Planning an Italy trip as a couple sounds exciting, right? You’re probably imagining long dinners under the stars, strolling hand in hand through quiet piazzas, sipping wine at a little table outside.
But let’s be honest—traveling together also brings out your differences.
Maybe you’re dreaming of slow mornings with cappuccino, while your partner wants to see every sight by 10 a.m. Maybe you’re picturing a cozy countryside agriturismo, and they’re imagining lively city streets filled with energy.
Over the years, I’ve helped many couples plan their Italy trips. I’ve seen what works—and what causes stress.
One thing that makes all the difference? Talking through your expectations before you start booking anything.
I’ve worked with couples who thought they wanted the same things—until they started choosing hotels or activities. Suddenly, they realized they had very different ideas of what the “perfect trip” looked like.
Some caught it in time and adjusted. Others didn’t—and spent part of their trip frustrated or disappointed.
In this post, I’m sharing 7 simple conversations to have with your partner ahead of time. These questions will help you avoid misunderstandings, plan a trip that feels good for both of you, and make the most of your time together in Italy.
1. What does ‘relaxing’ mean to each of us?
Relaxing doesn’t mean the same thing to everyone. For one of you, it might mean lounging at a café for hours with a book. For the other, it might mean wandering through museums, taking a cooking class, or hiking up to a scenic viewpoint.
If you don’t talk about it, you could end up frustrated—one of you wanting to slow down while the other keeps moving.
Ask each other: “When you picture relaxing in Italy, what does that actually look like?”
This way, you can plan downtime that feels good for both of you. Maybe it’s alternating slow days and busy days. Or agreeing on a few hours of solo time to recharge.
👉 Tip: If you’re staying in a city, book a hotel with a rooftop or a quiet courtyard. If you’re staying in the countryside, check that your agriturismo has a pool or garden. These small details give you built-in relaxation spots—without needing to go anywhere.
A couple I worked with last year planned four nights in Florence and felt exhausted by day three. They hadn’t realized how crowded and busy the city would feel. We added a countryside day trip mid-week, and they told me later it was their favorite part of the trip.
2. What’s one must-do or must-see for each of us?
You don’t need a jam-packed itinerary. But it’s important to know what matters most to each of you.
Ask each other to name one non-negotiable experience or place. This keeps you both from feeling like your top priority got skipped.
For example:
- One of you might dream of a wine tasting in Tuscany.
- The other might want to see the Colosseum.
Once you know your must-dos, you can build the trip around them—and avoid resentment later.
👉 Tip: Write them down and check which ones need advance tickets. Some attractions, like the Uffizi Gallery or Vatican Museums, sell out weeks in advance.
A couple I know skipped booking their top-choice cooking class until they arrived—and couldn’t find an opening. If it’s truly a must-do, reserve it ahead of time.
3. How comfortable are we with spontaneity vs structure?
Some people love having every day planned out. Others want room to wander and decide on the spot.
Neither approach is wrong—but mismatched styles can cause friction.
Talk about how much structure feels right. Maybe you book a few key things in advance but leave afternoons open. Or agree to pre-plan the first few days and see how you feel.
Finding middle ground early will save you from arguments later.
👉 Tip: Italy rewards flexibility, but some things need booking. Balance pre-planned tours with open time to explore local neighborhoods, markets, or cafes.
One couple I worked with decided they’d each get to plan one “structured day” while leaving the rest flexible. They loved taking turns being “in charge” and it gave each of them ownership of a part of their trip.
4. How do we want to balance tourist spots vs local experiences?
Do you want to check off every “bucket list” attraction? Or skip the crowds and focus on small, authentic experiences?
Some travelers love the energy of famous sights. Others feel overwhelmed by crowds and prefer quiet streets and local spots.
Talk about your ideal mix. For example:
- “I want to see the Vatican Museums, but I don’t need to tour every big church.”
- “Let’s do the Colosseum, but spend the next day exploring lesser-known neighborhoods.”
👉 Tip: Build sightseeing days around early mornings or late afternoons. Many famous sights are busiest midday. This small adjustment gives you time for relaxing lunches, exploring markets, or wandering quieter streets.
I had a couple who skipped the Leaning Tower of Pisa but spent a morning biking along the medieval walls of Lucca (my favorite corner of Italy!). “We didn’t miss the tower at all,” they told me. “But that bike ride was a highlight.”
5. What’s our budget—and what’s worth splurging on?
Money disagreements can sneak up on couples during a trip.
Be upfront about your spending expectations now. Talk about:
- How much you’re comfortable spending per day
- Where you’re okay splurging (accommodation, food, activities)
- Where you’d rather save
For example:
- “I’d love to splurge on a nice hotel for 2 nights, but I’m fine with budget places the rest of the trip.”
- “Let’s save on dinners so we can do a private boat tour.”
👉 Tip: Budget for small “surprise” expenses. In Italy, it might be an impromptu wine tasting, artisan shop purchase, or taxi when your feet are tired. Giving yourselves a buffer makes saying “yes” easier in the moment.
It’s easy to regret blowing your budget early on souvenirs, which could result in you having to skip something else you were looking forward to. Leave room for the experiences you’ll remember—not just stuff.
6. How much time do we want to spend together vs solo?
You don’t have to be glued at the hip every minute. Even couples benefit from solo time while traveling.
Ask:
- “Would you enjoy a few hours to yourself some days?”
- “Are there activities you’d like to do solo?”
For example:
- One of you explores a museum while the other shops or relaxes at a café.
- One takes a morning cooking class while the other sleeps in.
Building in solo time gives you both space—and makes shared experiences even sweeter.
👉 Tip: Use solo time to recharge before busy travel days. A quiet afternoon reading or journaling about your trip is often just what you need to be ready for the next adventure.
One client told me she loved walking early mornings alone while her husband slept in. “Those solo walks were the best gift—I came back feeling calm and excited to explore together.”
7. What are our biggest travel pet peeves?
We all have little things that drive us crazy. Travel only magnifies them.
Ask each other:
- “What really bothers you when you travel?”
- “What’s something I might not realize frustrates you?”
It might be lateness, indecisiveness, overpacking, complaining, or wanting to stop for photos every few feet.
By talking about pet peeves now, you can head off unnecessary frustration. Maybe it’s as simple as agreeing to split up if one person wants more time at a site.
👉 Tip: Write down a couple of “ground rules” for the trip based on your pet peeves. For example:
- “No checking work emails at dinner.”
- “If we’re tired, we can skip anything without guilt.”
One couple I worked with told me they had agreed on a phrase: “let’s pause this.” If an argument started brewing, they’d say it—and revisit the topic later when emotions cooled. It’s a great idea and a proactive way to preserve the calm energy of your trip.
Final Thoughts
You don’t need to agree on everything. But being clear about your priorities, preferences, and pet peeves makes a big difference.
Couples come back from Italy happier when they’ve had these conversations ahead of time. Their trips are smoother, more personal, and less stressful.
Take 30 minutes to ask each other these 7 questions. It’s a small step that sets you up for a trip you’ll both love.
👉 Want extra help building an itinerary that fits both your travel styles? My Italy Unrushed guide walks you through exactly how to do that.
Leave a Reply