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Italy, Southern Europe & Mediterranean

Tuscany: Florence San Gimignano & Pisa

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You are viewing the 2026 itinerary. Select your departure year
20252026
8 days From $1,595 $1,495 per person
4.5 stars(14 reviews)
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Experience the essence of Tuscany’s celebrated medieval towns and Renaissance cities from the historic spa town of Montecatini Terme

Travel among a group of like-minded travelers led by a professional tour manager
Save up to $500

2026 Early Booking Offer: Save up to $500 per person on select vacations departing November 1, 2025 through December 31, 2026.

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Mobility Rating 2

2026 Tour code: TUS26

About the tour

Savor the glorious colors, aromas and flavors of Tuscany on a vacation highlighting the true beauty of this beloved Italian region. Discover the great Renaissance city of Florence, visit historic Il Borgo Machiavelli for a tour and dinner, and explore the iconic monuments of Pisa, including the Leaning Tower.

Explore the stunning sights of Siena, the ancient hill town of San Gimignano with its distinctive towers and have the chance to circle beautiful Lucca on a gentle bike ride along its ancient walls - experiencing fabulous views across the terracotta rooftops.

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Unforgettable Experiences

Discover the many wonders of Florence
Discover the many wonders of Florence
Known as the ‘Jewel of the Renaissance’, Florence is a feast for the senses, bursting with great art, fabulous food markets, palazzo gardens, and glowing with soft light shimmering across the Arno River.
Explore the medieval city of Lucca
Explore the medieval city of Lucca
Take a gentle bike ride along Lucca’s ancient ramparts above the terracotta rooftops, or wander the delightful street on foot, discovering ancient piazzas and exquisite churches.
Visit the famous landmarks of Pisa
Visit the famous landmarks of Pisa
On a guided tour of one of Italy’s most well-known cities, visit its iconic Leaning Tower and ornate Romanesque Cathedral in the Field of Miracles, a UNESCO World Heritage site.
Step back in time in San Gimignano and Siena
Step back in time in San Gimignano and Siena
Perfectly preserved and unique in character, explore both San Gimignano, with its astonishing 14 towers rising up from a golden cluster of ancient buildings, and Siena, known for its festival of bareback horse racing.

What’s included

Itinerary

Day 1 - Meeting up in Montecatini Terme

Your vacation begins in the Tuscan town of Montecatini Terme, our delightful base for the next seven nights. This picturesque spa town is set in glorious Tuscan countryside and is split into two parts. The lower town is known as Montecatini Terme, while on the hill above us is the Old Town of Montecatini Alto.

Our beautiful family-run hotel is in Montecatini Terme and has been offering guests a warm welcome for many generations. After meeting the Tour Manager and group, we gather for dinner at our hotel, renowned for its friendly service and excellent facilities.

Includes
  • Dinner
Day 2 - Exploring Montecatini Terme at leisure

There's nothing like the feeling of waking up in surroundings as beautiful as Tuscany, and today you are free to see more of Montecatini Terme independently. Among the facilities at our central hotel are an inviting outdoor swimming pool (usually open from May to October) and a sun terrace for warmer days.

Heading out into the attractive town, you may wish to visit the 18th-century Terme Tettuccio, where you can sample the different healing waters and look around its lavish Liberty architecture, marble-lined pools and fountains, and Art Nouveau tiles. Each year from April to October, the town hosts the Montecatini Opera Festival in various venues, including the spa complex.

The historic quarter above us, Montecatini Alto, is an enchanting place to explore, and can be reached by a funicular railway, which runs late into the evening and offers wonderful views over the valley. Here, you can find many idyllic piazzas, pretty sidewalk cafés and two charming Romanesque churches. Montecatini Alto also offers an excellent choice of eating places, from relaxed osterias to traditional ristorantes.

Includes
  • Breakfast
Day 3 - A day in Florence, the ‘Jewel of the Renaissance’

Today is a vacation highlight as we travel by rail to the Renaissance city of Florence. We enjoy a guided tour of the city's treasures, including the iconic, red-tiled Duomo, the Santa Maria Novella Church and the Ponte Vecchio, the famous 14th-century bridge.

