Monfalcone to Florence

Having decided to fly to Trieste (price to Milan doubled within a couple of hours) ... the next decision is what train to get ...

The journey from Monfalcone (near Trieste airport) to Venice is on a regional train where there is no discount for advance booking ... with the flight arriving at 14:35 ... the 15:07 departure (arriving into Venice Mestre at 16:37 and S Lucia at 16:49) should be doable without flight delays, otherwise the 16:07 arrives into Venice Mestre at 17:37 and S Lucia at 17:49 - the price to go into S Lucia is 8.95 eur in economy or 13.50 eur first class

The decision is what to do on the Venice to Florence leg ... in case the flight is delayed it's probably too risky to make an advance booking on the 17:09 departure from Venice Mestre (which arrives into Florence S.M. Novella station at 19:35), in which case the walk-up fare is 43 eur in economy ...

But it would be safe to book the 18:27 departure from S Lucia (18:39 from Mestre) which would be 29 eur in economy or 39 eur first class, and arrives into Florence S.M. Novella station at 20:35 ... that would give either 1.5 hrs or half an hour (depending on whether the flight was on time) to get reacquainted with the Grand Canal ...

london to italy for the jubilee weekend

Looking to go to Florence from Sat 2nd June to Tuesday 5th June

Flights to the nearby airports (Florence / Pisa / Bologna) are either too late or too early ... so there seem to be two reasonable options:

STaNsted - Trieste
dep 11:35 and arrive 14:35 for 76 gbp, and then get the train from the nearby Monfalcone station (no need to go into Trieste itself) at 15:07 arriving into Florence (via Venice) at 19:00 for 38 eur (58 eur in first class) or the later 16:07 departure which arrives into Florence at 20:35 for 48 eur
LHR - Milan Linate
dep 9:25 and arrive 12:30 for 142 gbp, and the get the train from Milan at 14:20 (or an hour later) arriving into Florence at 16:05 for 49 eur

On the return journey, there are options from Rome to Luton (dep 19:35 arr 21:15 for 98 gbp), or Milan to Gatwick (dep 21:50 arr 22:40 for 109 gbp) ... but since it would be good to check out the leaning tower, the options from Pisa are:

Pisa to Luton departing at 16:25 and arriving at 17:45 for 131 gbp
Pisa to Leeds Bradford departing at 16:20 arriving at 17:45 for a ridiculous 33 gbp.  The 19:15 departure from Leeds arrives into Kings Cross at 21:28 and costs 60 gbp, or 89 gbp in first class