Italy welcomes over 60 million tourists annually, many over 50. While navigating ancient cobblestone streets and historic piazzas might seem daunting, Italy is one of Europe’s most accommodating destinations for solo travellers over 50.
Planning a trip to Italy solo or with your best friends doesn’t have to be overwhelming. With the proper preparation and knowledge, you can create the perfect trip that balances cultural experiences with comfort and accessibility. From solo-friendly accommodations to relaxed itineraries, our guide will help you craft the ideal Italian adventure at your own pace.
Choose the Best Time of Year to Visit Italy
There are many myths about visiting Italy in the shoulder months, and the belief that spring and autumn are the best. Still, for the most visited cultural cities, those months are peak season, due to all the events and the cooler temperatures. The summertime of mid-June to mid-September is peak season for all coastal towns and those regions for outdoor experiences. So while summer brings warmth, it also brings the crowds to well-known destinations such as Cinque Terre, Amalfi Coast, Sicily, Sardinia, all coastal areas, and the beautiful Italian countryside.
Winter is the best time for budget-minded travellers
If you don’t mind travelling in the winter months, winter offers lower rates, and you’ll save lots of money on accommodation with shorter lines at attractions. In fact, in the early winter months of November and December (until the 15th) and again after the 10th of January until the end of February, you are likely to score 30-40% discounts off the standard hotel prices in any city, including Rome, Venice, Verona, Milano, Turin, Naples, Bari, and more.
Spring and Autumn are low season for Sicily + Sardinia
For a great experience with mild temps and fewer crowds, visit Sicily and Sardinia in April-May and from the end of September through the whole month of October, since these months are low-season with lower prices and no families and kids around.
Summertime is best for the Dolomites and outdoorsy people
The peak seasons for the Alps and Dolomites are mid-June to mid-September. The lower season is from mid-September to the end of October; however, the weather may not be ideal for hiking, and most huts close around mid-September.
Draft the core itinerary
If you plan to visit Italy for the first time, you will have the most visited ancient cities on your itinerary. Venice (3 days), Milan (1-2 days), Florence (2-3 days), Rome (4 days), and Naples (3 days) are a must, and you will need 10-14 days to cover all of them. If you have limited time, you may want to skip Milan and Naples and focus on the top three Italian Cities of Rome, Venice and Florence. It’s all about your priorities and interests. Look for places that match your interests in culture and art, historical sites, food experiences, or outdoor adventures.
Pro Tip: I recommend branching out your core trip itinerary by including one or two half-day trips to the countryside with a food and wine tour or a train ride to visit a small heritage site off the beaten track. That will add more value to your trip and provide a slower pace for relaxed sightseeing. Remember that Italy has more hidden gems than any other country, so you will never fall short of ideas for off-the-beaten-path places in Italy.
Want insiders’ help to plan your Italy Trip? Check our Italy Trip Planning Services
Compare and book flights to Italy
This is the first step of your Italy Trip plan. Flights to Italy in summer are notoriously more expensive, so if you plan to come to Italy in July or August, you need to book at least 6 months ahead to find a good flight deal. If you travel in springtime, like April or May, you need 4-5 months ahead for October. You may find a good deal on flights even 2-3 months ahead for the winter months.
While there are many online comparison sites for flights, I highly recommend SkyScanner as the best. It infacts adds all low-cost airlines in their searches. Use this tool to gain overall information about all options and then drill down. You can set up alerts and get them delivered to your mailbox.
Pro-Tip. For Italy, book international flights at least 5-4 months before departure to ensure you get a good deal. I recommend this tool from Skyscanner to search for flights to Italy.
Book accommodation in Italy
Once you have finalised the itinerary for Italy and booked your flights, you must work on booking where to stay. It also takes considerable time to search accommodation platforms, read hotel reviews, and pick suitable places that match your requirements. Because the process is quite time-consuming, as a rule of thumb, I highly recommend booking hotels with free cancellation for your peace of mind. Once you have a first round of bookings, you can always find something better if you are not 100% happy and find a replacement.
Pro Tip: For Italy, the best platform is booking.com, which works best and has the most comprehensive hotel listings.
I highly recommend staying centrally located in safe hotels for a short stay in Italian cities. This will help you optimise your time and better navigate the city on foot. For the countryside, staying in a private home such as an Airbnb or an agriturismo can be a great choice, as it takes advantage of the local produce most family-owned agriturismos and private homestays offer.
If you travel solo in Italy, check the type of rooms listed to ensure that hotels care for solo travellers and offer single rooms or a low upgrade for staying solo.
Pro Tip: Here is our Venice Guide with 30+ hotels where to stay.
Choose the best way to get around the country
To fully enjoy your Italy Trip, you must optimise your time while travelling around the country and make the most of the logistics. Make good use of the Italian train network. Forget about hiring a car in Italy unless you plan to explore the Tuscany countryside or vast areas not well-connected by trains or other means of public transportation.
