Perfect two-week itineraries in Italy

Vacation blueprints for your trip to Italy so you can get the most out of your two-week vacation, no matter where you want to go

• Itineraries
• Guided toursFirst thing you should know: you can't see all of Italy in just two weeks. Trust me. I've spent approximately seven years of my life there, and have yet to scratch the surface (and four of those years—spread out over nearly two decades—were spent writing guidebooks and being, for all intents and purposes, a professional tourist).

Doesn't mean we can't have a great time trying to cram in as much Italy as possible! Here are some perfect itineraries that so just that. Please take a moment to read the "How these itineraries work" page so you can get the most out of each sample vacation blueprint (and find out such things as what I mean by "sane" and "insane" variations).

Insane two-week Italy itineraries

Ultimate Italy: The Best of Italy in Two Weeks
(Rome—Pompeii—Amalfi Coast—Florence—Hilltowns of Tuscany & Umbria [San Gimignano, Siena, Assisi, Perugia, Monteriggioni]—Pisa—Cinque Terre—Venice—Verona—Lake Garda—Milan—Lake Como) » more

The Insane Whirlwind: Italy's Greatest Hits in Two Weeks
(Rome—Pompeii—Hilltowns of Tuscany & Umbria [Orvieto, San Gimignano, Siena, Pisa]—Cinque Terre—Florence—Venice—Verona—Lake Garda—Milan) » more

Sane two-week Italy itineraries

The following three itineraries are all variations on the same thing—you get to see all the greatest hits of Italy—but each also takes about two days to devote to seeing one region a bit better: either the Amalfi Coast, the hilltowns of Tuscany ad Umbria, or the Northern Italian Lakes.

The Sane Whirlwind: Italy's Greatest Hits in Two Weeks—Amalfi Coast edition
(Rome—Naples—Pompeii—Amalfi Coast—Capri—Siena—Florence—Pisa—Cinque Terre—Venice—Milan) » more

The Sane Whirlwind: Italy's Greatest Hits in Two Weeks—Tuscan Hilltowns edition
(Rome—Pompeii—Hilltowns of Tuscany (Siena, San Gimignano, Pisa)—Cinque Terre—Florence—Venice—Milan) » more

The Sane Whirlwind: Italy's Greatest Hits in Two Weeks—Lakes edition
(Rome—Pompeii—Pisa—Florence—Venice—Lake Garda—Lake Como—Milan) » more

Other plans for two weeks in Italy

The Perfect 10 Days in Sicily
(Palermo, Monreale, Segesta, Erice, Marsala— Selinute—Agrigento—Piazza Armerina or Caltagirone or Ragusa—Siracusa—Noto or Etna—Taormina—Cefalù) » more
* Add a few days at the beginning and end in Rome and you've got two weeks total

Two-week Italy tours from trusted partners

If you prefer someone else to sweat the logistics details, take care of the driving (or train tickets), and provide a professional guide for all the sightseeing, consider an escorted tour. Not just any tour, mind you, but one that allows you a measure of the kind of freedom independent travel offers.

Why I recommend these tours

You'll notice that most of the tours briefed below are small, limited to 12 people (at most 16). In the case of the Select Italy packages, they're essentially private tours including lodging, guided walks and side trips each day, and often most of the transport from place to place.

No giant lumbering buses here. You travel on local trains, city buses, ferries, and the occasional private car or minivan.

Airfare is not included—though most of these companies can arrange it, often at discounted rates—leaving you free to find the cheapest fares on your own.

Also, none of these tours are "all-inclusive"—and that is a very, very good thing.

Most of the classic, "all-inclusive" tours out there offer the lowest common denominator of travel experiences, traveling firmly in the deepest ruts of the established tourist routes. Instead, these low-priced guided trips come with plenty of options to customize your days and your vacation can remain your own—only with the benefits of a professional guide.

With this kind of tour, some of the sightseeing admissions are included but some are not. That way you can pursue the activities that appeal most to you. Some in the group can hit the local museum, others go shopping, and others simply wander the medeival streets and maybe get a cappucino at a cafe.

