Florence • Chianti • Val d'Orcia • Lake Como • Rome
Three days exploring Florence on foot. Two days driving a convertible through Chianti and the Val d'Orcia. Two days on the shores of Lake Como. Then three days in Rome before flying home. Along the way — Michelin-starred dinners, hidden trattorias, vineyard sunsets, private boats on the lake, and early morning runs through Renaissance streets, cypress-lined countryside, and lakeside promenades.
Nonstop to Roma on Italy's flag carrier
$7,653.86 total • $3,826.93 per person • Nonstop
Airbus A350-900 • Lie-flat leather seats • Every seat has aisle access • Business Base fare
ITA's A350 business class is built around Made in Italy — the seats, the sommelier-curated wine, the chef dining at altitude.
Every seat converts to a fully flat bed with direct aisle access. Center pairs share a lowerable divider, so you can sit side by side in your own private cocoon. 17" touchscreen, USB & AC power, noise-cancelling headphones.
ITA partners with Michelin-starred Italian chefs each season. Four-course dinner with aperitivo on boarding (Campari Spritz, Neapolitan pizza bites), espresso, limoncello digestivo. The return flight from Rome features the full chef-curated menu.
Wines from Tuscany, Piedmont, and Veneto — flight attendants trained on pairings. QC Terme spa amenity kit (Italy's luxury spa brand) with Marvis toothpaste. The A350 is one of the quietest wide-body jets flying.
Book center-section seats (the 1-1 pairs). The divider lowers so you sit together. Window seats face outward — great for solo travelers but isolating for a couple. For a honeymoon, center is the move. Check FlightAware closer to departure to confirm the aircraft type.
13 days through the heart of Italy
Three days in the birthplace of the Renaissance
Three days on foot. The Duomo to the Oltrarno, Uffizi to hidden wine bars, with the Arno turning gold at sunset every evening.
Our Pick Intimate, family-owned. Steps from the Arno and Ponte Vecchio. Concierge can arrange running routes and personal trainers.
Full Gym Alternative if gym access is a priority. Technogym-equipped fitness center, full spa. Right on the main piazza.
Luxury Ferragamo family's flagship. Suites with private terraces overlooking the Arno and Ponte Vecchio. Rooftop bar, personalized concierge, gym.
18th-century palazzo, one of the world's great wine cellars. Book weeks in advance.
MapInside a Byzantine tower at Hotel Brunelleschi. Only 20 seats.
MapTerrace dining on the Arno, views of Ponte Vecchio. Lungarno Collection (Ferragamo family). Pure, honest Tuscan cuisine.
MapVoted best trattoria in Italy, 2023. Historic, decisive Tuscan flavors. The Florentine steak is definitive.
MapGiant schiacciata sandwiches — truffle cream, prosciutto crudo, stracciatella. The best sandwich in Florence. Line moves fast.
MapTwo days driving through Chianti & Val d'Orcia in a convertible
The two most iconic drives in Italy. Day one: the Strada Chiantigiana winding south through Chianti vineyards, stopping for wine in Greve and steak in Panzano. Day two: the Val d'Orcia — La Foce's famous S-curve cypress road, Pienza, and Brunello in Montalcino. Top down, golden light, no schedule.
Night 1 A working wine estate surrounded by vineyards and olive groves. Rustic luxury, good food, quiet at night.
Resort Gym + Spa A private wine estate with a 2-star Michelin restaurant, spa, gym, yoga, and vineyard suites overlooking the Val d'Orcia.
At Rosewood Castiglion del Bosco near Montalcino. Chef Temperini's garden-to-table cuisine on a panoramic terrace. Book with hotel.
MapAt Castello Banfi, Montalcino. Tuscan cuisine with Pugliese creativity. Vineyard setting.
MapTwo nights on Italy's most romantic lake
Deep blue water, Alps behind, pastel villages on the hillsides. Varenna is quieter and more romantic than Como town — and directly accessible by train from Milan.
Pool + Spa Lakefront infinity pool, spa, gym. Terrace dining with panoramic views. Splurge pick.
Charming Right on the water in Varenna. Historic, family-run, with a lakefront terrace restaurant. More intimate and affordable than Bellagio options.
Romantic A 14th-century villa surrounded by terraced botanical gardens cascading down to the lake. Terraced gardens down to the lake.
Varenna Intimate lakeside restaurant on Varenna's main square. Fresh lake fish, handmade pasta, and a wine list focused on Lombardy and Piedmont.
MapSunset Terrace dining with panoramic lake views in Bellagio. Sunset dinner spot.
