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 — La Dolce Vita, not Top Gear. 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
The honeymoon starts the moment we board. ITA's A350 business class is built around Made in Italy luxury — from the seats to the sommelier-curated wine to the Michelin-starred 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 — perfect for sleeping.
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
The city that invented the modern world. Every street is a museum, every piazza a masterpiece. Three days to wander from the Duomo to the Oltrarno, from the Uffizi to hidden wine bars — with the Arno turning gold at sunset every evening.
Our Pick Intimate, family-owned, deeply romantic. 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.
The crown jewel. 18th-century palazzo in central Florence. Exceptional wine cellar (one of the world's greatest). Book weeks in advance.
MapInside Hotel Brunelleschi. Tradition meets innovation in a Byzantine tower. Only 20 seats — incredibly intimate.
MapOn the Arno with views of Ponte Vecchio. Pure, authentic Tuscan cuisine. Part of the Lungarno Collection (Ferragamo family).
MapMassimo Bottura's Florence outpost. Italian-Mexican-South American fusion inside the Gucci Garden. As beautiful as it is delicious.
MapBest in Italy Voted best trattoria in Italy 2023. Historic, decisive Tuscan flavors. The Florentine steak and peposo are musts.
MapRomantic One of Florence's most romantic restaurants. Natural wine-forward. Oltrarno neighborhood. Perfect first-night dinner.
MapPure Tuscan Near the Uffizi. No pizza, no ketchup (literally on a sign). Cured meats, slow-cooked ragù, courgette flower paccheri.
MapViral Dimly lit, romantic date-night spot. Hotels recommend it too. TikTok hype confirmed real.
MapChef-Driven Four generations. Handwritten daily menu. Orange wine from tiny unknown Tuscan vineyards.
MapBudget Gem Family-run near San Frediano gate. Remarkably cheap, remarkably good. No reservations — arrive early.
MapViral Florence's oldest gelateria (1929). The pistachio affogato is the star. Confirmed worth the hype.
MapViral Florence's oldest gelateria (1929). The pistachio affogato has 50M+ views. Quick stop, confirmed worth every bit of hype.
MapViral Dimly lit, romantic date-night spot run by a Hapsburg prince. Hotels recommend it. TikTok hype confirmed real.
MapViral "The best sandwich in the world" — 100M+ TikTok views. Giant schiacciata sandwiches with truffle cream, prosciutto. 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, the medieval perfection of 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, incredible food, and that unmistakable Chianti silence.
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. Impeccable service and stunning vineyard views.
MapLegend The world's most famous butcher in Panzano. Steaks, poetry recitals, and unforgettable theater. A pilgrimage.
MapViral The most Instagrammed road in Italy. The winding cypress-lined road near Chianciano Terme has billions of views. Drive it, don't just photograph it.
MapViral The world's most famous butcher recites Dante while cutting your Fiorentina. His "meat hymn" videos have 20M+ views.
MapViral A medieval village built around a natural hot spring pool. The "free thermal baths of Tuscany" TikToks get millions of views. Soak post-run.
MapTwo nights on Italy's most romantic lake
The jewel of northern Italy. Deep blue water framed by Alps, pastel-colored villages cascading down hillsides, villas dripping with wisteria. Varenna is the quieter, more romantic alternative to touristy Como town — and it's directly accessible by train from Milan.
Pool + Spa The most iconic hotel on the lake. 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. Stunning grounds for morning strolls.
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. The ultimate sunset dinner spot on Lake Como.
MapVarenna Casual lakefront bar right on the water. Perfect for aperitivo at golden hour — negroni with the Alps reflecting in the lake.
MapViral "The most beautiful villa in the world." Star Wars and Casino Royale filming location. The garden photos break Instagram every summer.
MapViral The "secret free beach" of Lake Como. Crystal clear water, mountain backdrop, zero crowds if you go early. TikTok's favorite Como swim spot.
MapViral "Lovers' Walk" — a cliffside path carved into the rock above the lake. The sunset videos from here get millions of views.
MapThree days in the Eternal City to close the honeymoon
The city where every cobblestone has a story. Ancient ruins and modern trattorias. The Colosseum at dawn, Trastevere at dusk. Three days to slow down, eat everything, and end the honeymoon the way it started — just the two of you, somewhere unforgettable.
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 Legendary rooftop restaurant & bar with the best panoramic view in Rome. 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. Legendary cacio e pepe and carbonara. THE Roman trattoria experience. No reservations — arrive early.
MapIconic Legendary salumeria, bakery, and restaurant in one. The carbonara and the cured meats are otherworldly. Book ahead.
MapClassic Roman Family-run since 1961, steps from the Pantheon. Traditional Roman cuisine done perfectly. The artichoke and amatriciana are musts.
MapExplore The neighborhood near the Vatican. Wander in, sit down, eat whatever they're making. Less touristy than Trastevere, just as delicious.
MapViral Go at 6 AM before the crowds. You'll have the fountain practically to yourselves for the coin toss. The golden light is unreal. Every Rome TikTok that goes viral was filmed at this hour.
MapStreet Food The best supplì (fried rice balls) in Rome. The cacio e pepe supplì went mega-viral — crispy outside, molten cheesy rice inside. Tiny spot near Campo de' Fiori.
MapHidden Gem Peek through the keyhole at the Knights of Malta door on Aventine Hill — a perfectly framed view of St. Peter’s dome through a garden tunnel. One of Rome’s best-kept secrets.
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.
THE signature Florence run. Climb up V. Michelangelo, past Santa Miniato al Monte, and be rewarded with a panorama of the entire city at the top. In July: go at 6 AM.
Map Route DetailsFlorence's biggest green space. 395 acres of meadows, river paths, and wooded trails. Extends along the Arno for up to 15 km. The "Central Park" of Florence.
MapA challenging uphill run to the Etruscan hill town of Fiesole with incredible views. Run up, take the bus back. In the footsteps of A Room with a View.
MapStart 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.
MapThe famous unpaved white roads winding through Chianti vineyards. Quiet, scenic, and unforgettable. Same roads used in the professional cycling race.
MapA circular route through the rolling Val d'Orcia landscape. Cypress trees, wheat fields, and two beautiful hilltop villages. Dreamy.
MapRun downhill through vineyards and farmland to the natural hot springs of Bagno Vignoni. Soak in the thermal waters post-run. Best recovery ever.
MapA stunning trail from Colonno to Griante along the western shore. Flat-to-moderate terrain with incredible lakeside views the entire way. The signature Lake Como run.
MapShort but gorgeous waterfront path through Varenna. Perfect for an easy sunset run or morning shakeout. Connect with the Passeggiata degli Innamorati.
MapA beautiful out-and-back through olive groves with panoramic lake views. Best in the early morning when the lake is glass-still.
MapRome's most beautiful park. Shaded paths, connect to the Pincio Terrace for sweeping city views. Steps from Hotel de Russie.
MapRun on ancient Roman cobblestones past catacombs, ruins, and umbrella pines. One of the most unique runs on the planet. Go on a Sunday when the road is car-free.
MapFor 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