Rome & Tuscany 🇮🇹

An Italian escape filled with history, food, wine & la dolce vita

Spend a few unforgettable days exploring Italy, from the energy and ancient history of Rome to the slower pace of the Tuscan countryside.

We’ll start in Rome, where ancient landmarks, charming piazzas, incredible food, and lively streets are around every corner. Explore the city’s historic center, see some of Rome’s most iconic sights, and enjoy plenty of time to wander, shop, grab an espresso, or discover your own favorite neighborhood.

Then we’ll trade the city for Tuscany, using a charming Tuscan town as our home base. Think rolling hills, vineyards, medieval streets, long lunches, and evenings spent enjoying the slower side of Italian life.

Along the way, we’ll have a mix of planned experiences and free time—including a special Tuscan experience where you can get a taste of the region beyond the typical tourist itinerary.

And, of course, there will be plenty of good food and wine along the way, from group dinners to time to explore local restaurants and cafés on your own.

The best part? You won’t be spending every minute on a schedule.

There will be time to sleep in, wander without a plan, find a hidden gelateria, browse little shops, sit in a piazza with a glass of wine, or simply take in the scenery.

This is Italy with a group—but on your own terms.

Come for the sights. Stay for the food, the friendships, and the stories you'll be telling long after you’re home.

Rome. Tuscany. New friends. La dolce vita. 🇮🇹

Touch down in Rome and settle into your hotel as the ancient city waiting just outside your door. Once everyone's checked in and had a chance to freshen up, we'll come together for the first time over aperitivo, Italy's beloved happy hour — think spritzes, small bites, and easy conversation as the group starts to take shape. Later, we'll go for an evening passeggiata (or stroll) and grab our 1 (of many) gelatos.

No itinerary pressure tonight, just good drinks, good company, and the start of a week you won't forget.

• 1 Drink + Small Bites included

• Gelato included

Start the morning slow with a hands-on coffee experience. Learn the difference between a cornetto-and-cappuccino morning and an espresso-at-the-counter afternoon, and leave knowing exactly how to order like a local.

Then hop in a golf cart and let Rome unfold around you. We'll see the Colosseum, the Roman Forum, the Trevi Fountain, and centuries of history, all covered in comfort without the marathon walking, with a guide filling in the stories behind every stop. The rest of the evening is yours to duck into a museum, browse the shops near the Spanish Steps, or just wander and let Rome surprise you.

Step into the smallest country in the world with a guided tour of the Vatican — walk through the Vatican Museums, marvel at Michelangelo's ceiling in the Sistine Chapel, and stand beneath the dome of St. Peter's Basilica. It's one of those experiences that photos never quite capture, and having a guide means you'll actually know what you're looking at (and skip the lines everyone else is stuck in). The rest of the day is free to grab lunch near the Vatican, wander back toward the city center, or check out the cool neighborhood of Trastevere!

Enjoy breakfast before we say arrivederci to Rome and make our way north to Florence, the heart of the Renaissance. Once we arrive and get settled, the afternoon is yours to explore the city your way. Wander through the winding streets, admire the architecture, pop into local shops, grab a gelato, visit a museum, or find a sunny piazza and settle in for some people-watching.

As the day winds down, we’ll meet back up as a group and head out to one of Florence’s beautiful viewpoints to watch the sun set over the rooftops and the Arno River.

Today, we leave the city behind and head into the Tuscan countryside, where rolling hills, vineyards, and olive groves stretch as far as the eye can see.

We’ll spend the day experiencing two of Tuscany’s best-known traditions: wine and olive oil. Visit a local winery to learn about the region’s winemaking and enjoy a tasting surrounded by the beautiful countryside. Then, discover another Tuscan staple with an olive oil tasting, learning what makes locally produced extra virgin olive oil so special.

Between tastings, take in the scenery, slow down, and enjoy the kind of day Tuscany was made for—good food, great wine, beautiful views, and nowhere else you need to be.

After our day in the countryside, we’ll return to Florence with the evening free to relax or continue exploring the city on your own.

Today, we’ll head out of Florence for a day in Siena, one of Tuscany’s most beautiful medieval cities. Take your time wandering through the winding streets, discovering hidden corners, admiring the stunning Piazza del Campo, and soaking up the slower pace of Tuscan life.

After exploring Siena, we’ll make our way back to Florence with some free time to enjoy the city on your own. Grab a final gelato, pick up a few souvenirs, revisit a favorite spot, or simply wander until you find somewhere you love.

Then, we’ll come together one last time for a goodbye dinner in Florence. Over good food and wine, we’ll celebrate the trip, share our favorite moments!

Enjoy one final Italian breakfast before checking out and saying arrivederci to Florence. We’ll gather for our group transfer to Florence Airport, giving you plenty of time to catch your flight home.

And just like that, our Italian adventure comes to an end—with new memories, new friendships, and hopefully a camera roll full of photos you’ll be looking at for years to come.

Until the next adventure… ciao, Italia! 🇮🇹✈️

*If you are flying out of Rome Airport, please contact hello@retirotravel.com