works as a first trip to Italy and for travelers who have seen Florence before and never left it. If you’d like Rome and Venice in the same trip, look at Rome, Tuscany and Venice. If you’re new to the way I work, here is how a tailor-made trip comes together, and I answered the practical question separately: is Italy gay friendly?
The route
A starting point, not a fixed menu: every day is shaped around you. Four nights in Florence and four in the countryside, with fast trains for the long legs and a private driver for everything in the hills, so nobody spends an afternoon looking for parking outside a medieval wall.
Days 1–4
Florence, Pistoia and Lucca
Day 1. You land in Rome, a private transfer takes you to the station, and a Frecciarossa puts you in Florence an hour and a half later. Check in at Palazzo Castri, then nothing planned: a walk, an early dinner. On purpose. The first day of a trip to Italy is for arriving.
Day 2. A morning in the Oltrarno, the artisan side of the river, in workshops where people have worked for thirty or forty years, most of them not in a shop window. In the afternoon, the Uffizi or the Accademia with a private guide and timed entry. Both close on Mondays, and the days are planned around it.
Day 3. Forty minutes by train. Pistoia has the same Renaissance beauty as the rest of Tuscany, without the tourism: it is still a city lived in by its own people. The Piazza del Duomo, the striped marble baptistery, and in Sant’Andrea a carved pulpit by Giovanni Pisano that most visitors to Tuscany never see. Lunch in one of the old osterie that still cook for the people who live upstairs.
Day 4. Lucca is still entirely enclosed by its walls: more than four kilometers of ramparts, now a promenade you can walk in an unhurried hour. Inside, San Michele in Foro stands where the Roman forum was, and the Piazza dell’Anfiteatro keeps the oval of a first-century amphitheater. In summer, an evening of Puccini by the lake at Torre del Lago can be added.
Days 5–9
Pisa, and the hills of Volterra
Day 5. A private driver for the move to the countryside, with Pisa on the way. The Camposanto comes first, the quietest half hour on the square, and then the cathedral, the baptistery and the tower. About an hour on to Borgo Pignano, in time for the evening on the estate.
Day 6. San Gimignano early in the morning, before the day-trippers. In the late afternoon, a family wine estate in the hills above Siena: a short cellar visit, then dinner at their table, in the garden if the weather holds. A driver takes you back.
Day 7. Siena is about forty minutes away: the Campo, the Duomo, the streets of the contrade. On the way back, if you feel like it, Volterra at sunset, a quarter of an hour from the estate.
Day 8. Nothing on the schedule. The pool for adults only, a cooking class on the estate, truffles in season. This is the day the whole trip is built to end on: the last days of a trip should give you your energy back before you go home.
Day 9. A driver to Florence for the fast train to Rome, or a car straight to Rome Fiumicino, about three hours. With an early flight, the last night moves to Rome instead.
Where you stay
Two stays and one change of hotel, chosen for character, location and quiet.
Palazzo Castri 1874, Florence
A nineteenth-century palace on Piazza dell’Indipendenza, about seven minutes on foot from the Duomo but in a different Florence: a square that has kept its residential life. Breakfast is in La Limonaia, the old orangerie, with the garden in view. It is where I book most of my clients when they want the city as a base.
Borgo Pignano, near Volterra
A medieval hamlet in the hills between Volterra and San Gimignano, restored as a small and very quiet hotel, with a pool for adults only. Open from late March to early November. It is where the trip slows down: four nights, and nothing you have to do.
Every property here is one I have stayed in or walked through myself, or one vetted by the local team I have worked with for years.
Before you arrive
Everyone you’ll meet on this trip knows who’s coming. The hotel has been told two men are checking in and the front desk briefed: one bed, no questions. The driver knows you’re a couple before you get in the car. The guides are chosen one by one and told the same. The restaurants are booked with the kitchen in the loop if there’s something to celebrate. I’ve been on the other side of every one of those moments myself; anyone who stiffens at the request doesn’t work with me. Traveling solo or with friends? Same people, same welcome.
More Italy
ROME, TUSCANY & VENICE
Three nights in Rome, four in Florence, two on the Grand Canal — three houses I know, and the long legs by fast train. 9 nights
NAPLES, CAPRI & THE AMALFI COAST
Three nights in Naples, two at Le Sirenuse in Positano, two on Capri after the last ferry has left. 7 nights
PUGLIA, THE ITALY I COME HOME TO
Five nights in one masseria, Lecce and the Salento, a night in the rock of Matera — the region I was born in. 8 nights
A free guide
Not sure this is your Italy?
The Curator’s Edit: Italy is my guide to six journeys I plan for gay travelers and how to tell which one is yours. Free, in your inbox within a minute.
Make this itinerary yours
This is a starting point, not a fixed package. Tell me your dates and how you like to travel — a night of Puccini at Torre del Lago, an extra day in Siena, the last night in Rome — and within two business days you will hear back from me with a first proposal for your trip, which we then shape together.
Francesco Mevoli
Founder, Gay Up Travel