The train network in Italy is excellent. We have two fast train networks: Frecce and Italo. Italo is a private network, whereas Le Frecce belongs to the Italian National Train System. They are both a Godsend as they connect daily with all the main cities, such as Milan, Rome, Naples, Florence, Bologna, Venice, Verona, Turin, etc. I highly recommend using fast trains in Italy for long-distance train rides.
You must book for fast trains 1-2 months ahead to ensure you get a seat. And if you can plan 3-4 months, you will likely get a good discount on train tickets, too. You can, of course, also use regional trains to get around Italy. But, I would only use regional trains for shorter distances to minor cities. Regional trains do not need to be reserved in advance.
Pro Tip: To search and book train rides with fast trains, only use the official websites: trenitalia.com and italotreno to find the best offers and deals. The best offers are only on Tuesdays- Thursdays. Avoid travelling over the weekend.
What about renting a car in Italy?
Italy is a great country that can be explored by train and public transportation. However, renting a car will be best if you explore the Alps, the countryside, or the islands of Sicily or Sardinia. Nonetheless, I warn you that driving in Italy is not something I would take lightly. Unless you have travel companions to swap the drive, a solo drive experience will be demanding. In that case, you’re better off with public transportation of trains, buses, and taxis.
Book Activities and Day-Tours
Once you have finalised the trip itinerary and allocated the right time to each place, drill down into the day-to-day things to do and the experience you want to have in each place. Plan a draft itinerary for each day, with the core activities (1-3) allowing lots of time for the unexpected and spontaneous activities. Regarding day-tours, only book those that are strictly necessary to be booked in advance.
Skip-the-line tickets at major attractions like the Colosseum, the Uffizi and the Vatican Museums save time and energy. Food tours, cooking classes, and artisan workshops let you experience Italian culture while seated comfortably.
Book organised and guided trips with moderation. The rule of 80% on your own and 20% guided can be a good starting point. Exploring places by yourself without being tied to the group’s schedules may result in being more rewarding in terms of flexibility and a relaxing pace.
If you instead want to include Sicily, Sardinia, or the Dolomites, consider adding a small group tour since they are all more demanding when it comes to exploring on a self-guided trip.
Look for tour companies that run small groups of 8-12 people and have an average pace that is not too relaxed or rushed. We at Rocky Travel run small group tours of Italy for over 50 who love to walk and explore places on foot, rather than sitting most of the time and make unique experiences with local tour guides.
Pro-Tip: Use GetYourGuide.com to book skip-the-line entrances to museums, activities, and day trips in Italy.
Looking for a tour in Italy? View our Italy Small Group Tours For Over 50
Check Requirements to enter Italy
You need a valid passport (at least 6 months from the date of your flight return ticket). As for VISA, if you are a US/CA/AUS visitor, check your local travel advisory for all the relevant information. You can stay in Italy for a maximum of 90 days on a traveller’s entry visa. See the links to the official websites below. Also, the planned ETIAS for Spring 2025 is not postponed to the last quarter of 2026. Here are the travel advisory websites for general guidelines about travelling to Italy:
US Travel Advisory for Italy
CA Travel Advisory for Italy
AUS Travel Advisory for Italy
Money Matters and Budgeting Tips
Let your bank know about your Italy travel dates to prevent card blocks. Bring a mix of payment methods – credit cards work widely in shops and restaurants, while cash helps at small stores and cafes. Use bank ATMs inside or outside banks (called Bancomat) for the best exchange rates and avoid currency kiosks. Most Italian businesses accept Visa and Mastercard, though American Express is not accepted anywhere. Keep € 50-100 cash for daily needs. Plan € 150-200/day for a budget trip to Italy, with € 250-300 for an average trip, and 400-500/day for a luxury trip. Also, make copies of cards and identification documents needed in case of loss.
Final Thoughts on Planning an Italian Adventure
Embarking on an Italian adventure as a traveller over 50 opens doors to unforgettable experiences, from savoring authentic cuisine to exploring world-renowned art galleries at your own pace. The key lies in thoughtful planning that prioritises comfort without compromising on the magic that makes Italy such a unique destination.
Pro Tips:
Learn the basic Italian phrases and common words to connect with the locals who will appreciate the effort and make your experience memorable. Know the Italian culture and customs. Check these things before travelling to Italy.
Looking for more ideas for your Italy Trip?
Day Trip From Venice to the Eastern Dolomites
The Best Small Towns of Northern Italy
Visit Trieste the pearl of North East Italy
Spend 4 days in South Tyrol Italy
What do to in Bolzano in Summer
If you find this free guide helpful in planning your trip to Italy, please support Rocky Travel using the website below with our affiliate links. We earn a small commission on booked tours, activities and accommodation at no extra cost to you. Thank you.
This guide is copyrighted and was first published on rockytravel.net on 16th March 2025.
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