14 Days in Italy Itinerary for First Timers: Rome, Venice, Florence, Amalfi Coast & Lake Como

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Best Time to Visit Italy

year-round, destination, vibe, spring, April, June, bloom, temperatures, comfy, crowds, manageable, cities, coastlines, autumn, September, October, perfect, cooler, golden sunsets, harvest season, Tuscany, tourists, summer, bliss, July, August, high-energy, buzzing, streets, heat, locals, vacay, coastal towns, packed, winter, November, March, quiet, cozy, festive, Christmas, beach towns, shut, season, shoulder season, weather, fewer crowds, shoulder seasons, April-May, September-October, comfortable, extreme crowds, prices, swim, water, warm, warmer, central Europe, avoid, peak season, Cinque Terre, Amalfi Coast, Easter, Rome.

2-Week Italy Itinerary Quick Glance

Day 1, Milan, Day 2, Day 3, Lake Como, Varenna, Bellagio, Menaggio, Day 4, Day 5, Venice, Burano, Day 6, Day 7, Day 8, Tuscany, San Gimignano, Val D’Orcia, Florence, Chianti, Day 9, Day 10, Capri, Day 11, Day 12, Amalfi Coast, Positano, Amalfi, Ravello, Day 13, Day 14, Day 15, Rome, Days 1-3, Pompeii, Days 4-6, Amalfi Coast, Day 7, Days 8-9, Days 10-11, Pisa, Cinque Terre, Day 12, Days 13-14, overnight, route, Sorrento, Days 2-4, Days 5-7, Days 8-10, Days 11-12, Days 13-14, quick glance, itinerary, 14 days, 2 weeks, stops, cities, regions, first time, highlights, destinations.

Getting Around Italy / Best Way to Travel

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Rome

Eternal City, introduction, Roman Empire, capital, Italy, old, new, ruins, 2000 years, Vespas, cobblestoned, streets, street vendors, selfie sticks, Fiumicino, FCO, international airport, city center, Leonardo Express, Roma Termini, 30 minutes, €14, taxi, €55, Terravision, €6.50, 45 minutes, Ciampino, CIA, budget airline, RyanAir, EasyJet, SITBusShuttle, €6, 40 minutes, €40, 25 minutes, Spanish Steps, Scalina Spagna, staircase, Trevi Fountain, famous, fountain, crowds, Pantheon, 120 AD, Roman temple, church, 609 AD, €5, €2, Piazza Navona, square, fountains, Largo di Torre Argentina, Julius Caesar, assassinated, 44 BC, €7, Colosseum, gladiators, ruins, €18, 25 years, Roman Forum, government buildings, ancient, Palatine Hill, aristocrats, emperors, Arch of Constantine, 302 AD, Via dei Fori Imperiali, dusk, Vittoriano, Victor Emmanuel II, first king, united Italy, Vatican City, smallest country, Catholic Pope, St. Peter’s Square, St. Peter’s Basilica, free, shoulders, knees, Vatican Museums, €20, €5, Sistine Chapel, Sundays, Castel Sant’Angelo, mausoleum, Hadrian, fortress, castle, wander, river, church, historic center, Trastevere, dinner, wine, Colosseum, Roman Forum tour, Capitoline Hill, sunset, Vatican Museums, St. Peter’s Basilica, gelato, shopping, piazza hopping, Circus Maximus, Orange Tree Garden, Aventine Hill, Pristine Sistine, Castel Sant’Angelo, Centro Storico, Piazza Navona, Spanish Steps, Via del Corso, Piazza del Popolo, Terrazza del Pincio, Villa Borghese, Borghese Gallery, 5 weeks, tickets, Spaghetti alla Carbonara, eggs, cheese, spaghetti, pork, black pepper, Cacio e pepe, cheese, pepper, pizza al taglio, rectangular, street food, quick lunch, Supplì, fried, breaded, rice, Bruschetta, garlic, olive oil.

