Postcards from Italy

So, You Want to Take a Multigenerational Family Trip to Italy…

It probably came up during a big holiday reunion dinner or weekend, when grandparents, aunts and uncles, cousins, and grandkids were all happily gathered around the table: why don’t we all vacation together this year? How about Italy?

Young travelers at a vineyard, Tuscany

(Photo by Concierge in Umbria via Flickr)

It’s a wonderful idea – and will make for the trip of a lifetime for everyone – but also involves some tricky logistics and careful advanced planning to make sure that the vacation is unforgettable for all the right reasons! If you are considering a family trip that includes everyone from grandparents to the newest arrivals, here are some tips from our years of experience arranging successful multigenerational Italy trips:

Discuss the Budget

No one likes to hash out money issues, and it may seem like this conversation will immediately take some fun out of the trip planning, but an open, honest discussion about your travel budget right off the bat will be key in avoiding problems and misunderstandings later on.


(Photo by Concierge in Umbria via Flickr)

Perhaps someone is treating the entire family, which simplifies the financial issue enormously, but travel expenses may also be shared among the extended family, who may have different travel budgets. Establish some basic parameters immediately, and begin to plan your trip accordingly. Decide on a category of accommodation affordable for everyone, establish if shared costs will be divided per person, and be clear about which expenses will be split evenly and which will be the responsibility of each person or family group.

Once you have the budget sketched out, many other travel details will fall into place more easily!

Make sure everyone is on the same page

With an extended family spanning generations (not to mention at least 50 years), you are going to have a variety of dreams and expectations about the “perfect trip”, so it’s a good idea to have those out in the open early in the planning process.

Perhaps the family with older kids wants to do a whirlwind tour of Rome, Florence, and Venice, while the family with toddlers would rather relax in a Tuscan villa with a pool and take (or opt out of) nearby day trips. Grandparents may have already visited parts of Italy, and either want to return to share these spots with their grandchildren or explore new areas.


(Photo by Concierge in Umbria via Flickr)

Have a fun and open brainstorming session where everyone gets to throw out ideas, and start compiling a list of destinations, interests, and activities that are appealing to everyone…or, at least, to a sizeable majority. From here, come to a consensus (usually involving a bit of compromise) about a rough trip plan.

Also, make sure everyone is realistic about any physical and mobility limitations that the oldest and youngest members of the family may have. No one wants to wear out grandpa or deal with an exhausted five-year-old, so it’s better to consider some down time or rest days during the planning, rather than be forced to change your action-packed travel itinerary along the way because it turns out to be more ambitious than practical!

Fontana di Trevi, Roma

(Photo by Concierge in Umbria via Flickr)

Choose a leader

Planning a trip for an extended group, be it family or friends, involves enormous amounts of time and coordination. After you’ve established some budget parameters and decided on a rough trip plan, it’s best to hand over the reins to one or two group leaders who can delegate specific tasks, coordinate research, gather all the information into one file, and help guide the family toward final decisions on transportation, accommodations, itineraries, and activities.

Even if you are using a travel planner, which we strongly recommend for tricky trips like extended family vacations, it’s a good idea to choose a family leader who will act as the main contact person between the planner and the family to help simplify communication and decision making for everyone.

Venezia, gandola ride on Grand Canal

(Photo by Concierge in Umbria via Flickr)

Make some decisions

It’s easy to get mired in options, but you’ll have to make some decisions pretty early and decisively, especially regarding accommodations and activities which may book up months ahead of time.

Accommodations: Both hotels and villas are excellent choices for large family groups, depending upon your travel itinerary. If you are visiting a number of cities, hotels are better as many guaranteed and vetted urban apartments or private rentals have a 7 day minimum. If you are staying in one area and taking day trips, you may want to opt for a villa with a kitchen and pool, especially if there are young children in your group who may have an eating or napping schedule which is easier to manage in a villa than in a hotel. Remember that everything happens later in Italy, from meals (especially dinner, often served only after 8:00 PM) to bedtime. It is common in Italy to see children out with their parents for dinner or an evening walk until midnight and beyond!

rome with kids 001

(Photo by Concierge in Umbria via Flickr)

Transportation: For groups of 8 or fewer, you have the option of renting a small van and driving yourself. For larger groups, you will have to rent two separate vehicles if you are planning on driving, as larger vans require a special license and are impractical on Italy’s narrow streets and tight parking lots. That said, consider hiring a professional driver to transport your family from city to city or on day trips in the area where you will be staying. Not only does it take the pressure off of family members to navigate and drive in an unfamiliar country, it also gives your group more flexibility to split up for a few hours or a day if some members want to take an R&R break or are interested in an alternative destination or activity. Driving in Italy can be stressful and the person driving often doesn’t get to see and experience, which is another reason to book a professional.

Activities: There are a number of activities that are perfect for family groups, including cooking lessons, custom kid-friendly museum and city toursboat trips, or, for active families, guided hikes or bike trips. Guided tours are a great way for families to explore a city, neighborhood, or museum without having to navigate a map and with all the insider and expert knowledge of a professional guide to make the visit come alive. Activities like cooking lessons or a day at sea are perfect to break up the routine a bit, especially for kids (or their parents) who are at risk of getting “churched-out” after a few days of art and architecture.


(Photo by Concierge in Umbria via Flickr)

Have fun!

Extended family trips are rare and precious, so make sure you enjoy it! Keep your trip as simple and easy as possible so you can concentrate on savoring the days with your family and making memories that will last a lifetime!

Related posts:

Planning a Group Trip to Italy? Start Here
A Note on Tour Guides in Italy
Why 2016 Is the Year for Italy

Travel Specialists

Maria Landers

Brian Dore