The idea that one *must* have a large boat to travel solo is absurd.
John Guzzwell circumnavigated in 20'
Trekka, for example. Serge Testa's
Achroch Australis was 12', and he circumnavigated in 1987. And let's not mention Lyn and Larry Pardey's boats
Serrafyn and
Taleisin, both of which were under 30' and both of which circumnavigated, admittedly, double-handed. And as many have pointed out, Albin Vega's are renowned for the number of circumnavigations and ocean crossings sailed in that sturdy little 27' craft.
The general
rule of thumb is buy the smallest boat you can live with, as EVERY
boating expense increases with
hull length. Bigger
engine required. Larger sail area. More sq metres to
paint and anti-foul, etc etc etc. As the route you're proposing is essentially extended coastal sailing, ocean-crossing store-carrying ability is not so much of an issue. At 4L/day, two jerrycans of water will last 10 days, and don't take up much room. But I do agree with the comments about the transom-fixed outboard - not a great option. Useful for exiting a marina. That's about it. A small inboard
diesel is a better bet, but even some 25' yachts have these.
One question I'd ask myself is: what sort of boat do I want to sail about in once retired to the Phillipines? If the missus won't sail with you, and moorings, lifts, typhoons etc all add to the cost of
boating in the Phillipines, then perhaps a smaller boat will, ultimately, be more economical and, in which case, putting up with smaller and slightly slower to get it there, might be a
price worth paying, as it will be (you said) a one off 'delivery trip'.
A smaller boat would be fine around the coast of Britain and
Scotland. One of the pioneer 'small boat cruising sailors' was artist Robert E Groves in his original
Sheila, 25' on
deck (28' with 3' bowsprit) launched 1905 and in which he sailed (and painted) his way around the Hebrides and Highlands, documenting his travels in the Humber Yawl Journal. He is one of the reasons our pursuit is what it is today. A pioneer of 'small boat cruising'. When he crossed The Minch in 1907 fishermen in Stornoway told him his was the smallest boat they'd seen cross The Minch. Period.
So be not afraid of "small" as small is (often) beautiful. In more ways than one.
That Rival Phil pointed to looked a very smart and competant yacht for your purpose, and at the right price point. But it might be too big for cruising the Phillipines waters. I've not been there myself, but from what I've read, much if it is shallow, which is probably why catamarans are so common so in that neck of the woods.
All boat-buying decisions involve compromise. Probably if you could afford (and handle) a 50' cat with all the fruit, your missus might grow to like sailing. But it's a big chunk of change to find out that she might not! lol
One thought I had that might be of assistance in your planning, and someone else flagged this by saying 'put the boat in a container' - this is *perfectly* feasible to do with a boat under 40', although a bolt-on keel might be essential, and in which case you could truck the boat overland from Port Said via Jordan and Saudi to the Gulf states, probably Bahrain..?? and then sail south from there, hugging the coast around
India and making a 'weather window dash' across the Bay of Bengal from Sri Lanka to Yangon and down the Mallacca Straits to
Singapore and so to the Phillipines via
Indonesia.
Very do-able, I'd have thought. And savings made in
buying a smaller boat initially (i.e. one that would fit in a container) would offset the cost of shipping across the Saudi peninsula. Note that I have avoided suggesting the direct route via Haifa,
Israel, as the Arab states often look askance at passports (never mind boats) entering from that country. Avoid offending.
It's possible to get a
ferry from Sinai to Jordan and avoid
Israel entirely. Were it not for the devastating war there, Turkey-Syria-Jordan-Bahrain would also be an option, alas, not at this geo-political moment.
So yes, buy your boat in UK, sail Scotland and the Irish Sea for a few months, take some lessons first, and by the time you get to the far end of the Med, you ought to have a handle on the point A to point B stuff.
And fear not the naysayers!! Good luck. Report back.