Need help planning your next date? Here’s a list of fun, unique, and romantic date ideas in San Mateo and the bay area.
For couples who are physically active, consider themselves foodies and favor unique experiences and good vibes.
Local perspective from a relationship coach in San Mateo, CA who also enjoys dating her husband!
Let’s start with things to do in San Mateo and bay area during the day.
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ToggleOutdoor Activities in San Mateo
Here are some really fun active ideas for your date!
Go hiking at Purisima Creek Trail and head south on Skyline to Thomas Fogarty Winery for wine and views.
Purisima Creek Redwoods Open Space Preserve is located on the western slopes of the Santa Cruz Mountains. Experience the magnificence of towering redwoods there (tallest trees in the world, up to 380 feet tall!) and breathtaking views of the coast including Half Moon Bay, which is visible from the northern part of the preserve.
Purisima Creek Trail is 5.8 miles long but the distance from the start to the end is only 2.1 miles along the road. Here is a great blog article on how to hike the Purisima Creek trail.
Thomas Fogarty Winery is located south of Skyline Boulevard, which is Route 35. Stop by for a wine tasting and to learn about sustainable farming practices.

Explore Half Moon Bay San Mateo to watch the sunset on the beach and walk through their cute downtown area.
Half Moon Bay San Mateo is 10 miles west of San Mateo with its beautiful California countryside, easy access to the beach, plentiful open space, lush rolling hills, farm land and state parks, It is easily one of the most serenely gorgeous places anywhere.
Things to do in Half Moon Bay: hiking, exploring downtown restaurants, shops and wineries, relaxing among miles of expansive sandy beaches.
Pick a day to visit Filoli Garden and enjoy the afternoon English tea together.
Filoli Garden is vibrant landscape of the Bay Area. The huge estate features 654 acres on the slopes of California’s coastal range. Roam the Georgian revival-style mansion, 16 acres of English Renaissance gardens, a 6.8-acre Gentleman’s Orchard, and hundreds of acres of Natural Lands with 6 distinct ecosystems and nature trails.
What you can do there: explore the Filoli family estate home, stroll the gardens, walk the self-guided trails, shop for trinkets at the Clock Tower Shop & Nursery, have an afternoon tea complete with tea sandwiches and mini desserts at the Quail Cafe, and visit the Staghorn Bottleshop which is perfect for the connoisseurs of fine wine, artisanal spirits, and curated bottles (Sat & Sun Only).
To figure out what to bring, which flowers are in bloom season and for other information, check out their website.
Enjoy Historic Murphy Avenue, a perfect date spot to walk around with plenty of parking, shopping and dining.
Perfect for history buffs, foodies and shoppers, Sunnyvale Heritage District is an hour south of San Mateo. The district is home to Historic Murphy Avenue, one of the tree-lined avenues featuring early 20th century buildings, eclectic shops and local galleries. Great for walking, shopping, enjoying California sunshine and occasionally stopping at a cafe, brunch or an ice cream parlor.
Take a walk through the San Mateo Japanese Garden and rose garden in Central Park, San Mateo.
Located in downtown Central Park is a 16.3-acre property, home to the Japanese Garden, in San Mateo Central Park , one of the finest gardens in California. Features a granite pagoda, tea house, koi pond and bamboo grove.
The Japanese Garden is beautiful throughout the year, but be sure to visit in the late Winter and early Spring when the cherry blossoms are in bloom. Be sure to feed the koi fish during Spring and Summer.

Hike up to the top of Sugarloaf Mountain Open Space to catch the sunset.
Sugarloaf Mountain Open Space is a 1.25 mile loop through woods to grassy hilltop in San Mateo. It’s a fairly easy hike, although one stretch is very steep. It takes 1 hour to hike. Enjoy the panoramic views. On clear days, you’ll be able to admire San Francisco, the bay, Santa Cruz Mountains, and East Bay hills.
For detailed instructions on hiking this trail, visit this helpful article.
Hike the Pedro Mountain Trail and relax at Montara State Beach, with its amazing view of the ocean.
McNee Ranch State Park is located in San Mateo County, in the Santa Cruz Mountains, east of Highway 1, and overlooks Montara State Beach.
To the east, McNee Ranch, also called Montara Mountain is a mountain habitat with trails and views of the coast. The ranch’s two-mile Pedro Mountain Trail connects to Montara Beach.
Montara State Beach is popular for sunbathing, strolling, nature study and surfing.
For park information and hours of operation, visit their website.
Indoor Activities in San Mateo and Bay Area
Now, for some indoor activities!
Problem solve at the escape room at Red Door Adventures/Hillsdale Mall.
Get a greater appreciation for each other’s skills and talents and work on communication and problem skills together while trying to solve the puzzle at the best escape room in San Mateo. So fun to do with your partner!

