Italy layers ancient history with everyday pleasures—espresso at the counter, evening strolls, and dinners that stretch into stories. Over 14 days, you’ll trace the Roman Empire, touch Renaissance art in Florence, and swim off the Amalfi Coast, all with a relaxed, family-first pace.

Rome sets the stage with the Colosseum and Vatican, yet it’s the piazzas and gelato that win over kids. Florence follows with sculpture, markets, and artisan workshops in the Oltrarno, plus an easy day trip through Tuscan hill towns. Naples is your gateway to Pompeii, coastal villages like Positano and Amalfi, and the island of Capri.

Trains connect the dots in under three hours, and ferries shuttle you to beaches and caves. Expect generous servings of pasta and pizza, comfortable walking days, and early starts for big museums. Dress modestly for churches, prebook major sights, and pack comfy shoes for cobblestones and archaeological sites.

Rome

Rome dazzles with gladiator arenas, soaring basilicas, and street-corner fountains that have flowed for centuries. Families love the mix: big-ticket history in the morning and relaxed neighborhoods like Trastevere after dark. Keep eyes peeled for SPQR manhole covers—little breadcrumbs to the city’s past.

How to arrive: Fly into FCO or CIA. Compare fares and routes on Omio (flights). From FCO, the Leonardo Express reaches Termini in ~32 minutes.

Days 1–5: Ancient icons, Vatican masterpieces, and kid-friendly exploring

• Colosseum and Roman Forum: Enter like a gladiator and get the big stories in digestible bites for kids on the Colosseum Arena Floor, Roman Forum and Palatine Hill Guided Tour.

  

  Expect 2.5–3 hours; strollers aren’t ideal on ancient steps—bring a carrier for little ones.
• Vatican highlights with no waiting: Save energy and attention spans with the Vatican Museums, Sistine Chapel & St Peter’s Basilica Guided Tour.

  

  Early entry keeps crowds manageable; dress shoulders/knees for the Basilica.
• See more, walk less: Zip between Trevi Fountain, the Pantheon, and Piazza Navona on the Rome Highlights City Tour by Golf Cart with Gelato.

  

  It’s a hit with kids and grandparents alike, and the gelato stop is a built-in bribe.
• Evening food tour in Trastevere: Taste suppli, porchetta, and Roman pastas on the award-winning Winner 2025 Rome Twilight Trastevere Food Tour.

  

  Guides weave history into bites—perfect for curious teens and foodie parents.

Local gems for families: Explore the hands-on Explora Children’s Museum near Piazza del Popolo; run the Circus Maximus greens; rent bikes on the Appian Way and visit the nearby catacombs.

Where to stay (family-friendly picks):

• Hotel Santa Maria (Trastevere; quiet courtyards, family rooms).
• Hotel Mascagni (near Repubblica; reliable mid-range, easy transit).
• The Beehive (budget-friendly, community vibe; private rooms for families).
• Browse apartments for extra space and kitchens on VRBO Rome or check rates on Hotels.com Rome.

Food and coffee—specific places we love:

• Breakfast/coffee: Roscioli Caffè for maritozzi; Tazza d’Oro by the Pantheon; Panificio Bonci near Vatican walls for pastries and pizza al taglio.
• Lunch: Pizzarium Bonci for inventive slices; Mercato Centrale (Termini) for a family food court with Roman classics; Pastificio Guerra near Spagna for budget fresh pasta to-go.
• Dinner: Taverna Trilussa (Trastevere) for carbonara served in the pan; Da Enzo al 29 for cacio e pepe; Flavio al Velavevodetto in Testaccio for slow-braised amatriciana.
• Gelato: Gelateria del Teatro (sage-lemon), Fatamorgana (creative naturals).

Shopping: Via del Corso for high-street brands; the Monti district for indie boutiques and vintage; Campo de’ Fiori market for picnic fixings; Eataly Ostiense for edible souvenirs.

Rome → Florence (morning of Day 6): Take a Frecciarossa high-speed train (~1h30–1h40, usually €25–€60 per adult) via Omio (trains). Book early for seat deals; travel light for easy boarding.

Florence

Florence is a compact treasure chest of Renaissance art: Michelangelo’s David, Brunelleschi’s dome, Botticelli’s Birth of Venus. It’s also wonderfully walkable, with gelato stops every few blocks and parks like the Boboli Gardens for sprawling playtime.

Days 6–10: Renaissance hits, markets, and a Tuscan countryside day

• Uffizi and Accademia: Reserve timed entries; pair David with a short stroll through San Lorenzo market. Pause at Orsanmichele to spot the guild statues—history you can “see.”
• Tuscany in one day: Siena’s shell-shaped piazza, medieval San Gimignano, Pisa’s Leaning Tower, plus a winery lunch on the Tuscany Day Trip from Florence.

  

  Ideal for families who want big scenery without renting a car.
• Pasta workshop (hands-on for kids): Roll ravioli and tagliatelle in a friendly studio on the Florence: Pasta Cooking Class—you’ll eat what you make.

  

  A delicious souvenir skill to take home.
• Optional half-day wine country sampler: For families with older kids/teens, the Small-Group Wine Tasting in the Tuscan Countryside offers scenic drives and cellar visits; many wineries provide grape juice tastings for kids.

