The 13 most original date ideas for Valentine’s Day on the Peninsula

Swap out the chocolate, the flowers & the table-for-two mania with a new approach.

Original 650 Illustration by Kaz Palladino/Awkward Affections

A lot of our Valentine’s Days have looked the same: scrambling to find a dinner reservation at the ‘right’ place and bracing for the crowds of other couples attempting the same. The fact is that even if we somehow managed to forget about the sheer volume of people who are out to dinner to celebrate February 14, the whole dinner-movie-flowers-chocolate routine feels overdone to us — and we’re guessing you can relate…?

These days, we’re of the opinion that the best of what the Peninsula has to offer in the name of romance actually takes place pretty far from the dimly-lit table for two. So whether you’re celebrating as a couple, with friends or going it stag, take a new approach to Cupid’s carnival and check out our picks for an off-the-beaten-path Valentine’s Day on the Peninsula.

Scenes and a menu lineup from a previous Off The Grid. via Instagram

Off the Grid

OTG is easily one of our favorite (and frequent) food festivals to hit the Peninsula. If you’re not familiar, these guys organize different combinations of food trucks in open-air, casual environments that make for great laid-back date spots. Their collection of food trucks will be up in San Mateo from 11am-2pm on the big day (Valentine’s food truck lineup includes soul food, Mexican, Korean). We understand being partial to dining out on Valentine’s Day — here’s a way you can avoid the usual chaos while doing so. Best of both worlds.

901 Mariners Island Blvd, San Mateo

Irene Tu appears to really enjoy Valentine’s Day.

Have a Laugh

Maybe you pride yourself on your sense of humor, even when it comes to love. You’re more of a Meg Ryan in ‘When Harry Met Sally’ than a Ryan Gosling in ‘The Notebook’ — right? We know (and admire) the kind. No better way to honor that goofy side than the What is Love Comedy Show at the Dragon Theatre in Redwood City; the lineup has several notable names on it, including Irene Tu, who’s appeared alongside comedians like W. Kamau Bell (Bell called her “hilarious”) and Dro Knows, a similarly up-and-coming talent. Dragon Theatre will offer two showtimes — one at 7:30pm and another at 9pm. Doors open about an hour beforehand for music and drinks for both shows. Tickets are $20 dollars in advance (here’s the link), $25 at the door and $30 for VIP balcony seating.

Dragon Theater, 2120 Broadway, Redwood City, (650) 493–2006

A previous practice at Hapa’s. (Via Instagram)

Romance, Booze and…Yoga

Downward Drinking Dog will give it to you straight: whether you’re celebrating a Valentine’s Day gone well or hoping to forget a date that went horribly wrong, there’s no better way to reset yourself than arriving at your mat… and sipping on an IPA while you do so. Downward Drinking Dog will host ‘Valentine’s Day Aftermath’ on February 17 at Hapa’s Brewing Company, where guests are invited to have their beer either during or after their practice (and maybe before, as well). It’s no secret that we’re fans of these guys: owners Lori and Patrick are easygoing, encouraging and enthusiastic on the drinks. No need to worry about embarrassing yourself in front of your date, if you’re planning on bringing one — no prior experience with yoga is required. Tickets are here.

Hapa’s Brewing Company, 460 Lincoln Ave #90, San Jose, (408) 982–3299

A preview of what Wavecrest has to offer. (Image via Facebook)

Easy VD (sort of) Hike

Peninsula Open Space Trust is hosting a two-mile walk/hike on the Saturday following Valentine’s Day through Wavecrest Open Space, just above Redondo Beach on the coast. This isn’t meant to necessarily be a Valentine’s Day celebration, but it’s a chance for you (and whomever you’d like to ask along) to enjoy the outdoors and maybe celebrate some romance at the same time. If you’re the laid-back type who’s especially tired of the sit-down dating scene, this has your name on it. Sign up for free here — just note that attendees are asked to RSVP by February 9th, one week in advance.

Wavecrest Open Space, Half Moon Bay, (650) 854–7696

Romantic scenes at Filoli: sunken garden pond,(via Filoli’s Instagram).

Valentine’s Day Tea at Filoli

Filoli regularly catches our eye as one of the most scenic spots on the Peninsula — their gardens are date-worthy regardless of occasion, and their tea room is just the cherry on top (of the freshly made scones they’ll be serving, in this case). This year they’re opening up their tea room for a special Valentine’s Day tea service on Thursday and Saturday afternoons; admission includes a full tea (sandwiches, scones, dessert and tea, obviously) as well as admission to Filoli’s house and gardens (perfect for a post-tea stroll). Tickets can be purchased in pairs, as a group or individually — check out the details here.

