The question I get more than any other: “Should I do one island or two?” Or three. Or, God help us, all four in ten days. And the answer I give more than any other is: “Fewer than you think.”
Here is the honest math. Each additional island on your itinerary costs you roughly half a day of real vacation time — check out of your first hotel, drive to the airport, fly, land, wait for luggage, pick up a new rental car, drive to the next hotel, unpack. That’s not travel, that’s logistics. And the extra interisland flight, the extra rental car, and the extra set of hotel nights all add up fast. For a lot of first-time visitors, one island done well beats three done in a blur.
That said, if you’re coming from the East Coast and flying 10+ hours to get here, I understand the temptation to see more than one place. This guide lays out the logistics so you can make the call with real numbers instead of guesswork — and then gives you three sample itineraries at 7, 10, and 14 days.