The afternoon is yours to enjoy at your own pace. Apart from breathtaking buildings and pretty piazzas, the city is the world capital of Renaissance art, which you can find in its many galleries, churches and Medici palaces. If you're planning to visit the Uffizi gallery it is important to book ahead. Another wonderful way to experience Florence is to stroll across the river to the Boboli gardens, a peaceful space with fantastic city views. Mercato di San Lorenzo is the city's largest market with fresh products, leather and local crafts, an indoor and outdoor dining area, and a Chianti wine booth. A place to warm up or cool down, depending on the season!

We make our return journey by train then walk the short distance to our hotel where we dine together this evening.

Includes
  • Breakfast, Dinner
Day 4 - Discovering Lucca and visiting Pisa’s Field of Miracles

This morning, we travel by rail to the walled city of Lucca, where you are free to explore for two hours. There's an included option to hire a bicycle, with a choice of single, tandem, or four-seater bikes, and a gentle ride along the ancient ramparts is a wonderful way to see the city.

Lucca is also a pleasure to explore on foot, but do pick up a map at the Tourist Office where our day starts. The maze-like center has an impressive Duomo, outdoor sculptures and striking piazzas - a 'must-see' is the Piazza Anfiteatro, formerly a Roman amphitheater. The city also has a botanical garden and a tranquil ornamental garden at Palazzo Pfanner. We regroup for a leisurely three-course lunch in a local trattoria.

This afternoon we continue by rail to Pisa, where we tour the famous Field of Miracles. Here, we see the iconic Leaning Tower and Romanesque Duomo - a cathedral which glows with white marble. We return to Montecatini Terme by train at the end of the afternoon, where you are free to dine independently.

Includes
  • Breakfast, Lunch
Day 5 - San Gimignano and dinner at Il Borgo Machiavelli

Today begins with a coach excursion into the Tuscan countryside, among ochre-colored hills, dotted with cypresses and secluded farmhouses.

Our destination is San Gimignano - an extraordinary medieval hill town known for its many towers. One of these, Torre Grossa, can be climbed. The number of towers in San Gimignano has dwindled from around 65 in the Middle Ages, but the skyline is so unique that it has been dubbed the 'Medieval Manhattan'. We have free time over lunch and into the afternoon to explore this absolute gem of a Tuscan town.

Later this afternoon, we visit the gorgeous Renaissance-era Il Borgo Machiavelli, set in around 600 acres of glistening vineyards and olive trees. Once home to the famous political philosopher, Niccolò Machiavelli, we look around the museum and the cellar before a highlight. In a glorious setting, we indulge in drinks and dinner in quintessential Tuscan surroundings.

Includes
  • Breakfast, Dinner
Day 6 - Exploring Montecatini Terme or beyond at leisure

There's another opportunity to get to know Montecatini Terme at your own pace.

If you haven't already discovered it, you could visit Montecatini Alto, the medieval old town. Here, you can admire views across the Tuscan hills and wander among the ancient townhouses, churches and medieval walls before choosing a café in which to enjoy lunch. Typical Tuscan cuisine is humble yet mouth-watering, even simple dishes are prepared with pride and great care. Try crostini di fegato, warm bread topped with chicken liver pate, or pasta drizzled with olive oil and shaved truffles, foraged from the surrounding hillsides. Another appealing option is to make the most of the frequent rail service to visit the coastal resort of Viareggio (50 minutes), the city of Bologna (two hours), or possibly to revisit Florence or Lucca. Of course, you may be content to simply relax and enjoy the facilities of our hotel.

For dinner this evening you are spoilt for choice for places to eat, in both Montecatini Alto or the town center.

Includes
  • Breakfast
Day 7 - Discovering charismatic Siena

Another vacation highlight awaits today as we drive to medieval Siena, where a labyrinth of narrow streets opens out onto sun-kissed piazzas.

