Honeymoon in Tuscany: A 7-Day Romantic Itinerary

Tuscany earns its reputation as a honeymoon destination through sheer density of beauty: a landscape of rolling hills, vine rows, and cypress trees that looks like a Renaissance painting because it literally inspired them. The Val d’Orcia appears on UNESCO’s World Heritage list not as an archaeological site but as a cultural landscape - a living piece of geography shaped by centuries of farming into something closer to art. Add some of Italy’s finest wine, excellent food, and a dozen medieval hilltowns to explore at your own pace, and you have the ingredients for a honeymoon built around pleasure rather than logistics.

This 7-day itinerary is designed around a couple with a rental car (essential), a preference for countryside and wine over beaches and nightlife, and a desire to go deeper into fewer places rather than racing between cities.

Tuscany is highlighted as an optional add-on to our 10–12 day Italy honeymoon itinerary, which covers Rome, the Amalfi Coast, Cinque Terre, and Venice.

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Getting There

Fly into Florence Airport (FLR) or Pisa Galileo Galilei Airport (PSA), or arrive via high-speed train into Florence Santa Maria Novella from Rome, Milan, or Venice.

Pick up a hire car in Florence or at the airport. Do not drive into Florence’s historic centre - the ZTL restricted traffic zone operates around the clock and cameras issue automatic fines to non-residents. Park outside the ZTL and walk or use trams.

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Where to Stay: Hotels by Budget Tier

Chianti Wine Country

Luxury:

• Castello di Casole (Four Seasons) - a restored 10th-century castle near Colle di Val d’Elsa, converted into a hotel with 41 rooms, vineyards, spa, and a restaurant using estate-grown produce. Rates from approximately €700–€1,800/night.
• Borgo Santo Pietro - a 13th-century hamlet near Chiusdino transformed into a 20-room luxury property with biodynamic farm, spa, and exceptional restaurant. Approximately €600–€1,400/night.

Mid-range:

• Relais Vignale (Radda in Chianti) - a converted Chianti estate with 38 rooms, pool, wine cellar, and an excellent restaurant. From approximately €200–€380/night. Walking distance to the village of Radda.
• Tenuta di Ricavo - a hamlet-turned-hotel in the forest near Castellina in Chianti, very quiet, with pool and beautiful gardens. From approximately €180–€280/night.

Val d’Orcia

Luxury:

• Adler Thermae Spa & Relax Resort (Bagno Vignoni) - a thermal spa hotel in a village whose main piazza is a natural hot-spring pool that has been in use since Roman times. From approximately €400–€800/night, usually sold as minimum 2–3 night packages.
• Rosewood Castiglion del Bosco - a restored medieval hamlet near Montalcino with Brunello di Montalcino vineyards, spa, and golf course. From approximately €700–€1,500/night.

Mid-range:

• Locanda dell’Amorosa - a historic estate near Sinalunga with a restaurant that holds a Michelin star. Approximately €180–€350/night.
• Agriturismo Il Rigo - a working organic farm near San Quirico d’Orcia, simply furnished but beautifully positioned in the Val d’Orcia landscape. From approximately €130–€200/night. Outstanding breakfast.

Siena Area

Luxury:

• Residenza d’Epoca il Casato - a palazzo in Siena’s historic centre, small and intimate. From approximately €200–€450/night.

Mid-range:

• Hotel Athena - reliable four-star in Siena, 10 minutes’ walk from Piazza del Campo, rooftop pool with city views. From approximately €120–€220/night.

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Day 1: Arrive Florence - Afternoon in the City

Arrive in Florence, pick up your hire car, and drop luggage at your first hotel. If arriving in the morning, the Uffizi Gallery merits a visit - book tickets well in advance, as walk-up queues in season are long. For an afternoon arrival, spend the time in the streets: Ponte Vecchio, Piazza della Signoria, a gelato at Gelateria dei Neri.

Dinner: Florence has excellent restaurants at every price point. Buca Mario (Via dello Studio) is one of the oldest restaurants in the city - traditional bistecca Fiorentina, ribollita, pappardelle with wild boar. Approximately €50–€80 per couple. For a special first night, Enoteca Pinchiorri holds two Michelin stars and is widely considered Florence’s finest table - book months ahead, approximately €200–€300 per person.

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Day 2: Florence to Chianti - Wine Estates and Hilltowns

Drive south from Florence into the Chianti Classico wine zone. The route through Greve in Chianti, Panzano, Radda in Chianti, and Castellina in Chianti passes through the most intensely photogenic part of the Tuscan landscape.

