Italy 2-Week Tours & Itineraries

Explore 42 trips designed by local kimkim specialists to get ideas for your trip to Italy.

The traditional two-week vacation is just enough time to plan the ideal Italian getaway. You could embark on a food and wine tour that involves pizza making on the Amalfi Coast, wine tasting in Tuscany, and sampling the famous hams of Parma. You could also explore famous cities like Venice, Florence, and Rome, laze on the sun-kissed beaches of the lesser-visited Puglia region, or go on a family adventure that mixes kid-friendly museums with fun walking tours and even gladiator training.

See our itineraries below or read our guide to the best 14-day trips in Italy.

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Cefalú at sunset
Map of Spectacular Self-Drive Tour Around Sicily - 14 Days
Spectacular Self-Drive Tour Around Sicily - 14 Days

Experience Sicily in all its glory by driving around the island in 2 weeks. Highlights of this tour include Palermo, a cultural melting pot with stunning monuments and vibrant local markets and Taormina, the elegant village famous for its Greek theater and the postcard views. You'll also visit Syracuse and Agrigento, with their archaeological masterpieces, and hike Mt. Etna—Europe's most active volcano.

Florence, Italy
Map of Highlights of Italy: Venice, Florence, Rome, Naples - 14 Days
Highlights of Italy: Venice, Florence, Rome, Naples - 14 Days

Discover the sights and delights of Italy on this two-week highlights tour. Explore the floating city of Venice, the Renaissance jewel of Florence, and the Eternal City of Rome. Ride a Vespa through picturesque Tuscany and discover the stunning Amalfi Coast. Soak up the culture, food, and wine while you fall in love with Italy.

Town of Positano on the Amalfi Coast
Map of Relaxed Amalfi Coast, Naples & Rome - 14 Days
Relaxed Amalfi Coast, Naples & Rome - 14 Days

Spend two weeks living La Dolce Vita on this relaxing getaway trip. Spend 4 days exploring rocky beaches and sprawling summer villas on the Amalfi Coast, then head to Sorrento for beautiful architecture and a cooking class. Go shopping in Naples' glass-roofed Galleria Umberto, then head to Rome to discover Roman ruins, cozy streetside cafes and serene city parks.

Village of Savoca
Map of Best of Sicily: Palermo, Syracuse, Taormina, & Catania - 14 Days
Best of Sicily: Palermo, Syracuse, Taormina, & Catania - 14 Days

If you have two weeks and a thirst for Sicilian sunshine, delicious street food, and fascinating culture, then this is the trip for you. Spend four days exploring Palermo's diverse history, shopping at bustling markets, and relaxing on sunny beaches. Visit Syracuse—home city of mathematician Archimedes—and explore the Old Town of Ortygia, then head to Taormina to hike Mount Etna and catch a performance at the ancient Greek Theater. End your trip with a street food tour and sunny views of the Ionian Sea in Catania. 

Monreale Cathedral in Palermo
Map of Venice, Florence, Amalfi Coast & Rome - 14 Days
Venice, Florence, Amalfi Coast & Rome - 14 Days

Spend two weeks delving into Italy's historic and cultural sites on this packed itinerary. Ride a gondola down Venice's Grand Canal and see art by Michelangelo and da Vinci in Florence. Explore Tuscany's medieval towns, then continue to the Amalfi Coast for ancient summer villas, limoncello, and seaside terraces. End in Rome to see the Vatican and explore eclectic neighborhoods. 

Village of Manarola
Map of Cinque Terre and the Italian Riviera - 14 Days
Cinque Terre and the Italian Riviera - 14 Days

Spend two weeks exploring the Cinque Terre to your heart's content on this packed itinerary. Start in the medieval village of Manarola where you'll learn traditional cooking from a local, then head up the coast to the beautiful town of Portofino to explore the rugged coast from the water. Continue to Genoa for medieval alleyways and a food tour, then end in Pisa to learn why, exactly, the famous tower leans.