Same goes for dining. I can think of nothing more depressing than being forced to eat all ogether at every meal (which entails diners only at touristy restaurants able and willing to accommodate large tour groups). Instead, with these tours you usually get most breakfasts, perhaps a special lunch or dinner or two (at an agriturismo restaurant, or a group picnic in a spectacular setting), but are otherwise left to find your own wondeful trattorie and osteria (though the guide can always provide recommendations).

Classic
Active
Italy +

Classic tours of Italy

Duration: 10 days
Cost: from $2,795
Book:

Italy Experience

Destinations: Venice, Cinque Terre, Pisa, Florence, Perugia, Spello, Rome

Travel to Italy and savour the many flavours of this gastronomic haven on a journey from the canals of Venice to the cobblestone streets of Rome. Explore historic sites and picturesque villages on this special food-lovers' adventure through some of the most incredible places in Italy. There is plenty of time to indulge in everything from fresh seafood and hearty wines to the finest balsamic vinegars and pesto in the world. This 10-day trip is sure to tantalise all the senses....

Included activities: Cinque Terre day pass, Enoteca wine tasting and lunch, Pesto class, San Giorgio Bell Tower, Traghetto across the Grand Canal, Welcome dinner in Venice
Accommodation: Guesthouse (2 nts), Hotel (7 nts)
Meals: 9 breakfasts, 1 lunch, 3 dinners
Transport: Bus, Ferry, Metro, Taxi, Train
Group size: Max 12

Duration: 13 days
Cost: from $2,199
Book:

ULTIMATE ITALY

Destinations: Venice, Lake Como, Cinque Terre, Pisa, Lucca, Florence, Siena, Rome

Description...

Included activities: Orientation walk in Rome, Orientation walk and winetasting in Siena, Piazzale Michelangelo visit in Florence, Lake Como boat trip, Visit to Pisa, Cinque Terre hike, Orientation walk in Venice
Accommodation: Hotels (12 nts)
Meals: No meals; budget €430–565 for meals.
Transport: Local bus, train, boat, walking
Group size: Max 15, Avg 10

Duration: 14 days
Cost: from $2,999
Book:

TREASURES OF ITALY

Destinations: Venice, Lucca, Cinque Terre, Rome, Naples, Amalfi, Sorrento, Pompeii, Mt. vesuvius, Herculaneum

Artists have always travelled to Italy to lift their spirits. This 2-week adventure offers you the same opportunity. Connect with the ancients at the ruins of Pompeii and in Rome and marvel at the Renaissance in Venice and Tuscany. You’ll explore tiny markets and walk the hills of Cinque Terre and with the gods in Amalfi. We’ve taken care of the planning so you’ll have plenty of time for solo exploring and optional activities. Connect with the culture—past and present—and discover what visitors have always known: the heart beats faster in Italy...

Included activities: Orientation walk in Venice and Lucca, Cinque Terre walk, guided tour of the ruins of Pompeii, including the suburban baths, day hike of the famous Walk of the Gods on the Amalfi coast
Accommodation: Hotels (13 nts)
Meals: 13 Breakfasts; budget €420-560 for other meals.
Transport: Train, private minivan, walking
Group size: Max 16, Avg 10

Duration: 15 days
Cost: from $2,711
Book:

Best of Italy

Destinations: Rome, Florence, Lucca, Pisa, Cinque Terre, Portofino/Italian Riviera, Asti/Piemonte, Milan, Lake Como, Venice

Starting in the "Eternal City" of Rome and ending by the canals of Venice, uncover the best of northern Italy. Experience classic Italian food, wine, history and style, and discover immense natural beauty while traveling through this spectacular corner of Europe. Marvel at the ancient wonders and modern attractions in Rome. Meet Michelangelo's David in Florence. Visit the gravity-defying Torre de Pisa. Cycle across the Tuscan hinterland. Soak up stunning views along the Cinque Terre coast. Sample local wines in Piedmont. Unwind by Lake Como. Explore charming canals and alleyways on a trip to Venice...