Pompeii

ancient Roman city, volcano eruption, Herculaneum, ash, excavated, frozen-in-time, Roman civilization, 2000 years, Roma Termini, Napoli Centrale, Circumvesuviana train, 40 minutes, Pompeii Scavi Station, €4, luggage storage, €8, 5-minute walk, Pompeii site, entrance, €18, 2-3 hours, free, first Sunday, month, tour group, €12, audio guide, Porta Marina, €8, Rick Steves, free audio guide, Herculaneum, history buff, Pompeii ruins, Napoli Garibaldi, Ercolano Scavi, storage lockers, 2 hours, pizza, lunch, Pompei Scavi, red line, 4 hours, Sorrento, Vesuvius, local bus, tickets, hike, crater, flies, guided tour, transport, skip the line, entrance tickets, private tour, three sites, Gulf of Naples.

Sorrento

charming, beautiful views, Bay of Naples, Mt Vesuvius, volcano, jumping-off point, Pompeii, Amalfi Coast, Capri, base, three nights, luggage, Positano, Amalfi, Pompeii Scavi train station, Circumvesuviana train, 40 minutes, €3, last stop, cobbled streets, Via S. Cesareo, Aperol Spritz, dinner, window shopping, taxi, Naples airport, day trip, 30 minutes, train, farm, food experience, olive oil, limoncello, wine, pizza making class, atmosphere.

Amalfi Coast

stunning, beauty, couples, honeymoon destination, Amalfi, Positano, steep cliffs, curvy roads, quintessential houses, SITA bus 5070, one hour, Positano, 1.5-2 hours, Amalfi, €10, 24 hours, unlimited rides, tabaccherie, cigarette shops, bus schedule, ferry, 40 minutes, €18-22, Positano, one hour, €25, Amalfi, sea conditions, private car, large group, €600, Rome, Positano, Amalfi, unreal village, midday crowds, Marina Grande, beach, swim, Amalfi Cathedral, €3, exterior, Path of the Gods, hike, cliffs, Bomerano, Nocelle, downhill, views, Sentiero degli Dei, Ravello, Villa Rufolo, €8, SITA bus 5110, 30 minutes, morning ferry, window seat, pesto spaghetti, Amalfi view, pastel alleys, Fornillo Beach, lemon sorbet, Angelo Café, sunset boat tour, prosecco, cliffs, pistachio croissant, Collina Bakery, Cathedral, Lemon Cake, Pasticceria Pansa Amalfi, Da Adolfo, boat access, beachfront, 1 pm, red fish, cocktails, Franco’s Bar, La Tagliata, home-cooked, family kitchen, cooking class, funicular, Capri town, 9:00 AM, Marina Grande port, chaos, ferry, Positano, beach, shops, limoncello, food, cocktails, Path of Gods Trail, Atrani, tunnel, Ravello, Villa Rufolo, Villa Cimbrone, Mozzarella di Bufala, Italian water buffalo, Salerno, Limoncello, lemon liquor, Pasta al Limone, creamy, cheese, lemon, seafood, pasta, pizza, Naples, wood oven, dough, tomatoes, mozzarella, olive oil, basil leaves.

Capri

celebrity-favorite, island, yacht-studded, waters, glowing-blue, grottos, upscale, shopping, boat, ferry, Sorrento, Positano, Amalfi, €28, 50-minute, Marina Grande, Faraglioni, arch, water, €21, hour-long, Blue Grotto, famous attraction, €18, rowboat, one hour, noon, 2pm, Piazzetta, Via Camerelle, Anacapri, artisanal shops, boutiques, Piazza Vittoria, chairlift, Mount Solaro, €11, 30 minutes, Villa San Michele, €12, views, Gardens of Augustus, €2.50, Marina Piccola, beach, hydrofoil, Naples, Capri Town, Bar Tiberio, espresso, Piazzetta, Via Camerelle, shopping lane, boat tour, Faraglioni rocks, funicular, local bus, Anacapri, Monte Solaro, panoramic view, Bay of Naples, La Fontelina, Il Riccio, chair lift, Monte Solaro, Marina Piccola Beach, Via Krupp, Giardini di Augusto, west side, Blue Grotto, Faro di Punta Carena, hiking, almond gelato, Buonocore, drinks, Giardino Mediterraneo, dinner, Villa Verde, Sciue Sciue, Ravioli Capresi Al Limone, gelato, shopping, island, funicular, porter services, taxis.

