Arrive at Toronto Pearson International Airport (YYZ) in Mississauga with plenty of buffer — for a family trip with a 16-month-old, two to three hours before an international departure is the sweet spot, especially if you’re checking bags and want time for last-minute diaper changes without rushing. If you’re driving, parking and the terminal shuttle can eat more time than you expect; if someone is dropping you off, keep the curbside handoff quick because Terminal 1 gets busy fast. Once inside, follow the signs for Air Canada check-in and security, and keep snacks, wipes, a spare outfit, and any medications in an easy-grab pouch so you’re not unpacking everything at the counter.
Head to the Air Canada Maple Leaf Lounge in Terminal 1 once you’re through security — this is the part of the day that can feel like a luxury and a lifesaver at the same time. It’s a good spot for a proper breakfast, coffee, and a calmer diaper change or bottle feed before boarding; lounge access depends on your fare or status, and if you’re paying outright, expect it to be pricey, but often worth it for one long-haul departure. Keep an eye on the board and give yourselves a few minutes of margin; Pearson can be a hike from lounge to gate, especially if you’re juggling carry-ons and a toddler.
Use the last stretch in the airport for a little movement at the Pearson airport family/quiet area walk in Terminal 1. Let your 16-month-old toddle, climb, and burn off energy so the airplane doesn’t feel like a prison sentence after takeoff. The family areas and wider corridors near the gates are usually the easiest places to do this without getting in anyone’s way, and this is also the moment to do a final diaper check, refill water bottles, and stash a couple of easy snacks in the seat pocket. Then settle in for the in-flight meal / rest on the Air Canada long-haul service — on a west-to-east overnight, the goal is simple: eat a little, hydrate, and sleep as much as the child will allow so you land in Italy as functional as possible.
After landing at Milan Malpensa Airport (MXP), keep your expectations low and your pace slow: immigration, bags, and moving through the terminal can take anywhere from quick to annoyingly long, especially if several flights arrive at once. If you’re continuing onward to Lucca, treat this as a transfer day, not a sightseeing day — grab only what you need, stay together, and give yourselves extra time if there’s any delay. By the time you reach your hotel near Lucca centro storico, the best move is to check in, order or pick up a very easy dinner, and call it an early night; the first evening in Tuscany is much more enjoyable when nobody is forcing themselves through a full meal or a late stroll.
Ease into Lucca with a slow wander through Piazza dell’Anfiteatro, the oval square built on top of the old Roman amphitheater. It’s one of those places that feels especially good first thing, before the day crowds settle in — about 45 minutes is plenty, and with a 16-month-old it’s a nice open space to let everyone decompress after the travel day. From there, it’s a short stroll through the Centro storico to Basilica di San Frediano, where the golden mosaic on the façade catches the light beautifully. Inside is quiet and cool, so it’s a smart stop before Lucca heats up; plan on roughly 45 minutes, and dress respectfully if you want to step inside without fuss.
When everyone’s ready for coffee and a diaper-friendly reset, head to Caffè Casali on Via Fillungo. It’s a classic Lucca stop for cappuccino, cornetti, and a proper sit-down break, and the location is convenient if you’re already moving through the historic center. Expect about €8–15 per person depending on whether you’re doing just coffee and pastry or adding juice/sandwiches. Afterward, take the easy route up to Passeggiata sulle Mura di Lucca; the tree-lined walls are the city’s best first-day move because they’re flat, scenic, and stroller-friendly. A leisurely loop or half-loop takes about 1.5 hours, and you can pause whenever you want for shade, views, or a snack.
For lunch, settle in at Il Giglio in Piazza del Giglio. It’s a refined but relaxed Tuscan spot that works well for a wedding trip arrival day — polished enough to feel special, but still comfortable if you’re arriving with family luggage and a tired toddler. Budget around €30–50 per person, more if you add wine or multiple courses. After lunch, keep the pace gentle and head to Giardini Pubblici di Lucca near Porta San Jacopo for a bit of open-air downtime. It’s a good place to let the little one stretch, run around a bit, or just people-watch while everyone recalibrates before the wedding weekend gets busy.
