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Headout: review, prices and reliability in Tuscany

Headout sells tickets and day trips in Florence, Pisa and Siena at prices that look discounted, but almost everything comes without cancellation and a fee can appear at checkout. It only works if you're sure of your date; otherwise there are more flexible choices, starting with the official sites.

Company
Headout Inc., New York, since 2014
In Tuscany
Florence about 247 products, Pisa 32, Siena 24, San Gimignano 20
Leaning Tower of Pisa
from €25, can't be cancelled or changed
Day trips from Florence
Tuscany €49, Chianti €67, Cinque Terre €99
Cancellation
none, unless the listing says otherwise
Refunds
issued within 7 days of Headout receiving the funds from the supplier
Support
+1 347 897 0100, support@headout.com

Updated 24 September 2026

The right question: can you afford not to change your plans?

Headout is a platform based in New York, on Nassau Street, founded in 2014, which claims over 56 million customers. It sells entry tickets, guided visits and day trips in many cities around the world, Florence included.

The whole verdict on Headout in Tuscany turns on one rule: unless stated otherwise, products can't be cancelled. If your trip is fixed and you know exactly what time you'll be in Pisa, this rigidity may not bother you. If you're travelling with children, depending on a train or keeping an eye on the weather, it matters a great deal.

What you'll find in Tuscany

At our last check Headout had about 247 products in Florence, 32 in Pisa, 24 in Siena, 20 in San Gimignano and just one in Lucca. There's no dedicated Tuscany page: you search town by town.

The most relevant offers:

  • Leaning Tower of Pisa: from €25, averaging 4.4 from about 5,000 reviews at our last check.
  • Uffizi: at our last check €28 struck through and a “discounted” price of €19.60.
  • Day trips from Florence: classic Tuscany from €49, Chianti from €67, Cinque Terre from €99.

Leaning Tower of Pisa: Headout compared

The Tower is on every platform, and it's the clearest case for seeing where Headout stands.

ChannelPriceChanges and refunds
Opera della Primaziale Pisana, official site€20time can be changed and order cancelled up to 2 hours before
Headoutfrom €25can't be cancelled or changed
Tiqetsfrom €25non-refundable and non-changeable
GetYourGuidefrom €24according to the listing's terms

The official ticket costs less and is the most flexible. The platforms' prices, on the other hand, move often, and we update the ones below regularly. If the official slots are sold out and you're looking for an alternative, compare the terms before the price.

Tiqets

Leaning Tower of Pisa & Pisa Cathedral: Entry Ticket

★ 4.5 (2,533 reviews) from €25

Book on Tiqets

GetYourGuide

Pisa: Entrance Ticket to Leaning Tower & Cathedral

★ 4.5 (14,459 reviews) from €24

Book on GetYourGuide

Read our full guide to the Tower and the Piazza dei Miracoli too, and our review of the Opera della Primaziale Pisana.

Day trips from Florence: how it compares with Tiqets and GetYourGuide

On day trips Headout isn't out of line with the market, but it isn't cheaper either. At our last check the classic Tuscany day trip started at €49, the same price as the most-reviewed Pisa–Siena–San Gimignano with lunch on GetYourGuide. Chianti started at €67, against €49.50 for the GetYourGuide winery tour, which had over 11,000 reviews at our last check. For the Cinque Terre the gap is even wider: €99 on Headout, from €49 on Tiqets and from €55 on GetYourGuide.

Itineraries and inclusions aren't identical, so price alone isn't enough. But with no cancellation as the rule, paying more for a less flexible product makes little sense. The alternatives are gathered in our guides to day trips from Florence and to wine tours.

