A Long Bike Commute from SF to South Bay with Alex

alex near the top of Mt Tam state park north of san francisco with a view of the hills and clouds and trees

Alex lives in San Francisco and regularly rides his bike on a long bike commute nearly 50 miles to work in South Bay. We asked him some questions about his story and any tips and tricks to help other people who work far away (especially for this specific Bay Area commute from San Francisco to the Peninsula or South Bay).

What got you started riding this long bike commute from SF to South Bay?

A long time ago I was just starting to enjoy working out more intensely, and a friend told me about someone who bikes from San Francisco to the South Bay for work and I was in awe. I didn’t think I would become one of those people too. However, once I started doing longer weekend rides I realized I could get a long bike ride in on a weekday too! The first few times I rode, I couldn’t sit in my chair comfortably at work. There are so many details that I’ve refined over the years to make it possible, but it’s definitely the hardest when you start. On top of that, when you start you’re not yet going consistently, so it’s harder to remember the ins and outs of how to prep for the ride.

Now I love riding into work with a large group. When I started it was mostly solo riding, sometimes with another friend or two. As the group picked up in size, it got more and more fun. Now we have amazing camaraderie in the group and we rarely have solo rides.

The math is simple: I could ride a bike ~2.5-3 hours into the office, or I can do a workout around home for an hour and take the shuttle in for 1-1.5hrs. If you can do the former, why not?

Four cyclists ride on Cañada Rd in the peninsula of the bay area with crystal springs reservoir in the background as well as the Santa cruz mountains
Riding along Cañada Rd with a group of other cyclist commuters! The more people on the ride, the more fun it gets.

How long have you been biking from SF to South Bay?

Looking at Strava data, my first ride to the office was on 10/30/2014. Ten years and counting!

alex rides his titanium road bike on a trail in the east bay hills

How do you choose your route? What’s your favorite bike route for SF -> South Bay?

There are two common routes: via Skyline Express and Bayway. Of the many times I’ve ridden to work (240 and increasing!), I’ve done Bayway once or twice. Bayway is great for when you’re starting, but it’s pretty tricky route-wise and not as interesting scenery. Skyline has climbs, a beautiful section along Cañada Road, and more.

Editor’s Note: There’s a website called SF2G that has all the route details, Strava ride links, and more info on the beginnings of these commute rides before Alex even started.

A cyclist rides a bike on a beatiful road with a body of water and mountains in the background
Cañada Rd is definitely the most beautiful part of the Skyline Express route.

What’s the best & worst bicycle infrastructure on your ride?

We ride two sections on the shoulder of highway 280 😵. That has to be the worst, but at least we don’t have to merge or cross any traffic since we get off at the first exit. This isn’t strictly necessary, but when we go with a group it’s fairly reasonable (and legal). The other ways take longer and have pedestrians. If you’re trying it for the first time or riding solo I’d recommend taking the more scenic route that doesn’t go on highway 280.

A cyclist rides on the shoulder of highway 280 with 4 empty lanes of traffic to their left
Riding on the shoulder of highway 280. It’s as unpleasant as it seems, but there’s an alternate route on a very nice bike path.

A group ride that I wasn’t a part of was once pulled over by a police officer for riding on the shoulder of 280, and it took some discussion before the officer realized it was in fact legal to ride on these sections of the highway shoulder.

A google streetview image of the entrance onramp of highway 280 where there is a sign that says pedestrians, motor-driven cycles prohibited
The start of the route that’s on the shoulder of highway 280. The sign says no pedestrians or motor-driven cycles, but human powered cycles are okay on this section! It’s still a small shoulder for some of the time.
Cyclists ride along a two way shared bike path in the peninsula of the bay area with a body of water and santa cruz mountains and fog in the background. Someone is wearing a Brazil cycling jersey

Another section I don’t like is the bridge that crosses over 280 on Sand Hill Rd going eastbound—Palo Alto put a green painted bike lane there recently which is better, but it’s still pretty dangerous. They need to build a dedicated bike/ped bridge instead or separate the traffic in a safer way. I tend to ride in the far right lane as soon as there’s an opening with cars, even if it means not riding in the bike lane.

Sand Hill Road green bike lane in between two car lanes on a bridge crossing 280. This is a dangerous looking street design.
This bike lane in between 2 lanes without any protection is no fun. Fast moving traffic makes this a stressful section of road.

The best spot on the ride is probably Cañada road. Nice big lanes, minimal traffic, nice visibility, etc. (Editor’s note: Cañada road is car free every Sunday from 9am-3pm for Bicycle Sunday, which a great time to enjoy this area outside of commute times)

Do you ride both ways or only from SF to South Bay?

Always one way! You typically get a tailwind or sidewind on north to south commutes, so going in the afternoon you’d get a headwind—and it’s often windier. I’ve done the ride there and back a few times, it’s just trickier. You need to be careful based on the time of the year for sunlight. I’m comfortable riding in the dark in the morning but at night there’s much more traffic, so I prefer not to ride in the dark at night.

