Northern Italy Family Girls Trip: 18 Days Through Venice, Florence, Tuscany, Cinque Terre & Rome (And What I Learned the Hard Way)

Let me be honest from the start: our first Northern Italy trip itinerary – 18 days as a family girls trip – was absolutely magical AND we tried to pack way too much in. My mom, her cousin, and I spent 18 days racing through Venice, Florence, Tuscany, Cinque Terre, and Rome – and while we created incredible memories, I learned some hard lessons about pacing, especially for multi-generational travel.

This isn’t going to be one of those ‘perfect itinerary’ articles where everything went smoothly and I pretend we nailed it on the first try. Instead, I’m going to share exactly what we did, what worked beautifully, what left us exhausted, and – most importantly – what I’d do differently now that I know better. 

Since this trip I’ve returned to Italy multiple times – including three months traveling from Sicily to the Alps. So trust me when I say I’ve had time to figure out what works and what doesn’t. That means my itinerary takes will likely look different from the rest out there. And, having since planned and taken several multi-generational trips, I’ve learned how to coordinate itineraries and pacing across three generations of women – not an easy feat.

Northern Italy Here You Come

If you’re planning a Northern Italy trip with your mom, daughters, sisters, or girlfriends, this article will save you from our biggest mistake: trying to see everything instead of experiencing the places that matter most. Because here’s the thing – Italy will still be there. You don’t have to do it all in one trip.

So keep reading to get the real story – tired feet, navigation failures, the dinner in Florence we still talk about, and the day in Rome when we were all secretly wishing we could just sit still for five minutes. Then I’ll show you how I’d redesign this trip for now.

This was our big one. For girls trips of every size and how to pull them off, here’s my full girls trips guide →

1. Our Actual 18-Day Northern Italy Trip Itinerary (At a Glance)

First Impressions Looking Back

Booking the Cinque Terre hiking trip with REI Adventures was the anchor portion of this vacation. My mom had never been to Italy, and it seemed a shame to go all that way and only experience one portion of the country – and to be hiking the whole time! That led to adding on a portion on the beginning through northern Italy. When we realized it was easier to fly out of Rome, we added on the end portion as well, as it seemed silly to fly out of a city that we wouldn’t stop and see! 

This ‘see-it-all’ mentality is how our little Italian vacation grew not only in length, but in the number of stops. There were so many amazing sights, moments, and memories made. With that, there was some exhaustion – the stress of driving, the depleted energy from hiking, the plethora of stairs, the constant travel – that could have been abated with fewer stops and a lighter itinerary.

Who This Trip Was For

There were three of us on the full itinerary – my then 60-something year old mom, her cousin, and myself. We met up with other friends for the Cinque Terre hiking portion, but everyone went their own ways before and after that section. When planning, we tried to incorporate our three travel styles, our must-sees, and overall energy levels. Sometimes we succeeded, while other times we were slightly off. But here’s the thing: those imperfect moments? That’s where the real stories are. The navigation fails, the ‘of COURSE there are more stairs’ laughs, the ‘what were we thinking’ moments we still joke about.

2. Venice (Days 1-2): Starting Swanky at the Gritti Palace

Day 1: Arrival + First Impressions

• Afternoon arrival from Seattle: Jet lag was REAL, but the excitement of arriving in Italy compensated for that
• Where we stayed: Gritti Palace (we splurged on points) 
• Evening: Wandering the streets of Venice, stumbling upon a lovely restaurant with outdoor seating and complimentary limoncello – it was actually the perfect first night
• The magic: Venice hits different even when you’re exhausted – the gondolas, the riverside patios, the bridges criss-crossing a city built on water. Venice definitely has a charm that can’t be denied.
• What worked: Not over-scheduling on arrival day 

