(MONEY Magazine) – One of the ironies of modern travel is that, although we typically spend thousands of dollars on a vacation, it's often the first $15 or so that we lay out--for a guidebook--that ends up determining how good a trip we have.

Problem is, bookstores are teeming with hundreds of travel guides, often several dozen on a particular location. And even if you found a guidebook you liked on an earlier trip, the other guides in the series may not measure up--in many cases, they're written by different people. Ultimately, discriminating among the popular general-interest guides requires two things most travelers don't have before leaving for vacation: time and in-depth knowledge about the place they're planning to visit.

That's where we come in. We found prominent travel and culture writers who are longtime residents of five popular urban tourist destinations--who better, after all, to judge a guidebook than a local?--and asked each of them to pick their favorites from among the most popular guides for their hometown (as determined by sales at Barnes & Noble and Amazon.com). Here's what they concluded.

NEW YORK CITY by Phillip Lopate

Lopate is a native New Yorker and the author or editor of 15 books, including Writing New York: A Literary Anthology.

The best guidebooks make us read them compulsively, gobbling up entry after entry like potato chips. I have only to think of past commentaries like the quirky, elegantly written 1939 WPA Guide to New York City (recently reissued for $17.95) or the architecturally indispensable, fearless (and now out of print) AIA Guide to New York City by Elliot Willensky and Norval White, for my mouth to water.

These supreme examples of New York guidebook writing overcome the fundamental challenge of the genre: They offer mountains of concrete, factual information without deadening or overwhelming the brain. The surest way to do this is to impose a strong viewpoint, not only tacitly, through inclusions or length of entries, but bluntly. I will give a lot for a guidebook that does not fear being undiplomatic and negative on occasion: I can trust its enthusiasms more, whereas a diet of pure enthrallment palls.

Of today's top-selling New York guidebooks, the best written by far--and the one that most seems to issue from a human being rather than a committee--is Frommer's '99 New York City ($14.95). David Doty, the guide's principal writer, has an ironic, somewhat bitchy style (as when he refers to the Whiskey bar in the Paramount hotel as "eternally trendy and inexcusably haughty"). He also has a well-balanced, insider-outsider perspective, discriminating yet accessible. He brings a savvy native's eye even to places that few locals (but countless visitors) actually go, noting, for instance, about the touristy Marriott Marquis Hotel: "On clear nights, the View, the three-story revolving rooftop restaurant, offers some good views; on cloudy nights, it offers only mediocre food and bad music."

Most guidebooks are addressed to the short-term visitor, and are consequently top-heavy with tourist "musts" that the local himself might skip. As a native New Yorker, I can honestly say that the places I depend on most to give me a real shot of New York are often what the guidebooks leave out. So it was a pleasant shock to find in Access New York City ($19) such casual glories as Russ & Daughters, the best lox and appetizer store in town; or Pomander Walk, that weird stage set of an alley carved into West 95th Street; or Fairway, where the produce is nonpareil; or the American Standard Building, an unsung 1924 masterpiece by Raymond Hood overlooking Bryant Park. Block by block, Access crams in those very grace notes that make the city livable.

The most visually appealing volume is the Eyewitness Travel Guide: New York ($24.95). Splendidly designed, bursting with color photographs of every important structure, including detailed closeups, it will save you the trouble of buying a hundred postcards, providing all the memory jogging you need.

My final assessment? I would buy Frommer's if I were a first-time tourist to the Big Apple; Access would be my choice if I yearned to know the city like a native.

WASHINGTON, D.C. by Anne Glusker

Glusker is editor of the Style Live section of washingtonpost.com.

Most visitors to the capital expect little more than monuments, museums and the machinations of government. And there's certainly enough of that to keep most people busy. But there are other sides to the federal city, few of which you're likely to discover without the kind of advice only an insider can offer. To my mind, Access Washington, D.C. ($19) is the guidebook that most successfully does it all. It offers the essential information--like how to get tickets to the popular White House Easter Egg Roll and which are the must-see sights at the National Air and Space Museum--and points you toward the city's less celebrated scenes, such as the incredible array of ethnic restaurants that have sprouted throughout the city and its nearby suburbs. (Access is right on the money, for instance, in suggesting Cafe Dalat, Queen Bee and Nam-Viet, three very good Vietnamese restaurants in the Little Saigon neighborhood that has sprung up across the Potomac River from D.C. in Arlington, Va.)

