Perfect Italy Vacation for Senior Travelers

Soak in Italy’s quieter side as you touch down in Milan and transfer to Lake Como. Mountain peaks shimmer in the glassy water surface, their rugged shapes contrasting reflections from colorful villas. Everything is narrow and mazy in the town, stores, and cafes spilling into one another yet maintaining a peaceful atmosphere. Your base is Bellagio, the most famous and most luxurious of the Lake Como towns. Check into your vintage hotel on the water and rest. You have more than two weeks in Italy, so it will be wise to slow down and work out any jet lag before setting off for the highlights and sights.

Regular catamarans crisscross Lake Como for an easy way to explore the romance of the water. Cruise to Varenna for a coffee, looking out at the villas owned by celebrities along its shoreline. Cross to Menaggio and listen for church bells, and then travel to Tremezzo and get a feel for small-town life. When you are ready, return to Bellagio and take a proper walk through the shops and streets. Antiques spill from one, oil paintings dominate other, and fashion boutiques stand in between. Bellagio’s gardens provide a serene place to spend an hour while the town’s old villas start the Italian sightseeing. This day is designed to be relaxed, and there is no specific itinerary, just a handful of beautiful places you could explore.

Bergamo is an old town frozen in time with hardly a stone out of place along the cobblestone streets. The city stands high on the hill, accessed via a funicular and a Venetian gate, and it is surprisingly light on tourists. Feast your eyes on the gilded beauty of Santa Maria Maggiore, inspect the sculptures and frescoes of Cappella Colleoni, and follow the colors from yellow to green across Piazza Vecchia. Some of the sights are hidden, revealed only when your guide takes you down an alleyway or through a tiny doorway. Some are for all to see, basking beneath the sun in a town that’s hardly changed for 300 years. Spend most of the day here then continue the journey to Milan, where you have a hotel in the heart of the city.

Da Vinci made his name in Milan, and his extraordinary works will provide your focal point to discovering the city. The Last Supper in Santa Maria delle Grazie, a painting that changed the art world in the 15th century is placed in the small, unassuming church and suggests how little known Da Vinci was before this masterpiece. Leonardo’s sketches in the Bramante Sacristy brings 1,200 pages that cover his elegant early work. And then move next to Biblioteca Ambrosiana where you can witness his only painting of a man, along with his relationship with Raphael. As you tour around Da Vinci and his works, you will also stop by Milan’s two greatest sights, a cathedral that took six centuries to complete, and the luxuriant interior of Galleria Vittorio Emanuele II.

It will be on to Venice by train and along the canals, a vaporetto boat taking you from station to hotel down the Grand Canal. The old city is compact, a string of small islands devoid of honking horns and traffic. The city is also a maze, a web of canals and alleyways that need a local guide for you to understand. On an orientation tour you will cover both, first a gondola through the city and then an easy walk in places where most get lost. While there is a sense of faded grandeur, a tour through Venice really impresses the beauty of vernacular architecture. Most of what you photograph and admire is not a typical highlight or sight to see, rather it is just what Venice is, a historical city slowly crumbling into the water.

Through Venice with a Venetian, you will travel the backstreets and the basilicas as you learn about the republic’s incredible past and uncertain future. The walk is a journey best done in the morning and before the streets and squares throb with afternoon crowds. You will end at St Mark’s Square and St Mark’s Basilica, two timeless highlights best understood when you know the context. This afternoon you can have time to discover Doge’s Palace or the Accademia Gallery, although you could squeeze both in if you have the energy. Continue the local Venetian experiences this evening with a church concert, the beauty of sanctified space really coming to the fore.

One era to the next, you will travel onwards with a relaxed, high-speed train journey to Florence and a day spent delving into the masterpieces of the Renaissance. Like Piazza della Signoria, where David used to stand, and Palazzo Vecchio is imposing and unperturbed by tourists. And then move to the cathedral, where Brunelleschi’s dome is beyond comprehension, as ineffable as any sight in Italy. Next will be the Accademia Gallery, where Michelangelo’s David now stands and is almost outshone by his Prisoners. There is not that much walking to get around these three sights, especially with such a centrally located hotel. Like Venice, Florence is surprisingly easy for senior travelers as the old urban core is compact and easy to get around, with countless cafes and restaurants.

You can look forward to more of the Renaissance today as you settle into the city. Begin with the Uffizi Gallery, Italy’s grandest art museum, where all the legendary names are represented. No other gallery has such a variety or abundance, as the Uffizi ranges from Botticelli to Leonardo and so many more. While the Uffizi has fame, some of the other Renaissance sights are easily missed.  Many church frescoes, historical villas, hidden palace rooms, and art galleries are overlooked by tourists, but your private guide will tailor an afternoon to your sightseeing interests. There will also be a lot of fun to be had by doing nothing at all, Florence being one of those cities where you can sit back on a piazza and watch the world go by.

