Italy in September or October: A Romantic Trip for Married Couples

Why Italy suits couples at this stage of life

Italy is built around the table, and that suits a long marriage. Dinner starts late and lasts. Nobody rushes you out. A plate of cacio e pepe in a Roman trattoria or hand-rolled pici with a simple ragù in a Tuscan town becomes the event of the evening, and the conversation gets a chance to go somewhere.

Then there's the passeggiata, the early evening stroll when whole towns walk the main street before dinner, arm in arm, grandparents included. Couples in their 50s and 60s fit right in. For Christian couples there's something moving about walking where believers worshiped and kept the faith for nearly two thousand years, then going back to your room and talking about what you saw.

Why September or October

July and August in Rome are usually hot and crowded, and hard on anyone who doesn't love standing in a line in full sun. By mid-September the heat often eases, and October days are usually mild and good for walking. Crowds thin somewhat, though Rome is never empty, and countryside hotels often come down from their summer rates.

It's also harvest season. The vendemmia, the grape harvest, runs through September and into early October across much of central Italy, and small towns hold food festivals called sagre for everything from chestnuts to porcini. If you don't drink, you'll still eat extremely well. The harvest is about far more than wine.

The trade-offs are real. Early September can still be hot in Rome. October brings more rain and shorter days. Some seasonal hotels and restaurants on the coast, in places like the Amalfi Coast and Cinque Terre, start closing as October ends. Pack an umbrella and keep a museum or two in reserve for wet mornings.

What you'll actually do

Give Rome four nights and don't try to see all of it. Go underground at the catacombs along the Appian Way, San Callisto or San Sebastiano, where early Christians buried their dead and carved symbols of hope into the rock. At San Clemente you walk down through a 12th-century church into a 4th-century church and then into Roman rooms below that. St. Peter's and St. Paul Outside the Walls round it out.

Assisi sits on the slope of Mount Subasio in Umbria, built of pale pink stone and quiet once the day-trippers leave. Stay overnight. The Basilica of St. Francis, with frescoes long attributed to Giotto, is the draw. Our advice is to save time for San Damiano below town, where Francis is said to have heard the call to rebuild the church. It's small, plain and easier to pray in.

Then settle into the countryside. Orvieto sits on a cliff of volcanic rock, with a funicular up from the train station and a striped cathedral with a glittering gold facade. In Tuscany's Val d'Orcia, Pienza and Montepulciano crown hilltops above rolling farmland; Pienza is known for pecorino cheese. In Umbria, Spello and Bevagna are smaller and quieter still.

A sample ten nights

This is the shape we'd start with. It uses trains for the long legs and a driver or rental car only in the countryside. The travel days are short, and each one ends early enough for a walk before dinner. Notice the empty day near the end. That's on purpose. A trip this long needs a day with nothing on it.

Too full? Make Orvieto a lunch stop instead of an overnight and give Assisi the extra night. Want the sea? Swap the farm stay for Sorrento or the Amalfi Coast, but know that those towns cling to cliffs and nearly everything involves stairs. Want Florence? Add two nights at the end and fly home from there.

• Day 1: Land in Rome, check in, walk to a nearby piazza and eat early. Jet lag wins tonight.
• Day 2: St. Peter's Basilica in the morning, a long lunch, a nap.
• Day 3: The Appian Way and the catacombs, then San Clemente.
• Day 4: The Pantheon, Piazza Navona and an evening walk along the Tiber.
• Day 5: Train to Orvieto. Ride the funicular up, see the Duomo and stay the night.
• Day 6: On to Assisi. Catch the evening light from the upper town.
• Day 7: The Basilica of St. Francis, then San Damiano.
• Day 8: Drive or be driven to a farm stay in the Val d'Orcia.
• Day 9: Pienza and Montepulciano, with cheese, bread and a slow lunch.
• Day 10: Nothing planned. Read, walk the farm roads, sit on the terrace.
• Day 11: Head back toward Rome and fly home.

Where to stay and how to get around

Stay central in Rome, within walking distance of what you'll see, even if the room is smaller. In Assisi, sleep inside the old walls. In the countryside, look at an agriturismo, a working farm that takes guests, where dinner is often cooked from what grows on the property. We'd take the room with the view over the room with the bigger bathroom every time.

The trains are the easy part. Regional trains reach Orvieto and Assisi from Rome, and fast trains link Rome and Florence if you want to add it. The Val d'Orcia is where a car pays off, though a private driver for a day or two is less stressful. If you do drive, learn about ZTLs, the limited-traffic zones in old town centers. Driving into one by mistake can mean a fine in the mail months later.

Pack light enough that each of you can lift your own bag up the steps of a train car. Many regional trains have steep steps, and small hill town hotels often have no elevator. One medium suitcase each plus a day bag is plenty for ten nights, especially since many farm stays have a washing machine you can use.

Making room for faith on the trip

Rome lets you read Scripture in place. Read Paul's letter to the Romans together in the weeks before you go, then read Acts 28 on your Appian Way day; Paul came into Rome along that road. Tradition holds that he's buried at St. Paul Outside the Walls, and it's worth standing there with his letter fresh in your mind.

For Sunday worship you can attend Mass in Italian and follow along, and Rome also has English-language congregations, Protestant ones included, if you'd like to sing hymns you know. In Assisi, early morning is the best time for prayer, before the tour buses arrive. On the farm, take your devotional out to the terrace and pray for each other by name. A trip this slow leaves room for it.

Practical tips

Italy is hard on knees. Hill towns mean steep streets, cobblestones and stairs, and the catacombs involve steps down into narrow, uneven passages. If either of you has mobility limits, tell us early. Orvieto's funicular, a driver who can drop you at the top of town, and choosing flatter towns solve a lot.

Pace is the other thing to plan. Jet lag hits harder than people expect, so keep the first two days light. Churches often close for a long midday break, and so do many shops in small towns, which is a fine excuse for lunch and a rest. Do your sightseeing in the mornings and late afternoons.

• Wear broken-in shoes with real grip. Smooth soles slide on old stone.
• Cover shoulders and knees for churches, especially St. Peter's and Assisi. A light scarf helps.
• Book the Vatican Museums ahead.
• Make lunch the big meal and keep some dinners light.
• Keep valuables zipped on crowded Rome buses and the metro.
• Skip the Cinque Terre unless you love crowds and stairs. It's busy even in fall.
• Check current passport and entry requirements for Europe well before you fly.