1. It took me far too long to finally make the excursion out to San Diego and I regret not getting there earlier in life. San Diego is a great place for a vacation and can handle either a regular weekend trip or up to a week of fun. The best weather in the U.S. (monthly average highs between 65 and 77 degrees) means you’re outside doing shit at all times. Not surprisingly that means a heavy majority of the female population embraces wearing bathing suits year round by being in seriously good shape. There’s obviously the beach lifestyle to embrace, but the downtown scene is lively as well. It’s filled with a younger crowd that’s looking to chill out and have a good time. Throw in really good Mexican food along (the other comfort food is pretty good too) and a nice ballpark and it’s hard not to give San Diego a shot.
2. There’s really not a bad time of year to visit San Diego. Unlike a city like New York where there’s things to do year round, San Diego’s weather allows everything to be done year round. The summer does make things that much more fun because you’re more likely to hit the beach when it’s in the mid 70s every day. That slightly warmer weather means clothing on the chicks, which is never a bad thing. The military crowd is more prevalent during the summer, which doesn’t impact things too much, but the younger crowd might want to be around in the late spring and early fall when the college kids are the most prevalent.
3. You actually have to make a hard choice on location when visiting San Diego. Your two options are to stay downtown or to stay out in Mission Beach or Pacific Beach (aka PB), which are basically the same thing.Downtown is what you’d expect it to be with hotels being within walking distance to Petco Park, and plenty of bars and restaurants. Staying on the beach puts you near a more laidback crowd while giving you easy beach access. My nod is to stay downtown because you can always drive to the beach during the day and then bounce around downtown at night. (Cabs also run pretty easily back and forth and will cost you about $35 between the two destinations.) There are plenty of brand name hotels downtown, but staying near the Gaslamp Quarter is key since you’ll be going out there. Those at the beach should look into an house rental and fall back on the motels/hotels along the water if the housing thing fails. Anything within walking distance of the intersection between Mission Boulevard and Garnet Ave will leave you within reach to all the places you want to go out.
4. The three main beach options in San Diego are PB, Coronado, and La Jolla. The obvious option for the younger crowd is PB because that’s where the rest of the younger crowd lives. It’s a pretty laid back setting since they banned alcohol and raft drinking in the water about six years ago. You can still enjoy yourself with some volleyball (just bring you’re A-game because these guys are out there playing every day) and those all-year bikini bodies we talked about earlier. Coronado is a nicer looking beach (it shows up on top 10 U.S. beach lists rather often), but is more family oriented seems it’s heavily populated with the military crowd. La Jolla is a nice combination of the two, plus you can check out the sea lions hanging out in La Jolla Cove. (Just don’t get disturb them because they’re less friendly than they look.) You can also find some sparkles in the Coronado and La Jolla sand as both areas contain some gold looking mica.
5. Planning your trip around a Padres game is a no brainer if you make it to San Diego during baseball season. Tickets are reasonably priced since you’re not in a big market, so hopefully your team is in town when you’re there. There are plenty of cool elements include the warehouse built in to left field and the beach, which is connected to a park in center field that can be accessed on the cheap. Qualcomm Stadium isn’t the nicest place to see a football game, but at least there’s an NFL team to enjoy. (The real question might be for how long?) San Diego State is a little out of the way, but their basketball team has been a legitimate program for numerous years now. Finally you can get your gambling fix on at Del Mar racetrack where they have twilight racing starting at 4p on Friday, which is followed up by a concert. (Find yourself a cougar.)