Included activities: Bicycle tour, Cinque Terre day pass, Duomo roof visit, Lake Como ferry pass, Milan half-day trip, Piazzale Michelangelo, Walk to Portofino and return boat ride, Winery visit
Accommodation: Hotel (11 nts), Private apartment (3 nts)
Meals: 2 breakfasts; budget €525 for other meals
Transport: Bicycle, Boat, Bus, Metro, Train
Group size: Max 12

Duration: 14 days
Cost: from $2,975
Book:

ITALY PHOTOGRAPHY TOUR WITH GARY ARNDT

Destinations: Venice, Lucca, Cinque Terre, Rome, Naples, Pompeii, Amalfi Coast, Sorrento, Herculaneum, Mt. Vesuvius

Save room in your luggage for extra memory cards, shutterbugs; on this travel photography tour through picturesque Italy, every second is a picture-perfect photo-op. From the inspiring ancient architecture of Venice and Rome to the rolling, impossibly lush hills of Tuscany, your shutter-finger is destined to get one hell of a workout. Best of all, you’ll get expert guidance in photography, travel writing and adventuring from our Wanderer-in Resident Gary Arndt, founder of Everything Everywhere, the internet’s most-visited travel blog. Between characteristic Renaissance flourishes, the somber beauty of Pompeii and plate upon plate of Tuscan cuisine prepared with the greatest care, the hardest decision you’ll have to make is which shot to frame first....

Included activities: Photo-workshops with Gary, Orientation walk in Venice and Lucca, Cinque Terre walk, guided tour of the ruins of Pompeii, including the suburban baths, day hike of the famous Walk of the Gods on the Amalfi coast
Accommodation: Hotels (13 nts)
Meals: 13 Breakfasts; budget €420–560 for other meals
Transport: Train, private minivan, walking
Group size: Max 16, Avg 10

Duration: 15 days
Cost: from $3,035
Book:

Italy Uncovered

Destinations: Venice, Gubbio, Assisi, Spello, Rome, Naples, Mt. Vesuvius, Pompeii, Sorrento, Amalfi Coast

From the romance of Venice to the laidback charm of the Amalfi Coast, take time to experience the true delights of Italy. Travel through the rolling hills of Umbria, visit medieval towns, soak up culture on a trip to Rome, explore the ruins of Pompeii and fall in love with the beauty of Sorrento. La bella Italia is diverse and fascinating - experience seaside scenery, rustic city streets and delectable cuisine, all infused with that passionate Italian spirit. Be charmed by the romantic aura of Venice city. Travel to Rome and discover ancient sites and modern delights. Ride a cable car to a hilltop basilica in Gubbio. Experience Umbria's religious heart on a visit to Assisi. Hike Mt Vesuvius. Find ancient artefacts in Naples’s Archaeological Museum. Explore the haunting site of Pompeii. Take in sun and sea on the Amalfi Coast...

Included activities: Archaeological Museum, Enoteca wine tasting, Gelato Making Demonstration, Guided tour of Basilica di San Francesco, Guided Walk Pompeii, Hike and cable car ride, Mt Vesuvius summit climb, Old Pompeii entrance, Orientation Walk Assisi
Accommodation: Hotel (14 nts)
Meals: 2 breakfasts, 1 lunch; budget €525 for other meals
Transport: Bus, Cable car, Metro, Train
Group size: Max 12

Duration: 15 days
Cost: from $3,400
Book:

Explore Southern Italy

Destinations: Bari, Matera, Alberobello, Lecce, Polignano al Mare, Trani, Naples, Pompeii, Sorrento, Amalfi Coast

See another side of Italy on this trip through the astonishing Puglia region, one of the lesser-known places in Italy. Let the history, culture and cuisine of southern Italy enchant you as you explore 9,000-year-old sassi dwellings carved out of rock in Matera, marvel at ornate frescoes in Lecce, wonder at the beehive-shaped trulli houses of Alberobello and be left breathless at the sight of the Amalfi Coast. Take in modern delights at Naples and Sorrento and see its contrast in Italy’s ancient past at Pompeii and Polignano on this unique tour in Italy...

