Best 21 Days in Italy

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

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

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+

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

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

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

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

Book ahead for the Uffizi to see Botticelli's Birth of Venus, da Vinci's Annunciation, and the world's greatest Renaissance collection

Climb 463 steps to the top of Brunelleschi's revolutionary dome for 360° views over Florence's terracotta rooftops

Book a timed slot to stand before Michelangelo's 5.17m marble David at the Galleria dell'Accademia

Join a small-group day tour through Chianti vineyards, medieval San Gimignano, and a Tuscan farmhouse lunch

Enter St. Mark's golden Byzantine basilica and the Doge's Palace — book the Palace in advance to skip long queues

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

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

Take the bus to Anacapri and descend by rowboat into the Blue Grotto's eerily glowing sea cave

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

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

Book months ahead to see Leonardo's Last Supper mural — only 40 visitors admitted every 15 minutes

Walk among 135 Gothic spires on the Duomo rooftop and admire 3,200 marble statues on Italy's largest cathedral

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

Drive through UNESCO-listed Val d'Orcia, stopping at cypress-lined roads, Pienza village, and a Brunello di Montalcino tasting

Swim from a private lido, rent a kayak, or sit on a villa garden terrace and watch the light change on the Alps

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