Morning: Greve in Chianti’s central piazza is an excellent first stop - excellent deli shops, the Falorni enoteca for olive oil and salami, and the beginning of the wine estates.

Afternoon: Private wine tasting at a Chianti Classico estate. Options vary from small family producers to grand historic cantine:

• Badia a Coltibuono - a 13th-century Benedictine monastery that has been producing wine since the 11th century. Guided cellar tours and tastings approximately €20–€40 per person.
• Antinori nel Chianti Classico - the estate of one of Italy’s great wine families, with a spectacular modern cellar designed by the Archea Associati firm. Tours and tastings approximately €30–€60 per person. Book ahead.
• Castello di Ama - known for both wine and contemporary art installations around the property. Tastings from approximately €25 per person.

Check into your Chianti estate hotel. Dinner at your hotel’s restaurant, or in the village - most Chianti towns have at least one excellent osteria.

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Day 3: Siena - One of Italy’s Great Cities

Day trip to Siena, 30–40 minutes from the Chianti heartland by car (park at the Siena Due parking garage outside the ZTL and walk in).

Siena rewards slow exploration more than any other Tuscan city. The Piazza del Campo - the shell-shaped central square - is one of the great public spaces in Europe, gently sloping, lined with Gothic palazzi. The Torre del Mangia (entry approximately €9 per person) gives the best view of the city from the top; expect a queue but the view justifies it. Guided Siena walking tours are a good option if you want the history explained as you go.

The Duomo: Siena’s cathedral (entry approximately €8 per person) is extraordinary - striped black and white marble inside and out, Nicola Pisano’s carved pulpit, Michelangelo’s early statues. In September–November, the Libreria Piccolomini floor mosaics are uncovered (additional fee, worth it).

Lunch: Il Bandierino, a small osteria near Piazza del Campo with an excellent lunch menu - pappardelle al cinghiale, ribollita, local Chianti by the carafe. Approximately €35–€55 per couple.

Afternoon: Walk the city’s lesser streets - the Terzo di Camollia in the north is far quieter than the tourist centre and has beautiful Gothic architecture.

See our Siena things to do and Siena hotels pages for more detail.

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Day 4: Montalcino - Brunello Wine Country

Drive south from Siena to Montalcino, the hilltop town that produces Brunello di Montalcino - considered by many critics to be Italy’s finest red wine. The drive takes about 40 minutes and passes through the northern edge of the Val d’Orcia.

Morning in Montalcino: The town itself is compact and extremely pleasant - a medieval fortress (entry approximately €5), good enotece with Brunello by the glass (starting around €8–€15 for younger releases), and panoramic views over the surrounding vineyards.

Private Brunello tasting: Book an estate visit for a serious tasting experience:

• Castello Banfi - the largest Brunello estate, with a castle, museum, and comprehensive tasting menus from approximately €30–€80 per person.
• Poggio di Sotto - smaller, very prestigious estate, private tastings by appointment.
• Col d’Orcia - a historic estate with organic vineyards and affordable tastings.

Lunch: In Montalcino - Osteria Trattoria Scame has excellent pasta and a wine list that goes well beyond what you’d expect. Approximately €40–€65 per couple.

Afternoon: Drive through the Val d’Orcia. Stop at the Cappella di Vitaleta - a small chapel on a ridge near Pienza, surrounded by cypress trees, that is one of the most photographed scenes in Tuscany. The late afternoon light here is extraordinary.

Check in to your Val d’Orcia accommodation.

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Day 5: Val d’Orcia - Pienza, Bagno Vignoni, and the Landscape

The Val d’Orcia is best experienced slowly, on roads that aren’t the main routes. Today is for the landscape itself.

Pienza: A remarkable Renaissance town planned in the 1460s by Pope Pius II as the ideal city. The Piazza Pio II at its centre, with the cathedral and papal palace, is perfectly proportioned. The main street is lined with excellent cheese shops - Pienza is famous for its pecorino, including fresh (fresco), aged (stagionato), and varieties wrapped in walnut leaves or truffle-dusted. Buy some for a picnic.

Bagno Vignoni: Not a tourist sight in the conventional sense - a village where the central piazza is a natural thermal pool, used since antiquity and still steaming. The pool itself is not for swimming (it’s a monument), but the spa hotels in the village use the thermal waters. A deeply unusual and beautiful place.

