Itinerary to Italy: Romantic Two Weeks

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Italy is a place I believe is romantic no matter where you are or with whom you travel. The romance factor is even more intense if you choose Italy as your honeymoon destination or vacation destination for couples.

Romantic can mean many things to different people. My ideal two-week itinerary for Italy is not for everyone. Not every couple will like my romantic Italy itinerary. I hope you find inspiration from the following to create your perfect itinerary.

A few general rules will apply before I begin to create the itineraries.

  • These trips will take place over a period of two weeks. It is not common for everyone to spend two weeks on holiday. You’ll need to adjust your plans if you only have a week.
  • Open-jaw tickets are a great option for travelers. They allow you to fly to one city and then to another without having to go back. This can waste time that you don’t have, so it’s worth checking out your open-jaw tickets options. It would be best to fly into Venice, and then out of Rome as per the itinerary.
  • I don’t think that my idea of a romantic getaway to Italy includes things like skiing, mountain biking, camping, and the like. You’ll have to do those activities yourself. I suppose I am a lazy romantic.
  • This is not a beach-centric itinerary. Many people associate a romantic vacation with lying on the beaches. You can book a week in Taormina or the Amalfi Coast and be very happy if that sounds like your ideal vacation.

You can tailor-make your trip to suit your personal tastes. You can follow my step-by-step guide to creating the perfect itinerary for Italy on any trip .

All-Seasons Romantic-Stroll-Worthy Italy

This itinerary is focused on historic towns, which are ideal for long, aimless walks with your loved one. There are many sights to be seen, but there isn’t much to do there that will make you run around like a mad person. Enjoy your vacation, relax, and spend lots of time looking into each other’s eyes.

This itinerary is not beach-centric, so it can be used regardless of the weather. While you might be more likely to stay in a cafe and enjoy a warm cup of tea than stroll through cobblestoned streets, cold weather is great for cuddling.

3 Nights in Venice

You’ll be able to explore Venice at your own pace after arriving in Venice in the morning.

Take a half-day tour to Murano, Burano and Torcello. Learn about Casanova’s ties with Venice. Book a gondola ride if you like.

Take the train to Verona after your third night in Venice. The faster trains take less than an hour.

Learn more about What to Do in Venice, and consult the Venice Travel Guide

2 Nights in Verona

Verona may be known as the city of Romeo & Juliet. But there is more to the city than that (admittedly tragic) story. You’ll be surrounded by beautiful old buildings if you choose a hotel in the historical center.

Visit the Roman Arena, where you can see an opera if it is during the summer opera season. Juliet’s balcony is a beautiful addition to the Roman arena. Wander the piazzas. You can take a day trip to Lake Garda, which connects towns with Verona in about 1-2 hours depending on where you live. If you want to see the lakeside scenery, or book a tour to the Valpolicella region north of Verona for wine tasting.

You’ll rent a car after your second night in Verona and begin the approximately 3-hour drive to San Gimignano. If you stay on the highway, San Gimignano does not have a train station. If you prefer to drive, Siena is a better option. The train ride takes between 3.5 and 4.5 hours with a few transfers.

3 Nights in San Gimignano

San Gimignano’s small size means that there are very few hotel choices. For maximum walking time, choose a hotel within the historical walls or an agriturismo with views and peace in the countryside. Regardless of your preference, inquire about the best place to park your car rental when you arrive.

This tiny town is crowded with day-trippers during the day and quiet at night. Wander wherever you want, visiting historical churches and climbing towers along the way. Day trips can be made with your GPS and car. You can take the GPS along on the journey and let the GPS direct you back to the hotel at the end of the day. You can visit Siena, Cortona or go wine tasting in Chianti. Or head to Florence and Pisa.

After spending the night in San Gimignano’s third, you will head to Assisi or Orvieto, both in Umbria. San Gimignano Orvieto takes just over 2 hours to reach, while San Gimignano Assisii takes about 2.5 hours.

2 Nights in Assisi or Orvieto

Orvieto as well Assisi, both historic hilltop towns, are romantic in their scenic beauty.

The cathedral of Orvieto is the main attraction. It also offers breathtaking views from its hilltop perch. Assisi, the home of St. Francis, is a well-known pilgrimage destination. It can get crowded sometimes, but it’s less crowded during daylight hours and on holy days.

You can choose which one you prefer, but I recommend that you make this your drop-off location so you don’t have to drive into the traffic jams of Rome. You can drop your car off at Assisi or Orvieto, but you won’t be able to find a rental car office to the north of Rome. From there, take a taxi to your hotel. It takes approximately 1.5 hours to take a train from Orvieto, Italy to Rome. The train takes approximately 2.5 hours to reach Assisi Roma.

3 Nights in Rome

Rome is not like the peaceful towns you visited up until this point, but it can be romantic if one has a relaxed attitude towards sightseeing.

I recommend booking main sight tours ( Vatican City, the Roman ruins at the Forum, Palatine Hill and Colosseum) with the “skip the-line” feature. This will save you from waiting in long lines that are unromantic.

Admire the Pantheon in wonderment; wander the Trastevere’s cobbled streets for a glimpse at Rome’s past; and then, relive a “Roman Holiday”, moment at the Mouth of Truth. On your return flight, you can start planning your next Italy vacation.

Learn more about things to do in Rome, and consult the Rome travel guides

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2 Responses to “Italy ITINARY: A Romantic Two-Weeks”

  • Elad Tsion:

    Excellent website!

    We are also a lazy couple so we plan to spend 2 weeks in March 18. It seems like a great idea. Are there any adjustments needed if we are starting in Rome? We don’t like to travel from one cathedral to another, but we love the idea of mixing good food with good views and being open-minded to try new things, especially when it comes to food.

    The thing I loved the most was that I didn’t have to drive all the way. It doesn’t make me feel like I’m on vacation.

    This itinerary can be used as an anchor. Any additional advice?

    • Jessica says:

      If you’re looking for a way to create the perfect itinerary in Italy, my article How to Plan It might help. This is the same method I use to plan my own trips.