Best 28 Days in Italy — Walking Tours

Visit the Pantheon, toss a coin in Trevi Fountain with the children, and stroll to Piazza Navona for gelato

Wander Trastevere's cobblestone lanes at sunset and eat supplì, cacio e pepe, and Roman pizza al taglio

Shop the Testaccio covered market and taste supplì, porchetta, and maritozzo in Rome's most authentic food neighborhood

Stroll from the Spanish Steps through the Baroque heart of Rome to the Trevi Fountain and Piazza Navona

Spend unscheduled time in Rome at your own pace — browse markets, linger at a café, or follow a last-minute lead

Sample 20+ tastings of Rome's best street food, wine, and local specialties across two neighborhoods at dusk

Pre-book Vatican Museums tickets to see the Sistine Chapel and Raphael Rooms without queuing for hours

Walk Rome's dark alleys at night and hear stories of murders, executions, and hauntings across centuries

Reserve a mandatory 2-hour slot at the Borghese Gallery, then let the children ride bikes and row boats in Rome's loveliest park

Make fresh ravioli, fettuccine, and pappardelle in a small-group Roman cooking class — great for children age 5+

Climb the dome of St. Peter's Basilica and walk the world's smallest country at the Vatican

Walk Florence's UNESCO historic center from the multicolored Duomo to the medieval Ponte Vecchio bridge

Walk across the medieval Ponte Vecchio and browse Oltrarno's leatherworkers, bookbinders, and mosaic workshops

Graze the Mercato Centrale's two floors of Tuscan street food — lampredotto, ribollita, schiacciata — and browse outdoor leather stalls

Spend unscheduled time in Florence — climb the Giotto Campanile, browse Oltrarno leather shops, or linger at a cafe

Take the 2.5-hour train to Cinque Terre and hike or ferry between five pastel fishing villages on the Italian Riviera

Take the 2-hour Frecciarossa to Venice and spend a day getting lost in canals, crossing Rialto Bridge, and visiting St. Mark's

Take the 1.5-hour train to Lucca and rent a bike to ride the Renaissance city walls circling the intact medieval center

Ride vaporetto Line 1 the full length of the Grand Canal past 200 Gothic and Renaissance palaces — then take a gondola through back canals

Take the vaporetto to the Murano glass museum and glassblowing demos — kids love the fire — then ride to Burano's candy-colored houses

Visit the Rialto Fish Market at dawn, cross the 16th-century stone bridge, and watch Grand Canal boat traffic below

Navigate Venice's back canals and medieval calli (alleys) away from the tourist trail, discovering hidden campi and craft shops

Spend unscheduled time in Venice — ride a vaporetto down the Grand Canal, find a bacaro, or sit in a quiet campiello

Walk Sorrento's clifftop center, descend to the fishing harbor, and take in views of Vesuvius across the Bay of Naples

Stroll to the clifftop park at the Gardens of Augustus — children love spotting the Faraglioni sea stacks from the viewpoint

Spend a free morning or afternoon in Capri — swim at Marina Piccola, browse boutiques in the Piazzetta, or walk to the Natural Arch

Walk Positano's steep narrow lanes, photograph its pastel dome from the beach, and swim at Spiaggia Grande

Catch the morning hydrofoil to Capri, visit the Blue Grotto, and browse the glamorous Piazzetta before the return ferry

Walk through Milan's 1867 glass-vaulted arcade and stroll the Quadrilatero della Moda — Via Montenapoleone, Via della Spiga

Spend a free half-day in Milan at your own pace — browse the Pinacoteca di Brera, sit in a Navigli cafe, or revisit the Duomo

Hike the Sentiero Azzurro coastal trail from Monterosso to Vernazza along dramatic cliffside paths above the Ligurian Sea

Swim and sunbathe at Monterosso al Mare's sandy beach — the only proper beach in Cinque Terre — with views of medieval towers

Take the train to the Ligurian coast and hike the coastal Blue Trail between Monterosso, Vernazza, and Corniglia

Cross the lake by ferry between Bellagio and Varenna, browsing pastel lanes, gelato shops, and silk boutiques

Spend a free half-day at Lake Como — visit Villa Carlotta's gardens, swim from a lido, or take the Bellagio funicular up to the fortress