Typical house facade
Map of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 14 Days
Explore Tuscany: Florence, Siena, Pisa, & Lucca - 14 Days

Discover why Pisa's famous tower leans so much (and why it's not the only one!), plus much more on this exploration of Tuscany. Start in Florence to see Da Vinci's 'The Annunciation' and other famous Renaissance works in the Uffizi Gallery. Look for treasures in the San Lorenzo market, browse shops on the medieval Ponte Vecchio, and explore history in the medieval cities of Siena and Lucca. End your trip with sweeping ocean views on the Cinque Terre hiking trail.

Sassi di Matera
Map of Laidback Puglia: Alberobello, Lecce, Bari - 14 Days
Laidback Puglia: Alberobello, Lecce, Bari - 14 Days

From fairytale Trulli homes to rocky sun-soaked beaches, this two-week trip to Puglia is perfect for travelers who want to see authentic Italy. See baroque architecture in Lecce, scrubby pine forests in Gargano National Park, and sunny southern towns of Otranto and Gallipoli. End your trip in the busy port city of Bari where a maze-like old town, deep-fried panzerotto, and 12th-century churches await.

Traditional Buranelli Cookies
Map of Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 14 Days
Food & Wine in Italy: Venice, Bologna, Florence, Rome, & More - 14 Days

Rome wasn't built in a day, but you can spend fourteen days eating and drinking your way through Italy's top culinary destinations! Go for a gondola ride in Venice, try the decadent tiramisu, and sample the local Cicchetti. Head to Bologna to see 11th-century architecture and try the Parmeggiano, then head to Florence to see Michelangelo's David and Leonardo's top works. Pair a bottle of Tuscan Chianti with a farm-to-table charcuterie board, then head west for four days on the sunny Amalfi Coast. Explore medieval fishing villages and learn to make the perfect Neopolitan pizza before capping your trip off with visits to the Sistine Chapel, Colosseum, and local gelateria in Rome. 

Italy
Map of Rome, Amalfi Coast, & Sicily - 14 Days
Rome, Amalfi Coast, & Sicily - 14 Days

Over  15 days you'll experience the highlights of Italy. In the capital Rome, you'll visit landmarks like the Colosseum and historic institutions like the Vatican. You'll then enjoy the pebble beaches and sun-kissed coast of Amalfi before venturing far south to Sicily, where a road trip will take you from Palermo to Mount Etna.

Evening sky over Santorini
Highlights of Italy and Greece: Rome, Florence, Venice, Athens, Mykonos, & Santorini - 14 Days

If you have two weeks to travel and want to see the highlights of the Mediterranean, this Italy & Greece itinerary is for you. Start the trip in Rome, where you'll explore treasures like the Vatican and the Colosseum. Continue to Florence and Venice for art museums and medieval palaces, then catch a flight to Athens — home of the iconic Acropolis. Spend your second week island-hopping in Greece, with wine tastings, sunset cruises, and much more.

Lake Garda
Map of Discover Milan and Italy's Lakes Region - 14 Days
Discover Milan and Italy's Lakes Region - 14 Days

Spend two relaxing weeks enjoying art, culture, and food. Shop for treasures at the Quadrilatero della Moda district and join the locals at the Navigli canals for high-energy nightlife in Milan. Spend four days on peaceful Lake Como, touring sleepy fishing harbors and learning to make the perfect pasta dish. Visit serene lakeside estates on Lake Maggiore, then end on Lake Garda for award-winning wine tasting and Tyrolean charm.

Exploring Cinque Terre
Map of Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days
Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Island of Capri on the Amalfi Coast
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome & More - 14 Days
Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome & More - 14 Days

Spend two weeks experiencing Italy's cities and Amalfi Coast in luxury. Start with a private tour of Venice to see ornate palaces and visit a traditional gondola workshop. In Florence, dine on world-class food and wine and go on a hot-air balloon ride above the Tuscan hills. Dive into history with priority access to the Vatican and a private tour of the Colosseum, then soak up the sunshine and ocean views on the gorgeous Amalfi Coast.

