Perfect Italy Vacation for Senior Travelers

St. Francis of Assis Basilica in Umbria, Italy

What to expect on this itinerary

The sights of Italy abound with mystery and legend throughout the breathtaking odes to history. Begin with Da Vinci in Milan, and then explore Michelangelo in Florence and the Vatican, continue to Assisi, Venice, Pisa, and Siena.  See Signorelli’s frescoes, Brunelleschi’s Dome and Bernini’s baroque, the canals of Venice and Bellagio on Lake Como. All of these are just the start on this handcrafted sightseeing tour for seniors as you will delve beneath the surface with expert guides to living the history that is often felt far beyond what any words can explain.

Countries Visited

Italy, Vatican City

Places Visited

Milan, Bellagio, Santa Maria delle Grazie, Pinacoteca de Brera, Venice, Florence, Cinque Terre, Tuscany, Siena, Il Campo, Assisi, Umbria, Rome, Pantheon

Suggested Duration

17 Days

Customizable Itinerary

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Day 1

Bellagio – An Opulent Town on Lake Como

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.

What's Included:

Transfer
Accommodation
Breakfast
Day 2

Bellagio – Cruising the Lake and Admiring the Vistas

Day 3

Milan – Seeing the Hidden Gem of Lombardy

Day 4

Milan – Discovering Leonardo Da Vinci

Day 5

Venice – Alleys and Canals of Venice

Day 6

Venice – Historical Walking Tour and an Evening Church Concert

Day 7

Florence – Michelangelo’s David and Brunelleschi’s Cathedral Dome

Day 8

Florence – All the Iconic Renaissance Sights

Day 9

Cinque Terre – An Unmissable Tower and Coastal Charm

Day 10

Cinque Terre – Free Day in the Mediterranean Villages

Day 11

Siena – The Magical Heart of Tuscany

Day 12

Siena – Stained-Glass Workshop and Dazzling Medieval History

Day 13

Orvieto – St Francis and Exploring Umbria

Day 14

Orvieto – Signorelli’s Frescoes and Colorful Pottery

Day 15

Rome – The Vatican Museums After Hours

Day 16

Rome – The Eternal City and All the Baroque

Day 17

Rome – Departure

Trip Highlights

  • Marvel at Da Vinci’s The Last Supper and explore the artist’s history in Milan
  • Discover the best of Rome from the Colosseum to Bernini’s baroque style
  • Rest and relax on the shores of Lake Como, with Bellagio the first stop on this itinerary
  • Drift down the Venetian canals in a gondola and get to know the city’s key highlights
  • Brunelleschi’s cathedral dome and Michelangelo’s David are just two sightseeing highlights from your time in Florence
  • Experience the St Francis story in Assisi and step back in time with a day in Bergamo
  • Indulge in the blissful heart of Tuscany with a two-night stay in Siena
  • Learn the artistic history of Orvieto, a quiet gem in the Umbria region
  • Take a boat between the villages of Cinque Terre, the classic way to see this colorful Mediterranean coastline
  • Visit the Vatican Museums after hours and be alone in the Sistine Chapel

Detailed Description

The sights of Italy are not just for your eyes. As Robin Williams tells Matt Damon in the 1997 movie Good Will Hunting, “you can’t tell me what it smells like in the Sistine Chapel.” The magical element of travel in Italy is how the sights and cities can make you feel. A church bell chiming as you gaze up at Da Vinci’s The Last Supper, the sense of spirituality that envelops Assisi, the sound of paddles, and chatter down Venice’s Grand Canal cannot so much be described as they are felt. The best of Italy’s sights are legendary pieces of Western history that cover art, architecture, Christianity, civilizations, and republics and make for history that you need to experience for yourself.

