In contrast, Edwards and I had a few initial conversations over the phone, during which he gleaned from me the goals and preferred style of my trip. After that, we corresponded almost entirely via e-mail. Edwards took it in stride when I had to change my dates three times, and happily revised the itinerary when I asked for more local flavor. When I was ready to book, he sent me a single invoice for the entire itinerary.

Timing and Pace
As I was narrowing down my travel dates, Edwards saved me from potential disaster by pointing out that the week before Easter—Semana Santa—is the busiest time to visit, with foreign families on spring break and Ticos (Costa Ricans) heading to the beach. Had I booked the international flights before hearing his warning, it would have been nearly impossible to find available hotel rooms, guides, and activities.

For my self-planned trip, I opted to rent a car and drive myself and my companion around, but I had trouble finding accurate drive times from point to point. Since I didn't want to miss a canopy tour or sea-kayaking trip, I never pre-booked an activity for the same day that I had to travel from one location to the next. And still it didn't all fit: When the drive from San José to Arenal Volcano took longer than I'd expected, I had to cut out the hike I'd hoped to go on that afternoon.

Edwards, on the other hand, was able to time his itinerary practically to the minute. Although he had to pre-book many of my activities since I was traveling during high season, he knew exactly how long to allow for every transfer and event, so that I could fit a zip-line adventure, nature walk, and spa treatment into a single day. The one time I fell behind schedule—wandering through the organic garden with El Silencio Lodge's charismatic chef—my guide deftly rearranged the afternoon's plans. I never felt rushed, and there was ample time for relaxation between the activities.

Accommodations and Guides
A good travel specialist adheres to the same code as this magazine's reporters: Don't endorse a hotel unless you've slept in its beds, eaten at its restaurant, and been in the care of its staff. It's for this reason that Edwards managed to choose better hotels than I did. Take the two properties near Manuel Antonio National Park: Mine, Si Como No, had a somewhat faded mass-market feel, while his pick, Arenas del Mar, had bigger, more elegant rooms and its own beach. Another perk: We were upgraded to a suite. Having opened only last October, Arenas was too new to show up on any of the Web sites I trolled for recommendations, let alone in the guidebooks, which are researched months before publication. Edwards also booked us into the new El Silencio Lodge, a chic, earth-friendly place where we had ultra-personal service as two of only three guests that night. The hotels I chose were acceptable and cost a fair amount less than Edwards's, but his offered higher standards of style and service.