- A persuasive, relaxed 2–3 week Italy itinerary tailored to include Rome’s Colosseum, old churches, wine country, tennis, hikes, and Lake Como boat days.
- Core route: 4 nights Rome → 5 nights Tuscany → 6 nights Lake Como; optional 3rd-week modules (Piedmont, Dolomites, or Venice/Prosecco).
- Built-in villa days, short drives, and flexibility for visiting Aunt Marge and possibly bringing the kids.
- Practical tips on car rental, ZTL, IDP, boats, tennis, budgeting, and timing.
- Booking checklist plus targeted Google search links for key reservations.
A note to my favorite Italian-food-loving movie buff
Picture this: You and me in the Colosseum’s underground tunnels where your favorite epics come to life, followed by twirling perfect cacio e pepe in a tiny Roman trattoria. Then we slow down in Tuscany with a glass of Brunello at sunset, and finish with a week on Lake Como—mornings of easy tennis, lazy boat days skimming past villas, and gentle lakeside walks. We rent a car, go at our pace, and spend as many days as we want simply relaxing at a villa. It’s Italy, unhurried—built for comfort, food, and a little adventure.
Trip at a glance (2–3 weeks, relaxed pace)
- Core 2 weeks: Rome (4 nights) → Tuscany/Chianti & Val d’Orcia (5 nights) → Lake Como (6 nights)
- Optional 3rd week (choose one module):
- Piedmont wine & food (Barolo/Alba), or
- Dolomites gentle alpine walks, or
- Venice & Prosecco Hills
- Travel style: Villa-forward, slow days, short drives, car rental outside big-city centers
- Interests woven in: Colosseum movie magic, old churches, tennis, wine, hikes, Lake Como boat days, family visit day for Aunt Marge, and kid-friendly options
Day-by-day: the unhurried 2-week plan
Rome (4 nights)
Day 1 — Arrive Rome, settle in
- Stay near the historic center (walkable to major sights); no car yet (Rome’s ZTL makes driving stressful).
- Stretch your legs with a passeggiata to the Pantheon and Trevi Fountain. Early night or light dinner.
- If the kids join: a short gelato stroll keeps the jet lag gentle.
Day 2 — The Colosseum you’ve always wanted
- Colosseum Underground + Arena Floor small-group tour (aim for morning or evening to avoid heat/crowds). Search: [Colosseum underground night tour tickets](https://www.google.com/search?q=Colosseum+underground+night+tour+tickets).
- Roman Forum and Palatine Hill at an easy pace (shade breaks).
- Dinner: classic Roman pasta tasting—cacio e pepe, amatriciana, carbonara—in Trastevere.
- Bonus for the movie lover: Search: [Gladiator filming locations tour Rome](https://www.google.com/search?q=Gladiator+filming+locations+tour+Rome).
Day 3 — Old churches and timeless art
- St. Peter’s Basilica (elevator to the roof if you’d like) and the Vatican Museums early-entry or late-entry timing.
- Caravaggio trail: San Luigi dei Francesi and Santa Maria del Popolo.
- Quiet gems: Santa Maria in Trastevere; Santa Prassede’s mosaics near Santa Maria Maggiore.
- Easy lunch and a siesta back at the hotel.
Day 4 — Food day (and flexible family visit placeholder)
- Rome food market walk or a hands-on cooking class. Search: [Rome Testaccio food tour](https://www.google.com/search?q=Rome+Testaccio+food+tour) or [Rome cooking class pasta and tiramisu](https://www.google.com/search?q=Rome+cooking+class+pasta+and+tiramisu).
- Afternoon free: If Aunt Marge is near Rome, use today for your visit. Otherwise keep it open for a nap or a slow stroll on the Appian Way (flat, scenic). Search: [Appia Antica bike rental](https://www.google.com/search?q=Appia+Antica+bike+rental).
- Evening: early trattoria dinner; pack for tomorrow.
Tuscany: Chianti & Val d’Orcia (5 nights)
Day 5 — Pick up the car; drive to your villa in Chianti (about 3 hours)
- Pick up the rental car outside Rome’s center (e.g., near Termini or an outer office). Avoid ZTL; set GPS to avoid restricted zones. Tips: [Italy ZTL zones map fines](https://www.google.com/search?q=Italy+ZTL+zones+map+fines).
