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Vacations By Rail · Independent rail vacation

Explore Tuscany: Florence & Siena

Eight-day independent Tuscany loop from Rome through Florence and Siena by train

Illustration of Explore Tuscany: Florence & Siena

Vacations By Rail's Explore Tuscany: Florence & Siena is an 8-day independent rail journey that departs from and returns to Rome. The trip uses Trenitalia high-speed trains to reach Florence, where you spend four nights, and then Siena for two nights. Days combine guided small-group tours of each city's art, architecture and food culture with private walking tours and substantial free time to explore independently. Day 2 brings a train journey through rolling hills and vineyards to Florence; Day 3 offers your choice of Cinque Terre villages by coach, boat and train, or a hiking excursion in the Arno Valley. Day 5 features a regional food experience with optional cooking classes at a farm near San Gimignano. Day 6 includes an afternoon Chianti wine estate visit and tasting. The trip suits independent travellers who want structure and guidance at key stops but also time to wander, as well as history lovers, food enthusiasts, and couples seeking a mix of organised activity and autonomy.

What to know before you look closer

  • Rail fares to and from Rome are booked separately from the from-price of USD 3,195; confirm the exact rail cost when booking
  • The Siena accommodation is noted by a guest reviewer as a bed and breakfast, not a traditional hotel; verify the property type matches your expectations
  • Many optional extras (Accademia upgrade, cooking classes, truffle hunting, Pisa tours) carry additional charges beyond the package price

Day by day

  1. Day 1overnight: Rome

    Arrive in the heart of the Holy Roman Empire: Rome

    Private transfer from the airport to a 4-star hotel, with time to explore Rome independently before an evening small group tour of the city's ancient architecture and sites.

  2. Day 2railovernight: Florence

    Into the rolling hills of Tuscany

    Private transfer to Rome's train station for a high-speed train to Florence, passing rolling hills, olive groves and vineyards. On arrival, transfer to a luxurious hotel followed by a private guided walking tour of Florence taking in the Duomo, Palazzo Vecchio and Giotto's Bell Tower (optional upgrade to include the Accademia and Michelangelo's David).

  3. Day 3railovernight: Florence

    Stacked villages and turquoise seas in the Cinque Terre

    Tour of the Cinque Terre's five fishing villages (Riomaggiore, Manarola, Corniglia, Vernazza, Monterosso) by coach, boat and train, with a local lunch, or alternatively a half-day hiking excursion through the Arno Valley from Bagno a Ripoli with a typical Tuscan lunch.

  4. Day 4overnight: Florence

    A free day among the history and gastronomy of Tuscany

    Free day in Florence to explore independently (e.g. the Uffizi Gallery, Piazza della Signoria), with an optional afternoon group excursion to Pisa (Piazza dei Miracoli, Leaning Tower with skip-the-line access) or an upgrade to a full-day tour of Pisa and Lucca.

  5. Day 5overnight: Florence

    The fresh and distinctive flavors of Florence

    Regional food experience with a local guide; optional afternoon cooking class at MaMa Florence, or an upgrade to a full-day tour with a cooking class at a family-run farm in San Gimignano and an afternoon in its historic center.

  6. Day 6railovernight: Siena

    Medieval sights and Italian delights in Siena

    Morning train journey to Siena, then an afternoon small-group tour of the Chianti region including a wine estate visit and tasting, a stop at the walled fortress of Monteriggioni, and another local winery.

  7. Day 7overnight: Siena

    Walking through Siena's layered cityscape

    Morning guided walking tour of Siena including Piazza del Campo, Palazzo Comunale, the Cathedral and the Basilica of San Domenico. Afternoon options include independent sightseeing, a small group truffle tasting, or a private full-day truffle hunting tour in Siena's woodlands.

  8. Day 8rail

    Tour conclusion

    Taxi transfer to the train station for a high-speed train back to Rome (about three hours), then an English-speaking driver transfer to Rome's international airport for departure.

The moments this trip is built around

  • Day 2High-speed Trenitalia train from Rome to Florence passes rolling hills, olive groves and vineyards before arrival at a luxurious hotel
  • Day 3Tour of Cinque Terre's five fishing villages (Riomaggiore, Manarola, Corniglia, Vernazzo, Monterosso) by coach, boat and train with a local lunch
  • Day 6Morning train journey to Siena followed by an afternoon small-group tour of the Chianti region with wine estate visit and tasting, including a stop at the walled fortress of Monteriggioni
  • Day 7Guided walking tour of Siena covers Piazza del Campo, Palazzo Comunale, the Cathedral and the Basilica of San Domenico

Included

  • Hotel accommodations for 7 nights
  • 7 breakfasts

Not included

  • Cancellation & Travel Insurance
  • Flights and Airport transfers

Questions travellers ask

Is train travel included?
Train travel within the package uses Trenitalia high-speed services between Rome, Florence and Siena. However, from-price covers the package accommodations and itinerary only; rail fares are booked separately.
Is this an escorted or independent tour?
Vacations By Rail operates this as an independent rail vacation with private and small-group guided excursions at each stop. Days 4 and 7 offer free time for independent exploration.
Which trains are used?
Trenitalia high-speed trains connect Rome to Florence and Florence to Siena, and return from Siena to Rome (approximately 3 hours).
What is included?
Seven nights of hotel accommodations and seven breakfasts. Most guided walking tours and small-group excursions at each stop are included; optional extras such as cooking classes, truffle hunts, and museum upgrades cost additional.
What hotels are used?
A 4-star hotel in Rome for one night, a luxurious hotel in Florence for four nights, and a property in Siena for two nights (described by a guest as a bed and breakfast with a view of Siena).
How much walking is involved?
Days include private and small-group guided walking tours of Florence and Siena. A half-day hiking excursion in the Arno Valley is offered as an alternative on Day 3.

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