Fortunately the place I work has a shuttle with bike racks that makes getting me and my bicycle home easy. For those who don’t, public transit can be an option. Caltrain has a bicycle car and makes it easy to take your bike onboard.

Editor’s Note: If you want to ride a long bike commute to work only one way and don’t have access to a shuttle or public transportation, you can make this work by driving in with your bike on the car. Once you drive in with the bike the first day, you park your car overnight and bike home that night. The next morning you bike into work, and on the way home you drive back with the bike again. This way you don’t have to ride your bike both ways, which can be overly time consuming for a long bike commute to work.

Alex's titanium road bike on top of twin peaks with a view of san francisco in the fog as the sun is rising
Not the SF to South Bay ride, but my bicycle up on Twin Peaks!

What do you eat in the morning to prepare for your ride? Eat anything on the ride?

I’ve changed between different things over time. I used to eat hard boiled eggs. Now I have it dialed in my breakfast to: (1) half caffeinated coffee equivalent to a single shot of espresso (2) a bagel from Schlok’s deli with lox and non-dairy chive cream cheese from KiteHill (3) a banana and (4) a glass of water. Sometimes I throw in a Belgian waffle if I’m hungry. 

On the ride I have two water bottles. Some people get by with one. I also have one Clif gel pack and a stroopwafel (Rip Van Wafel).

And when I get into the office I usually eat a quick second breakfast—single shot Americano and a breakfast burrito—depending on how hard the ride was!

A group of cyclists in the dark on the side of the road discussing things or fixing something. You can see dawn in the background
Sometimes it’s still dark when we start the ride.

What time do you wake up? And what time does that get you to work?

You know, this is where I wish I could improve. I wake up a lot earlier than most people that join the ride. My alarm is set for Tues/Thurs at 4:45am to leave by 6am. Most people wake up at 5:30 and roll out immediately. I need to eat, finish my coffee, use the restroom, take the dogs out, etc. I want to figure out how to just roll out and go!

I’ll get to the office typically between 8:40-9am if we don’t have any mechanical issues on the ride. Fortunately issues are rare, but they do happen. I carry flat fixing tools for simple fixes, but a handful of times I haven’t been able to finish because of a slashed tire, broken spoke, etc. In these cases I’ve had to be picked up. My toolkit consists of an extra tube, patches, a 2 dollar bill to boot the tire (2$ instead of 1$ for good luck 🙂), a CO2 inflator, a mini pump, and tire levers.

A cyclist fixes a flat tire while one road bike is upside down on the side of a two way shared bike trail in the bay area
Sometimes a flat tire happens.

How do you handle being sweaty when you get to work?

I use the showers at the office. I also leave a backpack (or two, or three, or more depending on my schedule) full of clothes at the office with a shower bag. I shower right when I get to the office to start the day.

Editor’s Note: Things like a small towel, wet wipes, a fresh change of clothes, and some deodorant can help if you don’t have showers available at your workplace.

What kind of bicycle do you use for commuting between SF & South Bay and where did you get it?

Alex's titanium road bike leaning against a pole. It's a tall bike.

I’m 6’8” so my needs on a bike are abnormal to say the least. I ride a custom road bike that I got from a great shop called Bespoke Cycles in San Francisco. It’s a titanium frame made by Seven Cycles. I have two road bikes (one new and one old, which I use on the trainer) and a gravel bike. I can ride any of them to the office. But I prefer my newer road bike 🙂

Editor’s Note: For any commute longer than 10 miles or so, a road bike is recommended for comfort and efficiency (or a gravel bike if the terrain calls for it). A commuter bike or my favorite Public C7 cruiser are not the kind of bikes you want to take on a ride this long. They may feel more comfortable at first, but become uncomfortable during longer rides.

Where do you normally park your bike after riding to work?

I try to park the bike in my office space but not in the way of other people. It really depends on your office situation. Just make sure that you don’t block any fire exits and you put your drivetrain facing the wall so that no one can easily bump into it!

Do you ride in all weather? How do you handle that?

Mostly. I’ll ride in all weather unless it’s raining (it doesn’t snow here). There are weather apps that let you track at a very detailed level what the weather is going to be like for the entire ride—from temp, wind, humidity, cloud cover, etc throughout the entire route. I look at the map both the night before and day of if I need to make any adjustments to the wardrobe selection for the day.

Editor’s Note: Check out Bike to Everything’s post on weather radar for some simple weather apps, as well as the bike specific weather app Epic Ride Weather.

Alex on a dirt trail with his helmet on  with lots of fog around him

What bike gear do you find useful for your long distance bike commutes?