Leave the rest of the day loose on purpose. Lucca is lovely when you’re not trying to do too much — a quiet evening walk back through the Centro storico, an early dinner if needed, and a relatively early night will make the next few days much easier. If you want to keep things simple, stick close to your lodging and avoid planning anything more ambitious than a nearby aperitivo; tomorrow is the better day for lingering.
Start early at Torre Guinigi in the centro storico while the air is still cool and the streets are calm. It’s one of Lucca’s signature climbs, and the reward is worth the steps: a sweeping view over terracotta rooftops plus the little grove of oak trees on top. Go soon after opening if you can, especially with a toddler in tow, because the stairwell is narrow and easier before it gets busy; budget about €4–5 per adult and plan on roughly an hour door to door. From there, drift onto Via Fillungo, Lucca’s main pedestrian shopping street, for a slow browse through local boutiques, baby-supply odds and ends, and any wedding-weekend errands you still need to sort out. It’s an easy street to wander with a stroller if you keep moving with the flow, and the whole stretch feels lively without being frantic.
Pause at Antico Caffè delle Mura on the city walls for a proper breather. This is the kind of stop locals use when they want a view, shade, and a little elegance without committing to a long meal; coffee, juice, pastries, or an aperitivo will usually run about €10–18 per person depending on what you order. Afterward, head to Mercato di Piazza del Carmine to gather picnic-style lunch bits — fruit, focaccia, cheese, snacks, and anything toddler-friendly you want on hand later. It’s a practical stop rather than a sightseeing one, so keep it loose and don’t overthink it. Then make your way to Osteria Baralla for lunch: this is classic Lucca, comfortable and unfussy, right in the heart of town. Expect hearty Tuscan plates, sensible portions, and a bill in the €25–40 per person range; it’s a good idea to book ahead for a weekend wedding period.
After lunch, give everyone a slower-paced reset at Orto Botanico di Lucca near Porta Elisa. It’s one of the nicest low-effort outings in town when you’ve got a small child and a full social weekend ahead: shady paths, quiet corners, benches, and just enough variety to keep things interesting without feeling like an “activity.” Plan on about an hour, maybe a little longer if your 16-month-old wants to toddle and explore. If the family needs a quiet break later, this is the kind of day that leaves room for an early return, a nap, or a relaxed dinner back near your accommodation — which, honestly, is exactly how Lucca works best before a wedding weekend.
Start gently at Chiesa di San Michele in Foro on Piazza San Michele — it’s one of those Lucca churches that feels grand without demanding a big time commitment, so it’s perfect before the wedding-day rhythm kicks in. Go early if you can; the square is calmer, the facade catches the light beautifully, and inside you can usually do a quiet 20–30 minute look around without feeling rushed. From there, it’s an easy stroll down Via Fillungo to Pasticceria Buralli, where you can keep breakfast simple: coffee, a brioche, maybe a savory bite if you want something more substantial. Expect about €6–12 per person; it’s the kind of place where you can be in and out, which is exactly what you want with a toddler and a schedule that may start to tighten.
After breakfast, wander over to Palazzo Pfanner near Via degli Asili for a slower, prettier pause before the ceremony. The garden is the real draw — tucked-away, elegant, and much quieter than the main streets — and it works well if you want one last peaceful family moment before the day becomes all about the wedding. Plan about an hour, and if it’s a warm June day, it’s a nice shaded break. For lunch, head to La Tana del Boia in Piazza del Carmine for a no-fuss meal that still feels properly Tuscan: think crostini, cured meats, hearty first courses, and a relaxed pace. It’s a smart wedding-day lunch because you can eat well without overdoing it; budget around €15–25 per person, and if you’re with the little one, ask for a quick table and keep it straightforward.