Chania shoreline
Mediterranean Coast Getaway: Amalfi Coast, Sorrento, Santorini, Crete, & More - 14 Days

Get away from the hustle and bustle of everyday life with laid-back visits to some of the Mediterranean's best beaches and coastal towns. In Italy, explore the cliffside fishing villages of Positano and Amalfi and enjoy Sorrento's sunny coast, making time for a day trip to the nearby resort island of Capri. Then, catch a flight to the Greek archipelago where you'll go wine tasting in Santorini, explore 3,000-year-old Greek history near Heraklion, and relax on Crete's famed beaches.

Vatican City
Map of Discover Venice, Florence & Rome - 14 Days
Discover Venice, Florence & Rome - 14 Days

Spend two weeks visiting Italy's top cities and world-famous winemaking regions. See ornate palaces and colorful bohemian islands in Venice, tour the Uffizi Gallery to see da Vinci's work in Florence, and climb the leaning tower in Pisa. Spend a day touring vineyards and small farms in Tuscany, then make—and eat!—the perfect pasta dish. Round out your trip in Rome for a visit of the Sistine Chapel and buzzing neighborhood wine bar.

italy
Map of Naples, Amalfi Coast, & Sicily - 14 Days
Naples, Amalfi Coast, & Sicily - 14 Days

You can do a lot with the traditional two-week vacation. Case in point, it's enough time to jaunt to southern Italy and tour beautiful locales like Naples, Pompeii, the Amalfi Coast, and the island of Capri. You'll even have time to road trip around the island of Sicily, enjoying incredible street food and touring ancient Greek ruins as you do.

Cinque Terre, Italy
Map of History and Nature in Italy: Venice to Rome - 14 Days
History and Nature in Italy: Venice to Rome - 14 Days

Combine the historical splendor of Italy with its natural charm in this 14-day tour, highlighting the ancient cities of Venice, Pisa, Florence, and Rome with sunset gondola rides, regional dishes in local neighborhoods, and guided walking tours, plus visits to many museums, art galleries, and monuments. Enjoy tasting wine in the picturesque hills of Tuscany, plus guided tours of Siena, Vatican City, and the Roman Forum. Swap lively city centers for outdoor experiences in Lake Como and Cinque Terre, like boat tours, day hikes, and traversing the seaside in search of colorful villages.

View of the Cinque Terre
Map of Florence, Cinque Terre, Rome, & Amalfi Coast - 14 Days
Florence, Cinque Terre, Rome, & Amalfi Coast - 14 Days

Your two-week getaway to Italy fits in cultural highlights and coastal beauty the country is famed for. Begin your adventure in Florence, admiring the art and architecture the birthplace of Florence offers before heading to Cinque Terre. Stroll through the colorful villages and admiring the coastline on a sunset cruise. From here, you'll visit Rome, where ancient history comes to life. Finish off your trip with a stay on the Amalfi Coast. Soak in the sunshine and discover the beauty of this enchanting area.

Villa del Balbianello
Luxury Italian & Swiss Lakes by Train - 14 Days

There's no need to choose between water or mountains on this two-week trip. You'll visit both the lakes and peaks of northern Italy and Switzerland, scouting out real estate that ranges from luxurious villas on the shores of Lake Como to Alpine hiking huts over the course of your trip.

Portofino harbor
Luxury Northwest Italy: Alps, Cinque Terre, Riviera, Lake Maggiore & More - 14 Day

The city of Alba is best known for its white truffles, sometimes referred to as the "diamonds of Alba" for how prized they are. Sample these truffles and other delights of Northwest Italy on this two-week trip which takes you from the shores of Portofino into the wine- and truffle-rich of the Piedmont. Continue to the medieval streets of Turin, up into the Alps, and back down to the shores of Lake Maggiore before you depart.

