Italy Vacation Packages
Curated Hotels & Services
Best Italy Vacation Packages
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Experience Rome - Florence - Venice
7 nights from $1,218*
4 Customer ReviewsCustomizable schedule, airline, hotel, and transportation choices, with a helpful and respectful customer service representatives.
Experience Rome - Florence - Venice
You'll find millennia of history and heritage in the Italian capital and its most famous cities! Let Tripmasters make your Italian holiday easy, visiting Rome (the Eternal City, with its stunning architecture and rich religious history), Florence (an artists haven with a surprisingly political past), and Venice (the romantic city set on canals); all contribute to the fascinating and diverse Italian traditions.
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Train from Rome to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Venice
- Hotel for 2 nights in Venice
Curated Experiences Based on Availability: - Rome Colosseum Tour
- Guided City Tours of Florence and Venice, visiting iconic sites and popular neighborhoods
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
Easily upgrade your vacation to a Luxury Private Guided experience, featuring upgraded hotels, curated private activities, and more, or try our flexible Essential Series package with hotels, transportation and optional activities that you can customize!
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Essential Rome - Cinque Terre - Florence - Venice by Train
9 nights from $1,269*
604 Customer ReviewsOverall Trip Rating: 2/10 Beautiful country, but major service failures across transportation and lodging severely impacted the experience. Train Experience: La Spezia ? Florence No seat selection offered when booking. Train was completely full, forcing uncomfortable travel conditions. Lack of seat assignment created stress and overcrowding. This is a service failure, especially for long-distance regional routes. Florence ? Venice No schedules offered or unclear schedule information take a very early travel no time for breakfast. Difficult to plan the day. Hotel Villa Carlota (Florence): 1/10 Major Issues Advertised air conditioning, but AC DID NOT WORK AT ALL. Staff acknowledged the issue and only offered: 1) A fan 2) Opening the window — not acceptable because The hotel is surrounded by trees Open windows attract insects: Furniture was old, worn, and not well maintained. Room was not clean, triggering your wife’s dust allergy immediately. You paid for two nights, but the room was so unacceptable we left after one hour. Why this is unacceptable Advertising AC and not providing it is false advertising. Allergens and unclean conditions violate basic hospitality standards. Offering a fan instead of fixing the issue is not a reasonable solution. You were forced to relocate hotels, losing TIME AND MONEY Summary Statement My trip to Italy was significantly affected by poor transportation and hotel services. Train routes from La Spezia to Florence and Florence to Venice offered no seat selection or clear schedules, resulting in overcrowded and stressful travel. The worst experience was at Hotel Villa Carlota in Florence, which falsely advertised air conditioning. The AC did not work, the furniture was old, the room was dusty and unclean, and my wife’s allergy was triggered immediately. Staff only offered a fan or an open window despite the hotel being surrounded by trees and insects. I paid for two nights but had to leave after one hour. This was an unacceptable experience.
Essential Rome - Cinque Terre - Florence - Venice by Train
Experience Italy by train!. Travel to Rome (famous for the Colosseum, Roman Forum, Vatican and delicious food), after that, Cinque Terre (five miles of rocky coast with five small villages overlooking the sea, in the midst of two capes with hundreds of miles of beautiful paths), next is Florence (home to many masterpieces of Renaissance Art and architecture) and finally, Venice (set on gorgeous canals, intimate Gondola rides and under sculpted bridges). Travel between these cities by very convenient train rides which allow you an opportunity to observe the lovely countryside.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Train from Rome to La Spezia (Gateway to Cinque Terre)
- Hotel for 2 nights in Cinque Terre Area
- Train from La Spezia to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Venice
- Hotel for 2 nights in Venice
Easily upgrade your vacation to a Luxury Private Guided Experience, featuring upgraded hotels, premium-class trains, and private activities including city tours and more!
