On these islands, a traveler can get by on $50 to $80 per day, or less, including food, lodging and, in some cases, air travel. From cheap airfare to cheap adventure, a Caribbean destination exists to suit the budget of most frugal travelers. Unless flights are included or discounted as part of a vacation package deal, the Caribbean Islands that are the cheapest to reach are the Bahamas (fly into Nassau), Puerto Rico and Cozumel. As of 2011, you can get to these islands for less than $400, round-trip.