Workation » Best Workation Locations and Why You Should Visit Them » Italy Workation – Working and Vacationing in Italy
Discover & Work in Italy
Italy is a country of passion, beauty, and pleasures making it a perfect Workation destination any time of year. Popular but with hidden gems with endless charm and famous cities, Italy can feel like the place everyone has already visited but the stretch of coastline, mountains, and historic cities turn the real-world destination into a place of fantastic dreams. Taste the incredible food, explore the beautiful nature, and visit cities that showcase the beauty of imperial Venice or the opulence of ancient Rome. An Italy Workation can be as quiet and secluded or as adventurous and immersive as you’d like.
Highlights
Italy is surprising and breathtaking, and blends the known with the neglected making it an incredible place for a Workation. Highlights for Workation in Italy include:
- Great infrastructure that includes trains, ferries, airports, and highways make it easy to travel between cities, towns, and islands.
- Wifi connectivity is strong across and cell reception is readily available, whether with roaming from a home carrier, a transportable wifi adaptor, or when using an international plan
- You are always close or even next to an historical landmark, natural panorama, or cultural presentation that can revitalize your energy
- Italy is on the Tyrrhenian, Ionian, and Adriatic seas with millennia of history dating back to before Magna Graecia showcasing hidden villages, delicious vineyards, and recipes steeped in ancient tradition
- Italian hospitality and friendliness is among the world’s finest, especially in smaller towns, and Workationing in Italy gives you the time and connections to experience the simple pleasures of life by engaging with the customs like a local

Italy is one of the most popular destinations in the world but still has neighborhoods, towns, cities, and regions that feel untouched by massive crowds. With gorgeous beaches, medieval walls, Roman fortresses, and elegant artwork, a few highlights of Italy include:
- The Roman Colosseum in Rome continues to stand tall above the city
- 4,723 miles of coastline that includes some of the most coveted towns and beaches in Europe such as the Amalfi Coast, Cinque Terre, and the Italian Riviera
- Italy is world-renowned for its cuisine, not just the ideas of pizza and pasta but regional dishes from places like Tuscany and famous Michelin-starred restaurants
- Museums like the Vatican Galleries, the Ufizzi Gallery, the Accademia del’Arte, the Archeological Museum in Naples, and more highlight the magnitude of history and beauty across the country
- Local and seasonal cuisine still take a prominent position, especially with the emergence of the Slow Food Movement and reconnecting with ingredients like truffle, cured meats, and local cheeses
- Cities like Rome, Florence, Pisa, and Venice highlight the traditional architectural, artistic, and historical treasures of Italy touching the Roman to Venetian empires
- Sicily is part of greater Italy but can feel like a completely different world with its own traditions, culture, and perspective formed by centuries of colonial rule
Italy combines the beauty of its picturesque coastlines with charming fishing towns, traditional hilltop villages with the rugged mountains creating a spine across the center and top of the country. The climate changes by region, supports flood plains and alpine peaks, but also shapes the exceptional cuisine found in each distinct area. During your Italy Workation package, you can experience how each region has its own flavors, ingredients, and ideas on what makes great dishes with activities like:
- A truffle hunt and tasting
- A hike on protected land
- A walking tour around one of Italy’s inspired historic cities and towns
- A boating excursion on the Venetian Lagoon or Adriatic, Ionian, or Tyrrhenian seas
- Visiting the coastline at a celebrated town or beach

Cities to explore in Italy
Italy’s cities and towns demonstrate the centuries and millennia of heritage that speak to the culture of today. Influenced by the lush hills and rugged mountain tops or the secluded seaside cliffs and volcanic soils, each region possesses its own set of customs with traditions locals are eager to share. The incredible collection of things to do and see in the following cities highlights the best options for an Italy Workation package due to the quality location, infrastructure, and connectivity:

Rome
Rome quickly introduces visitors to its nickname, “The Eternal City.” Layers upon layers are quickly revealed around the historic city center, where cobblestone streets weave between medieval tower homes and the ancient empire emerged grandeur in the form of the Colosseum and Roman Forum. Equal parts romantic, charismatic, and chaotic, Rome has a special flavor unlike anywhere else in the world.
History feels monumental and graspable, with artistic treasures at your fingertips displayed in the countless museums found across the city. Locals live their lives in the tradition of La Dolce Vita, focusing on the sweet little pleasures that exist each day while tasting great food, sipping delicious wine, and talking with friends as the city passes by. Feast on the art and architecture, the flowers and historic decorations, or the cuisine to enjoy the timelessness the Eternal City offers making it one of the best cities in Italy for Workaiton because it immediately immerses visitors in the joys of the past with the comforts of contemporary life.
Highlights
- The Colosseum walls and interior
- Vatican City with St. Peter’s Basilica and the Museum Galleries
- The famous Baroque monuments that include the Trevi Fountain, Spanish Steps, and Piazza Navona
- The cafes, restaurants, and shops along the luxurious and opulent Via Condotti
- The gorgeous combination of lavishness and prestige in the Borghese Gallery and Gardens

Tuscany
Tuscany is unquestionably Italy’s most famous region and for good reason; the landscape itself is as famous as the towns and cities, conjuring images of rolling hills, rows of cypress trees and estates sprawling with grape vines. Practically overflowing with ancient and medieval history, the scenery shining with emeralds also delivers the iconic medieval towns crowning the famous hills, where towers, defensive walls, and cobblestone streets reveal antique restaurants steeped in tradition or artisan shops showcasing customs passed down for centuries.
Michelangelo’s David in Florence, Pisa’s Leaning Tower, the wines of Montepulciano, or the horse races in Siena each add a unique texture to the culture, history, and charming personality of the greater region. In Tuscany, you can slow down and taste the flavors, witness some of the Western World’s most notable artworks, and find how the perfect landscape can shape your work-life balance on an unforgettable Italy Workation package.
Highlights
- The legendary dome of Florence’s cathedral and renowned artwork of in the city’s museums
- The Leaning Tower of Pisa and architecture of the Piazza dei Miracoli
- Siena’s cathedral and the mosaics decorating the floor
- Wine in the Val’Orcia
- The cuisine demonstrating centuries of cucina povera traditions translated into modern times

Venice
Venice can feel opulent and, while connected to Italy, worlds away in how it enchants, enraptures, and shapes the perspective of visitors. Walkways stroll beside and open to panoramas of the famous canals. Secret corners hide away local neighborhoods where history comes alive. Golden mosaics glow and shimmer in the light highlighting Byzantine history and illustrious images of the preserved past. The Grand Canal features the luxurious palaces of a bygone era, when the Republic rules as an Empire across the Adriatic Sea and beyond.
Enticing neighborhoods, serene islands, artisan crafts, and delicious small dishes known as cicchetti represent the elaborate local culture often ignored in Venice, overshadowed by the famous domes of St. Mark’s Basilica and the gondolas cruising on the water. But Venice is all these things and more, embracing a history of romance and power, expansive grandiosity and intimate charms creating an Italy Workation package experience unlike anywhere else in Italy or the world.
Highlights
- The mosaics of St. Mark’s Basilica and the secret rooms of the Doge’s Palace
- Views from the canal on a gondola ride away from the Grand Canal
- Art and architecture in the Scuola Grande di San Rocco
- Life and goods displayed almost daily in the Rialto Market
- Artisanal islands of Burano and Murano
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