Along with dozens of diplomats, ambassadors and a neat line of docile British government ministers, I sat in the dazzling Louis XIV style splendor of Lancaster House in January, taking in not just her long-awaited Brexit vision
, but a full on whiff of the mansion's grandeur.
For the next installment, May has picked Florence: a sparkling jewel of a city by any measure.
In choosing Florence's historic beauty over the more drab backdrop of Brussels to break the Brexit logjam, Britain's PM may be succumbing to the perennial end-of-summer lure that Chianti country holds over many Europhile Brits.
Or, she may have picked central Italy in order to remind the often self-important EU officials of the continent's soft underbelly.
-- Florence's infamous diplomat, politician and master of duplicity -- might have factored into May's thinking when selecting a location for speech.
Europe's troubles are more exposed in Florence's gracefully aging architecture than in the glass and concrete HQ construct that is the European Union's headquarters.
Less than a year ago, all the talk in this part of the world was of Italy being on a crash course to follow the UK out of the EU.
Its young, amiable Prime Minister Matteo Renzi had bet his political career against the need of the nation to reform its economy. Anti-EU populists -- in the guise of both nationalists and leftists -- helped end his gamble.
In short, for May, Italy is a simple cypher for Europe's ills: A rich North riven with nationalism and a poor South struggling to cope with waves of refugees.
Florence has its feet and pockets in the prosperous north, but many vineyards and olive groves in the rolling hills surrounding the city struggle to pay their way.
A speech here sucks oxygen from Brussels' inflated vision of one Europe fitting all.
But May won't be the only leader revealing their view of a future Europe this weekend.
Early next week, France's energetic President Emmanuel Macron will put his shoulder to the Sisyphean challenge of shifting the EU towards the path he prefers.
And at elections this weekend
, German Chancellor Angela Merkel is expected to handily secure a fourth term in office. Once liberated from the constraining shackles of fighting a domestic campaign, Europe's most powerful leader can let herself loose on her vision for Europe's destiny.
Merkel's aims may be more circumspect than Macron's more vaulting vision, but then for Germany -- Europe's economic power house -- the EU is working. Change will likely come cautiously.
Brussels, to this point, has brushed off Britain's advances much as a frustrated shopper might whoosh away wasps between them and their choice of fruit.
In Florence, May will hope to drown out the EU's increasingly angry buzz and steer Brexit discussion back toward a more mutually agreeable, diplomatic drone. One where the worker bees of Brexit known as sherpas can focus on facts and figures and ignore the emotions in both Brussels and London.
Brussles has become an increasingly implacable wall to May and her Brexit secretary David Davis's demands for a speedy EU divorce. She is desperate, ahead of her party conference in a few weeks, to part the gathering clouds of discontent that threaten her leadership with some sign of success in Europe -- be it from a solid kick to the EU's sensitive nether regions -- as some in her party want -- or a caressing of its ego.
Or, a combination of both of the above. Something to improve the odds of a quicker agreement, reduce the risk of failure and cast herself in a better light -- if only in the short term. Florence might be just the ticket: plenty of history, not just the political dark arts of Machiavelli, for a crafty speechwriter to weave into her own narrative for the future of Europe.
The city's charm is like butter on hot toast: it soaks into every pore, a richness of flavour that lasts long after the swallow. If May can emulate these qualities then she might finally break the Brexit logjam.
She will be hoping her words convince the EU27 that she is a serious negotiator and does have a vision for Brexit that she can deliver on and finally get trade talks between the EU and the UK going.
EU negotiators are telling their UK counterparts to table substantive plans on rights of EU citizens, on Northern Ireland and on settling the exit bill.
Until May's foreign secretary -- and in the eyes of many, leadership rival -- Boris Johnson penned his own 4,000-word Brexit vision last week, the mood music in the run up to Florence was vaguely in May's favour.
Leaks that the UK could offer to pay around £20 billion over two years
to plug would-be holes in the EU's budget and two or more years of transition after the talks deadline March 2019, perhaps keeping the UK inside the single market and EU Customs Union, might go some way to cooling the EU's perceived anger towards the manner in which Britain has gone about these negotiations so far.
But this kind of fudge wouldn't please everyone. Johnson and others have bridled at Britain paying a hefty bill that the EU has said could ultimately be around €100 billion.
So something for everyone maybe: the EU gets commitment from the UK that it will continue to meet its EU budget obligations until the end of this period (2020). The UK gets the transition that it wants. And the thorny issue of the final bill gets kicked down the road -- at least for a bit.
It wouldn't thaw the Brexit talks overnight, but might just hint that the winter of Brussels' discontent is less chilly than before.
Johnson's intervention though, what ever it does to May's calculus, will have reminded the EU that they may want to keep their thermals to hand a little longer. May has plenty more discontent awaiting her at the Conservative party conference.
Not for the first time, Johnson has soured the scene in Europe, and also not for the first time he says again he really is in lockstep behind May's leadership.