America's Best Cities for Winter Travel 2010
Mark Downey / Alamy
No. 3 San Juan, P.R.
The island high season is likely a big factor in Puerto Rico’s top three debut for winter. Being No. 3 for weather and No. 4 for cocktails probably doesn’t hurt, either. It’s not just about lazing on the beach, though: San Juan also ranks in the Top 10 for historical monuments.