Ocean photographed from atop a hill.
Rocky coastline.
Down by the Bay
Down by the Bay
Down by the Bay
Two people walking on a path surrounded by bare trees and toward the water

Down by the Bay

5.0 (3 reviews)

From $39

You don't have to go far from home to have an epic adventure! The scenic viewpoints and easy trails are endless on this trip. And while you won't see watermelons grow, there are tons of fantastic local eateries along the way.
When to Go Any day of the week
ends near Half Moon Bay, California

Choose your format:

  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

essentials for your trip

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package...

$5

Trip Highlights

  • A unique WWII photo op
  • The tastiest local cafes and breweries
  • Epic views around every corner
  • Wildflower blooms (March - June)
  • A haunted lunch stop
  • Multiple recommendations included on every stop

How Long Is This Trip?

Please see the approximate driving distances below. This just includes round-trip driving distances and not time spent at stops.

Don't see a city close to home listed below? Send us an email with your departure location and trip choice(s), and we'll give you an idea of the round-trip driving distance from home.

From San Francisco: 1 hour and 30 minutes / 60 miles

From Oakland: 1 hour and 50 minutes / 80 miles

From Fremont: 2 hours and 4 minutes / 96 miles

From San Jose: 2 hours and 10 minutes / 103 miles

From Santa Rosa: 3 hours and 26 minutes / 160 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

When Can I Go?

Days of the week: Any day

Seasons: Year-round

Not recommended: Holidays

Shipping & Returns

Shipping: Free shipping on orders over $100. Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

Down by the Bay

5.0 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

Explore All Road Trips

Frequently Asked Questions

View All FAQs

What People Love About Our Trips

Rated 4.9/5.0 stars

What an Amazing Day!

Our daughter gave us this for Christmas and we finally pulled it out this week, July now. We love a road trip and loved the mystery of each new step. Great things to see and experience. Great restaurants to enjoy. I’ve recommended it to all my friends. Amazing.

Donna S. 🇨🇦

First Time…There WILL be a second!

Knowing the area we went I was very pleasantly surprised. We saw things I did NOT know existed! One of the stops was closed however we were able to walk up to it for a photo.

Mary Y. 🇨🇦

Great day away!

Did this trip with my mom for Mother’s Day. Lots of quaint little stops and places to explore! They also gave a few options at each stop so you could choose your own adventure! Will definitely be doing this again, had a wonderful time!

Megan M. 🇨🇦

Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

More Experiences You'll Love

2,328 verified reviews

See Where Our Road Trips Took Them

“It was such a fun experience!”

@traveling_foodqueen

"The most fun, stress-free way to explore Ontario”

@ thevacaygirl

“Trust me, you need to try this”

@the_winged_rhymester

“I still can’t get over how fun it was”

@her.travel.adventures

“Guess Where Trips thinks of everything”

@wanderfarspendless

We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.