From Signorelli’s frescoes in Orvieto to Brunelleschi and Bernini, this tour discovers the very best of Italy as you delve beneath the surface on your 17-day journey. There are eight overnight destinations with two nights in each, and the itinerary has been designed for senior travelers to minimize travel time and keep walking to manageable levels while still covering a large part of the country. Various stops are incorporated into the journeys, like Bergamo en route to Milan and Pisa on the way to Cinque Terre. Accommodation is in the heart of towns and cities, so you are never more than a few hundred yards away from grand sights and restaurant choices. Local guides lead the way in each destination, their understanding of their home helping you look far beyond the postcard photos.

Kick-off in relaxed style on Lake Como with two nights in Bellagio easing you into the vacation. Explore Bergamo before moving to Milan, where day four is dedicated to the religious art and influence of Leonardo Da Vinci. Take the train to Venice, a city that crams so many sights into a tight area. You will travel on a gondola here of course, as well as experiencing an evening church concert. Florence is next, with Michelangelo’s David just one of the famous highlights. There is an incredible history here, and you will follow the artistic trail through all the domes, piazza, and palazzos.

Check out Pisa on route to two days in the Cinque Terre for a good place to unwind and reenergize halfway through the tour. Here you can take a boat to old fishing villages and spend plenty of time in the cafes as the Mediterranean glistens below. Siena is next as the heart of Tuscany is revealed from the paleo horse ring to a hands-on stained-glass workshop. From Tuscany to Umbria, you will stay in traditional Italy with destinations like Assisi and Orvieto practically untouched over the last two centuries. Rome will be your final stop, and you will experience the Vatican Museums after hours and without the crowds, discover what remains of ancient Rome, and travel forward through the city’s baroque and neoclassical styles on a tour of sights for an unforgettable place to finish.  Consider reading some of our travelers’ Italy for Seniors tour reviews for more ideas to perfect your dream Italy vacation.

Starting Price

$5,600 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 2498 reviews

Review: Italy Family Vacation, Milan, Rome, Florence, Venice, Parma, Modena, San Gimignano, Lake Como, Dolomites Snowmobiling

Thanks for helping me organize my family (of 10 with diverse age from 15 to 63) trip to Italy, from Dec 17 to Dec 31. Whilst different member of my family have different expectation and requirement, I would like to comment you and your team on having planned an excellent trip that not only met each and everyone's interest and expectation but truly exceeded it.

Your planning have brought us to the lovely cities of Parma, Modena, Florence, Orvieto, Civita Di Bagnoregio, Naples, Rome, Venice, Cortina d'Amprezzo and back to our starting point Milan. Throughout the trip, we have a well balance itinerary that covered

- beautiful churches such as the Duomo in Milan, Rome, Florence,

- archeological site like Pompeii, Colosseum, Roman Forum, Pantheon, Pisa, Verona (learning more about romeo and Juliet)

- great local eating places (recommended by the guides you chose)

- lovely country side and unique sight in San Gimignano, Civita Di Bagnoregio, Orvieto, Lake Como,

- great gallery likes Uffizi, Academia

- Interesting activity such as Snow Mobile excursion in Cortina, Learning Cooking 

- Shopping activities

With so much, yet your team immaculate planning never have us rushing from sight to sight, we were both able to enjoy and learn as much as we can of each sight and at times added more activities.

The team of guides you chose, have truly turn stone and history into exciting stories that the provided the group deeper understanding of the sights we visited and saw. Really like to thank each on of them like our guides in Florence, Pisa, San Gimignano, Orvieto and Civita Di Bagnoregio, Naples and Pompeii, Rome, Verona, Venice and Milan.

But most importantly, thank you for getting our driver, he truly ensure our comfort whilst driving steadily through jams on our way to Naple and snow storm on our way to Cortina d Amprezzo and also took very good care of us ensuring we know what to do where we have no guides and leaving us clear instruction when we needed help. He is truly a wonder.

I will definitely tell my friends heading to Italy about this company.... A wonderfully great experience.

