Tips for multi generational travel in Italy

Regardless of the specific destinations included in an Italy itinerary, multi generational trips require a unique approach to planning. This type of trip needs to work for different energy levels and different schedules (naptime!) while allowing quality time together and an amazing experience for travelers of all ages. This summer I planned a trip for 18 of my own family members, ranging in age from 2 to 72. In this post I share five tips for multi generational travel: what to consider if you’d like to plan a this type of trip in Italy. I include examples from my own trip this summer, and suggestions based on other multi generational Italy trips I’ve planned for clients in the past.

Our group listening to the guide, who was about to take us on a hike and give an intro to rock climbing for anyone interested.

Multi generational travel tip #1: Carefully consider accommodation

What to think about…. You are taking this trip to be together, but do you want to be in one house or would people prefer to have nearby yet separate spaces? Do you want be in the countryside with a rental car, or would you prefer to get around by train, and be able to walk out your front door to go to dinner? Would you like to have a front desk available with helpful staff to answer questions, an onsite restaurant or bar where you can order a drink — or is a private villa a better fit for your group?

What we did this summer….. The group wanted to spend time together during fun daytime activities, but our family is spread far and wide, and we’re all used to having our own space. Some families needed an afternoon break for naps or downtime, while others had specific breakfast routines and wanted their own kitchen. There were several family members who didn’t know whether they would be able to join, so we were looking to book a place where we could add or cancel rooms if needed, with a nightly (not a weekly) rate. Booking nightly also allowed some travelers to arrive a day later and depart a day earlier and pay only for the days they stayed, which they appreciated. Finally, although the adults in our group were okay with driving in Italy, we wanted to be walking distance to a town to allow the older kids a bit of independence.

In the end we found the ideal accommodation: we booked self-catering accommodation (read: apartments) that were in one building. The building had a front desk with incredibly helpful staff, a playroom for the kids, a breakfast room which they let us use for evening gatherings, a laundry room, balconies and views, and free parking — yet was a short walk into the center of town. If you’re going to the Dolomites and interested in our specific accommodation, I would highly recommend it: Ciasa Antersies.

What I’ve planned for clients in the past...   For smaller groups, a hotel or city apartment works well. Booking 3 or 4 rooms in a centrally located hotel allows people to get around by train, make use of a helpful front desk, not worry about breakfast, and have many options for walking to dinner. Apartments offer the convenience of a central location and the flexibility of a kitchen. Countryside farmhouses, called agriturismi, are also excellent for family gatherings: guests get to know the owners, have breakfast included, and learn about the animals or the wine or olives or other crops produced. I have had many conversations with clients about villas, and a private countryside villa can certainly be a fantastic solution. However a villa has its limitations. First, any countryside location requires a rental car, which means everyone in the group must be okay to drive in Italy. Also, if you’d like to keep accommodation flexible for travelers who may join your group, a villa is not an expandable accommodation. And finally, villa rentals in Italy are in the vast majority of cases, Saturday-to-Saturday rentals only.

Sitting on the terrace of my cousin’s apartment drinking Prosecco after a day of walking in those mountains over there.

Multi generational travel tip #2: Plan and pre-book structured yet flexible activities

What to consider…. Do not book your accommodation and then plan to “see what people want to do” every morning, or you will not go anywhere before noon. Book based on interests and make sure there’s some structure – but not too much – to the trip.

What we did this summer…. We had a set meeting time for a pre-booked activity every morning at 9.30 am, but afternoons were flexible. Even with a planned meeting time, there was always someone who forgot something in their room and just had to run upstairs. [Meanwhile, someone else would order a coffee while they waited, and the kids would run off to play on the swings while they were waiting….]. Our morning activities included guided historical hikes, a cooking class, exploring local towns and museums, wine tasting, and one full day excursion: an easy but long bike ride to Austria. After the morning activity, we’d have lunch and then the youngest and the eldest headed back for naps or downtime while the rest of us extended our afternoon with our local guide. We’d then regroup for pre-dinner drinks and dinner.

