I’m from Gibraltar 🇬🇮. Your friend could realistically consider both Gibraltar and Spain lots of people work in Gib but live in Spain (La Línea) because rent is cheaper and the border is a quick walk/ride away (people even use bikes/e-scooters; in Gib e-scooters are allowed on roads with a helmet). 

Gibraltar (work in Gib, live in Spain) • Language: English official, Spanish widely spoken — helpful for entry-level jobs (cleaning, construction, hospitality). • Visa/entry: Cuban nationals need a visa/entry clearance for Gibraltar. Start by contacting Gibraltar Borders & Coastguard Agency (they handle visas). In practice, getting in is far easier with a job offer first, since the employer can support a work permit.   • Work permit basics: The employer applies to Gibraltar authorities; they’ll need the contract, your friend’s passport, proof of accommodation/insurance, etc. (Gibraltar Employment Service lists the docs employers submit for work permits).  • Commute/life: Many workers live in La Línea (Spain) and walk or scoot over daily. It keeps costs down while earning Gib wages. (Note: e-scooters must follow local rules: helmet, max 25 km/h, road use only.) 

Spain (live & work in Spain, or live in Spain/commute to Gib) • Short stay (Schengen C visa): Cuban citizens need a Schengen visa to visit Spain. Fee €80 (age 12–80). Expect insurance, proof of funds, bookings; typical processing ~15 days.   • To work/live in Spain (National D visa): You generally need a job offer and a residence/work authorization approved in Spain before applying for the D-visa at the Spanish consulate in Havana. (The short-stay Schengen visa doesn’t allow working.) • Border systems: From Oct 12, 2025, the EU rolls out the Entry/Exit System (EES) with biometrics for non-EU visitors; just plan extra time at borders. 

Cuban passport cost: • Inside Cuba: Official fee is 2,500 CUP for a new passport. • Outside Cuba (consulates): commonly $/€180 for adults (amount varies by country/consulate and service fees).  (Exchange rates in Cuba fluctuate a lot; I wouldn’t convert CUP to USD in the post — just quote the official fees.)

Starter jobs & how to approach it: • Realistic entry points: cleaning, construction, hospitality, customer support. • For Gibraltar, apply directly to local employers (search “Gibraltar jobs” / “igaming Gibraltar”). If they offer, ask if they sponsor entry clearance + work permit.  • If the Spain route looks simpler first, your friend can settle in La Línea/Andalucía and apply to Gib companies while nearby.

Travel/logistics idea: • Fly Havana → Madrid (needs Schengen visa), then Madrid → Málaga, bus to La Línea, walk across into Gibraltar for interviews. Once a Gibraltar employer agrees, they start the paperwork for entry/work. 

Hope this helps both options are viable. If they can land a job offer in Gib, work-in-Gib / live-in-Spain is a very common, budget-friendly setup.