Leave the afternoon open for the wedding venue / ceremony location in Lucca — this is the part of the day where it’s best not to plan anything else. If you’re staying nearby, most of central Lucca is walkable, but with a toddler it’s worth allowing extra time for dress changes, heat, and the inevitable last-minute “where are the shoes?” moment. After the ceremony and celebrations, if everyone still has energy, finish with a celebratory aperitivo at Piazza dell’Anfiteatro. Late evening is lovely there: the square glows, the mood is festive, and it’s easy to find a spot for a drink and snacks without committing to a full second dinner. Keep it light — €12–20 per person is a good estimate — and then call it an early night so the next day in Tuscany doesn’t feel like a recovery mission.
Start with a soft countryside escape at Villa Reale di Marlia in Marlia, just outside Lucca — it’s exactly the kind of post-wedding reset that works well with a toddler: open lawns, shaded walks, and enough space that nobody feels rushed. Plan on about 20–25 minutes by taxi or private car from the center, a little longer if you’re coming by bus. The gardens usually open late morning and admission is roughly €12–16 for adults, with younger children often free or reduced. If you go early, you’ll get the best light on the fountains and avoid the hottest part of the day; bring water, sunscreen, and a stroller that handles gravel paths reasonably well.
Head back into town for a sweet stop at Pasticceria Taddeucci on Piazza San Michele — this is one of those classic Lucca breaks that feels more local than touristy if you time it right. Grab a pastry, a gelato, or a quick espresso at the counter; budget about €5–10 per person depending on how indulgent you get. From there, it’s an easy walk to Museo Nazionale di Palazzo Mansi, a good midday shift when you want shade and calm. The frescoed rooms and historic interiors are elegant without being overwhelming, and tickets are usually around €5–8. After that, keep lunch simple and reliable at Trattoria da Leo, just a short stroll away near Piazza San Michele — order the house specialties, local pasta, or a straightforward meat dish, and expect roughly €20–35 per person. It’s the kind of place where service is efficient and nobody minds a family with a small child.
After lunch, slow the pace down with a wander toward Terrazza della Repubblica by Piazza Napoleone. It’s a very easy place to let a 16-month-old stretch, and the whole area feels spacious compared with the tighter streets inside the center. A coffee, a gelato, or even just a bench break works well here; most cafés around the square are open all afternoon, and this is the part of the day when Lucca feels especially relaxed. If you need to burn off a little toddler energy, this is the moment to do it without committing to another “official” sight.
Wrap the day at Enoteca Vanni on Via del Fosso for a quieter adult-friendly finish. It’s central but tucked away enough to feel like a proper pause rather than another big outing, and it’s ideal for a glass of Tuscan wine, a few snacks, or a soft drink while the baby settles. Expect about €10–20 per person depending on what you order. Go earlier in the evening rather than late — around aperitivo time is best — so you can keep the night easy and still have energy for tomorrow.
Start at Piazza Napoleone, which is one of the easiest “meet everyone here” spots in Lucca because it’s big, central, and forgiving if you’re juggling a stroller, a coffee, and someone who’s still waking up. Aim for a relaxed arrival around opening-of-day energy rather than a strict schedule; 30 minutes is enough to let the toddler stretch, admire the open square, and get everyone oriented without feeling like you’re already sightseeing hard. From there, it’s a short, easy walk into the old town to Domus Romana in the centro storico — a quick archaeological stop that gives the day a different texture from churches, gardens, and wall walks. Plan on about 45 minutes; it’s compact, usually around €5–8, and works well as a “smart but not exhausting” stop before the day heats up.
For coffee, pastries, and a proper pause, head to Caffè Santa Zita near Piazza San Frediano. This is the kind of place that feels very Lucca: unhurried, practical, and good for a mid-morning reset. Expect to spend roughly €6–12 per person for espresso, cappuccino, brioche, and maybe a juice or water for the little one. If you’re heading toward the hills afterward, this is the moment to buy a couple of extra snacks and confirm the taxi or driver for Bagni di Lucca; once you leave the center, you’ll be glad you did. The drive into the Val di Lima is usually around 35–45 minutes depending on traffic, and the scenery shifts quickly from city stone to cooler green valley views, which is a nice change after several days in town.
