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1. Where to Go: Napa
Napa is perfect for a day trip or, better yet, a weekend getaway. If you really want to make things special, we recommend booking a sunrise hot-air balloon ride. While you do need to get up extra early for this one, the views of Napa Valley are more than worth it for the experience.
What to Wear: We suggest light layers. Maxi dresses or skirts with additional top layers make the perfect pairing. Make sure to bring a jacket along as it can get a bit windy. We're all for adding a denim jacket (scroll up for proof).
Where to Shop: HeidiSays. This is one of our favorite shops and has a great mix of designer options to keep you stylish and cozy—in the air and when you're back down to Earth. HeidiSays is located at 2426 Fillmore Street.
2. Where to Go: Top of the Mark
If dinner and dancing is your thing, Valentine's Day at Top of the Mark will have you jumping for joy. Not only does the rooftop bar at the top of the Mark Hopkins Hotel offer amazing views of the city and a glamorous downtown vibe, but the live band makes it impossible to sit still.
What to Wear: Skip cliche color options like pink and red for this dinner date and opt for a classic LBD. Sometimes the more understated the look, the more you stand out. If you do need a pop of color, we recommend a bold, red lip.
Where to Shop: Elizabeth Charles. A high-end boutique in Pac Heights, it's filled with lust-worthy designer goods from Carven, 3.1 Phillip Lim and Acne Studios. It's the perfect spot to find that special look. Elizabeth Charles is located at 2056 Fillmore Street.
3. Where to Go: Crissy Field
Not every February 14th activity requires a large budget. We're lucky that SF has some of the most scenic views in the world. For a low-key date, we're all about a bike ride along Crissy Field. If the weather is favorable, throw in a picnic on the Marina Green with spectacular views of the Golden Gate Bridge for an idyllic way to spend an afternoon.
What to Wear: Keep your outfit casual with boyfriend jeans and a pair of classic white sneakers. There's nothing better than being comfortable yet still stylish. Just, add a hat, some chic sunglasses and pedal away.
Where to Shop: Les Merchantes. We love this boutique, which features local designers and trendy accessories. While best known for its beautiful caftans, you'll find a selection of dresses, sweatshirts, graphic tees and more. Bonus: The shop is located in nearby Ghirardelli Square so you can pick up some chocolates en route. Les Mechantes is located at 900 North Point Street.
4. Where to Go: Sundance Kabuki Cinemas
There's nothing better than the classic dinner-and-a-movie date. Sundance Kabuki Cinemas combines the best of both worlds. Grab a bite and a cocktail beforehand, or enjoy during the movie.
What to Wear: Since you're heading to the movies you don't need to get overly dressed up. Try mixing feminine and edgy pieces like a chiffon dress with a leather jacket and booties.
Where to Shop: Union Square. We know it can be touristy but it really is a great shopping area. Hit up Post Street first, which has Zara, Saks Fifth Avenue, DSW, and H&M.
5. Where to Go: Barrel House Tavern
If you're looking to get out of the city but a trip to Napa or Sonoma is too far, check out Sausalito's Barrel House Tavern. Aside from the great food and drinks, it's located directly on the water and offers stunning views of the Bay and the city. After dinner, take a stroll through ever-charming downtown Sausalito before taking a ferry back to the city.
What to Wear: This spot tends to see it all in terms of attire, but that doesn't mean you can't get dressed up. Instead of a dress, try a slightly different option like a jumpsuit. Still special but also keeps you warm on the Ferry ride.
Where to Shop: BellJar. With an eclectic mix of gorgeous dresses, stand-out jewelry, and funky home decor, it's a great spot to find unique pieces that you can show off while taking in the views of the Bay—or anywhere. BellJar is located at 3187 16th Street.