In 2000, he set up a company, Craggenmore, to buy and restore the 23-acre estate, including the manor, grounds and village. Borgo di Colleoli was roofless and home to thousands of pigeons, but Hogg spotted its potential as the heart of a development that is making owning a Tuscan home possible for many who thought it beyond their purse or hassle threshold.
The main house, Il Palazzo, is now a hotel that holds some of the Borgo's 60-plus apartments, the rest being in converted outbuildings. Every step was overseen and approved by the Italian fine arts ministry. The ministry were so happy with Craggenmore's work that they are allowing it to restore the ruins in the adjacent valley, turn them into 17 apartments and incorporate them into the Borgo.
There are three types of ownership at Borgo di Colleoli: freehold, fractional ownership and membership. This last is the entry-level option, buying you one week a year for 20 years and starting at £12,000 for a studio, rising to £25,000 for a two-bed. As with all ownership at the Borgo, members can use the hotel facilities and concierge service, including collection from Pisa airport, to which Ryanair flies from Dublin, Prestwick and Stansted. "Membership is a way to test the water," says the sales and marketing director Steve Carmichael.
Craggenmore offers a smooth transition from one kind of deal to another. Membership can be cashed in at any time or rolled into a freehold fractional ownership. There at six types of this at the Borgo, beginning at £52,000 for a studio, rising to £85,000 for a two-bedroom. Fractional owners receive six weeks' use a year.
Freehold ownership comes either as an outright usage package or a rental guarantee deal, such as Susan Segal from London opted for. An interior designer who commutes between London and New York, she wanted a hassle-free Tuscan bolthole.
"I love Tuscany but wasn't interested in buying a place and doing it up, or having the responsibility for looking after it when I wasn't there," says Segal, who, nine months ago, bought her one-bed apartment freehold for £210,000, which included furnishings and service and maintenance charges.
She opted for a rental guarantee deal, which entitles her to six weeks' use of her apartment each year, at three days' notice, plus a guaranteed 5 per cent return on her investment for a minimum of three years.
For Segal, it's ideal to have an onsite restaurant and wine bar and a concierge to organise airport pick-ups. She sees it as a better return on her money than the small one-bedroom flat she sold in London to afford the sale. Segal reckons her investment is now worth £240,000. The 17 valley apartments just released for sale on a freehold and fractional basis, although still raw ruins, have already attracted interest from existing members. Freehold prices start at £225,000, rising to more than £700,000.
It's not surprising that investors and pleasure-seekers alike jump at developments like the Borgo. They see a user-friendly ownership option Italy otherwise lacks. Most overseas purchasers underestimate the cost and complexity of buying and renovating in Italy.
Spying a chance to add fine dining to the Borgo's attractions, Hogg invited Glaswegians Rodney Doig and top chef David Maskell, formerly of Gordon Ramsay's in Glasgow, to establish their own restaurant Il Secoil on the premises.
Doig began his career at Nicolson's in Edinburgh, where JK Rowling wrote the first Harry Potter book. "I keep waiting for a character clutching a corkscrew and glass of wine to go swaggering through her novels," he jokes. But these are serious restaurateurs - Maskell has won plaudits for his nouveaux Tuscan menu and Doig's 700-bottle wine "library" has won an award.
Together with the five Scots on the Borgo's sales team, Doig and Maskell are now fluent in Italian, have passable suntans and form a little Caledonian community in the heart of Tuscany. During the reconstruction work, locals from the nearby village of Palia were invited to celebrate Hogmanay. Later, the attractions of the kilt had to be explained to the Borgo's Italian waiting staff when Burns Night rolled around.
In the late 19th century, many Italians fleeing famine and corruption ended up in Scotland. Most of them were from Tuscany. "Legend has it that they set off for America but got lost and washed up on the west coast of Scotland," Hogg says. However accidental, it was a marriage made in heaven, as anyone who's enjoyed an espresso and ice cream after a night on the malts will testify.
Hogg reckons the immigrants stayed put because of the similarities between the Tuscan and Scots landscapes, both being so very green, rolling and studded with trees and towers.
Hogg has long been part of the annual holiday exodus to Tuscany. "I love it, I've been coming here for years, and was thrilled to find this project," he says.
Borgo di Colleoli is offering three nights preview visits for £299 per couple, including flights, bed and breakfast at Il Palazzo and airport pick-up.
Available through Craggenmore (0870 243 0314); www.viewtuscany.com; and Aylesford (020-7351 2383)