Help
Talk to usPlan my trip
← All Holidays

Small-group departure · Italy

The Pearls of Tuscany – 8 Days

An 8-day Tuscany tour through Florence, Pisa, Siena, Val d’Orcia, Pienza and Montepulciano, with winery tasting, guided city walks and 4-star stays.

The route3 cities.
Loading map…
8 days, 7 nightsDuration
3 citiesWhere you sleep
3 nights in Florence and 2 nights in Siena in centrally located 4-star hotels, with breakfast daily.Meals

Why this journey

Travel through Tuscany at an easy, rewarding pace, starting in Florence with time to settle into a city-centre 4-star hotel before stepping out to explore one of Italy’s most admired Renaissance cities. The tour blends guided walking and free time, so you can take in Florence’s historic centre, admire its landmark squares and bridges, and choose whether to add the optional visit to Santa Maria del Fiore and Brunelleschi’s Dome.

The route continues to Pisa for a full-day excursion that includes the Piazza dei Miracoli, the Cathedral and the Leaning Tower, with entry tickets and guided visits included. From there, the journey turns deeper into Tuscany’s wine country and hill towns, beginning with San Gimignano for a tasting experience before reaching Siena, where the medieval centre, Piazza del Campo and the Duomo give the city its unmistakable character.

Days in Siena and the surrounding countryside balance sightseeing with time to enjoy the atmosphere at your own pace. The program then moves into Val d’Orcia, one of the region’s most scenic landscapes, with cypress-lined roads, rolling hills and a stop at the Chapel of Madonna di Vitaleta. You also spend time in Montalcino, known for its fortress and Brunello wine, before continuing to a farmhouse-style stay in San Quirico d’Orcia.

The final part of the trip brings in two of Tuscany’s most appealing towns, Pienza and Montepulciano. Here you can wander Renaissance streets, taste Pecorino cheese, and experience the wine culture that defines this part of Italy. With private transfers, English-speaking assistance on key touring days, and a mix of city stays and countryside accommodation, this 8-day Tuscany holiday is designed for travellers who want history, wine, and classic hill-town scenery in one trip.

Trip highlights

  • 01Stay in centrally located 4-star hotels in Florence and Siena, with a farmhouse-style stay in the Val d’Orcia area.
  • 02Explore Florence with a guided walk through its historic centre and time to enjoy the city at your own pace.
  • 03Visit Pisa’s Piazza dei Miracoli with Cathedral entry and a Leaning Tower climb included.
  • 04Enjoy a wine tasting stop in San Gimignano on the way to Siena.
  • 05See Siena’s Piazza del Campo and Duomo with a guided visit of the historic centre.
  • 06Travel through Val d’Orcia’s UNESCO-listed scenery with time in San Quirico d’Orcia and Montalcino.
  • 07Discover Pienza and Montepulciano, with Pecorino cheese and Vino Nobile wine highlights.
  • 08Private transfers and an English-speaking driver on countryside touring days keep the route comfortable and efficient.

Day-by-day itinerary

What's included

Included in your trip9 items covered in this fare
Hotels2
  • 3 nights in Florence and 2 nights in Siena in centrally located 4-star hotels, with breakfast daily.
  • 2 nights in a farmhouse-style stay in the Orcia Valley area with breakfast.
Transfers2
  • Shared excursion to Pisa with round-trip coach travel.
  • Private transfers included as per the programme.
Entrances1
  • Entry to Pisa Cathedral and the Leaning Tower.
Guides3
  • 3-hour guided visit of Florence’s historic centre.
  • 3-hour guided visit of Siena’s historic centre.
  • Guided tour of Pisa with an expert tour leader.
Experiences1
  • Winery visit in San Gimignano with wine tasting.
Plan and pay separately5 items not covered by this fare
Flights1
  • International flights are not included.
Taxes1
  • City taxes are not included.
Meals1
  • Lunches and dinners are not included unless specifically mentioned.
Personal Expenses1
  • Tips and personal expenses are not included.
Optional Tours1
  • Optional private visit to Santa Maria del Fiore and Brunelleschi’s Dome at additional cost.

Your hotels

Hotels are named on your confirmation — all are of the stated category.

Meeting & drop-off
You're met atFlorence city centre hotel
You're dropped atFlorence city centre hotel or onward transfer on request

You leave from a different place than you arrive — book an open-jaw flight, not a return.

Arrival and departure transfers are arranged according to the programme. Private transfers are included as specified in the itinerary.

