# Experiences on Demand 2027: Book During Your Stay | Doorways

> Private tours with art historians, chefs and archaeologists in 12 Italian cities, from about $60 per person for a group. Book direct with Context Travel, no markup.

Source: https://villavacations.com/experiences/on-demand/

In partnership with Context Travel

# Experiences on *demand*

Every tour is led by a working art historian, archaeologist, or chef. Twelve Italian cities, no markup, direct booking.

12

· Italian cities

125

· private tours

4.9★

· Trustpilot · Context Travel

![Rome](https://villavacations.com/wp-content/uploads/2026/06/eod-rome-colosseum.jpg)

The Eternal City

### Rome

**23** private tours · from **$66** per person

See Rome experiences

![Florence](https://villavacations.com/wp-content/uploads/2026/06/eod-florence-uffizi.jpg)

Renaissance HQ

### Florence

**24** private tours · from **$59** per person

See Florence experiences

![Venice](https://villavacations.com/wp-content/uploads/2026/06/eod-venice-grand-canal.jpg)

La Serenissima

### Venice

**18** private tours · from **$65** per person

See Venice experiences

![Siena](https://villavacations.com/wp-content/uploads/2026/06/eod-tuscany-siena.jpg)

Medieval Tuscany

### Siena

**5** private tours · from **$85** per person

See Siena experiences

![Lucca](https://villavacations.com/wp-content/uploads/2026/06/eod-tuscany-lucca.jpg)

The walled city

### Lucca

**1** private tour · from **$77** per person

See Lucca experiences

![Bologna](https://villavacations.com/wp-content/uploads/2026/06/eod-context-bologna-welcome.jpg)

Food capital

### Bologna

**6** private tours · from **$74** per person

See Bologna experiences

![Lake Como](https://villavacations.com/wp-content/uploads/2026/06/lake-como-hero-maria-serena.jpg)

The lake

### Lake Como

**2** private tours · from **$84** per person

See Lake Como experiences

![Milan](https://villavacations.com/wp-content/uploads/2026/06/eod-context-milan-welcome.jpg)

Lombard capital

### Milan

**10** private tours · from **$74** per person

See Milan experiences

The chaotic south

### Naples

**13** private tours · from **$75** per person

See Naples experiences

The tower city

### Pisa

**1** private tour · from **$99** per person

See Pisa experiences

A whole world

### Sicily

**17** private tours · from **$118** per person

See Sicily experiences

Shakespeare's city

### Verona

**5** private tours · from **$70** per person

See Verona experiences

Why Context Travel

## Tours led by *scholars*, not scripts

Context's guides are working art historians, archaeologists, chefs, and academics in the city you're standing in. Groups stay small — usually six or fewer — so the conversation is real, not a megaphone.

Context Travel is a certified B Corp, Doorways' editorial partner on the mindful-travel side. We share the same standards on who books a private guide and who waves a flag.

**Independent rating**

4.9 / 5

**Reviews**

4,000+

**Years**

20

**B Corp certified**

Yes

Custom request

## Want something *not on the list*?

A private cooking class with a Michelin chef. A vineyard with the founder. A truffle hunt in November with the dog who actually finds them. Tell us the brief and we'll have our partner build the experience around your week.

[Request a custom experience →](https://villavacations.com/contact-us/)

Experiences are delivered by [Context Travel](https://www.contexttravel.com/?ref=Doorways_Villa_Vacations), our B Corp-certified partner. Bookings made through these links may earn Doorways a referral commission, at no additional cost to you. Doorways does not mark up Context Travel pricing.

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Doorways Villa Vacations, Italian villa specialists since 1994. Book through a travel advisor: https://villavacations.com/contact-us/