Ferry across the palm-lined shores of Garda Lake
Map of Cycling Northern Italy: Dolomites to Venice, Slovenia to Croatia - 14 Days
Cycling Northern Italy: Dolomites to Venice, Slovenia to Croatia - 14 Days

Featuring two weeks of cycling through beautiful and diverse landscapes in northern Italy, you'll also pedal along the Slovenian and Croatian coastline. Begin your journey in Bolzano, the gateway to the Dolomites, and work your way south to Peschiera before turning east to Venice and following the Adriatic Sea around the Gulf of Trieste, where you'll end along the Istrian coast in Croatia's Poreč. Discover romantic Verona, marvel at architectural masterpieces in Vicenza, and soak weary muscles in thermal waters in Padua.

Riva del Garda, Lake Garda
Map of Mountains and Lakes in Northern Italy: The Dolomites, Lake Garda, Verona & More - 14 Days
Mountains and Lakes in Northern Italy: The Dolomites, Lake Garda, Verona & More - 14 Days

On your two-week trip to Italy, experience the beauty of alpine living in the Dolomites and on Lake Garda. Visit unique museums and quaint towns, including Ortisei and Cortina d'Ampezzo. Go hiking and ride funicular cable cars, marveling at the panoramic views. Stay in the historic towns of Riva del Garda and Desenzano del Garda, and take a guided tour of the Roman villas and castles protecting the lake.

Explore the Vatican City with your little one
Map of Leisurely Italy With Small Children: Rome, Sorrento, Amalfi Coast & Naples - 14 Days
Leisurely Italy With Small Children: Rome, Sorrento, Amalfi Coast & Naples - 14 Days

Take two weeks to explore Rome and some of Italy's most popular coastal cities with this itinerary designed to make traveling with babies and toddlers simple. Private tours to Roman highlights like the Vatican, Colosseum, and Palatine Hill will make sure you can move at your own pace before you head to the coast. In Sorrento and the Amalfi Coast, plentiful free time allows for maximum flexibility and time to lounge on the famous beaches. Finish your trip in Naples, where everyone can enjoy making pizza and exploring the ruins of Pompeii.

Cinque Terre coastline
Map of Rome, Florence, Cinque Terre, & Venice - 14 Days
Rome, Florence, Cinque Terre, & Venice - 14 Days

Start your trip in Rome and visit the legendary Colosseum. Admire the Sistine Chapel and stroll through the streets of its buzzing nightlife. See Michelangelo's 'David' sculpture in Florence, meander through piazzas and across the famed Ponte Vecchio bridge before exploring the colorful, seaside villages of Cinque Terre. Finish off in Venice, shopping for carnival masks and handblown art.

View of the Florence skyline
Map of Florence, Rome, & the Amalfi Coast - 14 Days
Florence, Rome, & the Amalfi Coast - 14 Days

This two-week trip through Italy takes you to it all. See Michelangelo's 'David' sculpture in Florence and meander through piazzas and across the famed Ponte Vecchio bridge. Visit Rome and admire the Sistine Chapel and stroll through the streets of its buzzing nightlife before finishing off on the incomparable Amalfi Coast and Capri Island for some leisure and beach time to complete your trip.

Lie out on the black sand beach of Stromboli Island
Map of Sicily Highlights Self-Drive Tour with Aeolian Islands - 14 Days
Sicily Highlights Self-Drive Tour with Aeolian Islands - 14 Days

Spend two weeks delving into Sicily's historic and cultural highlights on this complete itinerary. Discover remote island settlements on Stromboli, meander and climb the narrow laneways and staircases in Modica, Ragusa Ibla, and Scicli,  and dine on fresh seafood in sophisticated Taormina. You'll begin and end in lively Catania and spend four nights on the Aeolian Islands before picking up your rental car and touring the Italian island from Palermo to Taormina, with Cefalù, Agrigento, and Syracuse in between.