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Experience Sicily: Chauffeured Collection (Palermo - Agrigento - Syracuse - Taormina)
9 nights from $2,389*
Experience Sicily: Chauffeured Collection (Palermo - Agrigento - Syracuse - Taormina)
Dive into Sicily’s ancient ruins and scenic shores in Italy. Uncover history, culture, architecture, and outdoor street markets with a passionate local guide in Palermo. Continue this trip in Agrigento (home to the Valley of the Temples with the best preserved Greek ruins outside Greece), up next is Syracuse (a former stronghold of the Greek empire; full of medieval and Baroque buildings). Enjoy door-to-door service with UNESCO stops at the Norman Castello di Caccamo, the world-famous mosaics of Piazza Armerina, and the ancient Necropolis of Pantalica before reaching Taormina (overlooking the Ionian Sea, with countless stores, cafes, piazzas, and breathtaking vistas), where you will take a day trip to mighty Mount Etna (renowned for its exceptional level of volcanic activity).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Includes:
- Flight into Palermo and out of Catania
- Transfer from Palermo Airport to Hotel
- Hotel for 3 nights in Palermo
- Transfer from Hotel in Palermo to Hotel in Agrigento via Castello di Caccamo
- Hotel for 2 nights in Agrigento
- Transfer from Hotel in Agrigento to Hotel in Syracuse via Piazza Armerina
- Hotel for 2 nights in Siracusa
- Transfer from Hotel in Syracuse to Hotel in Taormina via the Necropolis of Pantalica
- Hotel for 2 nights in Taormina
- Transfer from Hotel in Taormina to Catania Airport
Curated Experiences Based on Availability: - Guided Tour of Palermo, visiting iconic sites and popular neighborhoods
- Mt. Etna Tour from Taormina
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
Try our flexible Essential Series package with hotels, transportation and optional activities that you can customize!
9 nights from $2,389*
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Curated LuxuryExclusive Rome - Sorrento - Amalfi (Chauffeured Collection)
7 nights from $3,299*
1 Customer ReviewI thought Tripmasters did a fabulous job, I really enjoyed my vacation. Everything was wonderful on land and sea. I had quite a few problems with Swiss air, some of which were communicated to your agent Lily, and others which occurred after. I am quite dissatisfied as I paid extra for both of my seat seats coming back, and they gave me all kinds of trouble from the booking onward. Ultimately, I was seated at the very back of the plane for the long flight from Zürich to Tampa, about 3 rows from the rear bathroom (lines in aisle etc) with a broken TV set and tray table— even though I had spent an extra $62 for this seat alone. The people next to me told me they had tried to upgrade and couldn’t—-So obviously these were not preferred seats in other words. I know this is not your company directly, but as you work with them, I thought you would like this feedback. I did report it to the person, but she was ineffectual. If possible, if you could put pressure on Swiss air to refund at least that $62 it would be helpful. I could show you messages about the seat before this, for Naples to Zürich where I’d had to fight to keep a seat that was the preferred rate I had paid. They gave me all kinds of trouble with that, but at least I did have a decent seat for that flight. I do believe that I am eligible for a $62 refund, and I’m hoping with your help that I would receive that from Swiss air or from yourself thank you
Exclusive Rome - Sorrento - Amalfi (Chauffeured Collection)
Discover the magic of Italy with our customizable guided journey: from the iconic landmark of Rome to dreamy, lemon-scented alleys of Sorrento and Amalfi. Explore UNESCO World Heritage site Pompeii and the cliffside splendor of Positano. Tripmasters offers flexible itineraries with hand-picked hotels and private transportation. Book your dream Italian getaway today!
