You want a vacation spot with Pacific beaches, wine tasting, San Francisco Bay views, amazing dining, cultural activities, great golf, endless recreational activities, microbreweries and cool selfie spots.  You’ll find it all in one spot: San Mateo County/Silicon Valley. 

When you land on the San Francisco Bayside, you can head for a selfie in front of the iconic Facebook sign or Hewlett Packard garage.  Or you might start your trip with a wine class at the top notch San Francisco Wine School in South San Francisco. (You can follow a class with a visit to Armstrong Brewery downstairs.)

Once you’re feeling smarter, try an urban wine tour in the city of San Carlos.  Walk from Domenico Winery to Cuvee Winery to Russian Ridge to Flying Suitcase to Old County Cellars, getting your tasting on!   Consider heading to Noelani’s for Hawaiian food (and music), and then walk up the street to Savanna Jazz to catch a show.

Still in the hunt for food and wine?  Grab a ride or hop on Caltrain to Redwood City, where you’ll endless sidewalk cafes. Upscale restaurants abound, such as Donato Enoteca, LV Mar and La Viga. Want nightlife?  Enjoy dinner and a show at Angelica’s or catch a musical at the Fox Theatre.  Feeling more casual?  Head over to Gourmet Haus Staudt, a German beer garden and site of the legendary the lost Apple phone prototype.  And speaking of beer, locals love Freewheel Brewing Company in Redwood Shores.   

As your itinerary progresses, you may opt to head south to Palo Alto for a gourmet meal at The Sea by Alexander’ Steak House or the historic  MacArthur Park , or to A. Space Gallery in Menlo Park for some art appreciation.  Make sure to hit the free Cantor Arts Center, home to the world’s second largest Rodin exhibit.

Another option is to head north to the City of San Mateo, where restaurants and outdoor dining establishments are in abundance.  Enjoy a high end dinner at Porterhouse Restaurant with dry-aged steaks, seafood at Pacific Catch or an eclectic menu at the Zagat-rated Pausa.   Want seafood overlooking a scenic lagoon? Opt for the Fish Market.

For culture, stop at Filoli Mansion and Gardens, a National Historic Landmark .  Filoli has been used in multiple TV shows and movies, including Dynasty, Nash Bridges, The Wedding Planner, Heaven Can Wait, and Rent.  Drive past Crystal Springs Reservoir and head “over the hill”, to the Half Moon Bay/Coastside.  Make a stop at La Nebbia Winery for a tasting and bocce ball and stop for fantastic local seafood at Flying Fish Grill or a farm-to-table meal at Pasta Moon on Main Street. (For a pub-style option, try the historic San Benito House.)

On Main Street, stop by Barterra winery for wine tasting and chocolate.   And speaking of chocolate, you do not want to miss Sweet 55, a Swiss chocolate confectionery.  More options: outdoor dining and music with a view at the Half Moon Bay Brewing Company or Sam’s Chowder House or exquisite Peruvian food right on the water at La Costanera.  Another not –to-be-missed spot is Moss Beach Distillery, complete with a resident ghost. You’ll want to hike Devil’s Slide in Pacifica, a spectacular paved hike along the cliff overlooking the Pacific. Feeling ambitious?  Try the Portola Discovery Hike, celebrating the discovery of San Francisco Bay 250 years ago.  Fun stops in Pacifica include A Grape in the Fog wine bar, the iconic Nick’s Seafood Restaurant and Pedro Point Brewing Company.  Nick’s and A Grape in the Fog feature regular entertainment.  visitsanmateocounty.com.