The Point Loma peninsula has a split personality. In the north, block upon block of houses spread over the peninsula's broad spine. Spacious military land and parkland (Cabrillo National Monument) encompass the peninsula's narrower south end. To get an inside look at the whole of the peninsula -- and at a leisurely pace to boot -- consider the circuitous, 16-mile-long bicycle route described here and arrowed on our map.
Pacific view, Point Loma
Begin at Collier Park, one block north of Voltaire Street and west of Nimitz Boulevard. Make your way southwest toward Sunset Cliffs Boulevard over the rectangular grid of residential streets on Ocean Beach's more serene east side. On Sunset Cliffs Boulevard, south of Point Loma Avenue, you approach the brink of the wave-battered Sunset Cliffs. These structurally weak bluffs, made of sandstone, are eroding at a rate that is among the fastest anywhere along the California coast.
At Ladera Street, turn inland and pedal sharply uphill for two blocks to Cornish Drive. Go left and continue on Cornish past Hill Street to Novara Street. (Hill Street may be used to short-cut the arrowed route, but it's extremely steep.) Curve right, following Novara Street, then Santa Barbara Street. Mission Bay, Pacific Beach, and part of the La Jolla coast may be glimpsed in the north. Use Tarento Drive, crossing Hill Street again, to reach Catalina Boulevard, where you turn right.
Catalina Boulevard becomes Cabrillo Memorial Drive as you pass the Navy reservation gate (public admitted from 9 a.m. to 5 p.m. daily). Using the bike lane on the road shoulder, enjoy the next 2.5 miles of undulating roadway, with bay and city views on the left, and ocean views on the right. At the road's end lies Cabrillo National Monument's entrance booth, a good place to turn around and pedal north back up the peninsula -- unless you want to pay the small fee to enter the monument and hobnob with the tourists.
Back outside the Navy reservation gate, go 1/3 mile and turn right from Catalina Boulevard onto Rosecroft Lane. Take short segments of Silvergate Avenue, Dupont Street, and Gage Drive. Turn right at Charles Street (a short and very steep uphill); make a left at Bangor Place; and make a right at Golden Park Avenue. Pause at Lucinda Street (one of San Diego's steepest streets) and decide whether your brakes can handle the descent. Walk -- don't ride -- down if you want to have more than a few seconds to enjoy the startling view of the bay and the city.
At the bottom of the Lucinda Street hill, curve around to Armada Terrace and continue descending to Talbot Street. Jog left to Evergreen, then later Willow Street, passing tidy homes, many owned by retired fishermen of Portuguese descent. After some further zigzagging, staying west of busy Nimitz Boulevard, find Capistrano Street and go across Nimitz (or else you may cross Nimitz at the traffic light on Chatsworth one block away). Pedal uphill on Capistrano to Tennyson, then go right and continue sharply uphill to Willow Street. Turn left on Willow and freewheel through the stylish but aircraft-noise-impacted Loma Portal district.
You may conclude the ride by returning to Collier Park, circuitous as always, on residential streets (arrowed on the map) overlooking Mission Bay and Ocean Beach.