Venice in $390s-$400s RT

Venice is romantic as hell (peep these Valentine's dates, by the way), which means it's at its best after the sun goes down.

Picture this: After watching the sunset from a gondola for two, you head for the nearest osteria—a small restaurant serving light meals, delicious cicchetti appetizers, and, most importantly, wine and spritz. After a couple (or more) drinks, you stroll over to the 11th-century church of San Vidal. The church houses some gorgeous Baroque-era art, but you're here for the show. Vivaldi's Four Seasons, naturally.

After the performance, it's time to head back to your room and get some rest so you can do it all over again tomorrow. And if you can't sleep, you can always just hit the streets... :-)