Treat Bagni di Lucca as your easy countryside exhale: not a packed itinerary stop, just a slower half-day with fresh air, river valley scenery, and enough space for the 16-month-old to move around. If you’re doing a light lunch or gelato while there, keep it simple and don’t over-plan; the point is the change of pace. Three hours is plenty for a wandering drive, a sit-down, and a bit of exploring without pushing anyone into overtired territory. On the way back to Lucca, aim to return with enough daylight left to reset at the hotel before dinner.
For dinner, Ristorante Da Giulio on the outskirts of Lucca is a solid, family-friendly choice after a countryside day — comfortable rather than fussy, with the kind of Tuscan menu that works well for a mixed group. Budget roughly €20–35 per person depending on wine and extras, and it’s the sort of place where an earlier seating is smarter with a toddler so the evening doesn’t run too late. After dinner, finish with a final Passeggiata serale sulle Mura — the wall circuit is one of Lucca’s best habits, especially at golden hour when the stone warms up and the city softens. Give yourselves about 45 minutes, keep it slow, and let this be the easy, lovely closing note on the Tuscany part of the trip.
Keep this as a very easy transfer morning: leave Lucca train station with enough buffer for tickets, bags, and a last diaper change, then settle in for the ride to Firenze Santa Maria Novella. If you’re traveling with a stroller, the regional trains are usually manageable, but it helps to aim for a departure before 10:00 so you arrive in Florence before the lunch rush and still have energy left for the day. Once you roll into the station area, it’s a short walk into San Lorenzo, and you can take your time getting your bearings rather than trying to “see everything” on day one.
For an easy first meal, head straight to Mercato Centrale Firenze in San Lorenzo. This is the kind of place locals use when they want options without the stress: pasta, pizza, sandwiches, grilled dishes, and quick desserts all under one roof, with plenty of space to navigate a toddler and bags. Expect roughly €15–25 per person depending on how hungry everyone is, and go with the flow instead of waiting for a sit-down restaurant — this is exactly the right lunch for a transfer day. Afterward, a slow walk through the market area is enough; the neighborhood around Via de’ Ginori and Via Faenza is lively but compact, so you won’t burn the whole afternoon getting around.
From there, make your way to Piazza del Duomo and keep it light: this is a “look, don’t overdo it” stop. The outside of the cathedral complex is the real win on a travel day — the marble facade, the bell tower, and the huge open square are impressive even if you don’t go inside, and that’s usually the kinder choice when everyone is tired. A few minutes’ wandering is enough before heading on to Basilica di Santa Maria Novella, which is one of the best Florence sights to save for a jet-lagged arrival because it sits conveniently close to the station and gives you a proper sense of the city without much walking. Entry is usually around €5–7, and it’s often pleasantly calmer than the big-name attractions, so you can enjoy the frescoes and cloister atmosphere without feeling rushed.
Finish with an early hotel check-in near Santa Maria Novella and treat the rest of the day as recovery time. This is the smart move in Florence with a 16-month-old: unpack, get everyone washed up, find an ice cream or a simple dinner nearby, and go to bed early so tomorrow feels like the real start of the city stay. If you do want one last gentle outing, the streets around Piazza Santa Maria Novella and Via della Scala are easy for a stroller stroll after dinner, and you’ll already be in the right part of town for a low-stress start to the next day.
Arrive at Stazione Milano Centrale and make this a clean, low-stress reset day: there are luggage storage options inside and just around the station, and it’s worth using them so you’re not dragging bags through the city. Give yourselves about 45 minutes to get organized, grab water, and let the toddler stretch after the train. From here, hop on the Metro to Porta Nuova or take a short taxi if everyone is already in “last-day mode.”
A relaxed walk through Piazza Gae Aulenti is the right way to start Milan if you want something open, modern, and stroller-friendly. It’s one of the city’s easiest places for a casual wander because the whole area around Porta Nuova is pedestrian-friendly, with benches, fountains, and space to move without feeling squeezed. If you want coffee, the branches around Corso Como are dependable, but don’t overthink it — this is more about soaking up the skyline and getting one last dose of Milan’s polished side.