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Review: Luxury Italian Vacation, Rome, Venice, Florence, Positano, Siena, Tuscany, Napoli, Amalfi Coast, Pompeii, Duomo, Colosseum

Our trip to Italy proved to be, indeed, 'fantastica'!  We traveled to Venice for 2 nights; by train to Florence for 2 nights where we stayed at the luxurious Palazzo Niccolini al Duomo; by train to Siena for 2 nights.  From there we speed-railed it by "TreniItalia" to Napoli where we were picked up in a private car to take us to the jaw dropping showcase Italian seacoast resort of Positano.  We stayed there for 3 glorious nights at the Covo dei Saraceni with the most breath taking views of the bay and the Amalfi Coast that you could ever see.  Finally, we were picked up in a private car and taken to Napoli for a train to Rome.  But first...we had a 2-hour stop with guided tour of Pompeii's ruins.  Finally, after training to Rome, we stayed at the quietly elegant Residenza di Ripetta hotel near the Piazza del Populo.

I've left out the most important parts which were the incredible tours that this Italy travel agency arranged for us.  We must've seen everything that this trip could offer.  And it was all done over two weeks.  We toured Venice during the calamitous weekend of George Clooney's wedding.  No, we couldn't go to the wedding but we had a fabulous time nonetheless!  Our agent and her team put us up at the quaint yet convenient Hotel Georgioni in Venice quite near the Rialto Bridge.  We had been picked up at the airport and water-taxied to our hotel.  During our fabulous 48-hour stay, we saw every nook and cranny of central Venice anchored by the eye-popping Piazza San Marco.  Included in our stay was a tour of the Doge's Palace with its art treasures galore and a tour of the markets area replete with a 30-minute gondola ride through a memory of photographs that I took that I will never forget.  The Rialto Bridge at night, along with the rest of Venice, is one of the most romantic sights in the world.  The lighting of this magnificent city at night is unforgettable.

From there it was on to the renaissance city and Medici capital of Florence to our luxurious hotel, the Palazzo Niccolini al Duomo right across the street from the magnificent Duomo itself.  We walked and toured everything; from the Accademia Gallery and the "David" masterpiece by Michelangelo to the Uffizzi Gallery and Vasari Corridor to the Ponte Vecchio where I bought my beautiful wife a golden ring the size of Sardinia.  We saw street musicians, vendors, activists and sellers of all kinds.  We even saw a Brahma bull towing a wagon hauling over a 1000 bottles of Chianti up the main street into the square.  The food? Indescribably memorable.  Just like all of Italy.  

On to Siena where the Medieval contrasts with the Renaissance of Florence beautifully.  These 2 cities, once rivals, are now bastions of art and relics dating back centuries...from every genius known to man.  Siena, with its massive "Campo" is the meeting point for all of Tuscany seemingly.  They run their horse race there every year around the Campo.  We didn't see it.  But we did see a huge nighttime sports car rally featuring the finest autos made by Ferrari, Maserati, Alfa-Romeo and others.

Taking the train in Italy is a far preferable way to travel than car.  We had the benefit of traveling in clean cars traveling almost 200 MPH in almost serene silence - with some of the greatest views ever.  It's fun...and grabbing a panini and a water is the perfect way to relax and have lunch aboard the train.  

Positano.  What can we say other than it was a 3-day dream.  Everything that you could possibly photograph is present in this sea coast paradise.  Staying at the singular Covo dei Saraceni provided us with a view out of our bedroom window that could stop time.  It was THAT beautiful!  The views of villas tucked into the mountains; the roads that snake their way down to the beach, the lovely little shops that adorn the narrow streets all make for fantastic photographs so compelling that friends would envy you and your experience.  From Positano, we took a day trip out to the Isle of Capri.  Capri, for us, was like Italy's Catalina Island - kinda honkytonk and overpriced yet still very fun.  Especially when you bus up to the top to take in the wildly sweeping and sometimes scary sights from Anacapri, the island's little town that's 'above it all.'  We toured the historic Villa San Michele with its stories of Axel Munthe, the one time owner and Renaissance man in his own right.

