Italy in December is a warm embrace of tradition: twinkling lights in historic piazzas, nativity scenes in church naves, and the smell of roasted chestnuts on cobblestones. From Milan’s Duomo to Rome’s Colosseum, winter brings quieter museums, easier reservations, and a festive rhythm perfect for families.

This 14-day itinerary traces a classic arc—Milan, Florence, Rome—with time for headline museums and hands-on experiences, plus kid-approved breaks for hot chocolate, gelato, and parks. You’ll ride Italy’s high-speed trains, which are fast, comfortable, and budget-friendly for families.

December essentials: pack warm layers, waterproof shoes, and a compact umbrella. Note holiday hours around December 24–26 and 31; prebook marquee sites (Last Supper, Uffizi, Vatican). Keep an eye on your belongings in crowded areas. With that, settle in for Italy’s winter magic.

Milan

Italy’s style capital mixes Gothic grandeur with Renaissance genius and modern design. In December, the Duomo’s marble spires sparkle and the Galleria’s giant tree turns shopping into spectacle. It’s also your gateway to Lake Como and snowy Alpine panoramas—easy day trips kids remember forever.

Top sights include the Duomo (and rooftop), Leonardo’s The Last Supper, Sforza Castle’s museums and gardens, the science-forward Museo Nazionale Scienza e Tecnologia, and the Brera district’s Pinacoteca di Brera. Families love the Triennale Design Museum’s interactive exhibits and the playgrounds in Parco Sempione.

Days 1–4 (Dec 16–19): Duomo, Last Supper, Sforza Castle, Lake Como/Alps

• Duomo and rooftops: Learn the cathedral’s 600-year story, then step onto the rooftop for sweeping views (great for older kids). Inside, the winter light is glorious for photos.
• Leonardo’s Last Supper: Limited slots—book early. The short, focused visit works well for families and sparks great conversations about art and history.
• Sforza Castle + Parco Sempione: Combine castle museums with an hour at the park. Add the Aquarium (Acquario Civico) for a kid-pleasing bonus.
• Day trip options (choose one):
  • Lake Como: Winter ferries, pretty promenades, and a relaxing cruise.
  • Bernina Red Train: A scenic snow-country adventure into the Swiss Alps.

Family-friendly Milan eats (mid-range, reliable): Start with panzerotti from Luini by the Duomo; pizza at Piz (short menu, fast turnover, friendly staff); fresh pasta at Pasta d’Autore; risotto and cutlets at Trattoria del Nuovo Macello (book ahead); snack through Eataly Smeraldo’s counters; sweets at Pasticceria Marchesi 1824 or hot chocolate at CioccolatItaliani.

Where to stay (center or near Cadorna/Centrale for easy trains): Search Milan stays on VRBO | Search Milan hotels on Hotels.com

Getting to Milan: Fly into MXP/LIN/BGY. Compare fares on Omio Flights (to/from Europe) or Trip.com Flights. From Malpensa, the Malpensa Express train to Cadorna/Centrale runs ~37–52 minutes.

Curated Milan activities (Viator, family-friendly; pick 1–2):

• Milan Duomo & The Last Supper Skip-the-Line Small Group Tour — Efficient, story-rich overview for all ages.

  

• Milan Super Saver: Skip-the-Line Duomo and Rooftop Guided Tour — Sunset rooftops are a winter highlight.

  

• Bellagio & Varenna: Small Group Tour from Milan with Boat Cruise — A winter-tailored Lake Como day perfect for families.

  

• St Moritz & Swiss Alps Day Trip with Bernina Red Train from Milan — Snowy scenery, epic photos, smooth logistics.

  

Local gems: Brera at dusk, Navigli’s canals for an early family apertivo, and Via Dante’s lights toward Sforza Castle. Check the Christmas village near Duomo/Galleria for treats and crafts.

Travel to Florence (Morning of Dec 20)

Train: Frecciarossa from Milano Centrale to Firenze S. M. Novella ~1h55; typical advance fares €25–€60. Book on Omio Trains. With kids, choose seats around a table and pack snacks.

Florence

Birthplace of the Renaissance, Florence is a living museum where domes and bell towers punctuate the skyline. December’s softer crowds make the Uffizi and Accademia more pleasant, and holiday markets pop up around Santa Croce.

Highlights: Brunelleschi’s Dome (or Giotto’s Bell Tower for fewer steps), the Uffizi’s Botticelli rooms, Michelangelo’s David at the Accademia, Ponte Vecchio at golden hour, Palazzo Vecchio’s family-friendly secret passage tours, and the hands-on Museo Galileo.

