There is a moment in Tuscany when the light softens, vines deepen to ruby and Florence exhales after summer. Autumn is when gallery mornings feel unhurried, truffle hunts return to the woods and vineyard roads run quiet under cypress and sky. This is the season we love most. Travel Seen curates the inspiration, the rhythm and the right addresses, then our partner brands secure the stays and the little touches that make it feel effortless.
Portrait Firenze
Florence
art, elegance, ease
Base yourself where Renaissance bones meet modern comfort. We pair style to mood, then our network handles suite strategy and smart timings.
Portrait Firenze places you beside Ponte Vecchio with Arno views worth waking for. Design, discretion and stroll-everywhere ease.
Four Seasons Hotel Firenze is a 15th-century palazzo wrapped in a private park with a serious spa and an outdoor pool that still catches October warmth.
Hotel Savoy sits on Piazza della Repubblica with modern glamour and the most walkable address for shopping, galleries and late lunches that turn into early evenings.
From any of these, we unlock quieter corners of Santa Croce, line up the best window tables at golden hour and time museum entries so you never feel rushed.
COMO Castello del Nero
Belmond Castello di Casole
The Tuscan hills
slow roads, vineyard rhythm
Leave the city on the scenic SR222 and watch the landscape open into neat vines and olive groves. Here, vineyard hotels give you space to slow down while driver-days make tastings simple.
Rosewood Castiglion del Bosco, Montalcino sits on a vast private estate with its own Brunello winery. Borgo life, rust-red lanes and villas with pools for friends who like room to breathe.
Belmond Castello di Casole brings ten-century drama with olive groves and terraces that glow at dusk. Classic Tuscany with service one step ahead.
COMO Castello del Nero blends frescoed halls with a wellness-first approach. COMO Shambhala mornings, long lunches and vineyard walks that unspool the day.
We’ll weave in truffle hunts near San Miniato, cellar tours in Montalcino and backroad viewpoints that never make the guidebooks. Our partners confirm the drivers, the reservations and the room keys waiting with your name.
A simple outline
that always works
Day 1 – Florence
Check in, timed gallery entry, river-light aperitivo, dinner within strolling distance.
Day 2 – Into Chianti
Driver via the SR222 with a pause for that light-struck viewpoint. Truffle hunt or winery lunch, spa hour at COMO or a terrace nap, firelit dinner.
Day 3 – Val d’Orcia
Brunello tasting in Montalcino, a slow drive over open hills to Pienza, last terrace coffee, late flight home.
Every trip is tailored which is why we start with your dates, pace and the mood you want to capture. Travel Seen shapes the flow, our partner brands secure the booking details.
Four Seasons Hotel Firenze
Hotel Savoy, Florence
Seasonal flavour
Markets brim with figs and chestnuts. Menus lean into porcini risotto and pappardelle with wild boar. White truffles arrive in late October then peak through November which makes autumn in Tuscany the moment for long lunches where the simplest plates taste the most luxurious. We’ll place the chef’s table on a bright-light day with a short road home.
Practicalities
we line up
Flights into Florence or Pisa with meet-and-greet on arrival
Private drivers for city to countryside and tasting days
Gallery entries without long queues
Restaurant and winery reservations timed for the light and your pace
Hotels and suites chosen for view, quiet and layout that suits how you travel
Because of our relationships, you’ll find smarter rooming, the right side of the building for sunrise or sunset and small touches that feel personal.
Ready when you are
Tell us your dates and wish-list. Travel Seen will shape a Florence-to-Chianti route that fits the season, then one of our partner brands will finalise the booking with preferred rates and the right value-adds.
Plan my Tuscany escape — curated by Travel Seen, booked through our partners
Interested? Call us on 0333 305 9912.
