Quick answer: Both cities restrict or complicate letting to visitors, and the question that separates them is what a landlord does next. Florence has students, hospitals, universities, international institutions and a professional economy to fall back on. Siena’s fallback is thinner, because its dominant private employer has been shrinking.
Every short-let underwriting has a hidden assumption: that if the plan does not work, the property can be let to someone who lives there instead. That assumption is doing more work than most buyers realise, and its value differs sharply between these two Tuscan cities.
What happens when plan A fails
Choose the city with the deeper fallback if the property is a letting business. In practice that is Florence, and the reason has nothing to do with the buildings and everything to do with how many unrelated employers can supply a tenant.
Choose Siena if the property is for use. It is smaller, quieter, cheaper and to many people more beautiful, and none of the fallback argument applies to a buyer who is not letting.
The condition that reverses it: a stabilisation of employment in Siena, or a Florentine restriction that reached residential letting as well as tourist letting. The first would restore the fallback; the second would remove Florence’s edge. Neither has happened and both are worth watching.
Why the fallback is the real variable
A tourist-letting model produces a headline yield that assumes a level of occupancy. Three things routinely remove that occupancy: municipal regulation, competing supply, and a soft season. When any of them arrives, the landlord’s position depends entirely on whether the property can be let to a resident instead.
The value of that option is not a property characteristic. It is an economic one, and it is set by how many independent employers in the city can supply a tenant with a salary.
| Fallback source | Florence | Siena |
|---|---|---|
| Universities | Multiple institutions and international programmes | An ancient university |
| Teaching hospital | Yes, at scale | Yes |
| Professional and financial employment | Broad, and growing with international institutions | Concentrated in one banking group |
| Artisanal and cultural sector | Substantial | Present, smaller |
| Public administration | Regional capital functions | Provincial |
That table is the whole argument. Both cities have real economies. One has more independent legs than the other.
The concentration in Siena, stated carefully
Around 2,200 employees of the Monte dei Paschi group work in the city, with more than 3,000 across Siena and Florence together and further employment in related industries. The bank was founded in 1472 and has been the city’s defining institution ever since. For a city of Siena’s size that is a defining private employer, and it is one whose future has been the subject of successive industrial plans and of union concern about staffing levels.
Two things should be said plainly about that.
It is not a prediction of decline. Siena has a strong visitor economy, an ancient university, a hospital, and a historic centre that will draw people regardless of what any bank does.
It is a concentration risk in the specific sense this page is about. A landlord whose tourist letting plan fails in Siena is looking for a resident tenant in a city where the largest source of well-paid private employment has been contracting rather than expanding. That is a materially weaker position than the equivalent in Florence.
What Florence’s own restriction does to this
Florence is not the open market it was. Tourist letting inside its historic core is now limited to the units already regularly operating during 2024, no further authorisations are granted within the UNESCO area, and the limit has since been widened; the Florence page covers the mechanics.
That makes the fallback question more urgent in Florence rather than less, because for a new entrant in the core the tourist route is not available at all. The difference is that Florence’s fallback is genuinely good: a well-located flat there lets to a student, a visiting academic, a doctor or a relocating professional without alteration and without much marketing.
A buyer in Florence today is therefore best advised to underwrite the residential outcome from the start and treat any tourist income as upside. A buyer in Siena should do the same and should be more conservative about what the residential outcome pays.
What each city is worth living in
Reverse the question and the ranking reverses with it.
Siena is a compact walled city with one of the most complete medieval centres in Europe, a strong civic culture organised around its contrade, a serious university and very little industry. It is quieter than Florence, cheaper than Florence, and for many buyers a more pleasant place to spend time.
Florence is larger, busier, more visited and more expensive. It has more of everything, including crowds.
For a purchase driven by use rather than income, that comparison points the other way, and it is worth being explicit about it because the two objectives are so often mixed in one decision. The Siena page covers the city, the Florence guide the Florentine market, and the Tuscany guide the region.
Testing the fallback before buying
Four checks, all of which can be done before an offer.
- Ask a local agent what proportion of their lettings are residential rather than touristic, and to whom
- Establish how long a plain two-bedroom flat takes to let residentially in that city, in weeks
- Compare the residential rent achievable against the tourist revenue in the underwriting, honestly
- Ask what happens to that residential rent if the largest local employer reduces headcount
Question four is uncomfortable and it is the point of the exercise. In Florence the answer is that several other employers absorb it. In Siena the answer is less comfortable, and a buyer who has asked it has priced something a buyer who has not is carrying for free.
Both models are built from the method in the rental yield guide. For the countryside around either city, which answers to neither analysis, Chianti and the Val d’Orcia show what a rural purchase actually involves, and the Arezzo and Siena comparison sets Siena against a working Tuscan town with a very different demand calendar.
What the numbers look like in each
An illustration of the shape rather than a forecast, comparing what a similar sum buys and earns.
In Florence, a two-bedroom flat outside the core lets residentially to a student household, a hospital worker or a professional at a rent that is modest against the purchase price but reliable, with short voids and low management. Tourist income, if the unit holds an established position, sits on top of that as upside rather than as the basis of the case.
In Siena, the same flat lets into a smaller pool. Student demand is real and the university is ancient, hospital demand is real and smaller, and the professional demand depends more heavily on one employer. Rents are lower, the purchase price is lower too, and the void risk is higher.