- Check into a countryside villa/agriturismo with a pool; many have or can arrange tennis at a nearby circolo.
- Easy dinner at the property or a local osteria.
Day 6 — Chianti wine and a driver (so we both enjoy it)
- Arrange a private driver for tastings (Castellina, Radda, Panzano). Search: [Chianti wine driver private tour](https://www.google.com/search?q=Chianti+wine+driver+private+tour).
- Long lunch overlooking vineyards; light evening at the villa.
- If the kids join: some wineries welcome families and offer juice tastings or farm animals.
Day 7 — Siena and an old-church masterpiece
- Stroll Siena’s Campo and the stunning Duomo (consider the Piccolomini Library).
- Optional stop: Monteriggioni (tiny walled village) for a short, level walk.
- Return for a late-afternoon swim.
Day 8 — Val d’Orcia postcard loop (gentle)
- Pienza (level walking, cheese tasting), San Quirico, Bagno Vignoni hot springs town.
- Optional abbey visit (Sant’Antimo) for a peaceful church moment.
- Picnic dinner back at the villa.
Day 9 — Villa day: tennis, nap, repeat
- Morning tennis (property court or nearby club—ask the host to reserve). Search: [Tuscany tennis court rental](https://www.google.com/search?q=Tuscany+tennis+court+rental).
- Afternoon by the pool; optional short golden-hour walk among cypress lanes.
Transfer to Lake Como (6 nights)
Day 10 — Scenic drive north to Lake Como (5–6 hours, with food-lover stop)
- Break the drive in Parma or Modena for lunch and a tasting: Parmigiano Reggiano, prosciutto or traditional balsamic. Search: [Parma cheese prosciutto tour](https://www.google.com/search?q=Parma+cheese+prosciutto+tour) or [Modena acetaia traditional balsamic visit](https://www.google.com/search?q=Modena+acetaia+traditional+balsamic+visit).
- Arrive and settle in Bellagio/Varenna/Menaggio or a quieter base like Cernobbio/Tremezzina.
Day 11 — First lake day: easy boat tour
- Start with a guided boat tour so you can relax and learn the shoreline. Search: [Lake Como private boat tour Tremezzina](https://www.google.com/search?q=Lake+Como+private+boat+tour+Tremezzina).
- Visit Villa Carlotta gardens (flat paths, benches) and/or Villa Balbianello (short uphill walk; you can also arrive by boat).
- Dinner on a terrace.
Day 12 — Self-drive boat fun + lakeside tennis
- Rent a small boat (typically up to 40 hp needs no license; confirm locally). Search: [Lake Como boat rental no license Bellagio](https://www.google.com/search?q=Lake+Como+boat+rental+no+license+Bellagio).
- Afternoon tennis: ask hotel/villa to book a clay court at a nearby club. Search: [Lake Como tennis court booking](https://www.google.com/search?q=Lake+Como+tennis+court+booking).
Day 13 — Gentle hike and a lazy lunch
- Greenway del Lago di Como (mostly easy lakeside segments; do a short section out-and-back). Search: [Greenway del Lago di Como map](https://www.google.com/search?q=Greenway+del+Lago+di+Como+map).
- Alternative: the Sentiero del Viandante from Varenna for a short scenic section. Search: [Sentiero del Viandante Varenna map](https://www.google.com/search?q=Sentiero+del+Viandante+Varenna+map).
- Evening gelato and people-watching.
Day 14 — Valtellina wine and alpine air (easy pace)
- Day trip up the valley (Sondrio area) for terraced Nebbiolo (a.k.a. Chiavennasca) tastings; choose 1–2 wineries and a slow lunch. Search: [Valtellina wine tasting Sondrio](https://www.google.com/search?q=Valtellina+wine+tasting+Sondrio).
- Option: short, flat riverside walk or cable car/funicular viewpoints in the region.
Day 15 — Churches and a final swim
- Como town: Duomo and the funicular to Brunate (great views; minimal walking). Or peaceful Piona Abbey near Colico by car. Search: [Piona Abbey Lake Como hours](https://www.google.com/search?q=Piona+Abbey+Lake+Como+hours).
- Afternoon free for packing and one last splash or espresso in the piazza.