Essential Highlights and Recommended Experiences:
- Discover the monuments and landmarks of the Roman Empire, such as the Colosseum
- Experience vibrant Roman traditions and culture with local markets, street food, and lively piazzas
- Visit Villa Comunale for panoramic views of the Bay of Naples and Mount Vesuvius
- Explore the artisinal heritage in old-town Sorrento and Amalfi while wandering the old-town alleys of Via San Cesareo to discover authentic tarsia (inlaid wood crafts)
- Enjoy a lemon sorbet in the piazza outside the mighty Duomo in Amalfi
- Travel by private car through the cliffside roads with stops at the charming vertical village of Positano and at UNESCO-listed Pompeii (tickets not included)
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.Includes:
- Flight into Rome and out of Naples
- Private arrival transfer in Rome
- 4-Star or better hotels 3 nights in Rome and 2 nights each in Sorrento and Amalfi Town
- Private driver from Rome to Sorrento with a stop at UNESCO-listed Pompeii (entrance not included)
- Private driver from Sorrento to Amalfi Town with stops at Stabia Archeological Site (entrance not included) and Positano
- Private departure transfer from Amalfi Town to Naples Airport
- Live phone and chat support
Included Private Activities (Based on Availability): - Colosseum Tour in Rome
- Food Tour in Rome
- Capri Island Cruise from Sorrento (Small Group)
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Rome | Sorrento | Amalfi
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Italy Suggested Vacation Packages
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Experience The Amalfi Coast: Chauffeured Collection (Naples - Amalfi - Sorrento)
6 nights from $2,410*
Find the soul of Italy in the warm glow of the Tyrrhenian sun! Walking down the streets of Naples (a vibrant, edgy city that defines La Dolce Vita, for which Italy is famous) you find markets and main atractions; but even better, you will enjoy unforgettable views over the sea cruising along the scenic Amalfi Coast (stunning cliffs, beaches and colorful villages with steep and narrow streets) and to Capri Island from Sorrento (a lively coastal town famous for its Limoncello liquor and a good base for visiting the ancient sites of Pompeii and Herculaneum). Your Chauffeured Collection Transfers ensure effortless exploration, with stops to discover: the Roman frescoes of Villa de Poppaea and Ravello, the Stabia Archeolofical Site and the beauty of Positano (dramatic vertical landscape, colorful houses cascading down to the sea).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Experience The Amalfi Coast: Chauffeured Collection (Naples - Amalfi - Sorrento)
Find the soul of Italy in the warm glow of the Tyrrhenian sun! Walking down the streets of Naples (a vibrant, edgy city that defines La Dolce Vita, for which Italy is famous) you find markets and main atractions; but even better, you will enjoy unforgettable views over the sea cruising along the scenic Amalfi Coast (stunning cliffs, beaches and colorful villages with steep and narrow streets) and to Capri Island from Sorrento (a lively coastal town famous for its Limoncello liquor and a good base for visiting the ancient sites of Pompeii and Herculaneum). Your Chauffeured Collection Transfers ensure effortless exploration, with stops to discover: the Roman frescoes of Villa de Poppaea and Ravello, the Stabia Archeolofical Site and the beauty of Positano (dramatic vertical landscape, colorful houses cascading down to the sea).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Includes:
- Flight into and out of Naples
- Transfer from Naples Airport to Hotel
- Hotel for 2 nights in Naples
- Transfer from Hotel in Naples to Hotel in Amalfi Town via Villa di Poppea and Ravello
- Hotel for 2 nights in Amalfi Town
- Transfer from Hotel in Amalfi Town to Hotel in Sorrento via Stabia Archeological Site and Positano
- Hotel for 3 nights in Sorrento
- Transfer from Hotel in Sorrento to Naples
Curated Experiences Based on Availability: - Guided City Tour of Naples, visiting iconic sites and popular neighborhoods
- Amalfi Coast Cruise
- Capri Island cruise from Sorrento
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
Easily upgrade your vacation to a Luxury Private Guided experience, featuring upgraded hotels, curated private activities, and more, or try our flexible Essential Series package with hotels, transportation and optional activities that you can customize!
6 nights from $2,410*
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Experience Rome - Florence - Venice - Lake Como - Milan
11 nights from $1,711*
The Ultimate Grand Tour: Rome, Florence, Venice, and the Northern Lakes!. Discover ancient Rome (the Eternal City) and its famous Colosseum, Florence (home of artistic Italy’s Renaissance) and Venice (set on gorgeous canals) before heading to the shimmering shores of Lake Como (known for the natural beauty of its setting and the handsome villas that line its shores), culminating in a special encounter with Da Vinci’s Masterpiece Last Supper in Milan (one of the fashion and high-tech capitals of the world).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Experience Rome - Florence - Venice - Lake Como - Milan
The Ultimate Grand Tour: Rome, Florence, Venice, and the Northern Lakes!. Discover ancient Rome (the Eternal City) and its famous Colosseum, Florence (home of artistic Italy’s Renaissance) and Venice (set on gorgeous canals) before heading to the shimmering shores of Lake Como (known for the natural beauty of its setting and the handsome villas that line its shores), culminating in a special encounter with Da Vinci’s Masterpiece Last Supper in Milan (one of the fashion and high-tech capitals of the world).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Includes:
- Flight into Rome and out of Milan
- Hotel for 3 nights in Rome
- Train from Rome to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Venice
- Hotel for 2 nights in Venice
- Train from Venice to Como
- Hotel for 2 nights in Como
- Train from Como to Milan
- Hotel for 2 nights in Milan
Curated Experiences Based on Availability: - Rome Colosseum tour
- Guided City Tours of Florence, Venice and Milan visiting iconic sites and popular neighborhoods, including viewing DaVinci's famous The Last Supper
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
Try our flexible Essential Series package with hotels, transportation and optional activities that you can customize!
