Europe · Italy · Self-guided

Italy with kids,
the real way

How we actually do Italy with the girls: Rome as a one-week home base, then Florence and a Tuscan hill town by train, from a family that spent three months living in Tuscany. Here’s the family trip to Italy we’d repeat, and what it costs from Boston.

By Kailah Fredette · Last updated June 2026 · 9-min read

The quick answer

How should you plan a family trip to Italy?

Use Rome as a one-week home base, then add Florence and a Tuscan hill town by train. We have been to Italy more times than we can count, including three months living in Tuscany with our girls, and the train beats a rental car almost every time.

Italy with kids, key facts
Flight from Boston	Boston to Rome (FCO), an overnight that lands mid-morning
Best months	April to June, or September to October
Cost cue	About $5,500 to $9,000 for a week, family of four, flights included
Best for	Ages 2 to 12
Getting around	Train. Book direct on Trenitalia to skip third-party fees

Some links below are affiliate links. If you book or buy through them, NOE may earn a small commission at no extra cost to you. We only recommend what we would book for our own family. Our disclosure.

Italy with little kids works best when you slow down. We’ve been to Italy more times than we can count, including three months living in Tuscany with our two girls, and the same lesson holds every time: book a comfortable home base, plan one thing a day, and leave room for the rest. Here’s the whole plan: one week, how to stretch it to two, and the honest costs from Boston.

Apr–June, Sept–OctBest time to go

2–12Good for ages

5–7 days in RomeIdeal length

~$5.5–9kRough budget (family of 4)

One week in Italy

Rome with kids: one home base, one outing a day

With young kids we don’t do a packed day-by-day plan. It falls apart by lunch. We book one base and treat it as a jumping-off point: one outing in the morning, back for a nap or a run-around, something small later. It makes for a calmer, happier trip.

Where to base yourself

Rome first, then slow down in Tuscany

Rome (one week) · add Florence / Tuscany (two weeks)

Rome is a fantastic, chaotic one-week base: ancient ruins double as the world’s best playground for a kid’s imagination, and gelato is a perfectly good daily goal. For two weeks, take the fast train north to Florence and a Tuscan hill town, where space to run is the perfect counterweight to busy Rome.

In Rome we stayed in a family apartment, and in Tuscany we based in a terrace apartment in downtown Montepulciano.

Book it

An apartment in Rome, then a base near Montepulciano

Neither of our places is on Vrbo, so these searches cover the same areas. In Rome, check for an elevator: plenty of historic buildings don’t have one.

Central Rome rentals Montepulciano Or have us book it for you

Links open Vrbo for 2 adults and 2 kids, two bedrooms minimum, no dates set. Vrbo can’t filter by kitchen, so check the listing before you book.

From that base, in easy reach

Colosseum & Roman Forum: we did the kids’ guided tour and it completely landed; go early.
A pasta-making class: Lucilla’s cooking class was a runaway hit with the girls.
Villa Borghese gardens: bike rentals, a little lake, room to run.
Gelato, daily: the real Italian kids’ ritual.
Trevi Fountain: toss a coin; go early before the crush.
A Tuscan hill town: the two-week reset, all space and slow mornings.

Two weeks in Italy

Two weeks in Italy with kids: Florence, Tuscany and Venice

With two weeks, don’t cram in twice as much. Keep the calm home base and reach the rest by train. These are the outings that were worth it with our kids.

Getting around

Take the train, and book it direct

Almost everywhere on this page is reachable by train, and we can’t recommend it enough with kids: no car seats, no parking, no white-knuckle motorway driving. The girls love watching Italy roll past, and you step off right in the center of the next town. One tip that saves real money: book directly at trenitalia.com or the official Trenitalia app, not a third-party reseller, which tacks booking fees onto the exact same seats.

~1.5 hrs by train

Florence

Duomo, gelato, and the carousel in Piazza della Repubblica: doable in a day, lovely over two.

Tuscan hill town

Montepulciano

Where we based in Tuscany: a terrace apartment in downtown Montepulciano, slow mornings and big skies.

If your dates line up

Venice at Carnival

We went during Carnevale: masks everywhere, pure magic for kids. A longer haul, best on a longer trip.

Pre-book the big experiences through GetYourGuide, and use code NOWHEREONEARTH5 for 5% off. With kids, walking straight in beats a queue every time.

How we really did it

Three months in Tuscany with Boundless Life

Our deepest stretch in Italy wasn’t a trip: we based ourselves in Pistoia for three months with Boundless Life, a program built for families who’d rather live somewhere than rush through it. The girls had a routine and a community of other traveling kids; we had a real home and the weekends free to explore.

From that base we ranged far: Rome, Florence, the hill towns around Montepulciano, Venice during Carnival, and Viareggio for its enormous seaside carnival. If slow, rooted family travel is what you’re after, it’s the single best way we’ve found to give kids a true sense of a place.

Pistoia · home base Rome Florence Montepulciano Venice · Carnival Viareggio · Carnival

Explore Boundless Life → Ask us about it

Thinking about a Boundless stay? Email us. We’re happy to share the honest version of what three months looked like, and we’ll keep you posted as we plan future family stays of our own.

Honest notes

What landed, and what we’d skip

What the kids actually loved

The kids’ Colosseum & Forum tour (a guide who can spin the ruins into a story is worth every euro), Lucilla’s pasta-making class (highly recommended with kids), gelato every single day, the open space of Tuscany, and the sheer spectacle of Carnival in Venice and Viareggio.

