1. How would you describe the spirit of San Diego?
The spirit of San Diego  is as free and easy as the seagulls soaring overhead. It is the type of place that invites you to take your watch off for a while, kick back under the sun, and enjoy the waves rolling in.
2. Where is the best place to go watch a beautiful sunset?
With so many beaches nearby, sunsets are a San Diego specialty. If I had to pick one, I’d have to go with Torrey Pines State Reserve. You can either watch the sun go down from the beach or up on the cliffs, surrounded by the park’s vaunted torrey pines, coastal scrub, and scurrying bunnies. As the sun dips down it lights up the sandstone cliffs of La Jolla and Del Mar with a warm glow. The best part is that it is generally less crowded than many other sunset vantage points.
3. Where do you consider the best places in town for cheap eats?
All of San Diego’s neighborhoods are full of great places for cheap eats. After a day at Pacific Beach, nothing hits the spot like the fish tacos at Taco Surf, a cool little hole-in-the-wall that has dozens of collectible surfboards hanging from the walls. Over in North Park, Chicken Pie Shop has got an awesome deal for starving student types that includes a chicken pie, mashed potatoes, veggies, a roll, and dessert for fewer than six bucks. Up in North County, you can stuff yourself on the cheap breakfasts at Pipes Café in Encinitas or drop in for a milkshake and diner grub at the 101 Café in Oceanside. My all time favorite, though, is a rural roadside spot I like to visit when I’m driving toward the desert on I-8. Located on Old Highway 80 in Pine Valley, La Posta Diner cooks up a mean burger and has the best chicken fried steak I’ve tried this side of the Mississippi.
4. If money is not an option, where is the best place to splurge for dinner?
Get your bank account in order and book a reservation at Bertrand at Mister A’s. I think most San Diegans will back me up on this one—it is a local institution for a reason. The food is regularly ranked best in the city, service is classy, and its rooftop position on Bankers Hill offers a glittering nighttime view of Balboa Park and downtown.
5. If you can only visit for 24 hours, what’s the best way to spend such a small amount of time in such a vibrant and diverse city?
That is a toughie. There’s so much to explore! Fortunately a lot of the city’s best assets are within an easy 10 to 15 minute drive of each other. If I wanted to plan a perfect day in San Diego, I’d probably start my morning out on the city’s waterfront. I’d pick up a coffee to go at Seaport Village and stroll on down the Embarcadero for a while. From there, I’d probably drive a few minutes up to Balboa Park for lunch at El Prado right in the middle of the park and walk off my indulgences at the park’s gardens and museums. As the mid-afternoon shadows lengthened I’d hightail it over to Mission Beach to lounge on the sand and wait for the sun to go down, picking up a sunset dinner at one of the restaurants on the boardwalk. Then, if I wasn’t totally pooped, I’d probably go downtown for a nightcap in the Gaslamp Quarter .
6. What do you consider the best place, or places, to stay on a budget?
San Diego lodging options are undeniably expensive, but it’s not impossible to find deals. One option for on-the-go singles or young couples is 500 West, a hotel/hostel hybrid located smack dab in the middle of downtown. Rooms are tiny and bathrooms are shared, but most nights a single will only run you $59. It is a step up from the local hostels and it’ll save you money for more drinks at the nearby Gaslamp Quarter. For families looking for value on the beach, I’d suggest Beach Haven Inn in Pacific Beach. There’s a pool and barbeque on the property, it’s less than a block to the boardwalk, and rooms are comfy. You can often snag a room with a kitchen for just under $200 come summertime. Just don’t count on that price around the Fourth of July, when beach rates go through the roof.
7. Let’s talk transportation. What is the best way to get around town?
Face it, this is Southern California we’re talking about, so if you really want to explore the nooks and crannies during a short vacation, you need a car. This is particularly true if you want to spend time exploring the beaches up and down the county’s coast. Still, it’s possible to take advantage of public transit and get a pretty full San Diego experience. While downtown, consider using public transit and your own two feet to explore pockets of the city like the Embarcadero, Little Italy, the Gaslamp Quarter, and Balboa Park. From downtown you can also take a water taxi to Coronado Island and walk to the Orange Avenue district and to the Coronado city beach. Downtown is also a great spot to pick up the San Diego trolley, which can take you to Old Town, Mission Valley, and even Tijuana.
8. If you’re going to San Diego for the weekend, what should you not forget to pack?
To me, a pair of comfortable sandals is key. It’s the quintessential fair weather accessory. And unlike sunglasses, suntan lotion and bathing suits, you can’t just buy a broken-in pair of walking sandals at a gift shop. Believe me, you’ll thank me. There’s lots of great walking to be done in the region, and it’s always 100 times more enjoyable when your feet are happy.
9. When is the best time of the year to visit?
My favorite time of year is early September. The weather and the water are still very warm and most attractions are still open for extended ‘summer’ hours, but the crowds have dissipated. Plus, if you surf or bodyboard you’re likely to catch an early fall swell for some great waves.