Montego Bay at $346 RT

Think your bland summer schedule needs a little kick?

We've got just the thing!

We scooped up some surprisingly cheap summer dates to one of the most iconic island spots in world. While this is technically wet season, the rain is usually brief and intermittent, so Montego is still popping with visitors through these months. If you prefer to travel over summer break, this is one of your better Caribbean options!

Plus, there are plenty of bars and cafes to duck into if you get caught off guard. There's nothing a brightly colored cocktail can't cure :-)

P.S. To get this deal, you have to book your departure and return legs separately. Google Flights makes this pretty simple, but remember to add that carry-on for the leg with United — they don't include it automatically like American does.