10 Out-of-the-Ordinary San Diego Date Ideas

Rent a 2-person kayak at The Catamaran Resort on Mission Bay and paddle over to the water show at Sea World – you get a “behind the scenes” view and you see the show for free. Bring some home-made snacks to munch on (I’m a sucker for the old school PB&J) while you watch and you’ll really score some points. Link to the Map

OB is not typically know for its romance (unless hanging with dreadlocked hippies makes your heart go pitter-pat), but there are some nice cliffs that over the look the ocean that make for a great picnic site. Hit up Olive Tree Market to pick up some wine and some snacks from their wide selection of meats and cheeses. Add a blanket and a sunset and you have a great date. Link to the Map

There is some prep required for this date. It only happens a few times a month, so you have to sign up for their email newsletter to make sure you don’t miss the date. It’s far better than your average putt-putt/mini-golf. A short 9-hole course looks spectacular when the night is lit up by multi-colored, glow-in-the-dark golf balls whizzing past. End the evening with a glass of wine and some pizza at Wine Steals, conveniently located at the end of the 9th hole. Link to the Map

These classes take place in a nice, intimate atmosphere where you watch a chef prepare a multi-course meal before your eyes. Afterwards, you are given taken home materials in case you really want to try cooking a dish for your sweetie that a professionally trained chef cooked for him/her (good luck with that one). Link to the Map

Thought gondola rides were just for Venice? Think again friends. You can hire your very own Gondola right here in San Diego! At The Gondola Company in Coronado you can hire a Gondolier to paddle you around the waterfront, showing off some of San Diego’s most expensive homes. Bring some strawberries and champagne for the ride to score points. Score bonus points if while on the gondola ride you announce to your date you just closed escrow on one of the house you just passed. Link to the Map

7. Concert on the Sea
Find yourself a friend with an inflatable boat & a little electric outboard motor (or take that kayak you rented in date #1). Park your car at Canon Street and take your choice of water-vehicles out to Humphreys for a Concert by the Bay.
You’ll find yourself among an entire lot of “boat people,” having a great time and drinking. Don’t forget your own bottle of wine, a bottle opener (there’s nothing worse than having a great bottle of wine and no way to open it) and a couple of glasses. It’s a 4 hour tour without a bathroom, so make sure you give your date fair warning. Stop in the loo before setting sail for Humphreys. Link to the Map

Nothing says “fun date” like doing something where you have the potential to die. Grab your sweetie and hop into a 10×10 basket attached to gigantic balloon, rented from Hot Air Flyer in Del Mar area. You’ll sail over Del Mar and Rancho Santa Fe fantasizing about owning one of the expansive estates you see below. Link to the Map

If you’re adventurous and like hiking, here’s a great one for you – Cedar Falls. Don’t get any ideas about cliff jumping from this site, just note down the directions – they’re the best description of how to get to Cedar Falls that we’ve seen.

Most people in San Diego don’t know that we have a beautiful waterfall in our own backyards. It’s 4.5 miles roundtrip and if you want to see the waterfall, you have to go in the spring (the rest of the time, it’s pretty dry).

If you go at the right time, you’ll also get to impress your date with all the gorgeous desert flowers. It is a strenuous hike, downhill to the waterfall, but the return trip is all uphill. Don’t forget your camera (lots of amazing photo ops along the trail), bring lots of water, a hat, sunscreen, a suit/towel if you want to swim and it’s a long day, so bring some food (sandwiches, power bars, you get the idea…).

Much love to Licia for this one! Everyone knows that Temecula is great for wine tasting, but with so many wineries, how do you know where to go? Here’s your 3-stop plan guaranteed to make a great date:

First, stop at the Wilson Creek Winery. You may have heard about their Almond Champagne, but have you heard of their Decadencia Chocolate Port? Both are delicious and unique drinks. Mix them together for to create an Almond Joy – its amazing!

Then move to Maurice Car’rie Winery for their baked garilc sourdough brie. They take a giant loaf of sourdough bread and stuff it with brie and garlic. It’s even more tasty than it sounds and you can’t beat it for $15.
Finally, finish off the afternoon at Calloway. Calloway is know for their fine selection of wines and the relaxing atmosphere at the winery is the perfect way to wind down your afternoon.

Best part about this path is that its easy to follow: Wilson Creek is at the end of the road that winds through the wineries and Calloway is at the beginning. Start at the back and move your way to the front. Link to the Map

11. BONUS – cheap date alert!!! Cinema Under the Stars.
This is really one for the guys to score some points – pure romance. Remember those old black & white Audrey Hepburn movies? Bogie & Bacall anyone?

It’s a little (and we mean little – only 30 seats) outdoor theater in Hillcrest that looks like someone’s backyard. Seats are $13.50, but if you reserve early (and it’s worth it if you do), you can snag one of their cozy 2-person cabanas. There are only 3, so plan ahead. It’s got a little loveseat where the two of you can snuggle up and enjoy an old romantic movie.

If you miss out on the cabana, no worries, they have fully reclining lounge chairs AND they provide blankets too! We can’t say enough good things about it – love it!