Day 2: Islands + Food Tour

• Morning/Afternoon: Visited Murano on our own via vaporetto, had the obligatory gondola ride, wandered around different parts of town sampling gelato 
• Why we loved this: Taking it at our own pace after travel exhaustion was a nice way to ease in
• Evening: We did a Progressive Dinner tour through Cannaregio (with Walks of Italy), which is a wonderful way to learn about the city’s culture while sampling local delights
• Highlight moment: Finding a gorgeous murano glass vase in Murano – I still regret not buying it!
• Energy check: Still recovering from travel, this was the right pace 

Day 3: Doge’s Palace + Departure

• Morning: Doge’s Palace and St. Mark’s Square and Basilica 
• Afternoon: Leaving for Florence 

3. Florence (Days 3-4): Art + Architecture Speed Run

Day 3: Arrival Afternoon

• Travel from Venice: Easy train, good transition – use trains in Italy when you can!
• Where we stayed: Gallery Art Hotel on the Arno (beautiful location) 
• Afternoon: Visited the Pitti Palace and Boboli Gardens,  strolled the Ponte Vecchio
• Evening: Sunset at Piazzola Michelangelo, dinner at an amazing pizza place called Gusta Pizza, followed by delish gelato 
• First impressions: Florence felt immediately more manageable than Venice 

Day 4: Duomo + David Marathon

• Morning: We booked a Duomo dome climb reservation, and we all made it to the top! Wandered through the markets and city center shops, soaking in the Florence feels
• Midday: Recovery and lunch, followed by an aperitivo on the rooftop with a view of the Duomo
• Afternoon: Booked an Accademia Gallery tour to see David & Stradivarius
• Evening: Found a spot on the piazza for an early dinner before heading back to the hotel with elated exhaustion 
• Real talk: This was a LOT for one day, especially with the climb 

Day 5: Uffizi + Out

• 9am: Early morning Uffizi guided tour – worth it to avoid the crowds
• Late morning: Picked up rental car at Hertz 
• Afternoon: Drove to Chianti 
• The crunch time: First time driving in Italy – how would we fare?? (Spoiler alert: my mom’s a pro on the Italian roads!)

4. Chianti Wine Country (Days 5-6): Where We Finally Took a Beat

Arriving in Wine Country

• The drive from Florence: Scenic and exciting – and while the country roads were windy, driving in Italy wasn’t nearly as scary as we thought it would be (thanks, Mom!)
• Where we stayed: Fattoria Tregole (2-bedroom villa/apartment) 
• First impressions: THIS is what we needed – quaint, charming, quintessential tuscan farmhouse vibes
• The pace shift: Finally, we could breathe 

Day 5: Arrival + Settling In

• Afternoon: Getting settled, exploring the property, a little wine tasting
• Evening: First Chianti dinner – delicious
• The relief: No schedule, no museum tickets, no rush 
• Why this worked: Built-in downtime for everyone 

Day 6: Cooking Class + Wine Tasting

• Activity: Cooking class at Fattoria Tregole (booked with room) 
• Why we loved it: Hands-on, delicious, educational 
• Wine tasting included: Local Chianti education 
• The vibe: Exactly what multi-generational travel should feel like 
• Favorite moment: The three of us making homemade pasta, then sitting down to enjoy our hard work

Day 7: Departure via San Gimignano + Pisa

• Morning: Checkout and drive towards the coast 
• Stop 1: San Gimignano (medieval towers) – quaint town that is quite touristy – we felt a quick stop sufficed
• Stop 2: Pisa and the Leaning Tower – since we were going through Pisa, we knew we had to check out the leaning tower….as did everyone else! 
• Afternoon: Arrive Santa Margherita, drop rental car 
• Real talk: This was a great way to optimize sightseeing and break up a travel day 

5. Cinque Terre (Days 7-14): Hiking The Italian Coast

REI Adventures Cinque Terre Hiking (Days 7-14)

Day 7: Santa Margherita Arrival

We arrived in Santa Margherita a day before our REI Adventures Hiking Trip was to start, and reunited with friends we hadn’t seen in ages who were joining us on this section of the journey. (REI Adventures portion officially started on Day 8.)