11 nights from $1,711*
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Rome - Florence - Venice: Chauffeured Collection
7 nights from $1,959*
Explore our favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers. Begin this twist on our classic Italy getaway in historic Rome (the Eternal City) where the Colosseum looms large and the Vatican's treasures await discovery, and after that, travel to Florence (the capital of Tuscany and cradle of the Renaissance), until you finally reach Venice (the intimate city set on canals famous for gondola rides). Enjoy private transfers between each city that allow you to avoid the hassle of train stations and explore the following scenic towns: Montepulciano (renowned for its exquisite Vino Nobile Wine), San Gimignano (characterized by its medieval architectural towers) and Ferrara (a well-preserved UNESCO-listed city with rich history).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Rome - Florence - Venice: Chauffeured Collection
Explore our favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers. Begin this twist on our classic Italy getaway in historic Rome (the Eternal City) where the Colosseum looms large and the Vatican's treasures await discovery, and after that, travel to Florence (the capital of Tuscany and cradle of the Renaissance), until you finally reach Venice (the intimate city set on canals famous for gondola rides). Enjoy private transfers between each city that allow you to avoid the hassle of train stations and explore the following scenic towns: Montepulciano (renowned for its exquisite Vino Nobile Wine), San Gimignano (characterized by its medieval architectural towers) and Ferrara (a well-preserved UNESCO-listed city with rich history).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Transfer from Hotel in Rome to Hotel in Florence via Montepulciano and San Gimignano
- Hotel for 2 nights in Florence
- Transfer from Hotel in Florence to Hotel in Venice (Piazzale Roma Terminal) via Ferrara
- Boat transfer from Venice port to closest hotel dock not included; guests must book it independently
- Hotel for 2 nights in Venice
Easily upgrade your vacation to a Luxury Private Guided Experience, featuring upgraded hotels, private transportation between cities, and private activities including a Colosseum tour, Florence city tour, Venice food tour, and more!
Find a package. We have many more!
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Bari - Lecce - Rome by Train
9 nights from $1,242*
Discover the fascinating Europe visiting Italy with this package. Combine Bari (a major hub on mainland Southern Italy and well known as a port, university city, as well as the city of Saint Nicholas), Lecce (renowned for its beautiful historical structures such as the Basilica di Santa Croce, the Porta Napoli and the Duomo) and Rome (Italy's treasure with two millennia of artistic achievement). These destinations are connected by Trains.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Bari - Lecce - Rome by Train
Discover the fascinating Europe visiting Italy with this package. Combine Bari (a major hub on mainland Southern Italy and well known as a port, university city, as well as the city of Saint Nicholas), Lecce (renowned for its beautiful historical structures such as the Basilica di Santa Croce, the Porta Napoli and the Duomo) and Rome (Italy's treasure with two millennia of artistic achievement). These destinations are connected by Trains.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Bari and out of Rome
- Hotel for 3 nights in Bari
- Train Bari - Lecce
- Hotel for 3 nights in Lecce
- Train Lecce - Rome
- Hotel for 3 nights in Rome
Find a package. We have many more!
Cities in Italy
- Rome
- Venice
- Florence
- Agrigento (Sicily)
- Alberobello
- Alghero (Sardinia)
- Amalfi Coast
- Amalfi Town
- Ancona
- Arezzo
- Assisi
- Bagno Vignoni
Cities in Italy
Explore Italy
Italy FAQ
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What is Italy known for?
From the Roman Empire to the Renaissance, Italy is famous for its huge contributions to the worlds of art, architecture, fashion, opera, literature, design, and film – the list goes on, and we haven`t even mentioned the food yet. The country has more UNESCO World Heritage cultural sites than any other country in the world.
Artistic masterpieces, medieval hill towns, majestic mountains, Mediterranean beaches, bustling markets and mouth-watering cuisine - Italy really is a country that has it all, and that's why it is one of the most-traveled destinations in Europe. -
What are the best places to visit in Italy?
There are so many highlights in this gorgeous country - from the canals of Venice to the museums of Florence and the surrounding countryside of Tuscany and its Hill Towns to the cobblestone streets of Rome to the cliffs of Positano… and beyond.