6. Honestly there aren’t enough vacation days in San Diego to enjoy all the Mexican food it can offer, but boy should you try. The best fish tacos in town are at Blue Water Seafood Market & Grill. The fish is as fresh as it gets, can be cooked in a variety of marinades, and comes out in 4 oz. portions per taco. Focus on the lemon-garlic butter marinade and the halibut if you can. (You wouldn’t be bad off throwing that halibut on a sandwich either.) The clam chowder is also something that would make New England proud. Next door you can lock yourself into some great taquitos and a super chimichanga at El Indio. They make their tortillas fresh every day. San Diego is known for its California burritos (steak and French fries predominantly) and you can get a version of that (the Surfin’ California burrito) at Lucha Libre across the street. Other names for your Mexican food lists should be JV’s Mexican Food (huge burritos), Clayton’s Mexican Takeout, Carnitas’ Snack Shack, and South Beach Bar & Grill.
7. There’s not just good Mexican food in San Diego. As previously stated, there’s plenty of good comfort foods. The best burger in the area comes at Hodad’s. There are three locations, including the one at Pecto Park, but you should head to the Ocean Beach location for the true atmosphere. Be prepared for a line at all times of the day, but you’ll thoroughly enjoy the bacon patties on your burger. (Yes, I said bacon patties.) You might not expect good barbecue in San Diego, but Phil’s BBQ hasn’t been featured on numerous shows because it sucks. Get the El Toro and the ribs. San Diego shouldn’t be known for pizza either, but it somehow just topped Trip Advisor’s list of best pizza cities. That’s obviously not a statement I agree with, but getting your share of Bronx Pizza and Pizzeria Luigi. The best brunch spot is Hash House a-Go-Go, where you’re obviously getting a type of hash. (The French toast aint bad either.) Mateo’s Hot Spot in PB is your go-to for late night hot dogs on the weekends. Finally you can class it up downtown with meals at Searsucker (get the duck fat fries, the short rib, and the shark), Market Grill, or J Wok.
8. The downtown bar scene in pretty of a major city. All the action is in the Gaslamp District. Whiskey Girl is your typical high-energy bar with top 40 music and dancing. The Tipsy Crow has a nice contrast between a low-key main floor and a basement dance floor to get dirty with top 40 and some old school hip-hop. Bootleggers is set for an older crowd, but can still be a nice hookup scene. Basic’s got a nice rooftop and is near the ballpark. The Shout House offers the dueling piano scene that’s gained popularity nationwide in recent years. Surprisingly there’s a pretty big club scene downtown as well. 207 in the Hard Rock is part bar, part club, but it has blown up as one of the best downtown spots. Float upstairs on the roof has a Vegas like pool scene on Sundays, but is pretty good at night too. The Andaz has the Ivy rooftop and the Ivy nightclub downstairs. Stingaree gives you three floors including a rooftop. Bassmnt has only been open since April, but is already attracting a large and attractive crowd.
9. The scene changes when you make it over to PB. The scene is much more low-key, as you’d expect on the beach, but that doesn’t mean people aren’t getting fucked up. Hitting the PB Shore Club is a must while you’re in town. Things get pretty intense there on Saturday and Sunday afternoons. The Red Bull slushies will get you all kinds of fucked up. People go there in their least-fancy dress, hang out, get blitzed, and hook up. The other main action in PB is at Tavern at the Beach. They remodeled the inside recently, but the scene is the same. It’s the closest thing you’ll get to a downtown bar out by the beach as the dance floor heats up on the weekend nights. Thrusters gives you similar DJ and lounge type action. If you want to go full on club, you can roll over to Bar West. The Firehouse, across the street from PB Shore Club, is a more relaxing experience with rooftop seating. Beachwood also has a good rooftop situation.
10. There are two other things that should be on your San Diego agenda. The first is something called flyboarding and is offered in the marina. You pay $150 for 30 minutes on a skateboard-type thing that has water pumped into it via a hose and then pushes water out through jets on the bottom. This allows you to raise above the water as the jets use the water push you away from the surface. It’s an unmatched experience for something looking for something different. Secondly, you’ll want to check out the numerous breweries. There are too many to cover (44 microbrews out right now) in one trip, but those of note include Ballast Point, Green Flash, Societe, Helm's, Thorn Streey, Karl Strauss.