Hawaii-bound? Get the scoop on Pleasant Holidays, Aston and TS Restaurants

No matter what kind of trip you plan, you’re going to encounter more than beaches and palm trees when you reach Hawaii. Chances are you’ll bump into Pleasant Holidays, Aston lodgings or TS Restaurants. In fact, you may wind up doing business with all three, as I did on a Hawaii trip in late October.

These companies are easy to overlook on the mainland, even though one is based in Westlake Village. But once you’re in the islands, they seem to be everywhere. Here, for newcomers to Hawaii and repeat visitors looking to connect a few dots, is a briefing on what to expect from Pleasant, Aston and TS.

Pleasant Holidays, a Westlake Village-based seller of tour packages, has been taking tourists to Hawaii since about the time the islands attained statehood in 1959. Pleasant also sells travel elsewhere, including Mexico and the Caribbean, and the empire also includes dozens of lobby activity desks throughout Hawaii.

What many travelers don’t realize is that since the company’s founders, Ed and Marilyn Hogan, quietly sold out their controlling share more than a decade ago, Pleasant has been a subsidiary of the Automobile Club of Southern California. So if your Auto Club travel agent suggests a Pleasant tour package, don’t be surprised.

But Pleasant gets plenty of customers from elsewhere too. It handles thousands of travelers every year, from penny-pinchers on up. (Lately, they’ve been advertising three-night Hawaii packages with airfare for $299 per person and up.)

On my trip, I wanted a four-night stay, cheap but fairly comfortable. Pleasant got me nonstop United flights to and from Maui, four days with a Hertz rental car and four nights at a Maui vacation-condo resort that is run like a hotel. The package price (not counting United’s baggage fees and snack assessments) was a very reasonable $1,235.

Before you book anything, of course, it’s best to check out some package-tour competitors, and if you’re new to the territory, you’d probably benefit from the advice of a travel agent. Among the big competitors on packages to Hawaii are Classic Vacations (an upscale vacation packager that is owned by Expedia); Gogo Worldwide Vacations (which focuses on sales through travel agents); and Apple Vacations (another packager that goes back to the late 1960s).

As for Aston, the company does run lodgings at South Lake Tahoe; Sun Valley, Idaho; and Lake Las Vegas, Nev. But Hawaii is the core of the 62-year-old business, and vacation condominiums have been a specialty for decades.

There are 26 Aston hotels and vacation-condo resorts on Oahu, Maui, Kauai and the Big Island. The brand name was born in the 1980s, then dropped in the late 1990s in favor of ResortQuest. But in the last decade, the company has been through two ownership changes. In early 2009, management decided on a “strategic repositioning”: It dropped the ResortQuest brand in favor of – you guessed it -- Aston.

My own Aston experience last month was at the Aston Kaanapali Shores, a vacation-condo resort that is run like a hotel and has has been offering sale rates as low as $132 per night. If you tease out the details of my package, that’s about what I paid.

With prices like that, nobody should expect the Ritz. And sure enough, I landed a non-view room, far from the beach and far from the elevator, too. I also had a forgettable lunch at the property’s lone restaurant. (Maybe I should have used the full kitchen in my room.) Also, for all the beauty of the white-sand beach in front of the hotel, I found that the shallows were full of holes and rocks—the stuff that body-surfing nightmares are made of.

But just about every time I walked through the lobby, it seemed full of happy customers, plotting their day’s adventures (with help from some Pleasant advisors). Trip Advisor’s citizen-critics rated the Aston Kaanapali Shores 11^th among 28 hotels in the Lahaina, Maui, a respectable showing. And the Trip Advisor masses recently rated the Aston Waikiki Beach Tower No. 1 among 94 hotels in Honolulu.

Aston might not be your choice for an over-the-top honeymoon. But if you have a budget to watch and a family to feed, its rates are tempting.

Another big Hawaii brand that competes with Aston is Outrigger, which develops and operates hotels and condos on the islands and beyond. Besides the 10 hotels and 15 condo buildings bearing the Outrigger and Ohana names on Oahu, Maui, Kauai and the Big Island, the Outrigger family companies also run the Ala Moana Hotel in Honolulu and the 8-acre Waikiki Beach Walk area (four hotels, six restaurants, 40 retailers). Outrigger had two hotels (Outrigger Reef on the Beach and the Outrigger Waikiki on the Beach) among Trip Advisor’s top 10 for Honolulu.

Here’s the thing about TS Restaurants: Whether you know it or not, there’s a good chance you’ve already eaten at one, probably while admiring an ocean view. There are a dozen, most of them big and casual, with menus leaning toward surf and turf and Yelp ratings in the 3 ½-star range. If you go, odds are that somebody will suggest you have hula pie (ice cream, hot fudge and macadamia nuts are involved) for dessert.

The company’s island eateries include Duke’s (with locations on Oahu, Maui and Kauai, along with mainland restaurants in Huntington Beach and Malibu); the Hula Grill (on Oahu and Maui); Kimo’s (Maui); Leilani’s (Maui); and Keoki’s Paradise (on Kauai).

The company, which goes back to the 1970s, has several mainland eateries, too: the Cliffhouse (in La Quinta), Jake’s Del Mar and the Sunnyside Lodge (a restaurant, bar and hotel on the west shore of Lake Tahoe). Unlike competitor Roy’s – which has built an empire taking Hawaiian fusion cuisine to California, Florida and beyond – TS so far still has more restaurants in Hawaii than in any other state.

Many of the TS restaurants are in or next to hotels. One of its busiest spots is Duke’s in the Outrigger Waikiki on the Beach, and the newest Duke’s, which opened in late 2009, is at the Honua Kai Resort, a vacation condo property that opened last year in Kaanapali, Maui. On its website, TS management vows to run “the friendliest restaurant company in America,” but of course restaurants grow their own personalities, and there are good days and bad.

On this last trip, I stopped in at Kimo’s in Lahaina and found myself confronting a cheeseburger as bland and disappointing as the sunset was gorgeous. Within 48 hours, however, I had drifted within the TS orbit again, this time fetching up at lunchtime in the dining room of the Hula Grill in Kaanapali. Great waiter. Good Kapulu Joe (Hawaiian barbecued pork), and addictive macadamia nut slaw.