The lily white (yet absurdly tan) communities of the Monterey peninsula open their doors to automotive enthusiasts this week, but most of them are keeping the gates manned by guards. Here’s how to buy, cheat, lie, and connive your way into all the events you want to go.

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(This story ran in August 2015 and is being republished for Pebble Beach 2016.)

Monterey Car Week or, simply, Pebble Beach, is a collection of events dedicated to the appreciation of the automobile. Confusingly, many of these events don’t occur in Monterey and only a small handful actually occur on Pebble Beach itself.

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If you’re among the wealthy set who can afford to be chauffeured about in a vintage Rolls Royce this guide isn’t for you. Your man Jeeves will know where to go and all of the sartorial advice will be second nature. This advice is for the common enthusiast, and “common” by Pebble Beach standards is anyone who wears less than $25,000 on their wrist.

Learn How To Blend In

Pebble Beach isn’t for the nouveau riche, although the peninsula is full of them around this time of year. You’d scarcely know it as, even at The Quail, astute Silicon Valley seed-funded seedling millionaires dress like the ancien regime. It’s the kind of place where a Maybach is less appreciated than a rusted vintage pre-war Benz.

Thus, the first key to surviving Pebble Beach is to blend in. Know where you’re going. Know the crowd. Act like you belong there. Do this properly and see everything without losing all your money.

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Specifically, when you’re at the Pebble Beach Concours you should act like your family tree is planted on fertile soil (ideally fertilized with the sweat of the working poor). When you’re at The Quail pretend like you invented “Uber for dogfood.” And when you’re at the Monterey Historics, pretend like you’ve got a vintage IMSA race car in your garage.

We’ll have a full costume guide tomorrow, but on every day that doesn’t begin in “Satur,” dress 20% foppier than you would in any other situation. On Saturday, break out your best blipshift (or maybe Jalopnik) t-shirt.

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If you’ve been able to buy tickets to every event that requires them in advance then you’re probably not going to have to worry too much. If you haven’t, you can usually find someone at a bar or restaurant who has an extra pass. Listen carefully, stand people drinks, and be flexible.

Worst case, if you see some cars you like in a parking lot or a putting green somewhere, just walk in like you know the place. If you get busted, you read this on Hooniverse.

Plan The Events You Want To Go To

There’s an event at Monterey roughly every 19 seconds, it seems, as well as countless parties. Here’s a list. It’s like New York Fashion Week, but for people who are too rich to ever be unfashionable.

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First, you should pick a good day like Wednesday or Thursday to drive up as you’ll see tons of vintage iron (or gilded sapphire) driving up the coast. If you see a McLaren being chased by a Citroën SM, a Cadillac ATS-V, a 2016 Mazda Miata, an RV and a Range Rover Sport SVR you know it’s us.

Once you arrive you need to come to terms with the act that you’re not going to get invited to most places and you’re not going to be able to do everything. Pick your battles and configure your schedule based on the likelihood of getting parking, needing passes, and seeing what you want to see.

The Tour d’Elegance on Thrusday morning is a great way to see some of the cars that often sit in garages out on some of the most bucolic roads in the known universe. You can finish the afternoon at the Automotive Film And Arts Festival or, if you’re in the mood to cash in your 401k, you can get into an absurd bidding war for a Fiat Jolly at one of the many auctions.

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Friday is the busiest day of the weekend and you’ll likely have to make tough decisions: Do you go to the Classic Americana or the Legends of the Autobahn? Realistically, you can probably do a few of these events before ending up at The Quail, which is the biggest event of the day. If you can’t get in The Quail, it’s one of the many events where the cars outside the gates are almost as interesting as the cars inside.

Saturday there are plenty of events, but there are only two that you have to go to. First, there’s the sarcastically-named Concours d’LeMons, which features cars too absurd or terrible to be admitted to the Concours d’Elegance. It’s fantastic. The best event of the day, however, is the Rolex Monterey Motorsports Reunion at Mazda Raceway at Laguna Seca.

That’s a mouthful, but seeing race cars of every vintage moving under their own power is moving. The cars are loud, gorgeous, and dirty. You could (and should) spend most of the weekend there.

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Sunday is the eponymous Pebble Beach Concours d’Elegance, which is harder to park at than to actually attend. Two years ago we had a press van from Chrysler and we just dropped it next to a bunch of other Chrysler minivans at their display. No one noticed.

I have mixed feelings about the Concours itself. The cars themselves are impressive and you run into some interesting folks (Derek Bell once made fun of my hat in a restroom while we stopped to grab a drink!). However, the fondling of very specific models and marques borders on the perverse and the inclusivity that I hope Jalopnik represents isn’t well displayed here.

Instead, a sort of standoffish miasma of exclusivity abounds there and certain people like to use their knowledge as a bludgeon against the curious. Live video of this event will be brought to you by MotorTrend if you can’t attend.

The absolute best part of the day is actually at dawn when the field opens and cars emerge from the thick fog and onto the manicured lawn. It’s worth getting up for.

Don’t Plan Anything

I have a friend whose dad likes to plan out every minute of his family’s trips to Disney World. The planning is the fun part for him and it makes the actual trips themselves increasingly miserable for everyone else.

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Don’t plan. Just do whatever. You can’t throw a driving cap without hitting at least a sweet MGB GT. Drive around, stop when you see something cool, sleep on a friend’s couch (we’re out of couch space before you ask).

Talk to people. Make new friends (with better couches). Have fun. There are a few haughty jerks with crankshafts shoved up their exhausts, but mostly Monterey attracts people who love cars so don’t be afraid to ask an older gentleman or gentlelady in the Carrozzeria Touring Aston Martin about their car and they’ll probably want to share.


Contact the author at matt@jalopnik.com.