07/27/2026
Senior trip to bounce around Italy - Lake Como, Milan, Florence, Pisa, Rome, Vatican
May 23 – Leave home.
May 24. Fly into Milan. Get to Lake Como - Direct trains run from Milano Centrale to Como S. Giovanni, taking about 40 minutes and departing every 30 minutes. Tickets cost roughly €4–€60 depending on the service and class.
May 24-27 - Lake Como: Cobblestone streets, stunning views of the lake and the surrounding mountains. Como Cathedral on Piazza del Duomo. Places to eat: La Punta –panoramic viewpoints and classic Lake Como atmosphere. Ristorante Bilacus – romantic setting with terrace seating and an elegant “evening out” vibe. Move around the lake via ferry visiting the towns of Bellagio and Varenna. Parco di Villa Serbelloni. The Basilica di San Giacomo on Piazza della Chiesa. Bellagio is also known for its shopping. Dispensa 63, a tiny family run restaurant on Salita Camillo. Benso Conte di Cavour, is a great place for lunch. If you’d like a lakeside view, Hotel Florence on Piazza Giuseppe Mazzini has a charming wisteria clad terrace. Breakfast at Caffe Varenna on Contrada Scoscesa. Villa Monastero & its botanical garden. Villa Cipressi gardens. Hike up to Castello di Vezio in the comune of Perledo for unparalleled lake views, start from Varenna harbor it takes 20 min to reach castle. Lunch at La Vista. Lover’s Promenade connects Varenna with Riva Garibaldi. Church of San Giorgio & St. John the Baptist. Gelato at Riva Gelateria. Dinner at Osteria Quatro Pass. Orrido di Bellano gorge and waterfall have a 5€ entry fee. Villa Balbianello.
May 27-29 – Train back to Milan: Arco della Pace, walk through Sempione Park, and visit Sforzesco Castle, and Galleria Vittorio Emanuele II. Marchesi 1824 for espresso or cappuccino with a small pastry before heading to the Duomo. Rinascente Rooftop for easy food and close-up views of the Duomo spires. Piazza Mercanti and San Bernardino alle Ossa. Teatro alla Scala, Brera, Parco Sempione, Santa Maria delle Grazie and The Last Supper guided tour. Dinner in the Navigli neighborhood. Gelateria della Musica is a good pick for pistachio, hazelnut, or chocolate-based flavors. Chinatown, especially dumplings, bao, noodles, or Chinese street food. Porta Nuova and see Milan’s modern skyline, including Bosco Verticale and Piazza G*e Aulenti. Via Montenapoleone, Via della Spiga, Via Sant’Andrea, and Via Manzoni as a short fashion district checkpoint.
May 29-June 1 – High-speed train, taking about 1 hour 40–55 minutes from Milano Centrale to Florence – Museum of San Marco, Piazzale Michelangelo, Basilica of San Lorenzo, Duomo, Campanile, Bargello, Uffizi Gallery, Ponte Vecchio, Church of Santa Maria Novella, Boboli Gardens, Florence Cathedral, Accademia, Medici Chapels. Places to eat: Il Bottegone, Caffe Scudieri, Caffe Gilli, Caffe Michaelangelo, Pizza Napoli 1955.
May 31 – take train, taking about 1 hour for €8.50–€16, from Florence Santa Maria Novella to Pisa – Borgo Stretto, lined with a pretty portico arcade. Palazzo della Carovana and the statue of Cosimo I de Medici in front of it. Leaning Tower, Duomo, Baptistery, Museo dell’Opera del Duomo, Santa maria della Spina, Cittadella Nuova Fortress, Chiesa del Santo Sepolcro, Keith Haring Mural. Places to eat: Caffe Carraia del Nicchio, Filter Coffee, Café Bistrot dell’ Opera, Osteria del Tumi, Osteria dei Cavalieri, Tuffo 13 Gelateria, Bocconcino, trattoria da Stelio, Pizzeria Quarto D’ ora Italiono
June 1-3 - high-speed train, taking about 1.5–1.6 hours from Florence to Rome – Colosseo (arena floor ticket and underground tour, buy online), Palatine Hill, Roman Forum (walk between Palazzo dei conservatori & Senatorial Palace), Trevi Fountain, Pantheon (free), Spanish Steps, Trastevere, Jewish Ghetto, Capitoline Hill. The Appian Way. Catacombs. Piazza Naona tartufo @ Tre Sacalini. Altar of Fatherland ride elevator. Church St. Louis. Church of the Gesu. Piazza Navona. Villa Borghese Gardens. Aventine Keyhole. Pasta, pizza, gelato (San Crispino, Venchi with Nocciolo Supreme).
June 3 - Vatican City – St. Peter’s Basilica (free 7-7) & Square (go 7:30 am to avoid line), Sistine Chapel (free), Basilica of St. John Lateran, Scala Sancta & The Holy of Holies. Clothes that cover shoulders and knees.
June 4 – fly home