What I’ve booked for clients in the past…. Family-friendly tours in art museums such as Florence’s Uffizi Gallery and Rome’s Vatican museums can bring history to life for the whole family. Local guides can lead the family on “scavenger hunt” type city walking tours to trick the kids in to learning about medieval history. Hands-on classes like pasta-making, mask-making, cheese-making or pottery painting are fun for everyone. In towns, the kids will often want to scramble up to the top of a tower while grandma & grandpa wait at a cafe in a nearby piazza, with the 2 year old who is chasing pigeons. Teenagers love adrenaline sports and can even ride in the back of a Ferrari. And, a day or half a day at the beach or on a boat is usually a lot of fun.

Easy – but long – bike ride to Lienz, Austria.

Multi generational travel tip #3: Have a plan for dinner

What to consider…. Breakfasts are often included with accommodation in Italy, and lunches can be figured out while you’re out and about. But don’t let the crowd get hungry and then start thinking about dinner. Wandering the streets of an Italian medieval hilltown at dinner time, looking for a table for two or four and discussing the options can be fun. But this approach for a table for 10 or more will leave everyone hungry and frustrated, or – best case scenario – seated at an ultra-touristy restaurant, looking at a menu in five languages.

What we did this summer…. We brought in pizza, did potluck-style dinners in the common room, booked a private wine tasting with food (and hired a babysitter), and went out a couple of nights for special meals.

What I’ve booked for clients…..  when people have an eating space large enough for everyone to gather, I usually book a private chef for at least one evening (and there are always leftovers). Ordering pizza is always great (call the local pizzeria and let them know you want it “da asporto” which means “to go” — and you may have to go pick it up). Another great way to eat at home without spending a lot of time cooking is to visit the local rosticceria – a sort of deli serving hot food – which has hot, pre-cooked main courses to serve buffet-style. A huge benefit of having a local cooking space is that the kids can eat early (Italian restaurants open for dinner no earlier than 7.30 pm) and then go to bed or play while the adults catch up on the day’s activities over a glass of wine – and then nobody has to drive home.

Several nights, we all contributed to a potluck-style dinner in the common room of our accommodation.

Our fantastic dinner at Pre de Costa restaurant. At sunset, those mountains turned pink.

Multi generational travel tip #4: Set Expectations

What to consider… Italy is a bucket list destination for many travelers. Some of your family members may want to get off the beaten track in Italy while others may want to see the country’s main sights or spend a few days at the beach. Your group may include luxury travelers and budget travelers, so you need to decide what sort of trip it’s going to be (with input, of course) and then set expectations.

What we did this summer… To decide what the itinerary would be, each person got one request. (Interests / requests included: not too hot even though it would be July (!), not too crowded, wine tasting, biking, kid-friendly, good food, cooking class, interesting history, not too far from Padova). We had a few travelers in our group this summer who had never been to Italy before, and when I told them we were spending a week in the Dolomites, they were disappointed that our itinerary didn’t include the main sights of Rome, Florence and Venice. They added ten days to the trip so that by the time they met up with us, they’d already visited Italy’s most famous tourist attractions.

What I’ve done for clients in the past… When I work with people, we spend a lot of time creating the overall itinerary. I brainstorm lots of ideas and send information and links about places and activities and accommodation I think they would like. All the expectations get set during this back and forth discussion, and we make sure that everyone’s priorities are met before we finalize their Italy itinerary.

Multi generational travel tip #5: Don’t be the leader

What to consider…. If you’re the person who is planning to kick start this plan into motion, pat yourself on the back! Planning this sort of trip is a lot of work, and you presumably would like to relax while on vacation with your family. You do not want to fill the role of tour leader for your group. So hire local guides and leave the fun in their hands. Even better, hire Italy Beyond the Obvious and outsource the planning.

What we did this summer….. Having worked as a tour leader in the past, I was happy to take on that role with my family, although I booked one activity with a local guide every day so that I wasn’t in charge of everything all the time.

What I’ve done for clients in the past… The multi generational trips we plan for people at Italy Beyond the Obvious usually start with a conversation in which my new client says that they don’t want to be responsible for creating the trip of a lifetime for every single person on the trip. It’s too much pressure, they tell me. And from there, I take over the Italy planning…