From island escapes to European classics, these are a few of the places I love to plan. Tap any destination to learn more, and know this is only a starting point.
Nearly thirty years of travel across 48 states and 18 countries sits behind these pages. When I recommend a destination, it is because I know what the trip actually feels like on the ground, not because it photographs well.
The destination is the last decision, not the first. What matters more is the shape of the trip: how far you want to fly, how much you want to move around once you land, whether you want a resort to hand you everything or a place to go explore, and what the week actually needs to cost.
If you want warm water and no planning stress, look at the Caribbean or Mexico. For a beach trip with real landscape behind it, Hawaii. For adventure and wildlife without roughing it, Costa Rica. For food, art, and history with fast trains between cities, Italy. For somewhere genuinely different from anywhere you have been, Japan.
Closer to home, Ireland is the easiest first trip to Europe, the national parks are the best family trip in the country, a road trip skips the airport entirely, and New York City delivers more in four days than almost anywhere.
Beyond these, I also plan trips to Greece, Bora Bora, Switzerland, Alaska, Sedona, Portugal, Iceland, and far beyond, plus cruises on every major line. If you have a destination in mind, I can plan it. These pages are simply where I get the most questions.
A destination wedding or honeymoon, a group getaway, a solo trip, a family vacation, or a milestone birthday each pull toward different places. The occasion changes the answer as much as the season does, which is why I ask about it early.
I start with how you want the trip to feel rather than where you want to go. Busy or quiet, beach or mountains, resort or exploring, how much you want to move around, and what your budget really is. Most of my clients come to me without a destination picked, and that is a better starting point than a fixed idea that turns out not to fit.
No. These are the places I am asked about most and know best. I plan trips worldwide, including Greece, Switzerland, French Polynesia, Alaska, Portugal, Africa, and plenty more. If you have somewhere in mind that is not on this page, ask me.
Mexico and the Caribbean are the easiest, usually one connection through Houston, Dallas, Atlanta, or Miami. New York and the national parks are straightforward. Hawaii and Japan are long travel days and need to be planned with that in mind.
Mexico, the Caribbean, or Ireland. All three are easy to reach, forgiving if plans shift, and gentle introductions to traveling abroad. Ireland in particular surprises people with how simple it is for a first trip to Europe.
Yes, and it is one of the things I am best at. Costa Rica, Hawaii, the national parks, and the bigger Caribbean resorts all let the adventurous people and the relaxed people each have their own day and still have dinner together.