Regional Foods, Emilia-Romagna
Map of Food & Wine in Bologna, Venice, Verona, Milan & Turin - 14 Days
Food & Wine in Bologna, Venice, Verona, Milan & Turin - 14 Days

Over 14 days, eat and drink your way through Northern Italy with this food and wine-focused itinerary. Tour the 11th-century University of Bologna and visit nearby Parma to enjoy fresh prosciutto and cheese. Explore the highlights of Venice and spend a half-day at Valpolicella wineries near Verona. Learn to make homemade pasta and discover the mouthwatering food scenes in Milan and Turin. Try street food, chocolate, and more wine and regional delicacies in Piedmont!

Balloon over Chianti
Map of Veneto and Tuscany for Active Families: Venice, Verona, Lake Garda, Siena  & Florence - 14 Days
Veneto and Tuscany for Active Families: Venice, Verona, Lake Garda, Siena & Florence - 14 Days

Families with teens who want to get out and explore (and find the perfect backdrop for their photos) should give this two-week itinerary through the Veneto and Tuscany a try. You'll start in Venice, where you can explore secret passages, craft your own masks, and paddle a gondola. Then head to Verona and Lake Garda, biking through both urban and natural attractions. Wrap up in the Tuscan cities of Siena and Florence with a hot air balloon ride, gelato-making, and more.

Basilica of Santa Maria Assunta in Aquileia
Map of Explore Northern Italy: Trieste, Venice, Milan, Bologna, & More - 14 Days
Explore Northern Italy: Trieste, Venice, Milan, Bologna, & More - 14 Days

One of Italy's biggest attractions has always been its food, and you can sample plenty of it over the course of these two weeks. You'll relax by the seaside, walk through former Roman cities, and hike over mountains as you make your way to various tasting and art experiences to satisfy all of your sense.

Italy
Map of Puglia & Sicily Highlights - 14 Days
Puglia & Sicily Highlights - 14 Days

This two-week holiday combines anthropology and history with a road-trip adventure in two of Italy's most unique regions. First, you'll tour Puglia, Italy's "heel of the boot," which is home to beautiful beaches and ancient cities. Then you'll fly to Sicily for a road trip from the cultural melting pot of Palermo to ancient Greek and Roman ruins—plus enjoy a jaunt to Mt. Etna. 

Grado Harbor
Map of Northeast Italy: Trieste, Venice, Verona, Lake Garda, & More - 14 Days
Northeast Italy: Trieste, Venice, Verona, Lake Garda, & More - 14 Days

Discover the Northeast of Italy on this 14-day adventure. Explore history and archeology in Trieste and Grado. Visit the Miramare Castle and walk in the footsteps of Rome's Caesar on a day trip to the UNESCO World Heritage city of Aquileia. Enjoy a romantic gondola ride in Venice and tour the city with a local guide. Learn the language of love in Shakespeare's Verona and taste regional Valpolicella wines. Relax on Lake Garda and visit charming villages by boat, then end your trip in Italy's unofficial capital, Milan, where Gothic architecture and designer shops await you.

Young child painting a carnival mask in Venice
Map of Family Adventure in Italy: Venice, Florence, Rome - 14 Days
Family Adventure in Italy: Venice, Florence, Rome - 14 Days

If spending two weeks traveling with the family through Italy's top cities and historic sites sounds perfect, then this packed itinerary is for you. Start in Venice to see ornate palaces and ride a gondola on city canals, then continue to Florence for amazing food, kid-friendly museums, and the rolling Tuscan landscape. End in Rome where the kids can follow Percy Jackson's adventures through Ancient Roman ruins. 

Temple ruins in Rhodes
Discover Greek & Italian History: Athens, Crete, Rhodes, Venice, Rome, & More - 14 Days

Explore over two thousand years of Greek and Italian history in this two-week tour. You'll kick things off in Athens to see the Acropolis and nearby historic villages, then explore maritime history in the Greek islands with two nights in Crete and Rhodes. Catch a flight to Venice in the north of Italy to continue your education of ocean-going empires, then travel south to end your trip in Rome and Naples to discover the world of the gladiators and ancient Pompeii.

