A new Wine Country luxury retreat is coming to downtown Healdsburg in 2026

Traveling with cigars can be challenging if you’re not prepared. The lack of preparation can lead to your favorite cigars getting smashed from inadequate storage, or they can peel because they weren’t kept at the proper temperature, among other issues. Sometimes you do all the right things, and still come away shaking your head.

I’ve been smoking cigars for two decades now, and it’s not beneath me to admit that I’ve made plenty of cigar travel mistakes in that span, and as recently as two weeks ago. You live, you learn, and hope you don’t waste a stogie on the next trip. My most recent cigar travel mistake is what inspired me to share these tips. Sure, there are plenty of articles out there offering similar advice. But this list comes from a cigar smoker and writer who has visited six countries and about a dozen states in the last year alone. And in that time, mistakes were made, and lessons were learned.

If you are like me, you grew up with stories of adventure. Whether you were fans of fictional adventure like Indiana Jones and Alan Quartermain, or you loved the true-life accounts of Ernest Shackleton and David Livingstone, there is a deep pull to venture into the unknown. The desire to abandon the Mon-Fri 9-5 in search of something deeper. You could spend your time thinking about hopping a boat and sailing the seven seas like the pirates of old. You could look up at the elusive peak of a mountain and believe it begs to be summited. You could stare into the depths of a jungle and wonder what treasures it hides beneath its canopy. No matter what kind of adventurer you are, you need to be prepared for whatever the world throws at you. I have climbed Salkantay Peak and explored the jungles of Peru. I have scanned the plains of Africa in search of a giant cat (the prospect of which was much more comforting than the actual sighting and wondering if I was far enough away). And I have disappeared into the secluded areas of Svalbard. One thing that remained constant was the need for the right pack.

Here is what I learned when packing for my adventures.

Savannah is one of those cities that seems almost too easy to like. The live oaks are dramatic. The Spanish moss does exactly what it is supposed to do. The brick sidewalks buckle in all the right places. The houses look like they were designed by people who understood proportion, shade, and the value of a proper front step. Even the light seems to arrive with better manners than it does in most places.

I have a built-in advantage when it comes to Savannah. We have family there, so we have been back several times, not just once for the checklist version of the city. I have also done a photography workshop there, which is a terrific way to learn any city. You get up early, stay out late, and pay attention to alleys, doorways, ironwork, reflections, and the way a city changes when the tourists are still asleep.