The comparison that matters is not gross yield but the spread of possible outcomes. Florence’s distribution is narrower because more employers can supply the tenant. Siena’s is wider in both directions.
Where the buyers come from
Florence draws international buyers at scale and has done since the 1800s, which supports resale and makes the market responsive to sentiment outside Italy.
Siena’s buyer pool is more Italian and more regional, with a smaller international component concentrated on the historic centre and the surrounding countryside. That makes it less exposed to international sentiment and thinner in absolute terms.
Both are slow markets by the standards of a city like Milan. An owner in either should assume that selling takes months rather than weeks, and should price the property to sell rather than to test the market if the timing matters.
Reading a city’s employment base before buying
The exercise this page describes generalises, and it takes an afternoon.
List the employers in the town that could supply a tenant with a salary sufficient to pay the rent you intend to charge. Count how many are genuinely independent of each other, since a hospital and a university are two, while a bank and its suppliers are one.
Establish the direction of travel for each. Growing, stable, or contracting, from public reporting rather than from an agent’s impression.
Then ask what happens to your rent if the largest of them reduces headcount by a tenth. In a city with four independent employers, the answer is that the others absorb it. In a city with one, the answer is that the rent falls or the flat sits empty.
That is the whole method, and it applies as usefully to a small town in Puglia as to a Tuscan city.
Where each city’s risk actually sits
Florence’s risk is regulatory and it is visible. The city has restricted tourist letting and the direction has been consistent, so a buyer knows what they are dealing with and can underwrite the residential outcome instead.
Siena’s risk is economic and it is slower moving. Nothing changes in a year, and a decade of employment contraction changes a rental market completely.
Of the two, the visible one is easier to manage, which is a reason to prefer Florence for a letting business even though its restriction is the more severe. A known constraint can be priced; a slow erosion of the tenant base is discovered late.
What a buyer gains by moving south
Siena is roughly 70 km from Florence, about 75 min by road, and the price difference is real, particularly outside the two historic centres. A buyer moving south gets more building for the money, a quieter town, and a market with less international competition.
What they give up is the depth of the tenant base and the breadth of the resale pool, which is the whole subject of this page.
That is a legitimate trade for a buyer whose purchase is primarily for use, and a poor one for a buyer whose case rests on letting income. Being clear about which of the two you are is worth more than any amount of comparison of price per square metre.
The countryside around both, briefly
A large share of foreign purchases in this part of Tuscany are rural rather than urban, and the analysis on this page does not reach them.
A farmhouse in the hills has no residential tenant pool to fall back on, because nobody rents a rural farmhouse on an annual contract in a district with no employer. Its letting season is short and its fallback is not another tenant but an owner willing to hold it and use it.
That is a legitimate purchase and it should be priced as a lifestyle asset with a partial income offset rather than as a letting business with a fallback. Buyers who apply city logic to a rural property are the ones who are surprised by the November occupancy figure.
Two calendars, briefly
Florence’s visitor year runs from Easter to November and its residential year is continuous, which is what gives the fallback its value.
Siena’s visitor year has two national spikes, around the Palio on 2 July and 16 August, and a broad summer either side. Its residential year runs on the academic calendar and on the hospital, both of which continue through the winter but at rents well below what a summer week produces.
An owner in Siena therefore faces a wider gap between the two revenue models than an owner in Florence does, which is another way of stating the same point: the fallback is not merely thinner, it sits further below the primary plan.
Frequently Asked Questions
What happens when the tourist letting plan fails. In Florence a property that cannot be let to visitors can be let to students, hospital staff, academics or professionals. In Siena the residential fallback is thinner, because the city's largest private employer has been shrinking and the alternatives are smaller.
Around 2,200 group employees work in the city, with over 3,000 across Siena and Florence, plus employment in related industries. For a city of Siena's size that is a defining private employer, and its position has been the subject of restructuring and of union concern over staffing across several plans.
No, and the page should not be read that way. Siena has an ancient university, a teaching hospital, a strong visitor economy and one of the most recognisable historic centres in Europe. What it does not have is Florence's breadth of alternative employment, which matters specifically when a letting plan needs a second option.
Because the headline yield assumes the primary plan works. Every short-let underwriting rests on occupancy that regulation, competition or a soft season can remove. What a landlord needs at that point is another tenant, and the value of that option is set by the local economy rather than by the property.
Not for new entrants in the core. The city capped activity at units already operating during 2024 and stopped issuing new authorisations in the UNESCO area, later extending the block. That is precisely why the fallback question matters in Florence too, and Florence has the deeper answer to it.
For a letting business, generally yes, and the reason is the depth of the alternative tenant base rather than anything about the buildings. For a buyer acquiring a house to use, Siena is smaller, quieter, cheaper and to many eyes more beautiful, and none of this argument applies to them.
A stabilisation and expansion of employment in Siena, or a further tightening in Florence that reached residential letting as well as tourist letting. The first would restore Siena's fallback; the second would remove Florence's advantage. Neither is a prediction, and both are worth watching.
It is a different market from either city and it answers to neither analysis. A rural property in the Sienese hills is bought for use and for landscape, its letting season is short, and its fallback is not a residential tenant but an owner willing to hold it. That should be priced as what it is.
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