Head over to Eataly Milano Smeraldo for an easy lunch that works well with a child and with a day still unfolding. It’s practical, fast enough, and gives everyone multiple choices without the decision fatigue of a sit-down ristorante. Expect roughly €15–30 per person depending on whether you go for a simple plate, pasta, or a more complete lunch. It’s also a good place to pick up edible souvenirs if you want to bring something home from Italy that won’t get crushed in transit.
From there, make your way to Parco Sempione, which is the best “everyone breathe now” stop on this itinerary. It’s a straightforward taxi or a manageable walk depending on your energy, and once you’re there, just let the day loosen up. With a 16-month-old, this is the moment for snacks, open space, and zero agenda; there are shaded paths, lawns, and plenty of room near the edges to pause without feeling in the way.
After the park, continue into Castello Sforzesco for a final classic Milan landmark that feels substantial without requiring a huge time commitment. You don’t need to turn it into a museum marathon — even an hour is enough to enjoy the exterior, the courtyards, and the sense of history that sits right in the middle of the city. If you do want to go inside, ticketed areas are usually reasonably priced, but for a final-day stop the outside and grounds are often the sweet spot, especially if the toddler is getting restless.
End with aperitivo in the Navigli district at Mag Cafe, which is one of those Milan evenings that feels properly celebratory without needing much planning. Get there a little before the busiest hour if you can; the canal area gets lively, and an earlier arrival makes it easier to find a comfortable spot. Expect around €15–25 per person for drinks and aperitivo service, and keep it relaxed — this is the “we made it through the wedding and the trip” moment.
If you have a little extra time after your drink, wander the canal edge a few minutes and then call it early. Navigli is at its best when it’s unrushed, but on a travel day with a small child, the smartest move is to enjoy the atmosphere, then head back and pack calmly for the flight tomorrow.
Keep the last day as simple and low-energy as possible: if you’re near Toronto Pearson Airport in Mississauga, plan to arrive at the terminal with the usual international buffer and do as little else as possible. If you’ve got a hotel nearby, this is the morning to use it well — one last shower, a proper bag check, passports, chargers, snacks, and a final diaper-stocked run through the luggage before you head into the airport. If anything is missing, the airport side of Dixie Road and Airport Road has the basic pharmacy-and-snack options, but honestly it’s better to be done with shopping before you leave for the terminal.
Once you’re through Terminal 1, head to the Air Canada Lounge for a calm breakfast and a reset before boarding. Expect the lounge routine to feel especially worth it with a 16-month-old: a quieter corner, coffee that’s actually decent, fruit, yogurt, eggs, and enough room to settle everyone without the chaos of a crowded gate area. If the lounge is busy, keep it short and easy — about an hour is plenty — then make your way to the gate early so you’re not rushing with strollers, carry-ons, and boarding documents. This is the time for one last water refill, a snack stash check, and a quick toddler energy burn by the windows or a quieter hallway.
On the Air Canada flight back to Toronto, the goal is not productivity, it’s survival and recovery. Rotate through sleep, snacks, diaper changes, and entertainment in whatever pattern gets you closest to calm; for little kids, the window seat and a familiar blanket or soft toy can make a huge difference. Long-haul westbound flights can feel endless, so treat the cabin like a moving rest day: eat when food comes, nap when the baby naps, and don’t overthink the schedule. If you’ve packed a spare outfit in the personal item, keep it handy — it’s one of those small decisions that pays off massively when the flight feels long.
When you land back at Toronto Pearson, give yourselves the full cushion for immigration, baggage claim, and the slow re-entry into Canada after a wedding-week marathon. With three adults and a toddler, one person can handle documents while another keeps the child settled and the third watches bags and stroller parts; that division of labor makes customs feel much less stressful. Once you’re through, keep the evening brutally easy: go straight home in Toronto, order something simple if you need dinner, and aim for pajamas, unpacking basics, and an early night. If you can manage it, don’t schedule anything else for the rest of the day — this is the soft landing after the trip.