Filoli, 86 Cañada Road, Woodside, CA, (650) 364–8300

Scenes from a previous West Bay season in 2014.

A Night at the Opera

Even if you’re a big believer in Valentine’s Day with an affinity for the classic when it comes to dating, it never hurts to stray from your regular routine. Dinner by candlelight is a solid idea, but a date to the opera? That’s romance, folks. Lucky for us here on the Peninsula, West Bay Opera is showing I due Foscari at the Lucie Stern Theatre in Palo Alto on Friday the 15th. West Bay is the second-oldest opera company in the West (after the San Francisco Opera); shows are truly high-quality productions, and English subtitles are always projected so that audiences can understand lyrics regardless of what language they might be in. Showtime is 8pm. Bring a date, shed some tears — you know the deal. Tickets are $85 for adults, $72 for seniors and $40 for students. Get yours here.

West Bay Opera at Lucie Stern Theatre, 1305 Middlefield Rd #1, Palo Alto, wbopera.com/contact or (650) 463–4900

(Image via Grape in the Fog’s Instagram)

Live Bluegrass Music

A Grape in the Fog is a fantastically quirky wine bar in Pacifica. Their love of live music, bar trivia and a good time is apparent in the many events they’ve put on in the past, and their location (literally steps away from the ocean) doesn’t hurt either. For Valentine’s Day they’ll have a live bluegrass performance featuring accomplished musical pair Jim Mintun and Avram Frankel. There’s no cover charge: just enjoy one of the many boutique wines on their menu or a small plate and some great tunes. On top of that, here are three words everyone wants to hear on Valentine’s Day: no reservation required.

A Grape in the Fog, 400 Old County Rd, Pacifica (650) 735–5854

Romance, on the water. (via Getty)

Sunset Kayak Tour

If you’re the outdoorsy kind (or your date is and you’re playing along in the name of love) REI will guide a kayak tour Wednesday night off of the Public Boat Launch in Redwood City. You’ll be just in time to watch the sunset on the water for Valentine’s Day Eve. Just think — no prix fixe menu to be found, and not a single overly-PDA couple in sight (although… no promises). And no stress, it’ll be a relaxed time; only a basic understanding of kayaking is required, as the tour is “beginner” level. Kayaks and all equipment are provided, though it’s requested that you bring your own headlamp. Make sure to reserve your spot here.

REI Mountain View Store, 2450 Charleston Rd Mountain View (650) 969–1938

(Image via the Los Altos History Museum’s Website)

History of Valentine’s Day

If all the chaos around making Valentine’s Day arrangements has you wondering why we even celebrate this holiday in the first place, this is basically the answer to your prayers. The Los Altos History Museum is offering free tours on February 9th that will answer all your questions. Topics of discussion will include the history of Valentine’s Day, its modernization and its place within society. There are two tours offered — one at 10am and one at 11:30am — that’ll leave you with plenty of time to enjoy the rest of your day and bask in the glow of (education about) love. Reserve your spot here.

Los Altos History Museum, 51 So. San Antonio Road, Los Altos (650) 948–9427

What’s sweeter than homemade sweets? (via Getty)

Something Sweet

Sometimes because of all the craziness that comes along with Valentine’s Day, we forget what’s really important. You know, the reason we’re even celebrating in the first place: the sweets. If you think like we do and consider Valentine’s Day the second coming of Halloween, cookie decorating at Fair Oaks Branch Library has your name on it (written in frosting, of course).

Librarian Maria Diaz-Slocum says that participants of all ages are welcome, so you’ll fit right in whether you’re on date or bringing the entire family.

“This is a multigenerational program, so younger and older people can decorate cookies together,” she said.

Fair Oaks Branch Library, 2510 Middlefield Rd, Redwood City (650) 780–7261

A table for two with a coastal view, at La Costanera in Montara.

Dine with a view

If you’ve been left unconvinced that Valentine’s Day doesn’t have to center around a dinner date, at least let us suggest some Six Fifty-esque places to make a reservation. Our picks for the sit-down route: The Mountain House in Woodside, notable both for its menu and the beautiful view of the woods from its all-glass dining room; La Costanera in Montara, which caters to our need for good Peruvian food and sea-side dining; and Alice’s Restaurant, a roadside fixture in Woodside that’s long had our heart for its tough-love type glamour. Alice’s also just put out a Valentine’s Day menu — tell your date to get anything they want.

The Mountain House, 13808 Skyline Blvd, Woodside (650) 851–8541

La Costanera, 8150 Cabrillo Hwy, Montara (650) 728–1600

Alice’s Restaurant 17288 Skyline Blvd, Woodside (650) 851–0303

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Sarah Klearman

East coast transplant working her way through all things Peninsula. On Twitter @SarahKlearman

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