Included activities: Archaeological Museum, Gelato Making Demonstration, Guided Walk Pompeii, Mt Vesuvius summit climb, Old Pompeii entrance, Roman amphitheatre, Underground village
Accommodation: Hotel (14 nts)
Meals: 2 breakfasts; budget €600 for meals
Transport: Bus, Metro, Train
Group size: Max 12

Active & adventurous tours of Italy

Duration: 15 days
Cost: from $2,110
Book:

Mont Blanc Circuit

Destinations: Italy: Courmayeur, Planpincieux; France: Chamonix, Le Bossons, Les Frasserands, Val Montjoie, Les Chapieux; Switzerland: Trient, Champex, La Fouly

Undertake one of the most dramatic walks in Europe. No amount of training can prepare you for the staggering beauty and degree of diversity that is contained within the Mont Blanc Circuit. Postcard perfect villages, cerulean glaciers, striking alpine vistas, challenging passes and rewarding days await on this walking adventure through France, Italy and Switzerland...

Included activities: Guided trek
Accommodation: Camping (with basic facilities) (13 nts), Camping (with facilities) (1 nt)
Meals: 14 Breakfasts, 10 Lunches, 13 Dinners; budget €150 for other meals
Transport: Cable car, Walking
Group size: Max 16

Duration: 10 days
Cost: from $1,317
Book:

TREKKING MONT BLANC

Destinations: Italy (Coeurmayeur), France (Chamonix, Les Contamines, Les Chapiuex), Switzerland (Val ferret, Champex, Trient)

Experience the rarified air of Europe as you trek the Alps from France to Italy and Switzerland on this active 10-day adventure. This challenging hiking circuit will reward you with mesmerizing views of glaciers, steep valleys and, of course, Mont Blanc itself. Travel across high passes and through Alpine meadows and recharge at night with delicious mountain cuisine in simple refuges. Challenge yourself to conquer one of the world's premier hiking circuits and uncover the alpine heart of Europe on this incredible journey...

Included activities: Seven days of escorted mountain hikes (demanding)
Accommodation: Hotels (2 nts), basic hotels (2 nts, possibly multi-share), mountain refuges (5 nts, multi-share)
Meals: 7 Breakfasts, 5 dinners; budget €240–315 for other meals
Transport: Local bus, walking, cable car
Group size: Max 12, Avg 10

Duration: 10 days
Cost: from $1,399
Book:

TREKKING IN THE DOLOMITES

Destinations: Calalzo, Cortona d'Ampezzo, Canazei, Bolzano

Beloved by mountaineers and nature lovers alike, the Dolomites sit perched atop northern Italy like a rocky crown. This exhilarating trip through the mountains features day treks through some of Italy’s most unbelievable scenery, with plenty of visits to small villages along the way to soak up the unique local Ladin culture and cuisine. Nights are spent in mountain refuges, where your hosts will ply you with hearty home-cooked meals. Eat up; you won’t find tastier mountain-trekking food anywhere else...

Included activities: 7 escorted day hikes in the Dolomites, 6 hearty home-cooked dinners of local produce, transfer between Calalzo to Cortina and to Bolzano
Accommodation: Mountain huts/refuges (6 nts), hotels (3 nts)
Meals: 9 breakfasts, 6 dinners; budget €160-200 for other meals
Transport: Train, bus, walking, minivan
Group size: Max 12, Avg 8

Tours to more than just Italy...

Duration: 10 days
Cost: from $1,599
Book:

ROME TO PRAGUE ADVENTURE

Destinations: Italy (Rome, Viareggio, Pisa, Cinque Terre, Florence, Venice), Austria (Vienna), Czech Republic (Prague)

This trip is perfect for the young, budget-conscious traveller eager to check a bunch of boxes off their travelling to-do list in one fell swoop. Beginning in Rome—the crucible of Western civilization—and wrapping up in beautiful Prague, you’ll sample the regional specialities and delicious wines of Italy, get in touch with the continent’s rich culture in famed museums and galleries, and compare dance floors in the nightclubs of Europe’s party capitals...