The "Bests" listings are a particularly attractive feature, drawing on the insights and tastes of notable citizens who are asked to name their favorite things about the city. Renowned chef Ris Lacoste recommends the jazz pianist downstairs at Kinkead's restaurant. And Terrie Sultan, a curator at the Corcoran Gallery of Art, suggests a visit to Georgetown's Dumbarton Oaks park--especially in the fall, when the chrysanthemums bloom. Both ideas take a somewhat standard tourist destination and put a smart twist on it (everyone knows about Kinkead's; few take note of the great music downstairs).

Another of the book's assets is its clear, crisp design. The Access practice of dividing cities into neighborhoods, which enables you to easily pinpoint attractions in relation to one another, is particularly suited to Washington, D.C. Although the Metro is clean, quiet, safe and reliable, the stops aren't very close together, and if you don't plan your excursions carefully you can find yourself in the middle of a long walk--a torturous scenario if you are visiting on one of the District's infernally hot summer days. So, for instance, it's quickly apparent that you could visit the National Gallery of Art and the Hirshhorn Museum on the same day but that you'd be well advised to leave, say, the U.S. Holocaust Memorial Museum for another day--even though all three are located on or near the Mall.

NEW ORLEANS by Andrei Codrescu

A commentator for National Public Radio, Codrescu is the author or editor of some 20 books. His latest, Messiah: A Novel, is set mostly in New Orleans.

New Orleans is a complex and mysterious city, the layers of which do not reveal themselves easily to the casual visitor. Looking over the raft of guidebooks on New Orleans, however, I find myself frequently impressed. I read, for instance, in Frommer's Irreverent Guide to New Orleans ($12.95), that in the French Quarter, "Quarterites are happily at home in various sleek condos, creaky attics, chic townhouses and quaint gingerbread cottages." I am one of those Quarterites, and I am quite happy here, indeed.

I also find that most guides do a fairly good job of pointing visitors to the city's hundreds of fine eating and drinking establishments. Full-time residents might even feel that the books reveal too much: I was almost angry to find, for example, that Fodor's '99 New Orleans ($14) lists my favorite French Quarter coffeehouse, Croissant d'Or. The last thing I want to see in the morning as I have my first grumpy cafe au lait is a group of tourists taking nearly an hour to figure out what kind of coffee they want. Is nothing sacred?

Still, New Orleans tolerates tourists because they are valuable to the economy. So, grudgingly, I'll point you to the best of the guides, which, for my money, is Randolph Delehanty's Ultimate Guide to New Orleans ($16.95). It is the most highbrow of the guides, includes solid architectural information, is sprinkled with literary references on the city, and has an insider's view of not only the city's sensuality but also her history. What's more, it is well written, making it a pleasure to read. The visitor trapped in a rainstorm in an old French Quarter hotel reading the Ultimate Guide will feel the city's spirit. Later, when the sun comes out, he or she will be gripped by something more than mere information.

New Orleans is, of course, renowned for fabulous food, and Delehanty is one of the few writers who comes close to doing its restaurants justice. The restaurant reviews in the Lonely Planet City Guide ($11.95) are also quite trenchant.

A distant second best to Delehanty's erudite book is Frommer's Irreverent Guide. Unlike, say, Fodor's, which does well with the obvious, it goes under the surface, noting, for instance, that Disneyfication is a real threat to the city--a fact that many others strenuously ignore in their boosterism.

Of course, nothing beats having a true native as a guide. My own treasure of never-revealed places is quite secret, but I'll let you in on one: Molly's at the Market, a great bar on Decatur Street filled with local wits. Go after 2 a.m. I'll say no more. It's a test: If you go there and like it, you're one of us. If you don't, that's fine too--your guidebook will no doubt lead you to a hundred other great joints.

SEATTLE by Jonathan Raban

Raban, whose most recent book, Bad Land, won the 1997 National Book Critics Circle Award, has written extensively about his travels in the U.S.