8 go inside0 walk through0 exterior only
Florence1 places
FlorenceEntrance included in the fare
Goes inside
Pisa1 places
PisaEntrance included in the fare
Goes inside
Siena2 places
San GimignanoEntrance included in the fare
Goes inside
SienaEntrance included in the fare
Goes inside
San Quirico d'Orcia4 places
San Quirico d'OrciaEntrance included in the fare
Goes inside
MontalcinoEntrance included in the fare
Goes inside
PienzaEntrance included in the fare
Goes inside
MontepulcianoEntrance included in the fare
Goes inside

Italy

IdealGoodFairAvoid
OctGood

Spring and early autumn are ideal to avoid the July–August crowds. Amalfi Coast is best May–Jun.

Rome
Average High
22°C
Rainfall
111mm
Venice
Average High
18°C
Rainfall
70mm
Florence
Average High
20°C
Rainfall
89mm
Amalfi
Average High
23°C
Rainfall
130mm
Essential

Documents and entry requirements

  • Guests are responsible for holding a valid passport and any required visa documents.
  • Check your travel documents well before departure, especially if connecting from outside the Schengen area.
Essential

Insurance and personal readiness

  • Travel insurance is mandatory for this tour.
  • Make sure your cover is suitable for sightseeing, transfers and any pre-booked activities.

Local costs to plan for

  • City taxes are not included unless stated otherwise.
  • Allow for meals not listed in the itinerary, tips and personal spending such as drinks, laundry and shopping.

How you travel on this tour

  • The programme combines private transfers with a shared coach excursion to Pisa.
  • Countryside days are best enjoyed with comfortable walking shoes, as town centres often have cobbled streets and uneven surfaces.

Where you stay

  • Expect centrally located 4-star hotels in Florence and Siena.
  • The Orcia Valley stay is in a farmhouse-style property, offering a more rural setting for the final nights.

Optional Florence visit

  • A private visit to Santa Maria del Fiore and Brunelleschi’s Dome is available at extra cost.
  • Availability for optional experiences is subject to confirmation.

Packing for Tuscany

  • Bring comfortable shoes for guided walks and hill-town visits.
  • A light layer is useful for evenings and for time spent in wine country and open countryside.

Tour pace and style

  • This itinerary combines guided sightseeing with free time in each key destination.
  • The route is designed to showcase Florence, Pisa and Tuscany’s hill towns without rushing the countryside sections.

Common questions

Is the Leaning Tower of Pisa ticket included?

Yes, the package includes entry to the Cathedral and the Leaning Tower on the Pisa excursion.

How many nights are spent in each destination?

The tour includes 3 nights in Florence, 2 nights in Siena and 2 nights in the Orcia Valley area near San Quirico d’Orcia.

Are meals included beyond breakfast?

Breakfast is included daily. Lunch and dinner are only included if specifically stated in the programme.

Does the tour include countryside transfers?

Yes, private transfers are included as per the programme, along with a shared coach excursion to Pisa.

Can the Florence Dome visit be added?

Yes, there is an optional private visit to Santa Maria del Fiore and Brunelleschi’s Dome for an additional supplement.

Policies & booking terms
Booking terms
  1. Full payment must be completed 30 days prior to departure, unless otherwise specified.
  2. All bookings are subject to availability at the time of confirmation.
  3. Travel insurance is mandatory and must be purchased prior to departure.
  4. Prices are subject to change due to fluctuations in currency exchange rates, taxes, or supplier costs.
  5. Guests are responsible for obtaining valid passports, visas, and any required vaccinations.
  6. Cancellations or amendments are subject to the applicable cancellation policy outlined in the package.
  7. The company is not liable for delays, cancellations, or changes due to unforeseen circumstances such as weather, strikes, or other force majeure events.
  8. All travelers must adhere to the local laws and customs of the destinations visited.
  9. No refunds will be issued for unused services, including but not limited to meals, accommodations, or activities.
  10. The company reserves the right to modify the itinerary or substitute hotels of similar standards if necessary.
  11. All special requests (e.g., room preferences, dietary requirements) are subject to availability and not guaranteed.
  12. Guests are responsible for any additional costs incurred due to personal expenses, such as phone calls, laundry, or minibar charges.
  13. Check-in and check-out times are subject to hotel policies and may vary by property.
✦AI trip designer

Want this trip a little different?

Tell Tulli what you'd change — hotels, dates, an extra city — and she'll price it with our team and come back to you.

You Might Also Like

All tours →