This is true, but if you can drive to southern Spain you can get an inexpensive ferry to Morocco. From there you can go as far south as you could want.
You can start in Cadiz, Spain for a longer trip than from Lisbon. Actually I don't know the rules for this "longer route" since you could go zig-zagging.
Have some fun in your life. Spain’s nightlife is legendary. Grab a RyanAir flight to somewhere new. Sometimes when making a difficult decision you’re doing so from a place of being emotionally drained; you’re running on fumes. Fill up that tank before you make any decisions of this magnitude. You’ve probably got the money to enjoy yourself a bit.
Some spot in the south of Spain, where there's so much to choose. Málaga and surroundings for international community (avoid Marbella if you don't want to burn your money in 2 days), but Cádiz and Granada are probably awesome too. Almeria has some very nice spots (Cabo de Gata) and Sevilla is worth visiting often.
Bonuses:
- North Africa round the corner. Actually there are two Spanish cities in North Africa, so you don't even need another visa to step on the continent.
- You also have Huelva and the Portuguese Algarve somewhat close.
- Very cheap flights to anywhere in Europe (my last Málaga - London Luton was £24) and easy to jump to Madrid or Barcelona for long haul.
I visited (from the US) some years back when I was briefly living in Spain. We bused to La Linea (the Spanish border town), then walked across the border, then across the runway (after waiting for a plane), to get the main, touristy part of Gibraltar. Just added to the surreality of visiting such a visibly-known place.
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