Romance in Rome & Tuscany
Begin your forever together in romantic Rome and Tuscany, where cobblestone streets, candlelit dinners, and unforgettable moments create the perfect honeymoon. Starting from $5,304 per person
Cortona Vacation Packages
Custom Cortona vacations, hand crafted by our Italy based specialists.
Plan Your TripExplore Our Cortona Vacation Itineraries
Family Vacation Rome and Under the Tuscan Sun Vacation Packages
Experience ancient Rome and charming Tuscany as a family. Explore, taste, and connect on an unforgettable Italian adventure. Starting from $5,442 per person.
Private Tour Excursion to Cortona & Montepulciano
Enjoy a bit of Hollywood in Tuscany, as we tour the towns used in “Under the Tuscan Sun” and “New Moon.”
Rome and the Tuscan Sun Deluxe Package
A perfect combination of history and culture in this itinerary that will bring you to discover Rome, the Eternal City and the Tuscan town of Cortona, a beautiful walled
Unique Italy: Rome, Florence and Tuscany Deluxe Package
A fascinating tour that explores in dept the center of Italy focusing in its two major art cities, Rome and Florence. Both homes to illustrious museums, history, magnificent churches
Custom Cortona Vacations, Designed Around You
Cortona, an Etruscan hill town in southern Tuscany made famous by Under the Tuscan Sun, gazes out over the Val di Chiana from its ancient stone walls. It rewards travelers seeking classic Tuscan atmosphere with fewer crowds.
Why Plan Cortona With a Custom Specialist
Most Cortona trips sold online are fixed and rushed. We work the opposite way, building your Cortona visit around your interests as part of a custom Italian vacation designed by our Italy based specialists. That means private local guides, access arranged in advance where it matters, and a pace that leaves room to enjoy the place rather than rush through it, with every detail handled for you.
Top Experiences in Cortona
Steep medieval lanes climb to panoramic piazzas, the Etruscan Academy Museum holds remarkable ancient bronzes, and the Diocesan Museum guards a luminous Annunciation by Fra Angelico. The surrounding countryside of vineyards, olive groves, and Etruscan tombs invites slow drives and long lunches, with Lake Trasimeno and Montepulciano within easy reach.
Planning Your Cortona Trip
We shape Cortona to fit your trip, whether it is the centerpiece of your vacation or one memorable chapter of a wider Italian journey. A typical visit blends private guided time at the highlights with free hours to wander, taste, and simply enjoy the atmosphere. Every day is built around you and refined until it feels right.
Cortona for Couples, Families, and Groups
Cortona works beautifully for couples, families, and small private groups alike. We calibrate the pace, the guiding, and the experiences to your party so everyone gets the version of Cortona they came for.
Food and Wine in Cortona
Cortona’s table is hearty Tuscan, built on bread, beans, olive oil, and the wines of the Val di Chiana and nearby Montepulciano. A wine tasting or a farmhouse cooking lesson brings the flavors of the hills to life.
Pairing Cortona With the Rest of Italy
Cortona pairs naturally with the surrounding region and Italy’s major hubs, and we design multi destination trips as a single seamless route so the journey between places feels effortless.
How Planning Works
Whenever you travel, planning follows the same path. We begin with a conversation about what matters most to you, design a first draft itinerary for your review, and refine it together until every day feels right before anything is confirmed.
Cortona Vacation FAQs
It depends on your pace and how Cortona fits your wider trip. Many travelers give a city one to three days, and we tailor the length to your interests, whether Cortona is a highlight or a stop on a longer route.
Yes. Private local guides, reserved access where it matters, and hands on experiences are a core part of how we design Cortona trips, arranged around your interests.
Spring and autumn generally offer the most comfortable weather and the fullest calendar. Summer is warm and lively, and quieter months trade energy for space. We plan around whenever you travel.
Absolutely. We design multi destination itineraries as a single seamless journey, pairing Cortona with nearby cities and regions so the transitions feel effortless.
Yes. Accommodations, private transfers, guides, and experiences are arranged as one coordinated plan, confirmed before you travel.
When you are ready, our specialists will design a Cortona vacation built entirely around you. Tell us how you like to travel and what you most want to experience, and we will handle the rest. Start planning your custom Cortona vacation today.
Explore more Italy vacation packages: Rome, Florence, Venice, Amalfi Coast, Tuscany, and more.
About this guide: This Cortona vacation page was written by the Italian born travel specialists at Trips 2 Italy, a custom tour operator that has designed hand crafted Italian vacations for over two decades, reflecting the first hand knowledge our team draws on when planning a private Cortona trip.