Northern Italy: Tuscany (2025)

Fly overnight to Florence, Italy

The capital of Tuscany, Florence is like an outdoor museum. The incredible architecture invites visitors to meander through its streets and let go. In the morning we will visit the Accademia Gallery and gaze upon Michelangelo’s David. In the afternoon after lunch in a traditional café, we will head out on a walking tour of this incredible city visiting Piazza’s and Basilica’s along the way. Late in the afternoon take time on your own to relax and enjoy this Tuscany dream city. Dinner will be a special treat as we head to one of Florence’s greatest restaurants Pensavo Peggio!

Head back out into the magnificent city for a second day of exploring. Stroll through the Boboli Gardens before relaxing at an authentic Florencian cafe. Grab a croissant and cappuccino for a walk through the historic district, a UNESCO World Heritage Site, for an afternoon of delving into an Italian cultural hub.

After a great night sleep we awake to a wonderful breakfast. It is then time to head off to the wine region as we embark on an incredible journey. Visiting the Gaiole region in Chianti we take in a wonderful wine tasting and stroll through the vineyards. But wait…it gets even better. We actually get to spend the night in a historic winery and hotel. After a traditional Italian dinner relax out on the veranda and stroll the manicured Tuscan gardens as you watch the sunset.

Today we leave the rolling vineyards and head back in time 1,000 years as we visit Siena. This historic city is a must see for anyone visiting Tuscany. As a UNESCO world cultural heritage site, the city boasts one of the largest medieval squares in the world the Piazza del Campo. Since the 1300’s the square has been the centerpiece of the city and an active market place with the famed fountain Fonte Gaia located here. In the afternoon there is time to take a relaxing walk through the city. For those who are adventurous, you can try ascending the Torre del Mangia! Take the 400 steps to the top and you won’t be disappointed as the views of the city below are simply breathtaking. You can also visit the cathedral, the complex of Santa Maria, or simply meander in and out of the many café’s and shops that line the streets.

After a wonderful breakfast in Siena we head to the famous town of Pisa. Of course we will visit the leaning tower, but there is also so much more to do in this incredible Tuscan city. Pisa, famous for its artisan shops, antique shops, and markets is sure to delight any visitor. You can walk along Corso Italia the main shopping district area, stroll along the cobblestone streets and pop in and out of churches and historic sites along the way. On this evening, we have a special treat planned as we conclude our stay by taking in a show at the famous Verdi Theater!

Just a quick trip from the center of the city, today we will head to the coast of the Pisa Region to the Natural Park Migliarino for a much needed relaxing day by the glistening sea. Kick up your feet and enjoy a delicious picnic beside the spectacular landscapes. Take a bike ride, try a horse riding lesson, or simply meander around the beach area to enjoy the weather on this Italian coast. To wrap up the calm day, we’ll sit coast-side for a delicious Italian dinner.

Arrive in Genoa, Italy, a beautiful port city. This hidden gem renders some beautiful museums and sights that aren’t overwhelmed with tourists. Venture to the Bigo Crane, an iconic symbol of Genoa, to experience a sweeping view of the gorgeous city from 40 ft above ground. After, we will wander the narrow, cobblestone streets to find the glistening gem-filled palaces, which eventually lead one of Europe’s largest city squares. Admire the Piazza de Ferrari, a statue with a large, beautiful fountain between the modern and historic centers of the city. Throughout the day we can pop in an out of the unique artisan shops and the authentic Italian eateries.

This morning we will wake up early and drive north to Milan, where we will spend the day in the global capital of fashion and design. As we travel to the Arco della Pace and roam around the bustling city streets. We’ll then head over to the Duomo di Milano: the spectacular Milan Catholic Cathedral with gothic style steeples pointing up to the heavens! Finally, we’ll head to the Sforzesco Castle, where we can check out the historic art treasures hidden in this medieval fortress, including Da Vinci and Michaelangelo.

We will enjoy the final few hours in the beautiful country before flying home.