I always put a little more sartorial effort into my Italy packing—more “looks,” nicer jackets, accessories like scarves, ties, and pocket squares from Drake’s, and of course, more shoes than usual or needed. It’s a culture that values these gentlemanly details.

If you're living in the northeast of the United States like I am, you're probably pretty fed up with the cold weather. Lately, I've been fantasizing about sunshine, beaches, and warm tropical breezes. My mind has been filled with thoughts of St. Bart’s, Antigua, Barbados, and the Bahamas—just name the Caribbean destination, I've dreamed about it. While I can't be there, I can make a fantasy packing list.

Florence, Italy is home to some very famous creations: Michelangelo's art and architecture (we all know the David), The Duomo, Gucci, and of course, my favorite Italian cocktail: the Negroni. Perhaps not so well known is that Panerai watches trace their roots back to Florence as well.

Sometimes the pleasure of wearing a watch is not paying attention to that watch at all. Sometimes, you don’t want or need to keep track of time—except perhaps to remind yourself that it's an acceptable hour to have a cocktail. You may not want that watch to count down the hours until you have to leave a magical vacation spot, and Kamalame Cay is one place where you want time to stand still.

I like a restaurant that encourages gents to look their best when they sit down for a lunch or dinner. Sure, “jacket required" can be an annoying rule, but some places need no rules to encourage you to present the best version of yourself. Aretsky’s Patroon is one such place, on East 46th Street in New York City.

As much as this beauty of a watch from Ralph Lauren is meant to inspire the spirit of safari, far-flung explorations, and pushing yourself beyond your limitations, I found it perfectly suited for my own desert adventure around aperitivo time at the hotel bar in Palm Springs, California.