Farm-fresh olives
Best of Mediterranean Food & Wine: Athens, Santorini, Crete, Tuscany, Rome, & More - 14 Days

Sample both Grecian and Italian fare on this two-week itinerary as you explore everything from Rome's busy piazzas to Santorini's beaches. You'll start your trip in Greece for equal parts culinary and archaeological education, with stops at the Acropolis and family-owned olive farms. From Crete, catch a flight to Bologna in Italy's Emilia Romagna region for local Parma ham and parmesan, before eating and drinking your way south through Florence to the capital city of Rome.

italy
Map of Rome & Sicily Highlights - 14 Days
Rome & Sicily Highlights - 14 Days

In two weeks you'll not only immerse yourself in the splendor of historic Rome, but you'll also embark on an unforgettable road trip around the cultural melting pot that is Sicily. In the former, you'll tour famous sights like the Colosseum and Vatican plus take part in a local cooking class. In the latter, you'll drive around the island at your leisure, stopping at historic and beautiful cities like Syracuse, Agrigento, and Taormina.

Pose in front of the iconic Ponte Vecchio Bridge in Florence
Map of Family-Friendly Highlights of Italy: Venice, Florence, Rome & Naples - 14 Days
Family-Friendly Highlights of Italy: Venice, Florence, Rome & Naples - 14 Days

With two full weeks, your family can embrace what Italy has to offer on this tour, focused on kids aged 5-12. You'll craft Carnival masks and follow engaging clues through the canals of Venice, then experience the Renaissance arts of Florence. Tour ancient sites, extensive art collections, and fruit-filled markets in Rome before you end your trip in Naples, home of both ancient Pompeii and some of the best pizza you can find.

Orvieto, in the Umbria Region
Map of Rome, Orvieto, Florence, & Verona - 14 Days
Rome, Orvieto, Florence, & Verona - 14 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint. Finish off your trip in the Veneto region, staying in the lovely and romantic Verona and visiting its neighboring city, Venice.

Gondola through the Venice canals
Map of Discover Venice, Tuscany, & Rome - 14 Days
Discover Venice, Tuscany, & Rome - 14 Days

From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.

Creating memories on the beach
Family Adventure in Italy & Greece: Rome, Athens, Naxos, & More - 14 Days

Bring the whole family to explore history, art, and nature on this kid-friendly 14-day trip to Italy and Greece. You'll kick things off in Rome, where activities like a city-wide scavenger hunt and an art class keep the little ones entertained. Next, catch a flight to Athens where you'll travel back in history to the time of the first Olympic Games. End the trip on the island of Naxos for family beach time, a catamaran cruise, and all-around relaxation.

Walk amid the salt ponds in Trapani
Map of Sicily Highlights Self-Drive Tour - 14 Days
Sicily Highlights Self-Drive Tour - 14 Days

Follow this two-week circuit around Sicily for unique cultural experiences, hiking adventures, and coastal relaxation. Begin on the northern shore in cultural-melting-pot, Palermo before heading to Trapani and the Aegadi Islands in the west. Wander amid Roman ruins and extensive mosaics in Agrigento, get lost in the baroque cities of Modica, Ragusa Ibla, and Scicli and their medieval centers, wind through crypts and catacombs in historic Ortygia, and relax along the Ionian Sea enjoying fresh-caught seafood in Taormina.

Ponte Vecchio in Florence
Map of Rome, Florence, Verona, & Venice - 14 Days
Rome, Florence, Verona, & Venice - 14 Days

Your trip starts with tours through Rome's historical core, Vatican City, and the Roman Forum, with walks through the Colosseum and to the top of Palatine Hill. Head to Florence to experience its historic squares, cathedrals, and museums. End your trip in Verona, visiting the infamous romantic of Shakespeare's love story and the floating city of Venice.

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