Finally, we finished with 3 days in exciting unstoppable "Roma".  Can there be any more excitement?  Any more history? Any more style?  We saw everything: the Colosseum, the Forum, the Pantheon, the Piazza Navone, the Carra Calla Baths, Circus Maximus, Palatine Hill, The Arch of Constantine, The Villas of Borghese.  We rowed boats, we road bicycle carts, we got lost.  Moreover, we ate gelato at the 150-flavors of Della Palma.  We heard stories about Roman Emperors and the various peccadilloes, their loves (and lovers!) and their battles.  Both won and lost.  

This whole trip will go down in our memory as arguably the greatest trip that we ever took.  We've been together almost 20 years and, thanks to our agent and her team at this travel company, we enjoyed our 2nd honeymoon to the max.  Not once in our 12-day itinerary did we have a hiccup.  Everything that our agency arranged for us from tours, to drivers to train departures and tickets etc went off without a hitch.  All the I's were dotted...all the t's were crossed.  I would recommend this travel agency as a 5-star travel agency to anyone who would ask.  I'd trust them completely.  Indeed, I have the pictures to last a lifetime.  I have memories that will last even longer.  

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Italy Vacation Review: Cinque Terre Rome, Firenze, Siena, Tuscany, Assisi

Great experience with this Italy travel agency. We would recommend Laura for anyone looking to make Italy their next travel destination. We went to cinque terre, Firenze, Siena and surrounding tuscan cities, Assisi and Rome in 15 days. All was awesome. Solid 4 stars.

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Italy Luxury Family Tour Review: Milan, Padua, Venice, Florence, Tuscany, Siena, Assisi, Cascia, Rome, Vatican City

In May, our family of five, all adults, took the best Italy tour from Milan to Rome. We visited Milan, Padua, Venice, Florence, the Tuscan countryside, Siena, Assisi, Cascia, Rome, and the Vatican. The tour was wonderful and well organized, thanks to our terrific Zicasso travel advisor. She was always available for questions and went out of her way to ensure all of our wants were accommodated in the trip plans.

The itinerary was well-thought out and we loved each of the destinations and the individual tour guides who educated us at the sites. They were thoughtful, informative, and interesting. Kudos to our agent for her excellent choices.

The hotels were also very good. We really liked the Tuscany hotel and would return there on our own. All of the hotels were well-located, which made for ease of getting around and walking the cities.

Our days were split between touring and having free time, which allowed us to explore on our own and spend time as a family. This schedule was perfect for us!

I would highly recommend this trip itinerary to anyone interested in seeing the north of Italy. Our agent did an amazing job attending to the details of the travel so we did not have to and providing special opportunities we would not have had on our own without a lot of hassles. We are definitely booking our next trips with her as she went above and beyond what we expected in her attention to us and our enjoyment of the trip!