Florence

birthplace, European Renaissance, art, David statue, Michelangelo, Birth of Venus, Botticelli, Napoli Centrale, Frecciarossa train, 3 hours, Firenze S. M. Novella, €86, €35-55, Rome, 1 hour 20 minutes, high-speed train, Brunelleschi Pass, €30, Duomo, Cupola, Campanile, baptistery, Duomo museum, crypt, Basilica di Santa Maria del Fiore, third largest church, Renaissance, free, massive line, Brunelleschi’s Dome, architect, steps, view, time slot, Campanile di Giotto, viewpoint, Battistero di San Giovanni, Byzantine mosaic, gold doors, Duomo Museum, Piazza della Signoria, Loggia dei Lanzi, open-air museum, sculptures, David statue, Ponte Vecchio, Medicis, cobblestoned, Piazzale Michelangelo, sunset, best viewpoint, Accademia Gallery, David, €16, €4, Uffizi Gallery, Birth of Venus, €25, €4, San Lorenzo Market, leather, food stalls, masterpieces, Renaissance, slowly, piazzas, Arno, terracotta rooftops, Duomo area, Ponte Vecchio, Santo Spirito, Uffizi Gallery, morning, Oltrarno, Piazzale Michelangelo, sunset, Tuscany, Chianti vineyards, hill towns, cradle, Renaissance, Duomo, Uffizi Gallery, Ponte Vecchio, Gustapizza, pesto, pizza, affogato, espresso, gelato, Vivoli, La Strega Nocciola, Buchetta del Vino, Chianti Classico, Tignanello, Tuscan vintages, Chianti, vineyards, wine tasting, Castello di Albola, sunset drive, cobblestoned, historic center, Medici Chapels, Mercato Centrale, Torre di Arnolfo, Basilica di Santa Croce, tombs, Uffizi Gallery, Ponte Vecchio, Santa Croce, Accademia Gallery, 8:15 AM, David, Brunelleschi Pass, Dome climb, sunset food tour, Oltrarno, Tuscany, Siena, San Gimignano, Chianti, car rental, Bistecca alla Fiorentina, beefsteak, thick cut, well done, Gelato, frozen dessert, milk, cream, sugar, Biscotti, cantucci, almond cookies, Prato, Crostini Neri, crostini di fegatini, crostini Toscani, chicken liver paste, bread, Vasari Corridor, Uffizi, Ponte Vecchio, Arno River, €43, Palazzo Pitti, Medicis, Boboli Gardens, €10, Santa Croce, Piazzale Michelangelo.

Tuscany

car, slow drives, random detours, views, car rental, Tuscan countryside, rolling hills, cypress trees, vineyards, picturesque, San Gimignano, medieval town, towers, panoramic vistas, UNESCO World Heritage, cobblestone lanes, gelato, Gelateria Dondoli, Tuscan sunsets, Val D’Orcia, Montepulciano, narrow streets, wine tasting, Ercolani Cellars, underground city, museum, free tour, 20 minutes, Il Corso, side streets, Pienza, pecorino cheese, alleys, Siena, Piazza del Campo, cathedral, Trattoria Latte di Luna, Funghi porcini e tartufo, truffles, mushroom pasta, Relais della Rovere, Colle di Val d’Elsa, rustic, elegance, Gelateria Dondoli, winery, pre-book, peak seasons, ZTL.

Pisa

quintessential, Italy, Leaning Tower, Pisa, random city, transfer station, Florence, Cinque Terre, cliché, photographs, Firenze S. M. Novella, Pisa Centrale, one hour, €10, luggage storage, €5, 30 minutes, 1.5-2 hours, €20, time-slot, Duomo, free, ticket, Baptistery, €8, €11, €27, combo, five-monument, six-monument, Chiesa di Santa Maria della Spina, Ponte Solferino bridge, bus, bus 1+, 15 minutes, cab, Tuscan city.