Oh, this depends on the time of the year for sure! I used to not ride with any long / warm clothing and now I need it 100% in the winter. It’s great to ride throughout the entire year and not have to worry too much about not having the right equipment. Shoe covers, different types of long fingered gloves based on the temperature, lightweight beanies under your helmet, clear glasses to protect your eyes even if it’s dark, just to name a few. In the summer just enjoy the ability to go short sleeves!

Editor’s Note: Check out Bike to Everything’s rain gear guide and winter bike commuting guide for some gear recommendations.

Let’s dive deeper into your wardrobe. What do you wear during your ride?

Here’s my full cycling wardrobe that I wear on rides with different weather. For longer rides a lot of these are more necessary for comfort than if I was commuting a shorter distance. And don’t cheapen out on the bibs, you want to make sure you have quality padding.

Alex on a sunny day with sunglasses, helmet, and cycling cap on with a nice cycling jersey

General attire:

  • Helmet: POC Ventral Air MIPS – make sure you have a MIPS helmet!!
  • Cycling cap: Specialized Reflect – this helps significantly with managing my sweat.
  • Sunglasses: Oakley Sutro Lite Vented w/ PRIZM Road lenses when the ride is predominantly light, then Oakley Sutro glasses with rose lenses in predominantly dark (aka winter) rides.
  • Shoes: S-works torch. Make sure you get shoes that are right for your foot. I also have custom orthotics that I got from Bespoke Cycles in San Francisco.
  • Socks: any cycling socks will do! Recently I’ve liked the comfort of the Rapha trail socks even when I’m not riding gravel.

Warmer rides (anything 45°F and up):

  • Bibs: Assos Mille GTO C2 Bib Short (there are newer models)
  • Jerseys: Rapha size XL jerseys fit me best, but I’m way taller than average—you will have more flexibility
  • Gloves: either no gloves if it’s warm enough, or some minimal gloves. I got these minimal gloves in Europe

Colder rides (anything below 40°F and lower):

How do you carry your work clothes and other things? A backpack or pannier?

Try and find a way to bring a backpack to work the day before. You can even bring more than one :). For example, just yesterday I brought in 4 bags of clothes because I knew that I wouldn’t be able to take the bus in the next few weeks. The trick is to leave your clothes and a waterproof laundry bag in your backpack. Leave your shower bag at the office and some street shoes. Always leave the street shoes at the office and swap back to your cycling shoes at the end of the day. And finally, see if you can scrounge up some old laptops that you can work on while you’re commuting back home. Save some e-mail work, non-compute heavy work to do on the commute home so that you don’t need your main laptop.

I will only ride to work if I have a bag at the office. The few times I’ve ridden where I need to take a backpack, I found my back and neck really hurt. Other people don’t have that problem at all though. If I were to get a rear rack, I’ve seen some people with this very nice, sleek, removable rear rack by Tailfin.

Editor’s Note: Alex doesn’t want to carry stuff, but I’m a big proponent of adding a rear bike rack even to a nice road bike and commuting in with your stuff in a pannier or some other bag! This can help if you weren’t able to pre-plan and bring a bag the day before.

What do you think is the longest distance that makes sense to bike commute?

I think 50 miles is pretty up there for a recurring commute. I’ve done the Half Moon Bay variation of the peninsula ride that’s ~75 miles with a lot more climbing. It was pretty rough and took a lot more out of me. But I think the sky’s the limit…I prefer not to think about some of those limits because not thinking about it allows you to break down some barriers that you thought may exist. It’s not a one size fits all solution, different people have different abilities and desires in the moment. Do what you think makes the most sense (or is nonsense and have fun) 🙂

How would you describe the bike culture around this SF to South Bay ride?

It’s awesome. Everyone’s supportive. The ride to work is both normalized and not normalized at the same time. The group we ride in is tough—we do drop some people on days we’re fast. But everyone respects that, we won’t leave anyone in a dangerous spot, etc. It’s almost like you don’t have to say a word to anyone in the group because we’re happy to be out there. Of course we talk about bikes while we’re riding though 😉

Editor’s Note: The SF2G Website has a lot of information for new riders along with many helpful links and a Google Group where people organize group rides down the peninsula.

Alex and a friend having fun while riding

What’s one piece of advice you’d give about bike commuting around San Francisco, the Peninsula, and South Bay?

If you’re thinking about doing a longer commute, find someone who does it and ask for more personalized advice! I’m sure they’d be happy to help. Many companies have cycling slack channels, e-mail groups, etc. Bike to Work Day is also a great time to do a longer commute with a lot of new people, where you might feel a bit less intimidated.

Anything else you’d like to share?

I love how cycling to work takes an otherwise boring commute and makes it fun. I’ve met people within the company I’m at that I would have never met before (fun fact: I might not even recognize them at the office unless they’re in their cycling clothes). When you’re doing something that many people might consider “crazy”, it’s a great way to build camaraderie. Shoutout to the crew who makes this ride even more fun!

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