What we’d skip or watch out for

Long museum days: the Vatican Museums are stunning but punishing with little kids; if you go, book skip-the-line and keep it short. Roman cobbles are rough on strollers, so a carrier helps. And midday August heat is brutal: aim for spring or fall.

Book it yourself

Everything we used for Italy

Flights from Boston

Boston (BOS) to Rome (FCO)

We search and book on Skyscanner. From Logan, an overnight that lands mid-morning is gold: the girls sleep most of the way.

Search live fares

Tickets & tours

The kids’ Colosseum tour

The guided Colosseum & Roman Forum tour for families was our surprise hit: pre-book it through GetYourGuide so you walk straight in; code NOWHEREONEARTH5 takes 5% off.

Browse things to do in Rome

Vrbo, two-bedroom rentalsWhere to stay

Already set to central Rome, two bedrooms, 2 adults and 2 kids. Check for a full kitchen before you book.

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AiraloStaying connected

An eSIM before you land: data the second we step off the plane, for maps and translation with two kids in tow.

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SafetyWingTravel insurance

We never fly without it: your home health plan usually won’t cover you abroad.

Price it for your dates

SafetyWing’s published per-adult rate for its travel medical plan; the final price is confirmed on their site.

TrenitaliaGetting around

Trains: book them direct. You can reach almost everywhere on this page by train, and it’s genuinely a joy with kids. Book straight on Trenitalia’s own site or app to skip the third-party booking fees charged for identical seats.

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What it costs

How much does a family trip to Italy cost?

Rough ranges for a family of four (2 adults + 2 kids), flying from Logan and staying in a place with a kitchen. Estimates to plan around, not quotes: season and how far ahead you book swing them a lot. (A long Boundless-style stay runs on a different model entirely: see Boundless Life or email us.)

One week · family of 4

$5,500–$9,000

all-in, flights included

Flights (BOS, x4)$2,600–$4,800

Lodging (7 nights)$1,500–$2,600

Food$600–$1,000

Activities + transit$500–$900

Two weeks · family of 4

$8,500–$13,500

all-in, with Tuscany + day trips

Flights (BOS, x4)$2,600–$4,800

Lodging (14 nights, 2 bases)$3,000–$5,200

Food (2 weeks)$1,100–$1,900

Activities + day trips$900–$1,700

Adding more kids? It’s mostly about the beds.

Kids don’t add cost evenly: lodging is the real lever. Two adults and one or two kids can squeeze into a one-bedroom with a sofa bed, but we book two real bedrooms so the adults aren’t in bed at 8pm. That step up is the biggest single jump in the budget.

Flights: a child under 2 flies as a lap infant for very little; every child 2 and over is essentially another full seat (~$650–$1,200 round-trip from Boston). Food rises gently; most attractions are cheap or free for young children.

Rule of thumb: +1 child ≈ one more flight seat + a step up in lodging size.

Flight figures reflect typical round-trip economy fares from Boston (about $650–$1,200 per seat depending on season). Swap the headline totals and line items for your own numbers once you’ve booked. Real receipts beat estimates every time.

Pack smart

The exact kit we pack with two kids

Lightweight stroller, the carry-on setup, and everything else that earns its space, in one tested list.

See the packing list →

From our trip

Italy, at three feet tall

Before you go

Read Rosie in Paris with them first

Kailah wrote and illustrated our Paris picture book, drawn from our family’s travels: a lovely way to get the kids excited about the world before wheels-up.

See the book →

Quick answers

Italy with kids: FAQ

How many days do you need in Italy with kids?

Our sweet spot is 5–7 days in Rome, enough for the highlights at a kid’s pace without burning out. With two weeks, keep the same base and add Florence and a Tuscan hill town rather than cramming in more.

Where should you stay in Italy with kids?

Rome (one week) · add Florence / Tuscany (two weeks): somewhere relaxed with room for the kids to run beats a ‘central’ address every time. We loved basing near Montepulciano in Tuscany.

Is Italy good for young kids and toddlers?

Yes. Keep days short, base somewhere with green space, and lean on the simple joys (gelato, ruins, a pasta class). That’s the whole NOE approach.

Do you need a car in Italy with kids?

Honestly, no. Almost everything we did was by train, and we’d choose the train over a rental every time with kids. Book directly at trenitalia.com (or the Trenitalia app) to avoid third-party booking fees. A car only really earns its keep deep in the Tuscan countryside.

What’s Boundless Life, and would you recommend it?

It’s a program for families who want to live somewhere abroad for a stretch rather than tour it, with schooling and community built in. We did three months in Pistoia, Tuscany and loved it. If a slow, rooted stay appeals, have a look or email us. We’re happy to share the honest version.

Is Venice good with kids?

We loved it, but we went during Carnevale, when masks were everywhere and the whole city felt like it was built for kids. It’s a longer haul from Rome or Tuscany, so we’d save it for a two-week family vacation in Italy rather than squeeze it into one.

Is Lake Como worth it with kids?

We think so. One of the coolest things we did with the girls was staying in a loft in Como and riding the funicular up the mountain to the lake overlook. We drove there from our Tuscany base; on a one-week Rome trip, it’s too far to add.

Keep planning: the best time to visit Italy · where to stay in Italy · what a week in Italy costs · the Italy scorecard from Boston · Greece or Italy? · validating train tickets · Paris with kids · the gear we pack · how we book every trip · all destinations

Italy with kids,the real way