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Sample Italy with this unique, customizable vacation package!. Visit Florence (home to Renaissance Art and architecture), then pick up your car and ...
You'll find millennia of history and heritage in the Italian capital and its most famous cities! Let Tripmasters make your Italian holiday easy, ...
Discover thousands of years of history and breathtaking coastal beauty across Italy's most iconic destinations! Let us make your Italian holiday ...
Explore some of the awe-inspiring wonders of Italy!. Enjoy a stay in Rome (the Eternal City), visiting its most famous landmark: the Colosseum; then ...
The Ultimate Grand Tour: Rome, Florence, Venice, and the Northern Lakes! Discover ancient Rome (the Eternal City) and its famous Colosseum, Florence ...
Planning a trip to Italy in 2027 means experiencing a destination that is evolving faster than ever. From the rise of immersive regional travel to major improvements in high-speed rail connections, Italy is becoming more accessible, flexible, and rewarding for independent travelers. While iconic cities like Rome, Florence, and Venice remain essential stops, there is a growing shift toward deeper, more authentic experiences in regions such as Puglia, Tuscany, and Cinque Terre. Whether you are drawn to Italy’s historic landmarks, culinary traditions, or hidden gems, 2027 offers new opportunities to customize your journey like never before. These travel trends highlight the best ways to explore Italy, blending classic experiences with modern convenience for a truly unforgettable adventure.
All packages featured are fully customizable, giving you the flexibility to plan a trip that truly fits your travel style. Our platform is designed with you in mind, meaning our itineraries aren't just lists of hotels, but intelligently mapped journeys that prioritize the best locations, the most relevant experiences, and the direct answers you need to plan with confidence.
Choose from top-rated, highly-vetted hotels and room types that match your specific search criteria.
Upgrade or adjust your flights and ground transportation for a smoother journey.
Add or remove tours, transfers, and local activities to make the itinerary uniquely yours.
Design Your Own Trip
Select up to 12 destinations!
Our Best of Italy vacation packages make it easy to experience the country’s most iconic destinations with seamless travel between cities, handpicked hotels in prime locations, and flexible customization options.
Discover Italy with our Chauffeured Collection (Door-to-Door Discoveries) vacation packages, featuring private car transfers between top destinations like Rome, Florence, and Venice, with curated stops at charming towns, local attractions, and UNESCO World Heritage Sites along the way.
Explore Italy’s rich heritage with our History and Culture vacation packages, featuring iconic cities like Rome, Florence, and Venice, known for world-famous art, architecture, and UNESCO sites. Discover ancient ruins and Renaissance masterpieces with flexible, customizable multi-city itineraries designed for immersive cultural travel.
https://tripmasters-pictures.s3.amazonaws.com/images/apkg/71/puglia_-_bari-1058017-500.jpg</todoimage> <tododescription>Relax along Italy’s stunning coastline with our Italian Seaside Resort vacation packages, featuring top destinations like the Amalfi Coast, Puglia, and Sicily, known for crystal-clear waters, charming seaside towns, and rich culture.
Discover Italy’s world-renowned heritage with our UNESCO Sites vacation packages, featuring iconic destinations like the Dolomites, Florence, Rome, Pompeii, and the Amalfi Coast. Explore history, art, and culture through customizable multi-city itineraries designed to showcase Italy’s most celebrated UNESCO World Heritage Sites.
Savor the flavors of Italy with our Italian Wine and Food vacation packages, featuring culinary hotspots like Tuscany and Sicily, known for regional cuisine, local ingredients, and world-class wines.
Italy, Austria and Czech Republic awaits you. Combine pleasant stays in Rome (the Eternal City, with its stunning Colosseum, Roman Forum and delicious ...
The hotel in Rome was Relais De L'Opera. Nice room and the customer service was great, they even hold your luggage for free after checkout if your flight/train is later in the day. On the other hand ...
Discover the best of France and Italy!. Combine Paris (the romantic City of Lights; shopping, dining, museums) and Rome (the Eternal City, with its ...
While the hotel in Paris wasn''t the best (insane amount of street noise and bus/trains shook the room constantly), the location of the hotel couldn''t be beat. Great location next to trains and ...
Italy, France and England are combined for your ultimate enjoyment!. Begin in Rome (the Eternal City, with its stunning architecture and delicious ...
Three fantastic capital cities in Portugal, Spain and Italy, combined into one unforgettable vacation for you!. Begin in Lisbon (the capital of ...
Italy, Portugal and Spain, memorable cities. Begin in Lisbon (the capital of Portugal; home of famed explorers, full or tradition, rich culture, and ...
Combine Spain and Italy, two of the most popular destinations in Europe, with this unforgettable vacation!. Discover Madrid (an active and attractive ...
Planning an Italian escape for 2027 requires a blend of classic inspiration and modern logistics. As the travel landscape evolves, our 2027 Customizable Vacation Packages have been re-engineered to prioritize flexibility, sustainability, and unparalleled connectivity. The headline for the 2027 season is the total transformation of the Italian transit network. With the entry of new high-speed rail competitors on major corridors like the Milan-Rome-Naples line, travelers can now enjoy more frequent departures and more competitive pricing, making multi-city "Grand Tours" more accessible than ever before.
Our 2027 vacation planner has been specifically updated to include "Second-City Clusters." While Rome, Florence, and Venice remain the heart of our offerings, we are seeing a 20% surge in demand for sustainable, deep-dive itineraries in regions like Umbria and Puglia. These packages now feature hand-picked "Masserias" and boutique stays that emphasize slow travel and local immersion. Whether you are seeking a 10-day classic route optimized for the new 2027 rail schedules or a bespoke luxury escape in the Sicilian countryside, our real-time pricing engine ensures you secure 2027 inventory before the peak-season surge. By choosing a customizable tour for 2027, you aren’t just booking a trip—you are securing a seat at the forefront of Italy’s most connected and sustainable travel era yet.
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.
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.
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
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.
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.
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.
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.
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.
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.