• Why we chose a tour: It takes the planning off your plate, particularly with activities that could be harder to coordinate on your own – finding hiking trails, getting the right passes, knowing when and where to go, etc. I always feel more comfortable doing these types of trips with a guide.
• Who this worked for: Different hiking abilities were accommodated, as well. Having multiple people and guides in the group allowed for people to naturally break up based on hiking pace and interest.
• Transition: Preparing for the hiking portion of our trip came with its own excitement (and a bit of stress!)

Days 8-10: Santa Margherita Base 

• Where we stayed: Our first stop was Hotel Jolanda in Santa Margherita (3 nights) 
• Why here: Easier access than staying IN Cinque Terre 
• What we did: The first day we hiked scenic trails around Portofino, visiting its harbor and the historic Abbey of San Fruttuoso. Treated ourselves to a boat ride back. We also hiked part of the Cinque Terre, from Levanto to Monterosso, our next stop.
• The advantage: More accommodation options, less tourist chaos 
• Highlight moments: Reuniting with old friends; having a red carpet rolled out for us (not really for us, but there none-the-less) on one of our hikes

Days 10-11: Monterosso 

• Where we stayed: Hotel Margherita 
• Why here: Was a natural stop as we made our way through the Cinque Terre
• What we did: Hiked from Monterosso to Vernazza, meandered through the small towns, savoring local pasta, seafood and wine
• Highlight moments: Celebrating my birthday with the crew here; dipping our feet in the sea after a long day of hiking

Days 12-13: Portovenere

• Where we stayed: Hotel Paradiso
• Why here: Final stop on the itinerary, and a spot not as many people make it to as it’s not officially part of the Cinque Terre – my favorite of the stops we made here! 
• What we did: We hiked on Palmaria Island for stunning sea views, and explored the beautiful Golfo dei Poeti (Gulf of Poets) and the historic center of Portovenere
• Highlight moments: Hiking down into the town, stunned by the views; final dinner with our friends before the next portion of our trip began

Day 14: Leaving the Coast

• Morning: Picked up rental car in La Spezia (Hertz) 
• Drive: La Spezia to Montalcino area 
• The transition: Leaving the coast to the Tuscan countryside again 

6. Montalcino Area (Days 14-15): Another Taste of Tuscany

Day 14: Arrival + Quick Brunello Experience

• The drive: La Spezia to Montalcino (long but beautiful) 
• Stop 1: To break up the drive, we stopped in Siena – a gorgeous tuscan town where I found a piece of art that still hangs in my house today!
• Where we stayed: Podere Brizio – a gorgeous, relaxing property
• Afternoon: We visited the town of Montalcino, doing a bit of brunello wine tasting, wandering the streets and getting our bearings
• Evening: We settled in and relaxed, having a wonderful dinner at our hotel
• The reality: One night = one evening and one morning 

Day 15: Pienza, Montepulciano + the Road to Rome

• Morning: Checkout and hit the road
• Stop 1: Pienza (the views we still talk about) 
• Stop 2: Montepulciano (quaint hilltop wine town I liked so much I went back for three weeks a year later) 
• Afternoon/Evening: Drive to Rome, drop rental car, arrive at hotel
• Real talk: Some people would say this is too much driving in one day. But honestly? I loved the quick stops. They broke up the drive and let us discover places we wouldn’t have planned for.

7. Rome (Days 15-17): The Grand Finale (with Slight Travel Fatigue)

Day 15: Arrival Evening

• Afternoon arrival: After full day driving from Montalcino 
• Where we stayed: Via del Corso Home (2 rooms, excellent location) 
• Evening: Trevi Fountain, Spanish Steps area 
• Energy level: Running on fumes but Rome adrenaline kicked in 

Day 16: The Triple Tour Marathon

• Morning: “Privileged Entrance” to the Vatican & Sistine Chapel (Roman Guy tour) – worth it to avoid the crowds
• Afternoon: time to wander, eat and shop our way through Rome
• Evening: Trastevere Locals Food Tour (same company.) I always love a food tour – pretty funny considering what a picky eater I am! Let’s just say my travel companions get twice the samplings on most stops. 😊 
• How we felt: Amazing but EXHAUSTED – the trip was finally catching up with us

Day 17: Colosseum + Roman Forum

• Morning: Leisurely breakfast, exploring the city center
• Afternoon: Colosseum Dungeons, Roman Forum & Palatine Hill tour 
• Evening: Final dinner, packing 
• Reflection: We packed a lot into our time at each stop, but I wonder if there was enough breathing room to fully enjoy it?

