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My husband, Chris, and I just returned from a bucket list trip to Italy to celebrate our 20th wedding anniversary. We spent ten days hitting all the key stops—Rome, Florence, Cinque Terre, and Venice. I’ll be the first to admit that ten days was not nearly enough to explore all of those places, but since our parents were watching our kids, we had to make the most of our limited time. We chose September hoping for fewer crowds than summer and slightly cooler weather. (Spoiler: the crowds were still very much there.)
Although we’ve traveled internationally before, this was our first trip to Europe, and I was a little nervous about planning. Now that we’re back, I don’t pretend to be an expert, but I did learn some valuable lessons that I can’t wait to share to help you plan your dream trip!
Plan Early
We almost didn’t go to Italy because 2025 is a Jubilee Year. (For those who don’t know, Jubilee Years are celebrated every 25 years in the Catholic Church, and millions of people make pilgrimages to Rome and Vatican City. It was estimated that an additional 20 million visitors would descend on Rome in 2025.) It goes against all my instincts to travel during high season, and Italy is already a popular destination in a normal year. I was genuinely worried about how our trip would be impacted.
But once we decided not to let fear of crowds scare us off, I started planning as if we were going during peak summer. And I wasn’t wrong – there were definitely big crowds and long lines at major tourist spots. Accommodations became extremely limited (and expensive) the closer our trip got. Not only did prices go up, but time slots and entire days sold out. Thankfully, because I booked our hotels and tours early, we were able to do everything on our list.
HOT TIP: Book your hotel early and keep checking prices. If they drop, you can rebook and save!
Give Yourself Time
Was four locations in ten days overkill? Absolutely. Do I regret it? Not one bit.
It depends on what kind of traveler you are, but Chris and I made the most of every moment. That meant early mornings, late nights, and well over 20,000 steps a day—but we did it.
Coordinating logistics was overwhelming, and it’s easy to overestimate what you can actually do in a day. On travel days, don’t plan any activities. Give yourself time to settle in, figure out how to get around, and breathe.
My recommendation? Spend at least three nights in each location. That gives you time to see the highlights, enjoy a little downtime, and build in a buffer in case of travel delays. We were lucky—everything went smoothly—but if we’d had train issues, it would’ve been tough to recover.
Do What You Want to Do… Not What You’re Supposed to Do
Italy (and Europe in general) is overflowing with incredible art and architecture. You could spend your entire trip inside museums, churches, and monuments—and that’s great if that’s your thing. But if it’s not? Don’t feel bad about skipping a museum or missing a “must-see” spot.
In Rome, we walked around the Colosseum and Pantheon but didn’t do the tours. In Florence, we skipped the Uffizi Gallery. Each of those would’ve been a half-day commitment, and we just didn’t have the time.
Make space for what you love. Into cooking? Take a class. A foodie? Skip the monuments and book reservations at top restaurants. Need movement to feel good? Bike through Tuscany. It’s your trip – spend it doing what makes you happy. (Your travel partner will thank you too.)
Make Reservations for Tours and Popular Attractions Early
We booked our tours through GetYourGuide, and I’m so glad we did. Even with advance planning, some of the most popular tours – like early entry to the Vatican Museum – were already sold out.
Every time we rolled up to a tour and walked past the massive lines, I silently high-fived myself. A few things I did right (or wish I had):
- Book tours for the earliest time slots to beat the crowds.
- Don’t plan more than one big tour per day. Between timing and location, it’s hard to coordinate—and you’ll burn out fast.
- Know where to meet your group and arrive early (usually 15 minutes before).
- Pay attention to what you’re allowed to bring—and what’s prohibited.
Pack Light
For ten days, Chris and I each had a carry-on and a backpack. I also brought a crossbody purse. That was it – and I’m so glad we didn’t have more.
Over the course of our trip, we had five flights (including connections), four hotel rooms, six train rides, and a water taxi in Venice. Here’s what I learned about packing:
- Good walking shoes are essential. I brought Allbirds (amazing!) and Birkenstocks. That’s all I needed.
- Bring a small packet of laundry detergent. We washed socks and underwear in the sink on day four – saved space and sanity.
- Compression packing cubes are your best friend.
- Leave the big styling tools at home. My hairdryer didn’t work (too much power draw), and every hotel had one anyway.
- Bring outlet adapters and make sure your USB/USB-C matches your chargers. Also: portable charger = lifesaver.
- Even if it’s hot, pack a wrap or long sleeve shirt for churches. You’ll also need shorts, dresses, or skirts that cover your knees.
Learn a Little of the Language
This was our weakest area. We listened to a podcast with basic Italian phrases before the trip, but I wish we’d spent more time learning conversational Italian.
We got by – there was usually someone who spoke a little English, and Google Translate helped in a pinch. But out of respect for our host country, it’s worth learning a few basics. We picked up some phrases by the end, but it would’ve been helpful from the start.
Final Thoughts
Planning a trip to Italy (or anywhere in Europe) can feel overwhelming – especially if it’s your first time abroad. It’s easy to get FOMO when researching and trying to see everything. But honestly? You’ll enjoy your trip so much more if you leave room for wandering, discovering things that weren’t on your list, and savoring a cup of coffee or gelato without stressing over whether it’s the “best” one.
Curious about what we actually did on our trip? I’ll be sharing highlights from Rome, Florence, Cinque Terre, and Venice in the coming weeks – stay tuned!
