Celebrate Your Anniversary in Tuscany

Land at Florence's Amerigo Vespucci Airport (or Rome Fiumicino with high-speed train transfer) and settle into your Oltrarno hotel across the Arno from the historic center. Florence rewards immediate wandering — the pedestrianized historic core is small enough to navigate entirely on foot, and an afternoon walk from the Ponte Vecchio through the narrow lanes of the medieval city, past leather workshops and gelaterie, is one of travel's simplest pleasures. Cross the bridge to the Piazzale Michelangelo at sunset for the most photographed panorama in Tuscany — the Duomo's terra-cotta dome, the towers of the Palazzo Vecchio, and the Arno curving through it all, turning gold as the sun falls behind the hills.

• ✦ Check-in at Oltrarno boutique hotel
• ✦ Ponte Vecchio afternoon walk
• ✦ Aperitivo at a Florentine enoteche
• ✦ Piazzale Michelangelo sunset panorama

Florence has more great art per square mile than anywhere on earth, and your skip-the-line tickets give you priority entry to the Uffizi Gallery (Botticelli's Birth of Venus and Primavera, Caravaggio, Raphael, Leonardo) followed by the Accademia (Michelangelo's David in the original gallery with its awe-inspiring scale still visible after 500 years). Between galleries, recover at a marble-topped cafe table with a macchiato and a cornetto — Florentine breakfast culture is a ritual worth honoring every day. Afternoon for the Mercato Centrale, Florence's spectacular two-floor food market where you'll taste prosciutto, Parmigiano, and the city's extraordinary cold cuts before choosing a restaurant for dinner.

• ✦ Skip-the-line Uffizi Gallery — Botticelli and Leonardo
• ✦ Accademia Gallery — Michelangelo's David
• ✦ Mercato Centrale food exploration
• ✦ Sunset Negroni in Piazza della Repubblica

After a Florentine morning coffee (stand at the bar like a local — café seating doubles the price), your private driver takes you south into the Chianti Classico zone between Florence and Siena — 40 minutes and several centuries back in time. Check into your farmhouse or castello in the rolling Chianti hills, drop your bags in a stone-floored suite surrounded by olive groves and vine rows, and immediately make for the estate cellar for a private tasting with the winemaker. Sangiovese-based Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano are three of Italy's greatest reds and all produced within an hour's drive — today you begin the education. Tonight: dinner at the farmhouse table with the estate's wine.

• ✦ Private driver scenic transfer through Chianti
• ✦ Farmhouse or castello check-in
• ✦ Private winemaker cellar tasting
• ✦ Estate farmhouse dinner under the stars

Meet your truffle hunter and his Lagotto Romagnolo dogs at the edge of the oak woods near San Miniato at 9am — the dogs work the undergrowth in ranging patterns, and when one freezes and begins to dig, you'll understand why white truffles command such extraordinary prices. Back at the farmhouse, your afternoon cooking class transforms the morning's truffles into fresh pasta with truffle butter and shaved white truffle, followed by bistecca alla Fiorentina over the open hearth. In the early evening, drive south to Siena for a sunset passeggiata around the extraordinary shell-shaped Piazza del Campo — one of the most beautiful public squares in the world — before dinner at a traditional Sienese osteria.

• ✦ Oak forest truffle hunt with Lagotto dogs
• ✦ Farmhouse truffle pasta cooking class
• ✦ Siena's Piazza del Campo at sunset
• ✦ Dinner at a traditional Sienese cantina

The Val d'Orcia is Tuscany's most cinematic landscape — a UNESCO-protected valley of rolling hills, lone cypress trees, and hilltop towns that have changed almost nothing since Ambrogio Lorenzetti painted them in the 14th century. Drive the famous Strada Provinciale 146 from Pienza to San Quirico d'Orcia — the cypress-lined road that appears on every Tuscany calendar — and stop at Pienza, the Renaissance ideal city built by Pope Pius II, for pecorino cheese tasting and a bottle of local wine. In the afternoon, take the waters at Bagno Vignoni — a unique medieval village built around an ancient thermal pool in the main piazza — and then soak for free in the natural hot springs at Bagni San Filippo in the forest below Monte Amiata.

• ✦ The famous cypress-lined road of the Val d'Orcia
• ✦ Pienza pecorino cheese tasting
• ✦ Bagno Vignoni thermal piazza
• ✦ Natural hot springs at Bagni San Filippo

Two of Italy's greatest wine towns sit in the southeastern corner of Tuscany, and today is their day. Montepulciano climbs in a medieval spiral to a summit piazza with panoramic views over the Val d'Orcia — taste Vino Nobile in the enoteca carved into the city walls, then descend to the floor of the valley for the drive through sunflower fields to Montalcino. The great walled hilltop town produces Brunello di Montalcino from 100% Sangiovese grapes aged for five years minimum — one of Italy's most age-worthy and celebrated wines. The Fortezza wine bar at the medieval castle ramparts pours 30+ Brunellos by the glass with views across the valley to Monte Amiata. Return to the farmhouse for a long last evening in the Chianti hills.

• ✦ Montepulciano medieval hilltop and Vino Nobile tasting
• ✦ Val d'Orcia valley drive through sunflowers
• ✦ Montalcino Fortezza wine bar with Brunello
• ✦ Farmhouse final evening in the Chianti hills

A final slow Tuscan morning — espresso in the farmhouse garden with the valley mist burning off the hills, one last walk through the vine rows, and the bittersweet business of packing. Your driver returns you to Florence or directly to the airport, but most couples with a flexible departure request one final hour at the Mercato Centrale for provisions: aged Parmigiano, vacuum-packed Cinghiale ragù, local olive oil, and a case of the estate's Chianti to ship home. Tuscany is the kind of destination that requires a return visit — the region is vast, the seasons change it completely, and you will have left towns unvisited and wines untasted that will call you back.

• ✦ Final farmhouse garden breakfast
• ✦ Last walk through the Chianti vine rows
• ✦ Mercato Centrale provisions shopping in Florence
• ✦ Private transfer to Florence or Rome airport