Trip overview This 2–3 week Italy plan balances relaxed villa time with a few well-chosen excursions so you can unwind, play tennis, enjoy wine, hike, and spend time on Lake Como — while still seeing Rome (Colosseum), historic churches, and visiting Aunt Marge. Two flexible approaches follow: a Relaxed Villa-Based plan (best if you want a slow pace) and an Active Multi-Region plan (if you want more variety). Both assume a rented car for countryside and Lake Como flexibility; driving alternatives are noted. Key priorities addressed - Lake Como: boat rental, lake tours, time to relax. - Rome: Colosseum, movie-related film locations, ancient sites, old churches, Vatican. - Food & wine: tasting dinners, markets, a cooking class or winery day in Tuscany. - Tennis: villa court recommendations or local tennis clubs. - Hikes: easy-to-moderate hikes (Lake Como, Cinque Terre or Dolomites/Gargano choices), scenic walks. - Visiting Aunt Marge and trying to include the kids if possible. - Slow pacing and accessible options (you mentioned you’re getting older). Comfortable transfers and rest days built in. Practical notes up front - Length: I give both 14- and 21-day variants. If you have 2 weeks, choose the shorter version; with 3 weeks you can add regions or more rest days. - Car rental: Reserve an automatic if you prefer not to drive manual. Expect ZTL (restricted traffic) in many historic centers (Rome, Florence, small towns) — park outside and walk or use public transit. Use toll roads (autostrade) for faster travel. - Pace: Plan 1–2 overnight blocks in each base; allow 2–3 consecutive days in a villa for full rest. - Book ahead: Lake Como boat rental, Colosseum timed tickets, Vatican, guided wine tours, and popular villas sell out in summer. - Accessibility: If mobility is a concern, I’ve marked lower-effort suggestions in each day plan. Relaxed Villa-Based Itinerary (recommended if you want to mostly relax) Structure (14 days) - Days 1–4: Lake Como base (villa) - Days 5‐8: Tuscany (villa near Siena or Florence) - Days 9–11: Rome (2.5–3 days) - Days 12–14: Flex days / visit Aunt Marge / return to a favorite villa or nearby coast Structure (21 days) - Add an extra week to linger in Tuscany or split time between Amalfi Coast and Rome; insert extra rest days and a slow drive through Umbria. Sample 14-day relaxed plan (detailed) Day 1: Arrival north (Milan or Bergamo) — transfer to Lake Como - Pick up car at airport (or hire driver). Drive ~1–1.5 hours. Check into a villa with terrace and (ideally) a tennis court. - Evening: Ease into Italy with a lakeside dinner. Low effort. Day 2: Lake Como — private boat rental & towns - Rent a small private boat (or captain-led) for half or full day. Cruise Bellagio, Varenna, and Villa del Balbianello area. Bring picnic or stop in a trattoria. - Late afternoon: light walk through town; early evening tennis if the villa has a court. Day 3: Lake Como — hikes & wine - Morning: easy hike (Greenway del Lago, or trails above Varenna). Choose gentle 1–2 hour routes. - Afternoon: wine tasting at a small local enoteca/organize a private tasting driver to a nearby Franciacorta winery (sparkling wine region near Brescia) or head to Como’s countryside. Day 4: Lake Como to Tuscany (or direct to Florence area) - Drive leisurely to your Tuscany villa (4–5 hours). Stop in Parma or Modena for lunch (great food stops). Evening: rest. Day 5: Tuscany — rest, tennis, cooking class - Morning rest or pool. If villa has tennis, morning match. - Afternoon: private cooking class or market tour followed by dinner. Day 6: Tuscany — wine day in Chianti or Montalcino - Full-day vineyard tour with tastings and lunch. Choose a small, family-run estate for a relaxed pace. Day 7: Tuscany — light hikes & hill towns - Morning: gentle walk in Val d'Orcia or a vineyard trail. - Afternoon: visit Pienza or Montepulciano (cheese, local wine, slow pace). Day 8: Travel to Rome (or stay another day in Tuscany if you prefer a slower arrival) - Train is an option: drop the car in Florence and take fast train to Rome (1.5h) to avoid city driving. Day 9: Rome — Colosseum & Ancient Rome (film-themed) - Book Colosseum & Roman Forum timed entry. Consider a private guide who can point out classic movie scenes (e.g., Roman