I first visited San Diego in 2005. My friend Cat and I traveled for a quick weekend from New York City and checked into Hotel Solamar, a Kimpton Hotel that had just opened in the Gaslamp Quarter, which, at that time, was gaining traction as the new nightlife go-to spot. The concierge handed us a map of San Diego, and, not having really researched the city, we were shocked to discover how massive it was. Just to give you an idea, San Diego sprawls 4,525 square miles, almost the size of the entire state of Connecticut. In hindsight, the fact that San Diego is chockfull of attractions, many vibrant neighborhoods (all with very different personalities), and an emerging nightlife district made us anxious, as we are a traveling pair who likes to really get to know a destination. There was no way one weekend would serve San Diego any justice. Consequentially, to ensure we didn’t stress the entire time we were vacationing, we parked on the beach for 48 hours to watch surfers and marines do what they do best on their sandy playground: surf and look good. I didn’t return to San Diego until eight years later when a group of friends wanted to take a leisurely weekend trip from Los Angeles, where I now live. Again, I had mild heart palpitations, knowing it had weeks’ worth of attractions to offer and, considering my natural ambitious flare, I would need to see all of San Diego to feel as if I truly visited the destination. So I convinced my friends to stay for a week. And even when I later returned to LA, I knew that I hadn’t seen it all…which means I have every reason to pay San Diego another visit.