Included activities: Sunset visit to Piazzale Michelangelo in Florence, Orientation walks of Venice, Vienna and Prague, visit to genuine Pilsner beer hall in Prague
Accommodation: Simple hotels/hostels (8 nts, sometimes multi-share), overnight train (1 nt).
Meals: Budget €220–€320 for meals
Transport: Train, bus, metro, walking
Group size: Max 16, Avg 10

Duration: 13 days
Cost: from $2,399
Book:

FRANCE TO ITALY ADVENTURE

Destinations: France (Paris, Beaune/Burgundy, Avignon, Nice), Monaco, Italy (Cinque Terre, Pisa, Florence, Rome)

Sip wine in Burgundy, feast on local delicacies in Provence, follow scenic tracks along Italy's Cinque Terre coast and raise your glass to the best of France and Italy. Over 13 well-paced days, travel from Paris to Rome and savour the region's cultural and natural highlights. Your expert CEO will take the hassle out of travel but leave you with plenty of free time to explore. Witness the grandeur of Paris and Florence's great masterpieces, relax on the beach and fall in love with the beauty of this region...

Included activities: Wine-tasting in Burgundy, visit to the Palais des Papes and Pont St Benezet in Avignon, visit to Monaco, Cinque Terre coastal walk, visit to Pisa, visit to Piazzale Michelangelo in Florence
Accommodation: Hotels (12 nts)
Meals: Budget €430–565 for meals
Transport: Local bus, train, walking
Group size: Max 15, Avg 10

Duration: 15 days
Cost: from $3,250
Book:

Barcelona to Rome

Destinations: Italy (Rome, Siena, Florence, Pisa, Cinque Terre), France (Nice, Arles/Provence, Carcassone, Pyrenees), Spain (Barcelona)

Lose yourself in three of Europe's most enchanting countries. From the vibrant streets of Barcelona, travel into the heart of the picturesque Spanish Pyrenees. Discover Provencal food and world-class wines then frolic with Europe’s high rollers in the French Riviera. Feast on breathtaking sights in the cliff-top towns of the Cinque Terre, see master works of art in Florence and marvel at the leaning Torre de Pisa. Call into beautiful Siena then conclude this European adventure tour in the ancient city of Rome....

Included activities: Arles Amphitheatre, Cinque Terre day pass, Cogwheel train to Nuria Valley, Hiking in the Pyrenees, Picnic Nice
Accommodation: Hotel (12 nts)
Meals: 8 breakfasts; budget €525 for other meals
Transport: Bus, Cog wheel railway, Metro, Train
Group size: Max 12

Duration: 17 days
Cost: from $2,659
Book:

ROME TO LONDON ADVENTURE

Destinations: England (London), Belgium (Bruges), Germany (Berlin), Czech Republic (Prague), Austria (Vienna), Italy (Venice, Viareggio, Pisa, Cinque Terre, Florence, Rome)

With just 17 days to play with, time is tight on this tour, but the possibilities (and options) are wide open. It begins in Rome, home to more ancient landmarks than you could shake a centurion’s spear at. From there, you’ll explore elegant Prague, cut loose in the clubs of Amsterdam and Berlin, and savour the historical charms of romantic Bruges before the whirlwind drops us off in England. Hang on tight...

Included activities: Sunset visit to Piazzale Michelangelo in Florence, visit to genuine Pilsner beer hall in Prague, bike trip round Berlin, sightseeing walk and visit to local brewery in Amsterdam, orientation walks of Venice, Vienna, Prague and Bruges
Accommodation: Simple hotel/hostel (14 nts, at times multi-share), overnight bus (1 nt), overnight train (1 nt).
Meals: Budget €350–550 for meals
Transport: Train, bus, metro, walking
Group size: Max 16, Avg 10

Duration: 17 days
Cost: from $2,749
Book:

LONDON TO PRAGUE ADVENTURE

Destinations: England (London), France (Paris), Switzerland (Interlaken), Italy (Milan, Rome, Viareggio, Pisa, Cinque Terre, Florence, Venice), Austria (Vienna), Czech Republic (Prague)

Paris, the Swiss Alps, the Italian Riviera, modern Bohemia—you’d be surprised how much of Europe you can pack into 17 days. This excellent whirlwind tour of Europe for younger travellers reads like a greatest-hits compilation of classic Europe experiences: The bustle of busy London, cultural exploration in the French capital, postcard-worthy scenery in Switzerland, trekking in Cinque Terre and a frosty mug of Pilsner in an authentic Czech hospoda at the end of it all....