Day 18: Arrivaderci, Italy

• Morning: Final Rome moments 
• The goodbye: Leaving Italy after 18 days 
• Overall feeling: Incredible trip, with SO much ground covered 

8. What I’d Do Differently: My Revised Northern Italy Trip Itinerary

The Core Problems We Had

• Too many destinations: 7 regions in 18 days = constant moving 
• Wrong priorities: Rushed through places we loved to fit in places that didn’t resonate 
• One-night stays: Montalcino felt like box-checking 
• No recovery time: Went straight from jet lag to go-go-go 
• Including “must-sees” that weren’t OUR must-sees: Venice is incredible, but can also overwhelming – and there’s so much of Italy I loved MORE 

My Honest Take: Skip Venice (or Rome, or both)

Here’s the thing: Everyone will tell you that you MUST see Venice and Rome. And look, they’re not wrong – those cities are iconic for a reason. But here’s what I learned: if you only have 15-18 days and you’re trying to experience Northern Italy deeply, those two massive cities can actually get in the way. 

Why I’d definitely skip Venice on this trip: 

• It’s expensive, crowded, and honestly overwhelming 
• Two nights was enough to appreciate it, but takes away time from other stops
• The smaller towns of Northern Italy gave us MORE of what we were actually looking for 

Why I’d consider skipping Rome on this trip (if you have to): 

• Rome is a whole separate beast – it deserves 5-7 days minimum 
• By the time we got there, we were exhausted and couldn’t appreciate it 
• Rome + Southern Italy could easily be its own trip 
• The energy of Rome is SO different from Northern Italy’s charm 

What I’d add instead: 

• Cortona: Tuscan hilltop town magic without the Chianti crowds 
• Lucca: Walkable Renaissance walls, incredible food, authentic Tuscany (the one stop here that I haven’t been to and am dying to visit)
• Bologna: Food capital of Italy, porticos, less touristy than Florence 
• Orvieto: A taste of Umbria – the smaller, less visited cousin to Tuscany
• More time in Montalcino/Val d’Orcia area to actually explore 
• An extra Tuscany countryside stay 

My Ideal 15-16 Day Northern Italy Itinerary (Version 2.0)

Option A: The “Real Northern Italy” Route (Skip Venice AND Rome) 

• Days 1-3: Florence (3 nights) – arrive, adjust, explore properly 
• Days 4-6: Chianti wine country (3 nights) – add that extra day 
• Days 7-9: Montalcino/Val d’Orcia (3 nights) – Pienza, Montepulciano, countryside 
• Days 10-13: Cinque Terre (4 nights) – base in Monterosso, slow coastal living 
• Days 14-15: Lucca (2 nights) – Walkable Renaissance walls, incredible food
• Day 16 Departure: Pisa airport (20 min from Lucca) or train to Florence
• Alternative ending: Bologna or Cortona instead of Lucca 

Option B: Keep ONE Iconic City 

• If keeping Venice: Skip Rome entirely, add Bologna or Lucca, fly out of Pisa or Florence 
• If keeping Rome: Skip Venice, add more Tuscany towns, fly out of Rome 
• Either way: Choose depth in the places that resonate over checking off “must-sees” 

Option C: The Tuscany Deep Dive (My Secret Favorite) 

• Days 1-3: Florence (3 nights) 
• Days 4-6: Lucca (3 nights) 
• Days 7-9: Chianti (3 nights) 
• Days 10-12: Montalcino (3 nights) 
• Days 13-15: Cortona (3 nights) 
• Days 16: Florence or Rome departure 
• This gives you six different experiences, all manageable, all connected 

