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Night out plans? This laid-back escape takes you to San Jose’s first food hall, San Pedro Square Market, where you can indulge in the best local flavors while chilling in a plaza with rows upon rows of string lights and live music. Then, you’ll catch the latest film at a drive-in movie theater. 


Here's your plan for a laid-back night in San Jose: Enjoy food at San Pedro Square Market, followed by a drive-in movie at West Wind Capitol Drive-In

San Jose: Food, Tunes, & Drive-In Movies🍿🎥

At San Pedro Square Market, enjoy an array of local flavors, drinks, and live music in a vibrant outdoor patio setting.

Food and Music

✅ Before you go
• There’s multiple parking garages available near or walking distance to the square. If you park in one of the city operated garages, you get 90 minutes free
• Street parking is also available and if you’re there after 6pm, it’s free on most streets 

💪 Pro tips
• Keep an eye out on traffic times, especially on the weekends when they fluctuate

Eat, Drink, and Chill at San Pedro Square Market 

Enjoy a classic movie experience at West Wind Capitol Drive-In, complete with cozy setups and a variety of films under the stars.

Drive-In Movie

✅ Before you go
• Buy your tickets online in advance: https://www.westwinddi.com/locations/capitol
• The first showing starts around 9pm with a second showing at around 11pm
• You will need a working car radio or portable radio to hear the movie

💪 Pro tips
• Bring anything to help you get cozy – blankets, pillows, etc. 
• Spots are on a first come, first serve so get there early to snag a good seat
• You can bring in snacks and pre-cooked food (like pizza) but no alcoholic drinks are allowed
• If you’re a first timer, finding your screen might be confusing so when in doubt, ask a friendly neighbor or check with the staff
• To allow for the best viewing, the parking spots are designed with a slight angle. If you have a lower bumper, stick to the spots that are on level ground or whose angle is smallest.  

Catch a Movie at the Drive-In Theater

I like to escape to San Jose where the food and vibes never disappoint.

And I can enjoy the latest movie release in a classic drive-in theater.

And if you're a foodie like me, this is going to feel like paradise.

This time around, we couldn't resist the tacos because

well, how could we pass on something like that?

But the soul of this place is really outside.

The patio was buzzing with live music and dancing.

We would have stayed here too, but it was time

to head to West Wind Capital Drive-In Theater.

Once in, we snagged a great spot right in front of the screen,

hit up the concessions for some necessary popcorn

Honestly, nothing beats the nostalgia here.

So we settled back, tuned into the movie's frequency,

Craving a laid-back escape? Save this plan for your next night in San Jose.

Escape to the windswept beauty of Point Reyes for a day filled with sparkling mead sipped among wildflowers, fresh oysters enjoyed with sweeping views of Tomales Bay, and rich, handcrafted cheeses from a family-run creamery. With stunning coastal scenery and indulgent local flavors, it’s the perfect blend of relaxation and discovery.

The Perfect Day Getaway to Point Reyes

Visit Heidrun Meadery in Point Reyes Station for a meadery tour and tasting experience featuring their naturally sparkling meads.

Mead Tasting

✅ Before you go
• Make a reservation at https://www.heidrunmeadery.com/Visit

💪 Pro tips
• The Meadery Tour and Tastings are only available on Saturdays from 1130a to 1230p
• If you’re unable to attend a tour, they have affordable tasting flights where you can sip and enjoy the beautiful scenery
• They have a Beekeeping Experience monthly on select Sundays where you can don a beekeeping suit and do the hand-extraction to jar up their estate honey to take home. Check their website for specific dates

Head to Heidrun Meadery

At The Marshall Store in Marshall, enjoy a hearty Shrimp Po’Boy while overlooking the splendid Tomales Bay views.

Shrimp Po'Boy Eating

✅ Before you go
• Check out their menu at https://themarshallstore.com/the-menu

💪 Pro tips
• Everything we ate was delicious, but our fave was the Shrimp Po’Boy Sandwich
• If you plan to eat outside, make sure to bring a jacket as it can get a bit chilly

Meet at The Marshall Store

Head to Point Reyes Farmstead Cheese Co. for a cheese tasting, where you can sample a variety of cheeses and meet the cows.

Cheese Tasting

✅ Before you go
• Make a reservation for a cheese tasting at https://pointreyescheese.com/pages/tastings-at-the-farm

💪 Pro tips
• Farm brunches and dinners are typically held in the Summer and Fall. Check out the dates and make a reservation at https://pointreyescheese.com/pages/farm-dinners-brunches
• They offer an assortment of cheeses to sample – the Gouda was my favorite!
• Say hello to all the cows on your ride there

Drive to Point Reyes Farmstead Cheese Co.

a unique winery specializing in naturally sparkling meads crafted from honey,

which they also make in-house and have different flavors.

We came for their meadery tour and tasting,

and it was so fun taking a tour throughout the space

and learning so much about how their meads are made.

and my favorite part of the tour was when my flute was being refilled.

We got to see the bees and their colonies hard

at work and even people racing to get more mead.

Check out the hidden spot under the tree,

but maybe not the twirl cheers combo that no one asked for.

