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14 Perfect Days in Hawaii

by Deborah Dunn | Published May 2008 | See more Condé Nast Traveler articles

There are some places you can't help but fall in love with at first sight and return to year after year. We've chosen some of the world's most beloved (and touristed) destinations and, with the help of the best travel specialists in the business, have ferreted out their secrets, their treasures, their unmissable experiences. The result is a series of step-by-step trips that will surprise and delight those who've never been to the destination before . . . or who have been a dozen times. Each of our highly detailed itineraries has been vetted and perfected by a Condé Nast Traveler editor, and each can be bought as is with just one phone call. Let the romance begin

The Challenge

Word of the Hawaiian Islands' staggering natural beauty got out long ago. This Pacific Ocean archipelago is one of the most developed in the world, with tourism so intrinsic to the economy that it accounts for more than a quarter of its revenue. Upwards of seven million visitors descend on the islands every year, gargantuan resorts line much of the coastline, tour buses pack the parking lots of the star attractions. No wonder some travelers see Hawaii as little more than a manufactured tropical paradise where there's little reason to venture beyond the hotel beach or pool. Those who know better face another predicament: Visitors to Hawaii are, in fact, spoiled for choice. The state has eight national parks, 400-plus beaches, thousands of hotels, and countless scenic hikes and drives. How to narrow the options? Where are the best snorkeling spots, rain forest trails, and ahi burgers? With limited vacation time, it's imperative to make every decision a good one.

The Solution

We sought the advice of several Hawaii travel specialists as well as in-the-know locals to devise the perfect two-week itinerary—one that will steer you away from the tourist track and right to the heart of Oahu, Maui, and the Big Island. Half this trip is dedicated to learning about the island chain's rich history and fascinating culture, often in places that few travelers ever see. The other half is playtime, in which you'll be swimming, surfing, hiking, horseback riding, trekking over lava fields, and kayaking to a secluded cove. At times you'll be in the company of an expert guide. Often you'll be on your own, armed with precise instructions on where to go, when to go, and even how best to get there. You could, of course, make your own travel arrangements (we've provided all the details), but if you'd rather not deal with the hassle, contact Hawaii specialist Judi Chaitman of Great Getaways (see cntraveler.com/travelagentfinder) and let her sweat the small stuff. Chaitman knows the islands' best tours and hotels, and thanks to her connections, her clients sometimes score great perks—from complimentary fruit baskets and chocolates to room upgrades. Although this itinerary is timed for May, Chaitman will customize it to suit the time of year you plan to travel.

Day 1: Honolulu (Oahu)

Depending on what time your flight arrives in Honolulu, you may be faced with that very thing you would've assumed taboo in paradise—traffic jams. Not to worry. The trip from the airport to the hotel is just ten miles, and if you rent a car with a navigation system, you'll be able to swiftly wind your way through the choke of cars, high-rises, and construction that brings to mind a tropical Los Angeles. Although you're in one of the world's most isolated inhabited islands, you're also in a thriving state capital, one with the energy of a university town and the clout of an economic powerhouse. Blend that with the vibrant ethnic mix of Oahu's inhabitants—Polynesians, obviously, but also Chinese, Filipinos, Japanese, Koreans, Puerto Ricans, and Portuguese, many descendants from early plantation workers—and you'll soon discover a heady exoticism like nowhere else on the planet.

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