Picnic in the Val d’Orcia: Buy pecorino, local salumi, bread, and a bottle of Brunello or Rosso di Montalcino in Pienza, then find a viewpoint off the main road. The lane between San Quirico d’Orcia and Pienza passes through classic Val d’Orcia scenery - hilltops, cypress rows, farmhouses.

Dinner: Your hotel restaurant, or in San Quirico d’Orcia - Trattoria al Vecchio Forno has outstanding ribollita and pici (thick hand-rolled pasta) with wild boar sauce. Approximately €30–€55 per couple.

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Day 6: San Gimignano and a Cooking Class

Morning in San Gimignano: The medieval Manhattan of Tuscany - a hilltop town whose 14 surviving towers give it a skyline unlike any other in Italy. Arrive by 9am before the day-trip coaches arrive from Florence. The town is genuinely beautiful inside: the Collegiata (duomo, entry approximately €6) has stunning fresco cycles, and the Vernaccia wine produced in the surrounding vineyards is one of Tuscany’s most distinctive whites.

Cooking class: Many agriturismo properties in the San Gimignano and Siena area offer afternoon cooking classes - typically 2–3 hours, covering pasta-making, local sauces, and desserts, ending with a dinner of what you’ve made. Look at cooking classes in Tuscany - or ask your hotel to arrange a private class.

Approximate cost: €120–€200 per couple for a private class; €60–€100 per couple for small-group.

Dinner: What you cooked, at the farmhouse or estate. Or back in your area, at whichever local osteria caught your eye during the week.

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Day 7: Return to Florence - Departure

Drive back to Florence for afternoon or evening departure. The route via the SS2 Via Cassia passes through some of the quieter Chianti landscape.

If your flight is in the evening, spend the morning at the Bargello museum (sculpture collection, approximately €9 entry) or the Brancacci Chapel (Masaccio frescoes, booking required). Both are quieter than the Uffizi and Accademia and worth the morning.

Final lunch: Mercato Centrale upstairs - an excellent food hall above the covered market in central Florence, with stalls for pasta, tripe, pizza, and a full bar. Good for a last Italian meal before heading to the airport.

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Romantic Extras Worth Adding

Truffle hunt: From September–November, book a morning truffle hunt with a local trifolao and their dog in the forest around San Miniato or the Crete Senesi. Typically 2–3 hours, ending with a lunch using the truffles you found. Approximately €150–€250 per couple. An extraordinary experience and completely unique to this landscape and season.

Hot air balloon: Sunrise balloon flight over the Val d’Orcia is one of the great views in Italy - the landscape from 400 metres in still air at dawn is extraordinary. Tuscany Ballooning and Ballooning in Tuscany both operate flights from the Val d’Orcia area. Approximately €280–€350 per person.

Horseback riding: Several Chianti estates offer guided horseback rides through vineyards. Good for 1–2 hours through the landscape at a pace that lets you actually see it. Approximately €60–€100 per person.

Thermal spa day at Saturnia: The natural hot springs at Saturnia in the Maremma region - waterfalls of 37.5°C sulphurous water cascading into pools - are free to access around the clock. About 90 minutes’ drive from the Val d’Orcia, worth a detour if you have a flexible day.

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Practical Notes

• Car hire: Book a mid-size automatic. Tuscany’s roads include some narrow lanes with passing places; an automatic reduces one variable. Most hire companies at Florence and Pisa airports offer this.
• Petrol: Fill up in towns - rural petrol stations can be hours apart in the Val d’Orcia.
• Cash: More essential in rural Tuscany than in cities. Many agriturismo properties and smaller restaurants prefer cash or may require it. Keep €100–€200 on hand.
• Wine shopping: Wine can be significantly cheaper purchased directly at the estate than in UK or US retail. Most Brunello estates can arrange international shipping, though the cost makes sense only for larger quantities.
• Dress code: Rural Tuscany has no formal dress requirements, but cover shoulders and knees when entering churches (you’ll visit several). Evenings at estate restaurants are smart casual.

Book Before You Go

• Tuscany tours and wine experiences - Chianti tastings, truffle hunts, and Siena day trips
• Car hire in Italy - essential for Tuscany; most hilltop towns and vineyards are not on public transport
• Private airport transfers - from Florence or Pisa airport to your accommodation
• Travel insurance for Italy

Book Your Trip

• Flights - Find the best fares to Italy
• Travel Insurance - Get covered before you go
• eSIM - Stay connected from landing
• Airport Transfers - Door-to-door from Florence or Pisa airport
• Car Rental - Compare prices across providers
• Tours & Activities - Browse Tuscany tours on GetYourGuide