Included activities: Picnic in front of Eiffel Tower in Paris, visit to historic city of Pisa, sunset visit to Piazzale Michelangelo in Florence, orientation walks in Interlaken, Milan, Venice, Vienna and Prague, visit to genuine Pilsner beer hall in Prague
Accommodation: Simple hotels/hostels (13 nts, sometimes multi-share), overnight bus (1 nt), overnight train (2 nts).
Meals: Budget €420–550 for meals
Transport: Train, bus, metro, walking
Group size: Max 16, Avg 10

Duration: 15 days
Cost: from $2,395
Book:

Berlin to Venice

Destinations: Germany (Berlin), Poland (Krakow), Czech Republic (Prague, Cesky Krumlov), Hungary (Budapest), Slovenia (Lake Bled), Italy (Venice)

Take the long road through Bohemia on this adventure-filled tour from Germany to Italy. Travelling from historical landmarks and medieval squares to magical hilltop castles and romantic canals, this is an architectural extravaganza that cannot be missed. Wander among imposing Iron Curtain relics in Berlin, experience bohemian hospitality in an underground Prague bar and stroll the banks of the sparkling River Danube on a visit to Budapest. With the freedom to choose your own adventure in each city, you'll be captivated by the mysteries that are revealed on this tour of Central Europe...

Included activities: Guided tour to 6 countries
Accommodation: Guesthouse (2 nts), Hotel (4 nts), Overnight sleeper train (1 nt), Pension (2 nts), Private apartment (2 nts)
Meals: 3 breakfasts; budget €450 for other meals
Transport: Bus, Metro, Private Bus, Train
Group size: Max 14

Duration: 24 days
Cost: from $3,849
Book:

EUROPE ENCOMPASSED

Description...

Included activities: Picnic in front of Eiffel Tower in Paris, Visit to historic city of Pisa, Sunset visit to Piazzale Michelangelo in Florence, Orientation walks of Venice, Vienna and Prague, visit to genuine Pilsner beer hall in Prague, bike trip round Berlin, sightseeing walk and visit to local brewery in Amsterdam, orientation walk of Bruges
Accommodation: Simple hotels/hostels (20 nts, sometimes multi-share), overnight bus (1 nt), sleeper train (2 nts).
Meals: Budget €500–700 for meals
Transport: Train, bus, metro, walking
Group size: Max 16, Avg 10

Tips & links

Don't overplan

I will freely admit to being as guilty as anyone of this, but: Please try not to overplan your trip to Italy. That's a two-fold plea:

Plan everything, but don't feel compelled to stick to the plan. I think it's a fine idea to work out all the details of what you plan to do—if nor no other reason than it will help you get a handle of what you are able to get done, and start making the hard choices of what you have time for and what you should leave for the next trip to Italy. (Always assume you will retrun!)

But then do not book absolutely every second in advance (that leaves no room to adjust things as you go to accommodate changing interests, sudden festivals, or unexpected invitations), and please do not attempt to stick to the schedule if it turns out to be overly ambitious and startrs making you miserable.

Rememeber Clark W. Griswold, the Chevy Chase dad in the Vacation movies, always bound and detemrined to get to WallyWorld come hell or dead aunties? Yeah, don't be that guy. No one in that family was having any fun.
Don't try to pack too much in. A vacation is not meant to be all about checking sights off a list or dashing from place to place to fit in as much as humanly possible. It's about enjoying yourself.

So do that. Enjoy yourself. Take a hint from the Italian concept of la bel far' niente—the beauty of doing nothing—and take a break from the sightseeing every once in a while.

Leave some time to stop and sip the cappuccino.