Cinque Terre

five lands, Italian, five villages, Monterosso al Mare, Vernazza, Corniglia, Manarola, Riomaggiore, 350+ steps, staircase, train station, village, Pisa Centrale, regional train, La Spezia Centrale, transfer, La Spezia, base, cheaper, Via dell’Amore, 2-day Train Card, €44-€69, unlimited, paid trails, train travel, Levanto, La Spezia, free, WiFi, Via dell’Amore, Riomaggiore, Manarola, sunset, Nessun Dorma, café, Instagram, Monterosso, Vernazza, Corniglia, hike, swimsuit, water, Florence, Monterosso, Vernazza, swim, harbor, villages, morning, pesto making class, Nessun Dorma, lunch, sunset, pizza, gelato, Riomaggiore, Manarola, Pesto alla Genovese, garlic, pine nuts, salt, basil leaves, olive oil, cheese, Liguria, Genoa, Focaccia, fluffy, oily, flour, water, olive oil, salt, rosemary, vegan, Farinata, chickpea flour, pancake, crepe, snack, white wine, vineyards, cliffs, Ligurian Sea, accommodation, scarce, booking, La Spezia, budget, public ferry, landslide, reconstruction, winter, tickets.

Milan

fashion capital, Italy, Last Supper, Duomo, Last Supper, painting, not-too-hectic, stop, two-week, tour, La Spezia Centrale, Milano Centrale, 3.5 hours, InterCity train, €22-€29, Florence, 1 hour 40 minutes, high-speed train, Last Supper, official site, 3 months, €15, €2, 15-minute viewing, Santa Maria delle Grazie church, first Sunday, free, €20, guided tour, €40, Roof of the Duomo, €14, foot, €16, elevator, official site, Galleria Vittorio Emanuele II, oldest, active, shopping gallery, Navigli Lombardi, canals, Starbucks Reserve Roastery, first Starbucks, Italy, Galleria Vittorio Emanuele II, glass dome, mosaic floor, Gucci, Prada, jet lag, Malpensa Express, airport, one hour, Trenitalia, Varenna, Duomo di Milano, Gothic spires, rooftop, panoramic views, Last Supper, Santa Maria delle Grazie, Starbucks Reserve Roastery Milano, latte, Duomo, €22, terrace, Basilica di Sant’Ambrogio, Basilica di Santa Maria delle Grazie, Last Supper, Galleria Vittorio Emanuele II, Lake Como, Bellano, Varenna, Bellagio, ferries, guided tour, Pinacoteca di Brera, 8:30 AM, Mondays, Castello Sforzesco, €5, Michelangelo, Pieta Rondanini, sculpture, foodie tour, La Scala, opera, tickets, Thursdays, Saturdays, Risotto alla Milanese, saffron, world’s most expensive spice, Cotoletta alla Milanese, veal cutlet, Wiener Schnitzel, bone, Panettone, sweet bread, candied fruits, raisins, Christmas, New Years.

Lake Como

different pace, elegant villas, calm waters, pastel-colored villages, peaceful atmosphere, day trip, Milan, couple nights, Como, Varenna, Bellagio, ferry, boat, villas, Varenna, viewpoints, lake, public ferry, private boat tour, villas, scenery, water, Villa del Balbianello, beautiful, Star Wars, public ferry, 30 minutes, swimming, relaxing, Trenitalia, one hour, Varenna, Hotel Du Lac, lake views, Villa Cipressi, Villa Monastero, gardens, Lugana wine, terrace, lake, Bellagio, Pearl of Lake Como, cobblestone lanes, panoramic views, Punta Spartivento, Salita Serbelloni, Via Giuseppe Garibaldi, colorful buildings, shops, Grand Hotel Villa Serbelloni, Bellagio views, coffee, Menaggio, lakeside lunch, Cafè Del Pess, Viale Benedetto Castelli, promenade, pastel houses, flowers, lake views, Bar Il Molo, sunset, gold, rose, risotto, Hotel Du Lac, ferry schedules, como-lake-ferry.it, seasonal, Como town, tight connections, Pescallo bay, Locanda Della Maria, San Giovanni area, ferry pier, breakfast, Hotel Don Ferrante, lake views, restaurant, Royal Victoria, swimming pool, gardens, wellness centre, restaurants, Borgo Le Terrazze, Grand Hotel Villa Serbelloni, Mandarin Oriental, spa, Villa Balbianello, boat tour.