Tiqets · 13:00

Cinque Terre: Day Tour from Florence

★ 4.3 (17 reviews) from €49

Book on Tiqets

GetYourGuide · 12 - 13 hours

Florence: Cinque Terre Day Trip with Optional Hiking or Pisa

★ 4.9 (6,091 reviews) from €55

Book on GetYourGuide

GetYourGuide · 5 - 6.5 hours

Florence: Chianti Wineries Tour with Wine Tasting

★ 4.5 (11,658 reviews) from €49.50

Book on GetYourGuide

Struck-through prices and fees: how to read them

On Headout you'll often see a struck-through price with a lower one next to it. That comparison is between two figures chosen by the platform, not with the monument's official price. Two details make the comparison even less straightforward:

  • a service fee may be added at checkout;
  • the price shown changes depending on the country and currency you're browsing from.

For the Uffizi the point is concrete. The museum's official price list has a full-price ticket at €25 if you buy on the day and €29 if you book ahead, and online sales go through tickets.uffizi.it. A price below the official list should make you ask what you're really buying: the time slot, the audio guide, whether the ticket is in your name, whether it can be cancelled. And pay no attention to wording that suggests an official link with the museum: you'll find the right channels in our guide to Florence.

Refunds and support

Where a refund is allowed, Headout starts it within 7 days of receiving the funds from the service supplier. In practice the timing also depends on the local operator, not just the platform.

Support is available on +1 347 897 0100 and at support@headout.com; there's also an Italian line on record, +39 02 4013 6894, worth checking before you rely on it. One simple tip: save a screenshot of the listing when you buy, terms included. If a dispute arises, it's the most useful evidence you'll have.

Headout reviews: what customers say

At our last check Headout had about 4.4 on Trustpilot from 63,500 reviews, with 74% five-star and 14% one-star ratings; on the App Store its rating was about 4.65. The average is good, but the share of very poor ratings is high and the complaints repeat themselves:

  • queues at the entrance despite the promise of skipping the line;
  • confusion over day-trip meeting points;
  • refused refunds;
  • prices that differ by country and currency.

Who it suits, and what to choose instead

Headout can work for a timed ticket you're sure you'll use, if the final price at the moment of purchase, fees included, is competitive. That's where the 2 out of 5 comes from: on the Tower it costs the same as Tiqets, but its day trips also come without cancellation as a rule, struck-through prices and checkout fees make comparisons murky, and refunds depend on the supplier's timings. For everything else, there are more sensible choices in Tuscany:

Frequently asked questions

Is Headout reliable?
Headout is an American company based in New York, trading since 2014. At our last check it had about 4.4 on Trustpilot from about 63,500 reviews, but with 14% one-star ratings. The problems mentioned most are refused refunds, queues despite the “skip the line” promise and confusion over meeting points. Its main weakness is how rigid its terms are.
Can I cancel a Headout ticket?
As a rule, no: Headout's general policy is that there's no cancellation unless the product listing says otherwise. For the Leaning Tower of Pisa the listing states it clearly: the ticket can't be cancelled or moved. Where a refund is allowed, it's issued within 7 days of Headout receiving the funds from the supplier.
Are Headout's discounts real?
Headout often shows a struck-through price next to the selling price. The comparison that matters, though, is with the official price: the Leaning Tower of Pisa costs €20 on the Opera della Primaziale Pisana site, against €25 on Headout. Bear in mind too that a service fee may be added at checkout and that the price shown varies with country and currency.
Does Headout sell official Uffizi tickets?
Headout resells Uffizi tickets, but it isn't the official channel: the museum's ticket office sells on tickets.uffizi.it, with a full-price ticket at €25 if you buy on the day and €29 if you book ahead. Be wary of any wording that suggests an official relationship with the museum, and always compare what the ticket includes.
How do I contact Headout customer support?
The main number is +1 347 897 0100 and the email address is support@headout.com. There's also an Italian line on record, +39 02 4013 6894, but check it's still active before relying on it. Keep your booking number to hand and take screenshots of the listing when you buy, cancellation terms included.

Sources

  1. Headout: official site
  2. Opera della Primaziale Pisana: prices
  3. Gallerie degli Uffizi: tickets
  4. Trustpilot: Headout reviews