Departure
Day 16 — Drive 1–1.5 hours to Milan (MXP or LIN) and fly home; return car at the airport.
Optional 3rd-week modules (pick one)
- Piedmont (4–5 nights): Base in Alba/La Morra for Barolo/Barbaresco tastings, truffle-forward menus, and slow food. Short vineyard walks, hilltop villages, and leisurely lunches.
- Dolomites (4–5 nights): Base in Alpe di Siusi or Val Gardena for cable cars to panoramic, mostly level meadow walks; spa hotels for afternoon soaks.
- Venice + Prosecco Hills (4–5 nights): 2–3 nights in Venice at a quiet sestiere, then 2 nights near Valdobbiadene for a sparkling wine finale and gentle vineyard strolls.
Aunt Marge and family time
- Aunt Marge visit day: Place it in Rome, Tuscany, or Lake Como depending on where she lives. We can reshuffle a rest day to fit her schedule.
- If the kids can come: Add family-friendly options along the way—Roman gladiator school, gelato or pizza-making class; in Como, an hour at a lake beach club (e.g., Lido areas) and the funicular; in Tuscany, a farm visit with animals and cheese tasting.
Why this trip is perfect for you
- The Colosseum, up close and cinematic: Stand where the epics were set, with a small-group, skip-the-line experience.
- Food you’ll dream about: Market bites, a cooking class, wine country lunches, and time to savor classics—without rushing.
- Comfort first: Villas, pool days, short scenic drives, and the freedom to do nothing at all when we want.
- Your kind of play: Morning tennis, easy hikes, and two boat days on Como. We go gentle on the knees and big on the views.
Practicalities and tips
- Car rental and driving:
- Pick up after leaving Rome; return at Milan airport. Request an automatic and a GPS. Consider full-coverage insurance.
- International Driving Permit is recommended. Search: [AAA International Driving Permit](https://www.google.com/search?q=AAA+International+Driving+Permit).
- Avoid ZTL zones in cities; fines are camera-enforced. Search: [Italy ZTL zones driving fines](https://www.google.com/search?q=Italy+ZTL+zones+driving+fines).
- Toll roads (Autostrade): keep cash/card handy or consider a tourist telepass. Search: [Telepass tourist Italy](https://www.google.com/search?q=Telepass+tourist+Italy).
- Boat rental on Como: Many operators rent boats up to 40 hp without a license; bring ID and card; book in advance in high season.
- Tennis: Pack lightweight racquets or ask the property about rentals; clay courts are common; morning bookings are cooler.
- Health and comfort: Plan midday breaks, use shade, and book skip-the-line entries. Most days have 1–2 set pieces plus generous downtime.
- Budget (we have some savings):
- Lodging: €220–€450/night for high-comfort villas/hotels; splurges available on Como if you wish.
- Experiences: Colosseum special tour €70–€150 pp; wine driver day €250–€450 total; boat rental €120–€300 for a half-day.
- Car + fuel + tolls: ~€60–€90/day all-in depending on car type and driving.
- Food: Trattoria dinners €20–€40 pp; special meals €70–€150 pp with wine.
- Timing: Spring and early fall are sweet spots (mild weather, fewer crowds). Summer works with early starts and siestas.
- Connectivity: Consider an eSIM or local SIM. Search: [Italy travel eSIM options](https://www.google.com/search?q=Italy+travel+eSIM+options).
- Travel insurance: Worth it for peace of mind. Search: [Italy travel insurance comparison](https://www.google.com/search?q=Italy+travel+insurance+comparison).
Quick booking checklist
- Flights: Into Rome (FCO), out of Milan (MXP/LIN)
- Lodging: 4 nights Rome, 5 nights Tuscany villa, 6 nights Lake Como
- Key reservations: Colosseum Underground, Vatican timed entry, Chianti driver, Como boats, one special dinner per region
- Car: Automatic, airport drop-off, full coverage
- Court time: Pre-book tennis mornings in Tuscany and Como
- Family: Check kids’ schedules and Aunt Marge’s location; place the family day accordingly
In short: This plan checks every box—epic Rome for your inner cinephile, phenomenal food and wine, old churches that feel like time travel, and a blissfully slow finale on Lake Como with boats and tennis. We’ll savor, not sprint. And if we fall in love with the villa life (we will), we can linger longer and let Italy come to us.