Hey mate, welcome to the chaos-it's the best kind once you get your sea legs! As someone who's been bouncing around as a full-time online tutor for about 4 years now (ex-history teacher myself), I haven't spotted any true "vacation packages" laser-focused on teachers with built-in remote setups or workshops. The industry's more fragmented, with general digital nomad workations dominating. But I've pieced together some solid, affordable beginner options in Bali and Portugal that play to teaching skills. Here's what worked for me or folks I know, with real costs and caveats:
Bali (super beginner-friendly vibe, but brace for scooter life and WiFi roulette):
- Outsite Canggu or Ubud: Not teacher-exclusive, but their 1-4 week workation packages (~$800-1,500 USD including co-working, accommodation, and some events) are gold for newbies. They host casual "skill-share" nights where you can pitch teaching workshops-I've done ESL speed-sessions there. Visa-wise, stick to the 30-day B211A tourist visa (free on arrival, extendable once for $35), but don't overstay; Bali's cracking down. Pro tip: Pair it with Preply or Italki setup beforehand-students don't care where you are if your internet holds.
- Alternative: Digital Nomad Asia retreats in Ubud (~$1,200 for 2 weeks, inc. yoga/coworking). They do occasional "freelance pivots" webinars that cover teaching gigs. Evidence from Nomad List: Canggu scores 4.2/5 for remote workers, with cafes like Crate or Dojo having solid NBN speeds.
Portugal (easier visas, more Euro stability, less humidity drama):
- Selina Lisbon or Porto workations: 1-week starters from €500-800, with desks, community events, and even "hustle workshops" on platforms like Outschool (perfect for classroom vets). Portugal's new D8 Digital Nomad Visa (launched 2022) is teacher-friendly if you prove €3,280/month income-apply via consulate pre-trip. I've seen teachers chain this with TEFL cert refreshes via local spots like International TEFL Academy pop-ups.
- Cheaper hack: Surf Office in Ericeira (€600/week). Beginner nomads rave about it for the surf + work balance, and they've got visa info sessions. Nomad List rates Lisbon 4.5/5, with fiber internet everywhere.
Real talk: These aren't "plug-and-play" teacher vacations-expect to hustle your own gigs via VIPKid, 51Talk, or TeacherOn first (I made $2k/month starting out). Bali's cheaper flights from the US/EU, but Portugal wins on safety/long-term stays. What's your teaching niche (ESL, subjects?)? That changes platform recs big time. Anyone else found teacher-specific deals I missed, or am I just jaded? Hit me with your must-haves! Safe travels.