Varnish, laid on thick and shiny, is the curse of the regional guidebook. The surprised resident finds his local supper haunt cracked up to be a serious rival to the Four Seasons and Lutece, and his modest neighborhood extolled as if it were Paris' Left Bank. Seattle--a medium-size city that has been dangerously awash in money for the past 15 years--is now riddled with luxury shops, hotels and restaurants, most of them rather bad. It could do with a tough-minded guidebook to sort out the innumerable geese from the meager handful of swans. One might have hoped that the popular guides published in New York City, like Access, Fodor's and Frommer's, would bring an alien and discriminating eye to bear on our pretensions. They don't, though Frommer's Seattle and Portland ($14.95) is the most restrained in tone and the most nearly realistic in its judgments.

The best guide to Seattle is the locally published Seattle Best Places ($16.95), but it should be read with the aid of a sharp paint scraper. Early editions (the current one is No. 8) were modeled on the British Good Food Guide and were admirably influenced by the GFG's tone of witty--and sometimes ribald--deprecation. Alas, the Good Food Guide has since gone soft, and so to some extent has Seattle Best Places. Michelin-style stars are promiscuously scattered over some very indifferent restaurants, and the prevailing mood is one of barely modified rapture.

Yet beneath the glossy finish there is much expert local knowledge in Seattle Best Places. I used it when I first came to Seattle in 1989, and I've been using it ever since; it's led me to many places I'd never have found myself.

Attempting also to examine the books from an outsider's perspective, I tested the most popular guides by quizzing them on a subject about which I'm blissfully ignorant--the Seattle music scene. Even the Lonely Planet Seattle ($14.95)--intended for the young and, presumably, hip--failed the test abysmally. Seattle Best Places scored high, with a concise but ample guide to some 40 joints where you can listen to everything from blues to zydeco, including a plausibly atmospheric description of each club ("You can get a hard drink at 6 a.m."..."sexually diverse"..."known for its stiff drinks and the fact that someone once got killed there"). It would be nice if the hard, inside-dope tone of the Nightlife section had rubbed off on the restaurant listings, where it is badly needed.

SAN FRANCISCO by Don George

After nine years as travel editor of the San Francisco Examiner, George is now travel editor of Salon.com.

When you've lived in the San Francisco area for two decades, knowing the best guidebook to the city is not just useful, it's absolutely necessary. Last year, 4.2 million people visited the Beguiler by the Bay, and many of them turned out to be distant relatives or friends of friends. It's always easier to say, "I'm sorry, but I'm busy this weekend" if you can follow with, "but here's a guidebook that will tell you everything I would've told you anyway."

Choosing one is not easy. My local travel bookstore devotes six full shelves to San Francisco guidebooks, including the popular Eyewitness Travel Guide: San Francisco and Northern California ($22.95), to which I briefly served as a consultant several years ago but which is not my favorite. Instead, the guide I would most highly recommend is Frommer's '99 San Francisco ($14.95).

Something in my iconoclastic heart recoils at the notion of choosing the guidebook equivalent of a Hilton or Holiday Inn, but Frommer's offers everything I want--an authoritative, reader-friendly introduction to the area's history and culture; a sensible, easy-to-understand geographical breakdown of the city itself; critically acute evaluations of hotels and restaurants; and practical, informed guides to both the most important sights and the lesser-known, easily overlooked sights that illuminate the spirit of the city.

The book begins by listing "Frommer's Favorite San Francisco Experiences," and Nos. 1 and 2 just happen to be two of my favorites as well: "cafe-hopping in North Beach" and "a walk along the coastal trail." I can think of no better introductions to San Francisco culture and scenery. I also like the Best Bets recommendations that begin the accommodations and dining chapters--useful tips that cover everything from the best family hotel (the Westin St. Francis) to the best eatery for cutting a business deal (Moose's) and the most romantic restaurant (Fleur de Lys). Amazingly, I concur with most of the book's judgments on where to stay, eat and visit.

If you can afford a second guidebook, I would recommend Hidden San Francisco and Northern California ($17.95). While its general information is not quite on a par with Frommer's, virtually every one of the insider tips that appear under the "hidden" designation (there's one every five pages or so) is a gem.