Pisa’s Leaning Tower is photogenic, but the old town’s real highlights are not as surrounded by camera-wielding visitors. Check out the marble cathedral and admire how the light shimmers across its floor. Stroll through the cloistered cemetery, as elegant a place as any to be buried. Walk across the Square of Miracles and find the Romanesque baptistery. After all of that, enjoy lunch away from the succession of tour buses. Pisa is on route to the Cinque Terre, where the pace of this senior travelers tour changes abruptly. After lots of sights and cities, you will now on the coast, where the experience concerns lazy cafes, Mediterranean vistas, and serenity.

Vineyards stretch across mountain slopes, squares of green above sea blue. Small hiking trails crisscross the land, lacing together villages that have only received roads during the last few decades. Mostly these fishing villages are alleys and steps, something that ensures everyone travels slowly. Your time in the Cinque Terre is a break from cities and sightseeing, but it is still a piece of history. As you sip on a cappuccino and eat fish, or pizza, on a terrace, there will be a sense that time will never move forward here. When taking a boat to neighboring villages, you may get the same feeling. You could choose to visit a few of the five, or pick one and spend the day taking it very slowly.

Traveling by car now, you will traverse Tuscany. Vineyards flow abundantly, casting the hills in green shades as towns dot the valleys, sometimes little more than a church spire and small square. The roads twist and turn, twist and turn some more, and then ascend to a 15th-century village or Gothic city. Siena is today’s final destination, and it will be quite a sight, like a living museum of marble and sculpture centered on world-famous Il Campo. It is here that Siena’s neighborhoods compete in the Palio horse race and you can almost imagine the rumbling hoofs. For a special dinner, you might head into one of these neighborhoods, known as a contrade to taste delicacies that may not be found outside this single contrade.

Siena’s history comes alive in its cathedral, where elaborate light flickers through the stained glass. You can learn of the rivalry with Florence and the medieval figures that shaped the city, particularly the architect behind a dramatic city hall tower. Siena is a friendly place, and you will meet local artisans today, learning the basics behind stained glass techniques. The afternoon is at your leisure and one place to spend it is an enoteca, a wine bar that also serves as a museum to Tuscan wine.

Columns and colonnades mark the Assisi entrance, glowing in the morning light as you ascend the hill. They suggest dramatic wealth and grandeur, yet the story here is one of poverty, as preached by St Francis. Such a juxtaposition of opulent architecture and St Francis’s beliefs makes Assisi one of Europe’s most intriguing historical towns. Follow in the saint’s footsteps before twisting into Umbria and the first of two nights spent on a working winery. Amid olive groves and vineyards, your cottage stands proud, offering glorious views across the land. Wine tasting and great food come as standard here, so sit back and absorb the Umbrian experience.

You will be staying at a winery just outside Orvieto, the grandest of the region’s hill towns. Here, in the chapel of San Brizio, you find a sight to rival any Michelangelo or Da Vinci – Signorelli’s frescoes. There are so many of them, cycles of life and death and resurrection. They cover ceilings and walls, not an inch without paint in this spiritual place. Staying alongside your local guide, you can see more of the medieval town. Back at your winery hotel, there is also time for a countryside walk or a guided tour of the vines.

It will be an hour by train to Rome, your final destination on this historical tour for senior travelers. Check into your hotel near the Pantheon and spend some time building your impressions of the city. Visitors are often delighted by how close together everything is in this city, with elegant piazzas a crossroads between sights like the Spanish Steps and Trevi Fountain. Today’s private guided tour will take you to the Vatican Museums after they have closed for the day. Everything is even more majestic without other tourists around, as the elaborate chapel ceilings and ornate Christian sculptures are far more impressive when all is quiet. Before the museums, you will have visited St Peter’s Basilica, the largest and grandest of all the world’s churches, and a moving place of pilgrimage for many. Then you can compare Michelangelo’s works, picking a favorite from Pieta and the Sistine Chapel.

So many sights have been seen so far, but can any rival Rome? The Colosseum in all its glory, the amazing Pantheon, the history at Palatine Hill and the baroque style that reenergized Rome in the Middle Ages are all yours to enjoy. On a leisurely day of exploration, you can take in Rome’s major highlights. But like other days on this tour, there will not be too much walking, and you are never far from a cafe enjoy when in need of a rest. In Rome, it is hard to prescribe an itinerary as everybody has a slightly different idea of where they would like to go, but your local guide knows the city in and out and can customize the day to your preferences.

After more than two weeks in Italy, you will depart with memories and pictures of so much history and wonderful experiences to remember for years to come.