I definitely needed sustenance at Marshall's Store

We headed to Point Reyes Farmstead Cheese Company,

where they're known for their cheese making.

We had to sample their cheeses and everything was delicious,

so I obviously need to have a photo op with the cow that started it all.

A serene, one-of-a-kind day spa experience in Freestone—featuring a Japanese tea garden, cedar enzyme baths, and a peaceful Zen meditation garden. Perfect for reconnecting with friends and finding deep relaxation in nature

One-of-a-kind day spa in Sonoma county 🛀🪷

Relax at Osmosis Day Spa Sanctuary in Sebastopol with serene Japanese gardens, cedar enzyme baths, and Zen meditation for sublime peace and detox.

Spa Day

✅ Before you go
• Book in advance – Cedar enzyme baths and group packages fill up quickly, especially on weekends. Book here: https://osmosis.com/home/
• Arrive early – Give yourself time to relax into the space and enjoy the tea garden before your treatment.
• Dress comfortably – You’ll be changing into spa robes, but loose, cozy clothing is best post-treatment.

💪 Pro tips
• Hydrate well – The cedar bath encourages detox through sweating, so drink plenty of water before and after.
• Bring a journal – The meditation garden is a beautiful space for reflection and writing.
• Don’t rush off – Leave time to linger in the Zen garden or hammocks after your treatment—it’s part of the magic.
• Stay quiet – Embrace the stillness—Osmosis is designed as a sanctuary, so keep voices low or enjoy silence.
• Go on a weekday – It’s quieter, more serene, and often easier to book prime times.
• Pair the cedar bath with a massage – The bath warms your muscles and makes the massage even more effective.
• Visit with a small group – 2–4 friends is ideal for shared experiences while keeping it peaceful. 
• Request the tea garden room – For the full experience, ask to enjoy your tea in the private garden-view space.
• Leave your phone behind – Truly unplug for the day; there’s little to no service anyway, and that’s the point.
• Plan for lunch nearby – Wild Flour Bread is just down the road and perfect for a post-spa treat.

Head to Osmosis Day Spa Sanctuary 

Sometimes day trips are noisy and overbooked,

but a quiet spa day in Sonoma County hits differently.

We escaped to Osmosis Day Spa in Freestone for a quiet day with friends.

it felt like we had entered another world.

We were greeted with a warm smile and soft robes,

sipping herbal tea while surrounded by koi ponds and sculpted pines.

This wasn't the thick mud bath we pictured.

the soft cedar and rice bran mixture cocooning our bodies.

The fermented bath improves circulation and naturally detoxifies the body.

it was a ritual we didn't know we needed.

Wander the box SF and sift through over 15 million vintage age items 

Here's your plan for exploring vintage treasures at The Box SF in SoMa. Enjoy

Wander a vintage warehouse 

Explore The Box SF in SoMa, San Francisco, a treasure trove with over 15 million vintage items, perfect for trinket enthusiasts and vintage collectors.

Vintage Warehouse Exploration

💪 Pro tips
• open drawers, lift up boxes, and really explore 

The Box SF 

Inside an unassuming building in Soma is the Box SF.

With over 15 million unique vintage pieces,

the owner has accumulated everything from matchboxes and stamps

to functional printing presses from the olden times.

Outside of this room is a mix of the most random and eclectic vintage items.

I really enjoyed looking through the stamp collection with

collectors items and stamps from around the world.

Rifling through boxes and pulling out drawers just to find more items

made the entire shopping experience feel like an Easter egg hunt.

If you're a trinket person or have an eye for a vintage,

Channel your inner Tiburon local with caviar from a sister-founded SF spot, then wrap up the afternoon with waterfront drinks at a classic favorite.

Here's your plan for enjoying caviar and light bites, followed by drinks in Tiburon

Caviar & Light Bites in Tiburon

At The Caviar Co. Tiburon Champagne Lounge, indulge in a wide selection of caviar and light bites on a sunny patio.

Caviar Tasting

✅ Before you go
• Book a reservation in advance: https://www.opentable.com/r/the-caviar-co-tiburon

💪 Pro tips
• Grab a patio seat if the weather’s nice
• They have eight types of caviar and four kinds of roe from around the world
• We loved the Ruby Caviar Flight, Chips & Dip, Charcuterie Board, and Deviled Eggs  


Enjoy Caviar & Light Bites

At Sam's Anchor Cafe in Tiburon, enjoy waterfront vibes with frozen drinks and light bites, no reservations needed. Join the waitlist and start with a drink at Malibu Farm Bar.

Frozen Drinks & Bites

💪 Pro tips
• No reservations, so join the waitlist and grab a drink at Malibu Farm Bar while you wait
• Their frozen drinks and mojitos hit the spot on a warm day

Grab Frozen Drinks & Light Bites

If you've been waiting for a sign to spend the day in Tiburon,

I've always been very curious about caviar,

but we did grab a seat outside since it was such a nice day.

We ordered a caviar flight with a few small bite options,

but beware, some of the caviar does pop in your mouth like boba,

we headed to Sam's Cafe for drinks right on the water.

we had to try a few of their fan favorites.

It just felt like the right way to end the day.

This was one of the best ways to spend an

afternoon and I'm now fully manifesting that Tiberal lifestyle.