Distance: 20.5-mile lollipop
Elevation gain: 1490 ft

This is another SF Bay shoreline ride with great views of the Bay and its attractions. It’s a bit more strenuous than the Golden Gate Bridge loop and less strenuous than the Conzelman Loop (note that mild elevation total), and less dramatic than either. It’s a fairly quiet, rolling ride through pretty woods and occasional $10-million homes to three uniquely charming Bay locales: Tiburon, Belvedere Island, and Belvedere Lagoon. As with all Bay Area shoreline riding, this ride isn’t about the work—instead, ignore your heart rate monitor, slow down, and take in the many delights that surround you. The ride profile is perfect for a recovery day: constant serpentining, back and forth, gently up and down. The road surface is borderline problematic but never bad enough to disturb your wa.

Now I will say something I say nowhere else in Bestrides: you might plan to do this ride when it’s busiest. Paradise Drive is Cycling Central on weekends—on my last Sunday there I saw perhaps 200 bicycles—and, while I’ve done it in solitude and loved it, there’s a kind of Woodstock (SXSW?) atmosphere on the weekend that’s exhilarating.

(Ignore the jagged elevation profile—the actual profile is mellow.)

https://ridewithgps.com/routes/37651823

Find a place to park around the west end of Paradise Drive. This area is fully built-up, with churches, schools, parks, and neighborhoods, so there are lots of options. I recommend the Nugget Market parking lot, just east of Harbor Dr. Ride east on Paradise Drive. In the beginning, it’s a multi-lane without appeal, but soon the build-up ends, the road goes to small 2-lane, and you’re into woods. You’re riding along the hilly shoreline of the Tiburon Peninsula, so views of north SF Bay, the Richmond-San Rafael Bridge, San Quentin, and the like are frequent through the trees and in the infrequent breaks in the foliage. There is the occasional house, but you’re on a sidehill so they’re largely above or below your line of vision, and anyway they’re typically much too rich and snooty to let you see them. A realtor’s billboard advertises $7-million houses (or are they bare lots?—hard to say).

The road rolls sweetly and never makes you work. Soon you hit a Y and Trestle Glen Blvd. splits off to the R. You don’t want it, unless you’re determined to ride a loop, in which case when you leave Tiburon on the ride home you can take Tiburon Ave. and use Trestle Glen to get back to Paradise. The far better ride is to ride Paradise Drive out and back, as I’ve mapped it.

Paradise Drive drops down into Tiburon, one of those Bay villages you never want to leave. You debouch at Shoreline Park, a grass strip with benches right on the water where the views of Angel Island, Raccoon Straits, the main Bay, San Francisco, and the Bridge are peerless and the people-watching is prime. Sailboats invariably are busy in the Straits, and usually there are dingy regattas underway in front of the Corinthian Yacht Club on your R. (“Corinthian” in sailors’ jargon means “amateur” or “in the true amateur spirit”—apparently the people of Corinth were great sportsmen.)

The tiny village of Tiburon consists of one small block but, as Spenser Tracy put it, “Every bit is cherce”—several good restaurants (which during the pandemic are serving at open-air tables on closed-off Main Street), an Italian bakery, small, tasteful shops, and two ferry terminals (to Angel Island, SF, and Sausalito). If you want to do the true Tiburon experience, eat at Sam’s, a restaurant famous for having its own boat dock.

At the end of one-block Main Street turn R (still on Main Street, in fact), immediately stay R at the Y to stay off Eastview St., and pass the quaint little shops of Historic (or Historical, as one sign puts it) Ark Row lining the street on your R side. It’s the kind of place where the buildings have plaques on them detailing their past lives. If you’re in the mood for food, I recommend Lola’s taqueria—get the free avocado salsa. Main turns into Beach St—stay on it and you’re swept onto Belvedere Island.

I love this place. This small, hilly rock is crammed with small streets and absurdly expensive, very old houses—perhaps the classiest place to live in the Bay Area if you’re a fan of Old Money. Or expensive cars—in Belvedere the cheapest car you’ll ever see is a Lexus. I passed a house with three cars in the carport: a Bentley, a Porsche, and a Tesla. The marina below you as you start making your way around the island is the San Francisco Yacht Club, whose name is the basis for a local trick trivia question: “In what town is the SF Yacht Club?” (The correct town address is “Belvedere Tiburon.”)

Because the slopes of Belvedere are very steep, the houses and gardens tend to be vertical, and they make for an architectural and horticultural fairyland. You can follow the shoreline, but if you’re craving more expansive vistas (or some serious climbing), explore the inland streets, where you can find 14% pitches. Golden Gate Ave.>Belvedere Ave. is the main bisector of the island, but since it’s the thoroughfare the house and garden viewing along it is poor—much better gawking along the smaller streets. I like Bella Vista Ave., but you have lots of options—just wander, and keep looking up (unusual posture for a cyclist). The views of the surrounding geography are stunning—to the northeast Belvedere Cove, Tiburon, Raccoon Straits, Angel Island; to the northwest Belvedere Lagoon; to the south Richardson Bay, Sausalito, the central bay and the Golden Gate Bridge. Sometimes it helps to sneak into someone’s parking lot for the best views.

As you leave Belvedere Island, with San Rafael Blvd. on your R, you’re passing what is to me a magical place: Belvedere Lagoon. This artificial archipelago of charming cottages each with its own dock has ever since my childhood seemed like the most idyllic place on earth to live. Our route essentially circumnavigates it. Take a moment to explore it via its side roads. You can’t see the best part—the backyard docks—but each of the bungalows is unique, tasteful, and lovingly kept up.

As you near large, busy Tiburon Ave. (in the neighborhood of Hilaria, though I see nothing funny about the place), turn R onto small Lagoon Rd., which parallels it, to avoid the traffic (hard to see). Lagoon Rd. returns you to downtown Tiburon. From there return to your car the way you came. Again, if you’re dead set against out-and-backs, from Tiburon you can take Tiburon Ave to Trestle Glen and go R on Trestle Glen to get back to Paradise, but you’ll miss out on a great return ride. It’s mostly slightly downhill, so it’s a faster, more up-tempo ride that the ride out.

Shortening the route: This ride is easy enough that you probably won’t want to shorten it, but if you do, ride to Tiburon and return.

Adding miles: The nearly limitless riding options nearby are detailing the Adding Miles section of the Golden Gate Bridge Loop ride.