Places I Don’t Recommend (Even Though Others Do)

Lake Como: 

• Gorgeous in photos, touristy in reality 
• Too far north if you’re focusing on Tuscany and the coast 
• Overpriced for what you get 
• Save it for an Alps/Lakes trip, or consider other lakes in the region

Milan: 

• It’s a business city, not a vacation destination 
• The Duomo is beautiful but not worth a special trip 
• Use it as a flight hub, not a destination 
• 4-6 hours max, then move on 
• If you want a northern Italy city experience, visit Turino – much more manageable with a great mix of charm and city bustle

Here’s my reasoning: After traveling to 45+ countries, I know what makes a trip memorable for me: walkable towns with soul, incredible food, wine country, authentic experiences over Instagram moments. Lake Como and Milan don’t deliver that for me, even though they might for others.

9. Budget Reality Check: What We Actually Spent

Total Budget Estimate per Person*

• 7-day Cinque Terre tour (including food, accommodations, hiking, guides): $5500 per person
• Trip Insurance: $500 per person 
• Independent portion of the trip, per person: (11 days)
  • Flights: $1,000-5,000 (depending on class)
  • Accommodations: ~$1,000-1,200 (sharing rooms) 
  • Tours/Activities: ~$600-800 
  • Transportation: ~$200-400 (trains + car split) 
  • Food: $400-600 
• TOTAL: Approximately $9,200-14,000 per person (not including flights) 

*These are our actual 2017 costs. Expect current pricing to be 30-40% higher, but the relative proportions between categories should remain similar.

Where We Splurged vs Saved

• Splurge: Gritti Palace in Venice (worth it) 
• Splurge: Guided tours and dinners (absolutely worth it) 
• Save: Snacks from the market when you’re not in the mood for a full meal
• Save: Public transportation when possible 

10. Practical Advice for Your Own Northern Italy Trip Itinerary

How Far in Advance to Book

• Tuscany countryside: 6+ months (limited inventory) 
• Cinque Terre accommodations: 4-6 months minimum 
• Venice & Florence hotels: 3-4 months for good selection 
• Tours (Uffizi, Vatican, etc.): 2-3 months 
• Rental cars: 1-2 months for best rates 

The Rental Car Question

When you need one: 

• Tuscany countryside stays 
• Val d’Orcia hilltop towns 

When you don’t: 

• Venice, Florence, Rome, Cinque Terre (trains are better) 

Our approach: Picked up and dropped off on the outskirts of the bigger cities (Florence, Rome) to avoid city driving and parking

Packing for 18 Days: What Worked

• The carry-on challenge: My mom managed it, I didn’t 
• Laundry strategy: Used hotel services and sinks with travel soap
• Shoes: Loafers, tennis shoes, and hiking boots
• The rental car advantage: Could keep luggage in trunk 

11. Is This Northern Italy Trip Itinerary Right for You?

Do a Version of This Itinerary If:

• You want authentic Northern Italy over iconic bucket-list cities 
• You value food, wine, and slower experiences 
• You’re okay skipping Venice and Rome (or saving them for another trip) 
• You prefer hilltop towns to major cities 
• You want to avoid the biggest crowds 
• You’re interested in going deeper rather than broader 

Choose the Traditional Route If:

• Venice and Rome are non-negotiable for you 
• You’re a first-time Italy visitor and want the classics 
• Your travel companions would be disappointed without the iconic stops
• You only get one Italy trip ever 
• You love big city energy and museums 

My Honest Recommendation

If someone told me I could never return to Italy again, would I be sad I skipped Venice or Rome on this trip? Probably. But looking back, I’d trade our rushed Venice stay for three nights in Cortona in a heartbeat. 

The truth is: You can see Venice and Rome on separate trips. But experiencing the soul of Northern Italy – the tiny wine towns, the hilltop villages, the places where locals still outnumber tourists – that requires time and intention. And if you’re spending days in Venice and Rome, you don’t have that time. 