  

Neighborhood strolls: Cross Ponte Vecchio into the Oltrarno for artisan workshops, then climb up to Piazzale Michelangelo for sunset. The Boboli and Bardini gardens give kids room to roam.

Where to stay:

• Hotel Davanzati (central, personable, great for families).
• Grand Hotel Minerva (rooftop pool—a unicorn in Florence, book early).
• Hotel Santa Croce (value near Santa Croce; walk to sights).
• Compare apartments and family suites on VRBO Florence or check hotels on Hotels.com Florence.

Food and coffee—where to refuel:

• Breakfast/coffee: Ditta Artigianale (specialty coffee); Caffè Gilli (historic pastry counter).
• Lunch: Trattoria Mario (hearty Tuscan classics; go early), All’Antico Vinaio (famous schiacciata sandwiches), Mercato Centrale (upstairs food hall for families with many tastes).
• Dinner: Gusta Pizza (wood-fired pies), Trattoria da Burde (old-school Tuscan), La Giostra (if you want a celebratory evening).
• Gelato: Gelateria dei Neri and La Carraia—two scoops, minimal regrets.

Shopping: Via de’ Tornabuoni for window-shopping Italian fashion; San Lorenzo leather market for belts and bags; Bottega dell’Olio & co. for olive oil, honey, and pantry gifts.

Florence → Naples (morning of Day 11): Frecciarossa to Napoli Centrale takes ~2h45–3h10 (typically €30–€75) via Omio (trains). From Naples, you can stay in the city or continue ~1h10 on the Circumvesuviana/Campania Express to Sorrento; for the coast and islands, ferries are on Omio (ferries).

Naples (Gateway to Pompeii & the Amalfi Coast)

Naples buzzes with energy—Baroque churches, underground Greek walls, and the birthplace of pizza. It’s the perfect springboard for Pompeii, Mount Vesuvius, Capri, and the cliff-hugging villages of Positano and Amalfi.

Days 11–14: Pompeii adventure, seaside villages, and island time

• Pompeii with an archaeologist: Bring the ancient city to life on the Pompeii Small Group Tour with an Archaeologist.

  

  Kids love the street ruts from ancient carts, mosaics, and bakery ovens. Bring hats and water—shade is scarce.
• Capri day trip: Ferry from Naples or Sorrento (45–80 minutes, ~€20–€45 each way) via Omio (ferries). In Capri town, ride the funicular, walk to Augustus Gardens for Faraglioni views, then head to Marina Piccola for a swim.
• Amalfi Coast villages: Base in Sorrento (easy transit) and visit Positano and Amalfi by ferry (spring–fall) via Omio (ferries) or by bus via Omio (buses) (~€5–€10). Positano’s Spiaggia Grande is great for a beach break; Amalfi’s Duomo stairs become a family photo-op.
• Mount Vesuvius: On clear days, ride up to the trailhead and hike the 20–30 minute path to the crater rim—short, dusty, rewarding views over the Bay of Naples.

Where to stay:

• Naples (city base): Hotel Piazza Bellini (family-friendly, central historic quarter), Hotel Royal Continental (waterfront promenade, pool in season), Grand Hotel Vesuvio (iconic seafront classic).
• Prefer Sorrento for the coast: Search family apartments and hotels on VRBO Sorrento or compare Naples vs. Sorrento on Hotels.com Naples.

Food—and the best pizza on earth:

• Naples pizza: L’Antica Pizzeria Da Michele (two-pizza menu, cash-only vibe); Sorbillo (more styles, busy but fun).
• Seafood: Trattoria da Nennella (spirited, family-style plates in the Spanish Quarter); Mimì alla Ferrovia (classic Neapolitan dishes near the station).
• Sorrento favorites: Pizzeria Da Franco (queues move fast), Trattoria da Emilia at Marina Grande (sea-view, simple seafood), Il Buco (special-occasion tasting menus).
• Sweets: Sfogliatella Mary in Galleria Umberto; in Amalfi, Pasticceria Pansa for lemon delights.

Shopping: Naples’ Spaccanapoli for nativity workshops and artisan souvenirs; Sorrento for inlaid-wood boxes and lemon products; Capri for linens and sandals. Pack olive oil, colatura di alici (anchovy essence), and limoncello (check liquid rules) as edible mementos.

Departing Italy: Trains from Naples to Rome’s Termini take ~1h10–1h20; connect to FCO by Leonardo Express. Book on Omio (trains) and compare flights home on Omio (flights).

Optional add-on from Rome (swap into Days 1–5 if desired): If you prefer to see the coast as a guided sampler without changing hotels, consider the Pompeii, Amalfi Coast and Positano Day Trip from Rome for a one-day “greatest hits.”

It’s efficient, especially for first-time visitors.

Budget tips for a 50/100 spend level: Mix sit-down restaurants with market lunches; book major attractions as skip-the-line to maximize time; choose apartments with kitchens for breakfasts; travel by train instead of renting a car; and target free hours (first Sundays for many state museums, select dates) when it fits the schedule.

Two weeks in Italy gives your family a taste of the country’s greatest hits without rushing. You’ll stand where emperors ruled, learn to make pasta by hand, and ferry between cliffside villages—memories that linger long after the last gelato.