Is it actually safe to travel on this budget?

Yes, provided you practice the same street smarts you would in any major city. Avoid displaying wealth, stay in well-lit areas, and be home by dark if you aren't familiar with the neighborhood.

How do I get between islands for $50 a day?

You don't. Inter-island flights are prohibitively expensive. Pick one island and explore it thoroughly to keep your daily average at $50.

Caribbean Travel on $50 a Day

To survive on $50 a day in the Caribbean, you must stick to local transport, prioritize public beaches, and cook your own meals using ingredients from local markets. Avoid resort towns entirely and focus on islands with robust local infrastructure like the Dominican Republic or Cuba.

Choose the right island. Avoid expensive hubs like Turks and Caicos or the Cayman Islands. Focus your budget on the Dominican Republic, Cuba, or parts of Jamaica where local guesthouses and public buses are plentiful.
Sleep in local guesthouses. Use platforms like Airbnb or local listings to find rooms in residential neighborhoods. Expect to pay $25–$30 for a private room with a fan, away from the tourist beach strips.
Eat like a local. Stop eating in restaurants. Spend $10–$15 daily at local markets on fresh fruit, bread, and rice. Cook in your guesthouse kitchen or stick to street food (empanadas, doubles, or rotis) which usually costs $3–$5 per meal.
Use public transit exclusively. Never take a taxi. Use public 'route taxis' (shared vans or buses) which cost $1–$3 per trip. If the locals ride it, you can too.

Is it actually safe to travel on this budget?: Yes, provided you practice the same street smarts you would in any major city. Avoid displaying wealth, stay in well-lit areas, and be home by dark if you aren't familiar with the neighborhood.
How do I get between islands for $50 a day?: You don't. Inter-island flights are prohibitively expensive. Pick one island and explore it thoroughly to keep your daily average at $50.