Venice

unreal, beautiful, crowds, sights, less-crowded hours, city, Milano Centrale, Venezia Santa Lucia, 2.5 hours, Frecciarossa train, €29, one month, €52, Regional train, €22, Verona, vaporetto pass, Rolling Venice Pass, €6, 29 years old, 3-day pass, €27, discounts, attractions, Piazza San Marco, Basilica San Marco, €3, shoulders, knees, high season, Campanile, bell tower, €10, Doge’s Palace, €25, €30, Bridge of Sighs, prisons, prisoners, Rialto Bridge, Accademia Bridge, view, Burano, Murano, colorful houses, lace shops, glassblowing, Fondaco dei Tedeschi, rooftop, views, Gondola, €80, 6 people, daytime, €100, sunset, vaporetto, San Marco, Carnival Palace, Cannaregio, gondola ride, Piazza San Marco, gelato, cicchetti, Venetian tapas, bacaro, Doge’s Palace, Rialto Bridge, vaporetto, Burano, colorful houses, lace shops, Vaporetto day pass, €25, quiet, atmospheric, romantic, day-trippers, canals, main streets, Basilica di Santa Maria Gloriosa dei Frari, Ponte di Rialto, Basilica Santa Maria della Salute, Peggy Guggenheim Collection, modern art, Teatro La Fenice, show, St. Mark’s Square, St. Mark’s Basilica, Bridge of Sighs, Murano, Burano, glassblowing, lace, Venice Marco Polo Airport, VCE, bus, €10, 25 minutes, Piazzale Roma, ATVO, water bus, €15, 1.25 hours, Alilaguna, taxi, €40, 20-30 minutes, Tiramisu, coffee-dipped, ladyfingers, whip, sugar, mascarpone, cocoa, Treviso, Veneto, Risotto al nero di seppia, squid ink, Aperol Spritz, Spritz Veneziano, prosecco, Aperol, soda water, Veneto, Belini, Harry’s Bar, San Marco Square, Prosecco, peach purée, NOT PIZZA, wood burning ovens, banned, fire, authentic, mosquitos, flooding, rain, July, 2018, 3 nights, expensive, overcrowded, Palazzo Veneziano, Palazzo Keller, water boat, Basilica di Santa Maria Gloriosa dei Frari, canals, hotels, accommodations.

Rome (End of Trip)

private transfer, Naples, Rome, Amalfi Coast Destination, L’Antica Pizzeria da Michele, pizza, legendary, chaotic, 1-hour train, Bettoja Hotel Mediterraneo, central, elegant, Trevi Fountain, coin, wish, Antica Osteria di Pietra, Cacio e Pepe con Tartufo, Colosseum, early entry, Vatican Museums, Sistine Chapel, St. Peter’s Basilica, Trastevere, Tiber, boho neighbourhood, Nanarello, Trapizzino, locals, Ma Che Siete Venuti a Fà, drink, L’Antico Forno Di Fontana Di Trevi, maritozzo, cream bun, pistachio croissant, Pantheon, Campo de’ Fiori, Piazza Navona, Osteria da Fortuna, pastas, pistachio tiramisu, Two Sizes, late flight, airport transfer, Piccolo Buco, lunch, queue, Vatican tickets, 15 minutes, time slot, official site, skip long lines, cost.

Italy Packing List

comfy walking shoes, walking, Milan, Florence, Rome, light layers, mood swing, scarf, shawl, churches, breezy nights, travel adapter, Type C, Type F, Type L, plugs, reusable water bottle, drinking fountains, free, sunglasses, sunscreen, Italian sun, hat, cap, mid-day strolls, light rain jacket, umbrella, weather, Italy, first timers, packing, essentials.

