Sideways. A movie about avoiding responsibilities, Southern California, and wine. When this movie came out, it struck a chord with wine-os everywhere. Myself included. Now, decades later, I still think of this movie pretty fondly. It makes you want to spend winding afternoons in the California countryside, sipping a Malbec (I’m also not fucking drinking merlot.)
If this kind of trip is up your alley, here’s how to plan a trip there on a budget.
How To Plan A Trip To Sideways Movie Locations
A majority of the film was filmed in Santa Barbara, so if you want a true Sideways experience, that’s the place to start. Santa Barbara has it’s own airport, and there are a lot of cheap flights from New York and Atlanta.
– Fly via United From JFK – around $200 one-way
– Fly via United and American From Atlanta – around $200 one-way
From the airport, there are a lot of ground transportation options and shuttles you can use. If you want to stay true to the film, you want to rent a car. However, the car that Paul Giamatti drove was a 1987 SAAB 900 Cabrio Turbo. This is where we hit our first snag, because you can’t exactly rent one of those.
You can rent a small car from Avis for a week for around $170-$200. But the appeal is really the convertible, right? A Ford Mustang convertible rental will run you about $488 a week. However, I did promise budget, so that isn’t going to work. So here’s another idea. Don’t rent a car.
You can Lyft or Uber from the airport, and sign up for a guided wine tour for around $150 per person. The tour will shuttle you around from place to place. There’s a ton of wineries in Santa Barbara that a lot of these tours hit. Then, all you need is to grab an awesome hotel deal or an Airbnb, and you’ve got a trip.
If you stick to the Santa Barbara area, go carless, book a private room at an Airbnb or hotel and get one of the winery tours, this entire trip will run around $1k for about three days and four nights. To only go to Santa Barbara.
Meh.
I mean, the whole exciting thing about Sideways is the idea of the open road with a buddy, right? Skipping from winery to winery up and down the California coast? It looks like they go everywhere. In reality, the movie filmed in Buellton and Solvang, two towns near Santa Barbara and if you based your trip on these locations alone, you would be driving back and forth between two small towns.
Double meh.
So instead of all that mess, you could try to capture the essence of Sideways with a DIY wine tour up and down the California Coast. You can still hit a few of the actual locations, but explore more the state has to offer. I got excited about this idea, so I made a map of the best wineries in Southern and Central California.
Basically, it’s a wine road trip from Santa Barbara to Santa Rosa. It’s under five hours, and there are a lot of great towns to stop on the way. Santa Maria, San Luis Obispo, San Jose, San Francisco, and Santa Rosa. You could rent a car from around $280-$300 for a week and drive it up the coast.
Once you finish the trip, you could just fly out of San Francisco. It’ll be around the same price as flying into Santa Barbara from JFK or Atlanta. But alas, another snag. Budget. On top of renting the car and getting gas, you’ll need to book lodging and any wine tour costs. Even for a week, you’re still looking at $1200.
Yikes.
So here’s the Drifty option. If I were taking the trip, I’d spread the adventure out over 3-4 days. I wouldn’t be there as long, but that’s still a decent amount of time to travel. Then, instead of a car rental, I’d take the train.
On Amtrak, a direct train from Santa Barbara to San Francisco is $44-$70 for a reserved coach seat. The total train trip is 8-10 hours. Now, I wouldn’t take it straight through, this gives me enough information to figure out how to chop it up. Here’s a map that includes all of the towns Amtrak drops up and picks up in:
So from the Santa Barbara Amtrak Station, you can hop on the Coast Starlight and hit San Luis Obispo, the Paso Robles Intermodel Station, Salinas, the San Jose Diridon Train Station, and finally, the train stop at Fisherman’s Wharf in San Francisco. All you need to do is figure out a few logistics and price it out.
Planning The Train Route
California (in my opinion) has one of the best train routes in the country. There’s a lot of flexibility and it’s super cheap for a stop and go train trip from Santa Barbara to San Francisco.
Santa Barbara, CA to San Luis Obispo, CA – $34
via 14 Coast Starlight (2h 46m)
San Luis Obispo, CA to Paso Robles, CA – $17
via 14 Coast Starlight (1h, 2 m)
Paso Robles, CA to Salinas, CA – $16
via 14 Coast Starlight (1h, 51 m)
Salinas, CA to San Francisco, CA – $16
via 14 Coast Starlight (3h, 47 m)
If you stick to the 3-4 day rule here, you can leave from Santa Barbara, pick a town or two to stop in, then end up in San Fran.
Finding Places To Crash Along The Way
Next, a place to crash. Cali is too expensive for my usual Drifty deals, but I found a few good options. For each location, I scoured Booking.com and Airbnb and found some private rooms and two really neat retro looking motels/hotels along the route.
Santa Barbara – Private Studio in Garden Setting, $65 per night
San Luis Obispo – Wine Cellar Guest Room, $100 per night
Paso Robles – Melody Ranch Motel, $110 per night
Monterey – Hotel 1110, $158 per night
San Francisco – Bedroom in quiet Potrero Hill, $110 per night
Safe average is around $100-$110 a night. Now, there are really cheap motels, but I always price things out for a solo traveler. I tend to be more cautious when it’s only me.
Finding Sideways-like Wineries
Now, wineries. There’s a ton of wineries in California. Some of these are actually in the film, and other wineries I found myself. Before you pick any out, there’s an important distinction to make. The vineyards shown in Sideways are in Southern and Central California. The prestigious, well-known California Wine Country is actually more north, above San Francisco. It’ll be a lot more expensive to do the trip up there, but there are over 400 wineries to choose from.
If your heart is set on Sideways (and rolling on a budget), here’s some wineries to check out near each train stop I listed above.
Santa Barbara
Santa Barbara is full of wineries, including Whitcraft Winery, Deep Sea Tasting Room, and Sanford Winery and Vineyards. But you probably want to save a lot of your energy for nearby Solvang, where a lot of the filming for Sideways took place.
Solvang
Solvang is near Santa Barbara, and includes a ton of Sideways wineries.
Noteworthy ones include Fess Parker Winery & Vineyard, Kalyra Winery, and Alma Rosa Winery & Vineyards.
San Luis Obispo
You can try one of many San Luis Obispo wine tours or take a DIY approach and check out Tolosa, Foremost Wine Company, and Filipponi Ranch.
Paso Robles
Paso Robles has a few wineries to choose from that are kind of spread out, including Eos Estate Winery, Sculpterra Winery, and Steinbeck Vineyards & Winery.
Monterey
In Monterey, you can get an awesome view of the beach while you’re sipping wine at Pierce Ranch Vineyards, Carmel Ridge, and other wineries near Monterey Bay.
As an experienced wine-taster, I’ll caution that many of these wineries will charge for wine tastings. I’ve never paid more than $10-$15 anywhere. I also always suggest calling to double check hours and availability. Some wineries limit tastings to days and certain times of day.
How Much This Trip Would Cost
I played it safe with this trip, and stuck to rates during the Fall. Still not a bad time to visit California. However, if you’re looking during more competitive seasons, rates will probably skyrocket. The 3-4 day Sept./Oct/ trip I mapped out above would cost around $700-$800. That includes:
– Three nights at an Airbnb or motel, at an average of $100-$110 a night
– The train tickets, between $60-$70 for one or two stops
– The flights there and back, around $400 roundtrip from Atlanta or JFK
– Additional costs for your own food and any wine-tasting expenses
And that’s it. Book in advance and drink all of the Merlot you want.
Have another movie you want us to build a trip idea around? Hit us up here and we might just pick your film.