Holiday, Gladiator references) and film-history anecdotes your husband will enjoy. - Evening: Trastevere for dinner (classic Roman food). Day 10: Rome — Vatican & Old Churches - Morning: Vatican Museums & Sistine Chapel (book skip-the-line). Afternoon: St. Peter's Basilica. - Late afternoon: visit Santa Maria Maggiore or San Giovanni in Laterano (beautiful historic churches; quieter than St. Peter’s). Day 11: Rome — slow day, meet Aunt Marge (if in/near Rome) - Flexible: arrange to visit Aunt Marge. If she lives elsewhere, use this day to travel to her city. Keep this day unstructured to prioritize family time. Day 12–14: Flex days - Use for recovery, local exploration, or to bring in the kids. Or drive to Amalfi Coast for 2 relaxed days (Positano/Amalfi) instead of extra Rome days. Active Multi-Region Itinerary (if you want more variety) - Lake Como (3 days), Cinque Terre or Dolomites (3 days for hiking), Tuscany (4–5 days), Rome (3–4 days), Amalfi/Capri (2–3 days if 21-day trip). - Swap hikes between Cinque Terre coastal trails (active but achievable) or the Dolomites (more alpine-focused) depending on fitness. Tennis options - Villas: Many higher-end villas offer private courts; request this beforehand. - Clubs: Lake Como (Circolo Tennis Como), Florence (Circolo del Tennis Firenze), Rome (Foro Italico has historic courts, but public clubs like Circolo Canottieri Aniene offer access). Book courts in advance. - Coaches: Hire a local pro for a private lesson for a fun, low-effort tune-up. Lake Como boat tips - Book a private or captain-led boat especially in high season. Small rental boats are widely available, but some docks require a license. - Suggested route: Como town → Brunate viewpoint → Villa Olmo → Bellagio → Varenna → Villa del Balbianello. - Consider a sunset cruise and a day with a hired skipper so you can relax and swim. Rome and the Colosseum for a movie-lover - Add a private guide who can introduce cinematic spots: Colosseum (many films), Via dei Fori Imperiali, the Spanish Steps (Roman Holiday), Largo di Torre Argentina (films), Cinecittà (studio tour) if interested. - Evening: enjoy a classic Roman trattoria and gelato. Logistics & comfort suggestions (because you mentioned getting older) - Book fewer hotel changes; aim for 2–3 home bases and day trips. - Hire private transfers for longer legs if you prefer not to drive long distances. - Choose first-floor or elevator-access accommodations if stairs are difficult. - Allow mid-day rests and avoid very long walking days; use taxis in towns with cobblestones. - Travel insurance and European health card check recommended. Booking checklist (what to reserve early) - Colosseum & Vatican timed tickets - Private boat/skipper on Lake Como - Villas with tennis court or confirm local club access - Wine tours and cooking classes - Car rental (automatic if preferred) and GPS or offline map app Suggested budgets & splurges - Moderate: mix of villa rentals, private boat half-days, some paid tours — mid-range restaurants, a couple of special dinners. - Splurge ideas: private boat for a full day, Michelin tasting dinner in Florence or Rome, a private driver for a Tuscany day, a boutique villa with heated pool and tennis court. Packing & health essentials - Comfortable walking shoes and a light daypack - Tennis shoes & attire + a couple of dressy outfits for nicer dinners - Sun protection for Lake Como boat days - Copies of important documents, meds, and a list of nearby hospitals for each base Family & Aunt Marge coordination - Contact Aunt Marge early to confirm her location and availability; plan the Rome/Aunt visit day(s) around her schedule. - If kids may come, set flexible lodging options (extra room or nearby rental) and activities they’ll enjoy (short hikes, boat day, pizza/cooking class). Final notes This plan is designed to be easily scaled up or down. If you prefer, I can convert either the Relaxed or Active plan into a day-by-day printable travel document with addresses, recommended villas, restaurant names, and links to book experiences (boat captains, tennis clubs, private guides). Tell me your travel window, whether Aunt Marge is in a particular city, whether you’d prefer the Dolomites or Cinque Terre for hikes, and I’ll tailor it further.