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Travel Review: Memorable Vacation to Italy, Florence, Tuscany, Siena, Antinori Winery Tour, Rome, Vatican Tour
Giuliana of this Italy travel company guided us every step of the way and created one of our most memorable vacations. The most impressive thing at the outset was how quickly she responded to our initial inquiry. We had never been to Italy, had not done a great deal of research, and had only a general idea of what we wanted beyond the dates (mid-May) and the cities we wanted to visit (Florence and Rome). Within a day, Giuliana submitted a detailed proposed itinerary based on a recent client request similar to ours. The proposal included various options that provided a great starting point for further discussion. She asked many questions, including our hotel preferences (small boutique, high-rise, how many stars, etc.) and suggested a number of venues that would expose us to Italy’s remarkable history and culture. The result was a vacation specifically suited to our personal tastes and interests. We spent four days in Florence and three in Rome. In Florence, we stayed at the Hotel Lungarno on the Arno River, a lovely small hotel in the heart of the city within walking distance to everything of interest, including the Uffizi and Academy museums, and the famous Duomo. It rained two nights, but we didn’t have far to go for a great dinner. The hotel restaurant was superb. One of the highlights of the Florence leg of the trip was a day tour of the Tuscany wine region that included a stopover in the historic town of Siena. We had lunch at the Osteria di Passignano, a restaurant at the Antinori vineyards where we were treated to a four course lunch and wine tasting and a tour of the winery. Fabulous. In Rome, we stayed at the Hotel Saint George. Another small, well appointed, boutique hotel, centrally located near the Tiber River, it provided access to all the essential venues, including the Vatican, Coliseum, Spanish Steps, etc. As in Florence, everything was in walking distance, including fine dining restaurants, pizzerias, espresso bars, and gelateria—and lots of places to shop. The hotel was comfortable, attractive, with a friendly and efficient staff, but we would not recommend the hotel restaurant. It was nice enough (although too brightly lit) but was virtually empty the night we were there and the food was just O.K. That wasn’t Giuliana’s fault since the hotel restaurant was not on her recommended list. We were just tired (it was our first night) and thought we’d give it a try. The hotel concierge made up for it, however, by recommending two great nearby restaurants for the remaining two nights. Neither was on Guiliana’s list, but they were terrific. A word about the logistical aspects of the trip: we viewed this as critical to the success of a customized tour with multiple venues and connections. We couldn’t have been more pleased. On arriving at Rome’s Fiumicino Airport, we were greeted by Aldo who drove us to the high-speed train to Florence. After sharing an espresso with us in the station café, he made sure we got on the right train, helped us with our bags, and took us to our seats. Similar service greeted us at every connection point during the trip. Our personal tour guides, Enza (Florence), Andrea (Tuscany), and Sylvia (Rome), were exceptionally knowledgeable, personable, and fluent in English. Giuliana telephoned us at several points during the trip to confirm that we had arrived at our destination, that the drivers were on time, and that the accommodations met our expectations. Very reassuring to know she was keeping such close tabs on things. In short, all elements of transportation and personal service were impeccable. Would we visit Italy again? Without doubt. The trip simply whetted our appetites. Would we use this company? We wouldn’t consider any other service. Next time, however, we’ll make more of an effort to visit the restaurants recommended by Giuliana.

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Travel Review: Luxury Italy Anniversary Vacation, Rome, Venice, Florence, Positano, Ravello, San Gimignano, Montepulciano, Tuscany

We took this trip last year, and I realized when I came back to Zicasso to plan our next trip that I had never posted a review.

This was a 25th anniversary trip for my husband and me. We splurged on this trip. We wanted something special. We were overwhelmed by a trip that not only met, but far exceeded our expectations. Our Italy travel agent planned every detail and stayed in contact with us throughout our travels. She gave us a flip phone and called us shortly after we reached each destination to make sure everything was to our liking. And when we did run into a slight problem with our gondola ride in Venice, I was able to get in touch with our agent on a Sunday, and she took care of it immediately. Every driver and tour guide she set us up with was professional and well-informed about their part of the country. And they all spoke English very well. We felt pampered every step of the way.

Even with 2 weeks to spend in Italy, it felt like a whirlwind trip. Our agent managed to fit in everything we wanted to see and do and some things we hadn't even known we wanted:  A gondola ride and a tour of St. Mark's in Venice; a guided trip to the Accademia to see the statue of David and to the Uffizi Gallery, as well as time to walk across the Ponte Vecchio in Florence; wine tasting in Tuscany, not only of Chianti but also Brunello di Montalcino (what a treat); visits to Siena, San Gimignano, Montepulciano, and others in the area; a guided tour of Pompeii; visits to Amalfi, Ravello, and an inland winery near the Amalfi coast; a private cooking class; guided tours of the Colosseum, the Forum, the Vatican Museum and St. Peter's Basilica.

My husband and I would wholeheartedly recommend this agent and her travel company to anyone who is planning a trip to Italy. 

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

28,000+ Verified Traveler Reviews