Annapolis, MD

21 Nov

Hello! Jess here,

We’ve just returned from Annapolis, Maryland!  The primary reason for the trip was because I was attending a three-day SailTime Base Owners Meeting. Annapolis is well known as the center of sailing and boating in the Mid-Atlantic. As soon as you enter the town, you immediately sense the nautical ‘vibe’. Almost everyone looks like they’ve just stepped off a sailboat. Scenic Main Street is lined with sailing stores and boutiques. If you’ve never been, I would suggest you go check it out… but only for a day or two.  (Pictured below Chris and I are on Main St.)

Not being a ‘hard-core’ sailor, I find the town a bit boring. Annapolis is the type of place where you enjoy good food, good wine and good company. When I typed ‘Annapolis’ into Trip Advisor, the top things to do where Sailing, Museums, the local Park, Dining and the United States Naval Academy. Yes, the academy is pretty neat, but unless you’re a sailor there isn’t much to do other than wander the cobblestone roads and check out the old architecture.

The meeting I attended was a gathering of the global SailTime base owners. It was very cool to be in a room filled with people from all over the world who do the same thing I do for a living and suffer the same frustrations and challenges. I learned a lot and had a very good time. If you’re interested in the fractional sailing program I manage, you can click here for more information!

During the meeting, sailing legend Gary Jobson lectured on sailing, leadership, teamwork and his past adventures. I do admire sailors for their love of adventure and their free spirits. Gary told us wonderful stories of America’s Cup Racing, the founding of ESPN, his many years of commentating sailing events for the network, his love for the sport and sailing mishaps he’s since learned valuable lessons from. Gary is not only an inspirational athlete, he is also an exceptional leader and speaker. I was very excited to meet him. Gary’s website can be found here. Pictured with gary is myself and my collegue Andrew. We manage the SailTime GTA base and program together.

If you’ve never heard of the America’s Cup, you’ve got to check it out. The America’s Cup is the oldest active Trophy in international sport!  As sailing has progressed throughout the ages, so have the sailors. originating on monohulls in 1851, the boats racing this year in the 34th America’s cup are lightning fast catamerans. The sport is INTENSE in every sense of the word. As I persue learning the sport of sailing, I hope to eventually crew on a race boat. These guys are the real deal.

Check out the America’s Cup on their YouTube Channel. Here is one of their latest videos: or here.

I had the privilege of seeing these boats live in action last summer in Newport, RI. They sail three times the speed of the wind- it’s almost unbelievable!  I intent to blog about the America’s Cup in the future- stay tuned!

When Chris and I travel throughout the USA, we often drive to Buffalo, NY and fly out of BUF on SouthWest. On our way home, we stopped for some Buffalo wings… when in Rome…

Until next time! Thanks for following along :)

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