Recently my wife and I enjoyed a trip to Hawaii for our anniversary. I brought along a pair of watches that I believed were well-suited to the kinds of things I'd be doing on the trip.
I brought the Omega Speedmaster Racing for swimming/hiking/sun bathing as it has a nice and comfortable rubber strap and it is a fairly rugged design. While it is not for diving, it's 100M water resistance makes it suitable for taking a dip in the pool to cool off.
The second watch I brought was my Cartier Pasha Chronograph as it could be dressed up for nice dinners with my wife.
So, I invite anyone that has just been on a vacation, is currently on vacation or has one coming up to share what watches they plan to bring and what kind of occasion they will be wearing each piece for. Hopefully we are a bunch that travels enough to keep this thread going for a while. Also, pictures welcome!