Starting at the Santa Barbara Fortress, our guided tour takes us past the Duomo, one of Italy's most magnificent churches, with statues by Donatello and Michelangelo and an elaborate mosaic floor. Our tour ends at the city's most famous sight, the incredible Piazza del Campo - a grand, shell-shaped piazza that's regarded as one of the continent's most beautiful medieval squares. This is the site of the world-famous Palio horse races, an extraordinary event which the city has celebrated since the 17th century, now held twice a year in July and August. After our tour, there's time to wander Siena's ancient streets independently, and you may like to try some of the cured meats and cheeses that are popular here, including Pecorino, or finocchiona.

We return to our hotel at the end of the afternoon and this evening we gather for our final dinner in wonderful Tuscany.

Includes
  • Breakfast, Dinner
Day 8 - Homeward bound

The many delights of Tuscany have been explored from our base in the elegant spa town of Montecatini Terme. On this vacation, we have uncovered the wondrous art and architecture of Florence and Lucca, the unique hilltop town of San Gimignano, magical Siena and Pisa's famed landmarks.

After breakfast, this morning it is time to check out of the hotel and continue your travels in Italy or make your way home.

Includes
  • Breakfast

Additional information

Please Note

Transfers can be arranged to/from Montecatini.  Please contact a rail agent for details. 

Departure times

Departure times vary based on selected rail vacation. This information will be provided in your final documents. For more information please speak with your rail specialist.

Mobility information

Due to the nature of our tours, they are generally unsuitable for those with restricted mobility. Please reference our Mobility Ratings Information, and if you’d like to discuss any particular vacation with us in this respect, then please don’t hesitate to call us at 1-877-929-7245.

Hotel

Grand Hotel Francia e Quirinale, Montecatini Terme

Grand Hotel Francia e Quirinale, Montecatini Terme

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Reviews

4.5 stars4.5 / 5 · 14 reviews

  1. 5 stars
    (9)
  2. 4 stars
    (3)
  3. 3 stars
    (2)
  4. 2 stars
    (0)
  5. 1 star
    (0)

Todd Peterson

5 stars

Submitted 20/Apr

Overall the tour was fantastic. The food at the main hotel was not what I would consider true Italian cuisine which is what we were hoping for. I can get fish anyway of the week as I live in Florida. The itinerary was what we had hoped for, all of the places had there own uniqueness to them. Suggestion would be to supply name tags lanyards for tour guests so we would not have to keep asking for names to be repeated. Lastly Qilly Albrow was the perfect tour guide for this group of travelers. She was very engaging and her thoughts and suggestions were always well received.

from Vacations By Rail
Hi Todd - Thank you for leaving this review - we greatly appreciate this kind of honest, direct feedback. We're glad to know you enjoyed the tour and will pass along your kind words to Tour Manager Gilly. Ciao!
1 comment

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Todd Peterson
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Cheryl Sherburne

5 stars

Submitted 21 Sep 2024

Everything was well organized and our guide David was awesome! I loved the fact we stayed in the same hotel and made daily trips to visit several beautiful cities. It was wonderful.

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Cheryl Sherburne
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Evelyn Cruzpino

5 stars

Submitted 03 Jun 2024

My husband and I thoroughly enjoyed the tour for itinerary, keeping the same hotel for each night of journey, and good balance of arranged guided tours to personal venture time. Tour manager Joanne Long was EXCELLENT! She made the entire trip most enjoyable with her friendliness, regional knowledge and accessibility by way of excellent communication before, during and after travel time together. Her high energy and professionalism kept a pleasant and cohesive atmosphere for the whole group to feel comfortable and at ease. Highly recommend this tour.

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Lynda Fontana

5 stars

Submitted 01 Jun 2024

The tour was phenomenal along with tour manager. Food, accommodations were exceptional. Only rough thing for us older generation was getting to and from train stations.

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Lynda Fontana
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Mary Maki-Rich

5 stars

Submitted 11 Oct 2023

Loved the leader, Gilly. Loved the amount of free time and planned time as well. Perfecto. Loved the food at Ercolini and Savi. Loved that it wasn’t based in Florence. Loved the size of the group.

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Mary Maki-Rich
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Kate

5 stars

Submitted 18 Jul 2023

It was perfect. The pace and places we visited were exactly as we'd hoped.

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Kate
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