Days 5–8 (Dec 20–23): Uffizi, Accademia, Duomo Complex, Oltrarno Crafts

• Uffizi + Accademia: Do these on separate mornings; reserve time slots. The new family audio guides keep kids engaged.
• Duomo complex: Consider the Baptistery and Museo dell’Opera del Duomo for quieter, equally fascinating stops; climb Giotto’s Tower if you prefer open-air steps.
• Oltrarno: Cross Ponte Vecchio to artisans’ workshops around Santo Spirito; pop into the Boboli Gardens for a winter stroll if the weather cooperates.
• Optional half-day: Pisa (Leaning Tower exterior and Field of Miracles) or Siena’s shell-shaped Piazza del Campo via regional train/bus—check Omio for times.

Family-friendly Florence eats: Sample stalls upstairs at Mercato Centrale (everyone gets what they want); wood-fired pies at Gusta Pizza; ribollita and bistecca (share!) at Trattoria da Burde or Trattoria Mario (lunch, no-frills, bustling); panini at All’Antico Vinaio (go early); gelato at Gelateria dei Neri or Vivoli; breakfast pastries at Scudieri by the Duomo.

Where to stay (near the Duomo/Santa Maria Novella for walkability): Search Florence stays on VRBO | Search Florence hotels on Hotels.com

Travel to Rome (Morning of Dec 24)

Train: Frecciarossa from Firenze S. M. Novella to Roma Termini/Tiburtina ~1h30–1h40; typical advance fares €20–€50 on Omio Trains. Aim for an early train to enjoy a festive Roman afternoon.

Rome

The Eternal City layers ancient forums, Baroque fountains, and lively trattorias into one open-air classroom. In December, nativity scenes adorn churches and Piazza Navona hosts a classic Christmas market—carousel rides included.

Must-sees: Colosseum, Roman Forum & Palatine Hill; the Vatican Museums & Sistine Chapel; St. Peter’s Basilica (dome climb for teens); Trevi Fountain; Spanish Steps; and Piazza Navona. Families appreciate Villa Borghese park, the Bioparco zoo, and the lesser-known Centrale Montemartini (ancient statues in a power station—kids love the contrast).

Days 9–14 (Dec 24–29): Ancient Rome, Vatican, Baroque Highlights, Parks & Markets

• Ancient Rome: Do Colosseum + Forum + Palatine on one day; book a timed entry. Bring a simple “spot the symbol” scavenger list for kids (eagles, laurel wreaths, SPQR).
• Vatican: Early entry helps. The Raphael Rooms and the Sistine Chapel are your art anchors; end at St. Peter’s. On Dec 25, most museums close—plan a light day of piazzas and lights.
• Baroque walking loop: Trevi Fountain → Pantheon → Piazza Navona (market rides, roasted nuts). Evening illuminations are magical.
• Green day: Rent bikes or a pedal cart at Villa Borghese; visit Galleria Borghese if your family enjoys sculpture (reserve ahead).
• Hands-on ideas: Pizza- or gelato-making classes are big hits with kids (evening slots are easiest around sightseeing).

Family-friendly Rome eats: Pizza al taglio at Bonci Pizzarium (near the Vatican) or Antico Forno Roscioli; thin-crust pies at Da Baffetto (go early); cacio e pepe at Flavio al Velavevodetto; Testaccio market for quick bites; suppli (fried rice balls) at Supplizio; gelato at Giolitti or Fatamorgana; espresso for grown-ups at Sant’Eustachio.

Where to stay (Centro storico or near Termini for easy transit): Search Rome stays on VRBO | Search Rome hotels on Hotels.com

Budget notes (target: 50/100): Favor family apartments with kitchens; use lunch for your sit-down meal (set menus are cheaper), then do casual dinners. Reserve big-ticket museums early at standard rates; most children under 18 enter free or discounted at state sites. City buses/metros are cost-effective; walk the historic centers where possible.

Getting home (Dec 30)

Fly out of Rome Fiumicino (FCO) or Ciampino (CIA). Compare on Omio Flights or Trip.com Flights. If you have a few free hours, take a last stroll through the Centro Storico for souvenirs and one more gelato.

Practical holiday tips: Many sites close early Dec 24 and on Dec 25/26; restaurants book up—reserve dinners for Dec 24–25 and Dec 31. Keep museum confirmation emails handy on your phone; arrive 15 minutes before time slots. Trains run holiday schedules—verify times on Omio Trains.

This Milan–Florence–Rome route balances blockbuster museums with down time, cozy meals, and festive streets. With fast trains and kid-friendly pacing, you’ll savor Italy’s winter sparkle—and leave with a camera roll of cathedral spires, Renaissance masterpieces, and smiles around every table.