Holidays to Italy for singles over 60, hosted from the moment you land

If you are in your sixties, travelling on your own and Italy is the first big trip on your list, Spice Escapes runs small hosted group holidays there that take the organising off your hands. A host travels with you, the group is around fifteen people, and some reach twenty, and you arrive to a ready-made set of people to share dinner, ferries and a glass of wine with.

Retirement, or a life that has recently changed shape, brings the time at last, but often nobody to go with. Italy is the country most people have meant to see properly for years. The trouble is the effort: flights that line up with transfers, ferries on a lake, somewhere to eat on the first night when you do not know a soul. These are the Italian holidays we run that remove that work.

Escorted tour or hosted holiday: which one suits a first trip

Many people searching for escorted tours of Italy for seniors picture a coach and a timetable from breakfast to bedtime. Our holidays work differently. The host is one of the group, there to make introductions, keep plans on track and make sure nobody eats alone unless they want to. Days are yours to fill, with company when you want it.

Our guide for first-time solo travellers covers the practical side in more depth, and your first group holiday walks through a typical week.

Lake Como, for a week of ferries and slow lunches

Lake Como Discovery is the trip we would suggest to anyone who wants Italy at an unhurried pace. It runs for several nights, with departures on dates to be confirmed, from price on request. Your host is one of our hosts. Availability: ask us.

You stay at the four-star Hotel Como in the city itself, ten minutes' walk from the historic centre, with a rooftop pool. Ferries run to Bellagio, Varenna and Menaggio whenever you fancy a day out, and the old funicular climbs to Brunate for the view down the lake. Each morning your host gathers everyone over breakfast to talk about the day, and in the evening the group meets in the hotel bar before dinner. Arriving on your own, you always know where people will be.

The hotel has proper single rooms as well as double rooms for sole occupancy, which is helpful when you are weighing up cost. Our single supplement guide explains how the price of a room to yourself is set.

Venice from the water, with every meal taken care of

If the idea of planning restaurants in Venice puts you off, All Inclusive Treasures of Venice settles it. The ship is your hotel, moored close to St Mark's Square, and all meals, drinks at the bar and a gala dinner are included on board. It is a short break of 4 nights on 19 Nov 2026 – 23 Nov 2026, from £929, hosted by Samantha Pike. Availability: Waitlist only.

The flights land at similar times, so the group gathers at the airport and crosses to the island by water taxi together. One afternoon the boat takes you across the lagoon to Burano and its rainbow-coloured houses, and there are optional visits to the Doge's Palace, Murano's glassworks and a food tour for anyone who wants them. We have written more about the trip in our Venice holidays article.

Puglia at New Year, when the first festive season alone feels hard

The first Christmas and New Year after retiring, or after losing a partner, can be the time of year people dread most. New Year in Puglia with WingsItaly gives you somewhere warm and sociable to be. It is 5 nights on 28 Dec 2026 – 2 Jan 2027, from £1,139, hosted by Claire Dymond. Availability: 15 places left.

Claire and Andrea Dal Moro of WingsItaly meet you at the airport and stay with you throughout. The group has the rooms at Hotel Tesoretto in Poggiardo to itself, and the first evening opens with a welcome aperitivo. There is a day in Lecce, the honey-coloured Baroque city often called the Florence of the South, and visits to the hilltop town of Specchia and to Galatina. New Year's Eve is a private five-course gala with a bottle of wine each, while a local celebration runs next door and guests drift between the two. Some of the programme is still being confirmed with the town councils, so ask us for the latest.

Rome, then the Mediterranean, without worrying about a missed ship

For a longer trip, Mediterranean Cruising Italian Style with WingsItaly starts in Rome and continues aboard the Costa Toscana. It runs for 8 nights on 6 May 2027 – 14 May 2027, from £1,928, hosted by Claire Dymond. Availability: 11 places left.

You fly to Rome a day early, so a delayed flight cannot cost you the ship. WingsItaly meet you at the airport, and there is an optional first dinner prepared by the sisters at Palazzo Lante, near the Pantheon. Andrea, who grew up between Rome and Sicily, hosts alongside Claire for the whole cruise, and your drinks package and gratuities are included on board. After Barcelona the ship stops in open sea for an hour of stargazing away from city lights.

What the group does for you that a solo booking cannot

• Arrival is handled. On each of these holidays someone meets you or the group travels in together, so there is no hunting for a taxi in a language you are still learning. Our Italian phrases guide helps with the rest.
• Dinner has a table waiting. The hardest part of travelling alone is often the evening meal, and the host makes sure there is always a seat with people you have started to know.

You can see every Italian departure on our Italy holidays page, browse our culture and discovery holidays, or read how our solo holidays work for the over 50s. Still choosing? Spain or Italy compares the two.

Questions people ask

Will I be the only one who has come on their own?

Almost certainly not, because most people who book with us travel on their own. The host makes the introductions on the first day, so you are part of the group from the start.

Is there a single supplement on the Italy holidays?

Yes, every holiday carries a cost for a room to yourself, and it varies by hotel and room type. Some hotels, such as the one in Como, have true single rooms as well as doubles for sole occupancy, and we will tell you the difference in price before you book.

How much walking is involved?

It depends on the holiday, and you choose how much you do each day. Venice and Rome involve walking on old streets and bridges, while Como and the cruise let you take things gently from a ferry seat or a deck chair.

Are the Italy trips protected?

Our flight-inclusive holidays are protected under ATOL licence 9046. Ask us about the specific trip you are considering and we will explain exactly how it is covered.

What if I do not get on with the group?

Everyone is free to spend time on their own, and nothing is compulsory. The host keeps an eye on how people are settling in and is the person to talk to if anything is not right.

Your next step: a conversation with Claire

You do not need to have decided anything yet. Claire Dymond hosts both the Puglia New Year and the Rome cruise, so she can tell you who the host is on each Italian trip, what a typical day looks like and which one would suit a first holiday on your own. Tell us what you have always wanted to see in Italy and what has stopped you going so far, whether that is the cost, the planning or not knowing anyone. Get in touch with the team and ask for Claire, and we will come back to you with dates and places.