MapVarenna Casual lakefront bar right on the water. Good for aperitivo — negroni with the Alps across the lake.
MapThree days in the Eternal City to close the honeymoon
Ancient ruins and modern trattorias. The Colosseum at dawn, Trastevere at dusk. Three days to slow down and eat everything.
Full Gym + Spa Gorgeous terraced garden, excellent gym, spa with hydropool. Steps from Piazza del Popolo and direct garden access into Villa Borghese for morning runs.
Full Gym + Spa Rooftop restaurant & bar with panoramic views. Full gym, Eden Spa. Walking distance to Villa Borghese and Spanish Steps.
Grand A grand palazzo from 1894 with Murano chandeliers, butler service, full gym & spa. Near Piazza della Repubblica. Classic Old World luxury.
Roman Legend Trastevere. Cacio e pepe and carbonara. The Roman trattoria experience. No reservations — arrive early.
MapIconic Salumeria, bakery, and restaurant in one. The carbonara and cured meats. Book ahead.
MapClassic Roman Family-run since 1961, steps from the Pantheon. Traditional Roman cuisine. The artichoke and amatriciana.
MapExplore The neighborhood near the Vatican. Wander in, sit down, eat whatever they're making. Less touristy than Trastevere, just as delicious.
MapThe best supplì in Rome — fried rice balls with molten mozzarella centers. A gourmet street food counter near Piazza Navona. Quick lunch between monuments.
MapA run for every morning — from Renaissance streets to lakeside trails to ancient Roman roads
July = early starts. All runs before 6:30 AM. Bring a hydration vest for anything over 10K.
Climb up V. Michelangelo, past Santa Miniato al Monte, panorama of the city at the top. In July: go at 6 AM.
Map Route Details Send to DeviceFlorence's biggest green space. 395 acres of meadows, river paths, and wooded trails. Extends along the Arno for up to 15 km.
Map Send to DeviceUphill to the Etruscan hill town of Fiesole. Run up, take the bus back. In the footsteps of A Room with a View.
Map Send to DeviceStart at Ponte Vecchio, head through Via de' Bardi, climb Via di Belvedere. City and hill views with almost no people despite being in the center.
Map Send to DeviceThe famous unpaved white roads winding through Chianti vineyards. Quiet and scenic. Same roads used in the professional cycling race.
Map Send to DeviceA circular route through the rolling Val d'Orcia landscape. Cypress trees, wheat fields, and two hilltop villages.
Map Send to DeviceRun downhill through vineyards and farmland to the natural hot springs of Bagno Vignoni. Soak in the thermal waters post-run.
Map Send to DeviceTrail from Colonno to Griante along the western shore. Flat-to-moderate terrain with lake views the entire way.
Map Send to DeviceWaterfront path through Varenna. Good for a sunset run or morning shakeout. Connect with the Passeggiata degli Innamorati.
Map Send to DeviceOut-and-back through olive groves with lake views. Best early morning when the lake is still.
Map Send to DeviceShaded paths, connects to Pincio Terrace for city views. Steps from Hotel de Russie.
Map Send to DeviceRun on ancient Roman cobblestones past catacombs, ruins, and umbrella pines. Go on a Sunday when the road is car-free.
Map Send to DeviceFor two people, 13 days / 12 nights
| Category | Estimate | Notes |
|---|---|---|
| Flights (2x RT Business) | $7,654 | CONFIRMED — ITA Airways AZ 621/620 |
| Hotels — Florence (4 nights) | €2,000–€4,000 | The Place Firenze (3 + 1 return night) |
| Hotels — Tuscany (2 nights) | €1,500–€3,500 | Chianti agriturismo (1) + Rosewood (1) |
| Hotels — Lake Como (2 nights) | €600–€1,500 | Royal Victoria / Villa Cipressi in Varenna |
| Hotels — Rome (4 nights) | €3,000–€5,000 | Hotel de Russie (Rocco Forte) |
| Convertible rental (2 days) | €500–€1,200 | Italian convertible, delivered to hotel |
| Dining | €3,000–€5,000 | 3–4 Michelin meals + local trattorias |
| Trains & Transport | €500–€800 | FCO→Florence, Florence→Varenna, Varenna→Rome, taxis, ferries |
| Activities & Tastings | €500–€1,000 | Wine tastings, museums, boat rental on Como |
| Fuel, Tolls, Misc | €200–€400 | 2 days of driving |
| Total Estimate | $20,000–$30,000 | Flights locked in. All estimates for two people. |
Book now — July is peak season