Where to Stay in Italy / Hotel Recommendations

Milan, Starhotels E.c.ho., stylish, comfy, train station, Hotel Dei Cavalieri Milano Duomo, sightseeing, Lake Como, Varenna, Hotel Du Lac, lake views, Venice, Carnival Palace, Cannaregio, Palazzo Veneziano, Hotel Donà Palace, Tuscany, Relais Della Rovere, classy, cozy, centrally located, Palagina, La Cascina, rustic charm, countryside, Hotel Palazzo Renieri, simple, clean, Capri, Positano, Casa Cinque, views, coast, Le Sirenuse, luxury, Hotel Savoia, middle ground, Rome, Bettoja Hotel Mediterraneo, central, sightseeing, Relais La Maison De Luxe, small, sweet, train station, bus station, cabs, accommodation guide, Beehive Hostel, $100, Termini, boutique, garden, New Generation Hostel, $180, budget, style, bright, modern, social lounge, Hotel Nazionale, $220, centrally located, spacious, historic, Hotel Artemide, $350, Via Nazionale, rooftop restaurant, spa, Albergo del Senato, $420, Pantheon, rooftop terrace, Baglioni Hotel Regina, $700, Via Veneto, opulent, Hassler Hotel, $1900, Michelin-star, panoramic views, Spanish Steps, Florence, B&B Hotel Firenze Novoli, $120, clean, modern, Hotel Davanzati, $170, Florentine charm, Room Mate Luca, $200, design, Hotel Calimala, $320, medieval walls, Duomo, The St. Regis Florence, $1000, elegant, historic, rooftop, Portrait Firenze, $1300, Ferragamo, river views, Cinque Terre, Alla Marina Affitacamere, $170, Riomaggiore, harbor, La Malà, $250, colorful, Hotel Porto Roca, $2100, clifftop, Ligurian Sea, Miralago B&B Apartments, $160, Bellagio, Pescallo bay, Hotel Don Ferrante, $180, lake views, Grand Hotel Villa Serbelloni, $1300, Bellagio, iconic, Mandarin Oriental, $1500, luxury, resort, Locanda Ca’ Zose, $170, Cannaregio, canal-side, Maison Boutique Al Redentore, $300, Giudecca, boutique, budget, mid-range, luxury, accommodations, neighborhood, per night.

Travel Tips for Italy

trains, major cities, scenic, Trenitalia, Italo, advance, rates, Amalfi Coast, private transfers, euro, buses, unpredictable, car, Tuscany, cities, ZTL, restricted traffic zones, skip-the-line, official websites, GetYourGuide, dinners, Capri, Florence, Rome, Positano, popular spots, book, fast, splurges, Sorrento, Praiano, budget, value, local SIM, Vodafone, TIM, eSIM, Google Maps, bookings, validate, ticket, fines, expensive, long-distance, train tickets, online, schedule, save money, Regional trains, station, flexibility, pick-pocketers, Roma Termini, official employees, backpack, facing, front, Venice, flooding, rain.

Itinerary Adjustments / Flexibility Options

Venice, Rome, reverse, itinerary, Pompeii, Capri, Naples airport, backtracking, cheaper flights, Milan, Venice, reversed, Siena, Milan, extra night, Florence, day trip, Lake Como, Milan, extra night, Capri, hectic, Amalfi Coast, Florence, Milan, Cinque Terre, two nights, Pisa, Italy, major destinations, 2 weeks, popular places, Sorrento, base, day trips, Pompeii, Capri, Positano, public transport, Tuscany, rental car, Rome, Tiburtina, Florence, Novoli, fines, traffic congestion, Montalcino, Val d’Orcia, Bagno Vignoni, Pienza, Montepulciano, Siena, San Gimignano, Greve in Chianti, Panzano, Last Supper, tickets, sold out, Pinacoteca di Brera, Castello Sforzesco, route, highlights, pace, slow, fast, logistics.

Who Is This Trip Perfect For?

couples, gondola rides, sunset, wine, coastal strolls, romance, families, history, pasta-making classes, gelato addict, friends, road trips, wine tastings, beach days, rooftop cocktails, group energy, Italy.

Final Thoughts

Italy, hearts, tastebuds, 2-week journey, iconic sights, jaw-dropping scenery, unforgettable flavours, dolce vita, vineyard sunsets, gelato, streets, trip, love affair, life, highlights, itinerary, popular places, next time, 2 weeks, planning, tough choices, major destinations, highlights itinerary, first time, less visited spots.