Descanso Beach Club is a stylish resort tucked between steep cliffs and footed by a sandy beach where you can stroll with drink in hand, or swim to your mooring from the shore. We enjoyed snacks and cocktails beneath massive market umbrellas and watched a mammoth cruise ship weigh anchor and disappear for points south. 

Yippee Kai Yay makes quick work of the sail from her homeport of Dana Point to Catalina Island.

Where cruise ships abound now, there were once steamships delivering merrymakers to Avalon, heady and high after drinking and dancing on the passage from Los Angeles. Sexy Chris-Craft shoreboats would zip them to the pier where mariachis, troubadours and townspeople would greet them. Millions of visitors traveled to Catalina this way, and with its proximity to Hollywood it became the playground of the stars. More than 500 movies and television shows have been produced on the island over the years, and remnants of films such as the palm trees from Mutiny on the Bounty and bison from The Vanishing American evoke those glory days. 

We learned all this at the new Catalina Island Museum—a sophisticated 18,000-square-foot structure in the heart of Avalon. This world-class museum features contemporary indoor-outdoor displays, programs in the 100-seat amphitheater and rooftop gazebo, along with engaging exhibits that convey the fascinating history of the island. Another historic must on our sightseeing tour was the Casino, a Catalina landmark since its construction in 1929. More than 11 stories high, its distinctive circular Moorish Art Deco design commands Avalon Harbor, and can be seen well out to sea.

The Casino has never been a gambling hall. Instead, it was the first theater built specifically to show talking movies. Its perfect acoustics provided a model for New York’s Radio City Music Hall, and the original 1,240-pipe organ, plus frescos, gold leaf and other decor remain intact. Atop the theater is a stunning ballroom, one of the leading dance halls of the Golden Age of Swing where Benny Goodman, Jimmy Dorsey and the like would perform while guests cut a rug on the 15,000-square-foot expanse of glossy hardwood.

That night we enjoyed dinner at the Avalon Grille, owned by yet more Wrigleys and family, the Rusacks; so we selected the exceptional Rusack Vineyards Pinot Noir from the wine list. The island’s El Rancho Escondido was previously an Arabian horse breeding facility but now chardonnay, pinot noir and zinfandel vines blanket the slopes where horses once loped. After an excellent dinner and moonlit promenade along Crescent Avenue, we retired to a comfortable night at the stylish Pavilion Hotel. 

Pulling up anchor the next morning we headed northwest along the rugged coast. Twenty-two miles long and 8 miles at its widest point,  it narrows to just a half-mile at the Isthmus. Formed by plate tectonics and volcanic activity, the shoreline is ragged, providing lots of nooks and crannies for anchorages, however its precipices descend deep into the ocean. The bonus is spectacular sea life, however anchoring can be dicey unless you have a lot of chain.

Luckily Catalina has more than 1,000 moorings, most of them along the eastern side of the island due to the prevailing westerly breeze. Traveling up the coast we passed many at Moonstone, White’s Landing, Hen Rock and Buttonshell, plus several tiny anchorages. Because the island lies at a northwest to southeast slant, locations are referred to as being at the East End (Avalon) or West End (from Two Harbors to the western tip). Two Harbors is so named because of Cat Harbor on one side and Isthmus Cove on the other, which was our destination and we made fat tacks up the coast, enjoying the breeze, until the desire for Buffalo Milk overtook us. 

Nobody is brave enough to wrestle a bison and milk it. A Buffalo Milk is a mixed drink created more than 40 years ago by a bartender at the Harbor Reef bar and restaurant. This frothy, sweet, yet potent cocktail is so iconic, if you ask someone if they’d like a Buffalo Milk, it is akin to an invitation to Two Harbors. 

Betsy and Barry enjoy a kayak paddle—a great way to explore the island.

Few communities could be as diverse as Avalon and Two Harbors. Whereas Avalon is charming and refined with fine dining and museums, Two Harbors is a flashback to the wild west. Dirt roads and rough-hewn buildings are cut into the primitive nip of terra firma, where visitors launch into adventure. You can mountain bike, hike, kayak, paddleboard, scuba and snorkel. Whatever gear you don’t have onboard is available for rent for private or guided excursions. There’s a tiny market ashore for basics and ice, plus heads and showers (bring your quarters). Next door the open-air Harbor Reef eatery switches on the live music at night, for a rompin’ stompin’ good time. 

For a more upscale retreat, Harbor Sands offers a Nikki Beach-style vibe with cozy, furnished palapas nestled atop powdery white sand. After stretching our legs on a hike to Lion Head point, I lounged like Cleopatra on a cushioned chaise while servers brought Yellowtail tacos and fried calamari: delicacies we can only dream of aboard Yippee Kai Yay, where boiled water and Top Ramen are typical race boat fare. Gin-colored water lapped beyond the swaying palm trees and for a moment, we felt thousands (not dozens) of miles from home.

There are hundreds more moorings up the coast at Cherry Cove, Fourth of July, Howland’s Landing and Emerald Bay, so after soaking up the fun (and food) at Two Harbors, we took a quick jaunt to Howland’s Landing. Like several mainland yacht clubs, Los Angeles Yacht Club has a private facility on Catalina where members can reserve a mooring and enjoy the tucked-away beach-side setting. Howland’s is rustic for sure, but we were more than content with the barbecue pit, picnic table, shower and head. Thankfully there was a club member willing to shuttle us ashore in their dinghy, although in the past I’ve swum to the beach to borrow one of the club’s loaner kayaks. 

Heading home, we chose to continue circumnavigating the island, following a familiar race track around the west end and south. Beating into the westerly can be exciting, but it is made palatable by water ballast tanks in our Class 40. Then we ran south past Cat Harbor, a long, skinny, south-facing inlet that offers the only moorings and protected anchorage on the back side of Catalina. We had also decided to forgo Little Harbor, a gorgeous compact anchorage because it is a bit too exposed and possibly shallow for our race boat. Gliding past China Point along the barren windward side of the island, daylight began to dwindle, taking with it the breeze. We rounded Church Rock, turned on the engine and pointed toward home. 

If you go

Moorings are plentiful on Catalina. Go to visitcatalinaisland.com to make reservations. There are no slips available and anchoring is not advised, unless you have abundant chain and are adept at deep-water anchoring. 

Shore boats operate in the larger coves; dinghies less than 14-feet can also be tied up at designated docks.

Catalina is a year-round destination however northerly Santa Ana winds (typically late fall to early winter) can create a dangerous lee shore. Do not go if Santa Anas are forecast, or if they develop be prepared to depart immediately. 

Plan to enjoy the abundant marine life in these pristine waters, but be familiar with Marine Protected Areas where fishing is prohibited. Bison are dangerous, do not approach them. For your own safety, stay on marked trails.

For activities, accommodations and information visit The Catalina Island Company at visitcatalinaisland.com.