So here’s my advice: Be honest about what kind of traveler you are. If you want Aperol spritzes in St. Mark’s Square and throwing coins in the Trevi Fountain, absolutely do Venice and Rome. But if you want wine tastings on Tuscan terraces, wandering medieval streets without crowds, and discovering places that feel like secrets – skip the icons and go deeper.

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Frequently Asked Questions

Conclusion

Here’s what I know now that I didn’t know back then: Italy isn’t going anywhere. Those hilltop towns in Tuscany, the canals of Venice, the chaos of Rome – they’ll all still be there when you come back. And you WILL want to come back.

We saw seven incredible regions in 18 days, and I remember them all – but I also remember being tired. The days we slowed down (Chianti cooking class, Montalcino rest stop) are what we talk about most. But it was all worth it – three generations of women navigating and experiencing Italy together. My mom’s face tasting Gusta pizza for the first time – pure joy. The meals, the wine, the landscapes we’ll never forget. Learning what we’d do differently for next time.

So take what worked from our itinerary, skip our mistakes, and give yourself permission to see less but experience more. Choose 4-5 destinations instead of 7. Leave room for that extra glass of Brunello at sunset, the morning you sleep in because you can. Because here’s what I know for sure: there will be a next Italy trip. And you’ll be so glad you didn’t burn yourself out on this one. Want to take the trip but don’t want to deal with the planning? Contact me and I’ll do the planning so you don’t have to.

And when you do slow down, when you choose depth over breadth, drop me a comment and tell me how it went. Because I want to hear about the long lunch in Pienza, the afternoon you spent doing nothing in Monterosso, the extra day in Venice that made all the difference.

Wherever you go, however you do it, I want you to have a trip to remember – for the right reasons. 

Happy travels, kindreds!

RELATED POSTS

• This was our big one. For girls trips of every size and how to pull them off, here’s my full girls trips guide.
• Want more Italian inspiration? Take a look at my 2 week Southern Italy itinerary that’s a perfect compliment to this one.
• Take a closer look at how I spent 3 weeks in Sicily
• If Cinque Terre made you crave more Italian hikes along the coast, my Amalfi Coast itinerary is perfect for you.
• We also had a mother-daughter adventure in the UK, spending a few days in the Cotswolds
• Ready to take a girls trip but can’t go all the way to Italy yet? Here’s some other great options: Best Girls Trip Destinations
• If you’re planning your own trip with family, read my Multi-Gen Travel Tips and what I learned traveling with my mom
• Already thinking about what to pack? My What to Pack for Japan article outlines a 431 system that will work in Italy, and anywhere. Grab your free packing checklist to make it your own.
• If you can’t get your crew together and you’re nervous about going it alone, take a look at my complete guide to traveling solo.
• Read all about what I learned traveling solo through Italy for 3 months.

HELPFUL LINKS

Ready to book? Here are my go-to resources for flights, packing, planning, and staying connected:

• Custom Trip Planning
  • Need help planning your 2026 travel? Contact me here for personalized itinerary assistance!
  • Want more information on the benefits of using a travel advisor? Learn more here
• DIY Planning
  • Event and car bookings: https://www.viator.com
  • Hotel and activity comparison: https://www.tripadvisor.com
  • Looking for Travel Inspiration? Follow me and check out my boards on Pinterest
• Small Group travel:
  • I did part of this trip with REI Adventures, who now partners with Intrepid for their group tours. I’ve traveled with Intrepid in Italy as well, and highly recommend them! https://www.intrepidtravel.com 
  • Other great small tour companies in Italy are Wild Sage and Salamander Adventures. I’ve traveled with both and had wonderful experiences.
• On Your Trip
  • Airalo eSim – was key for using my phone while not paying for crazy international charges. This made using google maps, making reservations, etc easy and cost-effective: https://www.airalo.com Use Promo code: ANDREA68732 for $3 off
  • Away is my favorite luggage I used to navigate Italy’s train stations and small cars: https://www.awaytravel.com