7:55 a.m.: Board the Pacific Surfliner at the Santa Ana Regional Transportation Center (1000 E. Santa Ana Blvd., Santa Ana, 800-872-7245). Really, you can board this Amtrak service at any of Orange County's train stations, but SanTana's version is the true charmer, a place that has scored cameos in Rain Man and True Detective. All that's needed is a craft brewery to open up here—Left Coast Brewing, are you listening?
8-10:59 a.m.: Enjoy the comforting choo-choo, which offers free wifi and sells alcohol. Although you'll only get views of the coastline in OC if you pass through San Clemente (and you definitely should on the way to San Diego), the Pacific Surfliner is still a gorgeous ride through Southern California—the industrial buildings of OC and southeast Los Angeles County, the majesty of Los Angeles' Union Station, the chaparral of the San Fernando Valley, fields of Ventura County . . . and finally, Ventura, SoCal's best-kept staycation secret. Unboard at the train station near the Ventura County Fairgrounds (10 W. Harbor Blvd., Ventura, 805-648-3376; www.venturacountyfair.org), and get a cab. If you're an Uber person, be warned: Ventura is so darn bucolic that sometimes, there are no Uber drivers working—WHOA . . .
11:06 a.m.: Have whoever drives you drop you off at Paradise Pantry (222 E. Main St., Ventura, 805-641-9440; www.paradisepantry.com) in downtown Ventura for brunch. This charming bistro offers soups, salads and sandwiches, but the true stars are the cheese platters, epic frontiers of fromage anchored by California-produced cheeses that you can purchase in the ever-growing market side, along with locally produced limoncello, wine, even hot sauces.
12:30 p.m.: Stroll around downtown's many thrift shops. Once you've walked off your lunch, hike up to Ventura City Hall (501 Poli St., Ste. 109, Ventura, 805-654-7800; www.cityofventura.net), perhaps the most gorgeous civic building in Southern California. The Beaux Arts-style building dates back to 1910, when it opened as the Ventura County Courthouse, and its hilltop perch allows views, on a clear day, straight to the Channel Islands. It's a steep hill that shows no mercy, so proceed carefully.
2 p.m.: Get a late lunch at Spencer Makenzie's Fish Co. (806 E. Thompson Blvd., Ventura, 805-643-8226; www.spencermakenzies.com). The fish burritos are nationally famous, but perhaps the best thing on the menu are the ahi pockets, which are essentially poke in a tofu cup. Make sure to buy one of the company's five incredible hot sauces before you leave; you'll never want to douse your fish tacos with anything else again.
3:30 p.m.: Ventura still doesn't have its boutique-hotel game going, so check into the Ventura Beach Marriott (2055 E. Harbor Blvd., Ventura, 805-643-6000). With comfy digs, a great bar and reliable wifi, it's a chain hotel worth the money, and it's conveniently located between downtown, the beach and the rest of Ventura.
5 p.m.: Ask the kind Marriott people to call up the Downtown Ventura Harbor Trolley (805-827-4444; venturatrolley.com) to pick you up. The trolley runs from 11 a.m. through 11 p.m. Wednesday through Sunday, connecting downtown all the way to the many pleasures of Ventura Harbor Village (1583 Spinnaker Dr., Ventura, 805-477-0470; www.venturaharborvillage.com). Best of all? The trolley is free.
7 p.m.: Ventura's beer scene seems to bring a new brewery each year, but a great place to start is Anacapa Brewing Co. (472 E. Main St., Ventura, 805-643-2337; anacapabrewing.com). Great food, great entertainment and great suds: Go with Pissy Pelican Pale Ale for something light, Benyhana Espresso for a hefty stout, and a Pierpont IPA for the win.
9 p.m.: Explore on your own. We can't tell you all our secrets, right?
8 a.m.: You better be in bed—this is a vacation, after all.
10 a.m.: Walk out of the Marriott and toward San Buenaventura State Beach, which is never crowded for reasons only known to God—so take advantage of this and relax some more.
Noon: Walk over to the Jolly Oyster (911 San Pedro St., Ventura, 805-798-4944; www.thejollyoyster.com), as awesome a fancy food truck as you'll ever encounter. Everything it offers is either sustainably fished or raised by Jolly Oyster in Baja California farms. And after you slurp down some oysters and clams? Do like everyone else, and stand the shells up in the beach sand—trust us.
1:30 p.m.: After freshening up back at the Marriott, head over to the Museum of Ventura County (100 E. Main St., Ventura, 805-653-0323; venturamuseum.org). In addition to strong permanent exhibits regarding Ventura history, it has a wonderful gift shop and a keen eye for seasonal showings. Check the museum's calendar, as the weeknight lectures series is both great and not (I've spoken there four times already, always to large crowds).
Once you finish with the museum, walk across the street for a quick tour of San Buenaventura Mission (211 E. Main St., Ventura, 805-643-4318; www.sanbuenaventuramission.org). You're probably rolling your eyes at this suggestion after a lifetime of ignoring the docents at Mission San Juan Capistrano, but just take some time from your godless lives and enjoy the self-guided tour filled with artifacts, rose gardens and a bunch of beauty.
3 p.m.: Get lost in the stacks at the Calico Cat Bookshop (495 E. Main St., Ventura, 805-643-7849; www.calicocatbooks.com). Run by a nice Scandinavian couple, the tiny store has a bit of everything but specializes in books of the West and first-editions.
4:30 p.m.: Make a quick stop at T&A Leather (8 N. Fir St., Ventura, 805-585-5804; www.tandaleather.com). Run by a charming AF gay couple, the store offers its own leather creations—wallets, key holders, purses, belts, bracelets and even skirts—all done in traditional leather crafting with a modern, steampunk flair. T&A also offers classes—sign up for one next time you visit.
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5 p.m.: Ventura's great contribution to Mexican food is corn burritos—what the rest of the world calls taquitos—and Parmesan tacos, which are nothing more than hard-shell tacos dusted with Parmesan cheese but are wonderful. Get them at Corrales Mexican Food (1951 E. Thompson Blvd., Ventura, 805-643-6138), a roadside stand just across the street from Spencer Makenzie's.
6:30 p.m.: Most of downtown Ventura's restaurants are slammed with out-of-towners at this time of the evening, so go where the locals kick it: The Tavern (211 E. Santa Clara St., Ventura, 805-643-3264; www.thetavernventura.com), located in a historic old home on the outskirts of downtown. Here are some of the better cocktails and drunk food in Ventura's slowly emerging food scene, but just as awesome is the seating: outside fireplace, inside couches and ready-to-party locals everywhere.
8:30 p.m.: VenTiki (701 E. Main St., Ventura, 805-667-8887; www.ventikiloungeandlanai.com) will probably be slammed right now, but it doesn't matter. Wait for a seat at this honest-to-goodness tiki lounge. Not only are the drinks fantastic, but you'll also be issued a passport that you can get stamped after trying each of its dozens of drinks; at the end, you get a commemorative cup. Bali hai!
10 a.m.: Start dreaming about Ventura being your second home, or at least your annual staycation. Fuck annual; make it monthly. See you next week!