May - August; November - January and all major holidays
Families descend upon San Diego as school holidays begin, and are sometimes disappointed with what they find. Locals know all about the dreaded May Gray and June Gloom, which bring a low-lying marine layer over the coastline for most hours of the day. During this time hotel rates are at their highest, and tourist attractions are crowded. Sunshine is a constant in July and August, making these months arguably the best time to visit San Diego, especially if you are looking for a family vacation while the kids are still out of school. A second wave of travelers arrives for the winter holidays, and even if San Diegans are shivering in their jeans and boots as temps drop to the low 60s (and—horrors—even into the 50s), most visitors happily wander about in shorts and T-shirts enjoying the comparatively pleasant San Diego weather. Bring a jacket or sweatshirt year round, as evenings tend to get a bit chilly, especially if you've toasted your skin bright red in the sun. For the most part, crowds are manageable even in the busiest months—except if you're trying to park at the beach. Make reservations well in advance for fancy restaurants, and it's good to arrive early (8-9PM or so) to clubs and bars. San Diego weather along the coast remains temperate all summer, ranging from the low-70s in the evenings to the mid-80s at midday. Inland is a different story, with the mercury rising into the high-90s in summer.
October; February - March
San Diego doesn't have much of an off-season. The climate's so perfect, with an average of 72 degrees and daily sunlight in some part of the county, that it's a popular destination year-round. Hotel rates vary with occupancy rather than seasons, though you can usually find a 10-20 percent drop in the off-months.
September; April - May
September is our favorite month in San Diego. The sun shines every day and the ocean temperature finally rises into the mid-70s. The crowds are gone and we can play on our favorite beaches without worrying about finding a parking place. September is the best time to visit San Diego for a romantic weekend getaway or last-chance beach trip before fall and winter hit. The one big drawback is the onslaught of the Santa Ana, a fierce dry wind that cracks sensitive skin and fuels wildfires. The weeks between Spring Break and summer vacations are good, as well, with restaurants and attractions premiering their latest creations and hotel room rates back in the reasonable range. We swear the food at our favorite hangouts improves as chefs get a bit of a breather and shops drop their tacky souvenirs in favor of more desirable merchandise.