Hit some golf balls at the driving range at Mariners Point.
Mariners Point driving range has clear target greens, yardage markers, and some mention a short game practice area with bunkers and greens.
Enjoy ice skating in San Mateo.
Check the Nazareth Ice Oasis website fir their public sessions schedule.
Experience the Sandbox VR in San Mateo.
A little pricey but definitely worth it for the fun experience. Sandbox is a futuristic VR experience for groups of up to 6 where you can see and physically interact with everyone inside, just like the real world. Inspired by Star Trek’s Holodeck, this exclusive world let you feel like you’re living inside a game or movie.
This probably sounds really out there, feel free to confirm whether this is for you on their website.
Learn to dance Tango and Salsa with classes at the Motion Arts Center in San Mateo.
You do not need to be dancers already. Show up in whatever attire you are comfortable in and take a beginner Latin dancing class at the Motion Arts Center in San Mateo. For information and a class schedule, visit their website.
Take a glass-blowing class at the Art Glass Studio inside La Nebbia Winery.
La Nebbia Winery is a boutique Winery located in the coastal town of Half Moon Bay. You can sit in their Garden and enjoy table-side service all year round and enjoy a tasting flight or buy a bottle to take with you.
What’s even cooler is that you can take an artistic glass-blowing class at this winery to get creative and learn a new skill together.
San Mateo Budget Date Ideas
Here are some budget date ideas for you and your partner, in case money is tight at the moment.
- If the weather cooperates go to a farmer’s market and have a picnic! There’s a great one at the College of San Mateo, and the Burlingame one isn’t bad either. Grab some snacks and a bottle of wine. Go to San Mateo Central Park and enjoy the Zen.
- Drive along Skyline. The transition from sunny hills into heavy woods within minutes is fun for out of towners, plus there are lots of hiking trails.
- Go to the computer science museum in Mountain View, get the Groupon tickets online.
- Drive-in movies! Bring dinner and snuggle to a good movie.
- San Mateo downtown movie theater has discount tickets Tuesday.
- Coyote Point ($6, cash only) and Seal Point (free) are great places to walk by the water.
- B Street and Vine in downtown San Mateo is relatively inexpensive for both wine and food. Not super fancy but nicer than most places in that price range.
- Get Pancho Villa to go, and eat it in the park enjoying the fresh air together.
- Split a sub sandwich and a bottle of wine from the grocery store. 🙂

Local Tips & Insights For Your Date Night In San Mateo:
- Date on Sundays. It’s a lot easier to get a table without reservations.
- San Mateo is a laid back city. If you’re looking for night life and fun, San Francisco is where you want to be. The Marina and Mission in San Francisco districts are great for nightlife.
- Public transportation is not the best in San Mateo. While San Mateo does have access to public transportation options like Caltrain and SamTrans buses, many consider the system to be not very comprehensive, with limited routes and potential inconvenience for getting around within the city, making it less than ideal compared to other Bay Area locations.
Restaurants in Downtown San Mateo and Bay Area
After a day full of activities, you will likely be wiped out and hungry. I have put together a list of restaurants in downtown San Mateo that will satisfy your craving. Below are gluten free restaurants in San Mateo as well.
- Mykonos in downtown Burlingame, 2 miles from downtown San Mateo, has amazing Greek spreads and small plates.
- Trapeze is in close proximity to San Mateo for quaint Italian.
- Dash in downtown San Mateo is great if you like Sushi.
- San Mateo ramen is a thing here. Ramen Dojo is pretty amazing. Himawari is also really good and has a nice jazz vibe with the records on the wall and music. Kajiken is a popular dry ramen place.
- Pausa in San Mateo. If you find yourself at Pausa, order the Sfumato cocktail from the dinner menu.
- Tamari in San Carlos is a Georgian restaurant. The lamb kabobs are the best.
- Mortar & Pestle. Backyard curry spot – hidden & chill.
- Gao is really, really good. There is a wait but I promise you it is worth it and not overpriced. You can get a drink at the bar upstairs while you wait as well.
- Espetus if Brazilian steakhouse is your thing.
- Amour Amour is one of the best date night wine bar and tapas spots in San Mateo. Great food, excellent wine selection, cute place, super friendly and family run.
- La Costanera for a nice Peruvian dinner.
- Sourdough lovers: Backhaus has a really crusty (in a good way) loaf and Copenhagen Bakery in Burlingame has a tangy loaf.
- Enjoy some yummy dessert/crepe cakes from Luluyum.
Gluten Free San Mateo (and nearby) Dining
- Asian Box in Burlingame has a gluten free kitchen! They really should advertise it more.
- Pausa is able to accommodate in case of celiac disease.
- True Food Kitchen in Palo Alto.
- Sweet Diplomacy bakery in Los Altos.
- Centonove in Los Gatos.
Now let’s get into things to do after the sun goes down!

Things To Do In San Mateo At Night
If you are ready for a long day followed by a fun night, here are some bar and night entertainment recommendations.
Bars In Downtown San Mateo and surrounding areas.
- Hop Dogma, Half Moon Bay Brewing or Fieldwork for beer. If you go to Hop Dogma, grab take out from the Peruvian food truck in the parking lot
- Fogbird for a good (expensive drink).
- Wunderbar has a nice speakeasy vibe to it (not open Sundays). It has excellent drinks, a great vibe, and is just a super relaxed date night place. It’s quieter and less crowded and the service reflects it. Reservations must be made way in advance.
- Dueling Pianos at Faith & Spirits is great for date night. Craft cocktails and live music nightly. It’s usually empty(ish) on Sundays so perfect for a chill date night with great drinks.
- Comedy Show: Grapes and Giggles at Domenico Winery.
Want to truly transform your relationship?
Dating each other is an important part in maintaining a healthy and happy vibrant relationship. This is a small and integral part of the overall work required to enjoy each other for years to come.
If you really want to take your relationship to the next level and gain insights & tools to transform your communication, understand each other’s needs on an intricate level and further uplevel the foundation on which your love was built, a dating coach is an amazing investment.
Want to have a heart to heart consult with a certified relationship coach?

About The Author:

Hi! I’m Julie, a certified relationship coach for couples and singles.
Through my work, I empower couples to break free from patterns of disconnection and not only envision but create a revitalized relationship where love is not only rekindled but strengthened. Together, we explore strategies to reignite passion and growth, fostering a profound connection that stands the test of time.
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before you go
A little love note from Julie
I want to tell you that I’m here for you. If you’re having a tough time with love or just want to make your relationship stronger, I can help.
Everyone deserves a happy relationship where they feel loved and understood. Let’s work together to make that happen for you.