Rome is one of the most iconic and most traveled cities in Europe and you could spend days getting lost in this amazing destination. The most picturesque spots in Italy might just be Cinque Terre and all the stops along the Amalfi Coast. Positano is the gem of the Amalfi Coast and is arguably the most beautiful and most charming town in the whole of Italy. -
When is the best time to visit Italy?
Like all popular European destinations, Italy sees visitors throughout the year - rain, snow or shine. And all of these are a possibility depending on when you visit Italy. Every season in this country has its charm, as well as its drawbacks, so when to go depends on your travel type and what activities you are interested in.
Generally speaking, the best times to visit are during the `shoulder seasons` which is spring (April to June) or fall (September and October) when there are fewer tourists, lower prices, and moderate temperatures. The summer months bring an influx of tourists and increases in hotel rates, and higher temperatures. The winter months are often grey, wet, and cold in the north but temperate south of Rome. Here is an overview of Italy in all four seasons that will help you decide what`s the best time of year for you to visit. For more information, check out: Best Time to Visit Italy -
How many days should I spend in Italy?
We recommend 7-12 days based on what you want to see and do. We offer flexible vacation packages so you can select your number of nights in each city, desired hotel and activities. We suggest a minimum of 3 nights in larger cities.
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What is the best way to get around Italy?
Whatever your pleasure, transportation in Italy is modern, easy to navigate and fits a variety of budget ranges.
By Car: If it's the open road you're after, renting a car is the best way to travel in Italy. All the typical car rental companies are available at the major airports. Specify automatic or manual transmission, as car transportation in Italy (and Europe, for that matter) is usually manual. On the small, winding country roads, manners usually win out, and major highways span the country to help ease access to the major cities. For more information on getting around by car, check out: Driving in Italy
By Train: Train travel in Italy is an excellent way to take the stress out of planning routes. Though you can't get to the smallest towns by train, the medium-sized and, of course, the major stops are on train routes. -
What is the currency of Italy?
The currency of Italy is the Euro. US dollars are not accepted. Please be sure to have the correct currency on hand or be prepared to exchange your dollars for euros upon arrival. Currency exchange desks can be found at the airport and many locations throughout the city. For more detailed information, consult our guide by clicking here Tipping in Italy.
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Do people speak English in Italy?
English may be spoken at your hotel and in the tourist areas, but not everywhere. We suggest you get a good English-Italian guidebook and familiarize yourself with common phrases such as hello, goodbye, excuse me and numbers 1-10.
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Why should I choose Tripmasters to book my Italy vacation?
One of the biggest advantages of using Tripmasters to book your Italy vacation package is choice. You can easily customize multi-city travel itineraries, choosing from a wide selection of curated hotels, activities, and transportation options. Our Italy vacation packages are perfect for travelers who love independence, but appreciate expert planning behind the scenes.
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Does Tripmasters offer luxury vacation packages to Italy?
Absolutely! Please visit our Luxury Vacations page to discover our bespoke private guided luxury vacations to Italy as well as Tripmasters own customization platform where you will find high-end hotels, exclusive activities, VIP experiences, and private chauffeured transfer services expertly curated for the discerning luxury traveler.
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What are the best vacation packages to Italy?
Experience Rome - Florence - Venice (7 nights)
Customizable Italy vacation packages featuring multi-city itineraries. Book best Rome - Florence - Venice by Train. Custom multi-city, multi-country Italy vacations.
Includes: Flight into Rome and out of Venice, Hotel for 3 nights in Rome, Train from Rome to Florence, Hotel for 2 nights in Florence, Train from Florence to Venice, Hotel for 2 nights in Venice
Curated Experiences Based on Availability: , Rome Colosseum Tour, Guided City Tours of Florence and Venice, visiting iconic sites and popular neighborhoods
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
Easily upgrade your vacation to a Luxury Private Guided experience, featuring upgraded hotels, curated private activities, and more, or try our flexible Essential Series package with hotels, transportation and optional activities that you can customize! -
Can I combine a vacation package for Italy with other countries?
Yes, you can combine with: San Marino
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Where can I go for $2000 in Italy?
- Experience Rome - Florence - Venice - Lake Como - Milan (11 nights from $1711)
- Rome - Florence - Venice: Chauffeured Collection (7 nights from $1959)
- Bari - Lecce - Rome by Train (9 nights from $1242)
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