Key-West-Sailboat

In order to write about life first you must live it. -Ernest Hemingway

Much has happened since I left you last. After spending a few days living the Key West lifestyle, I finally settled into a routine that was much less FOMO driven. The last few nights were spent wandering the streets with a cigar in my hand and Hemingway on my mind.

Which sounds as odd to me as it does you. Although I’m an aspiring writer, I’m much more likely to read Andy Andrews or Donald Miller than I am Tolstoy or Faulkner.

Yet, there was something transcendent about reading Hemingway while walking in his footsteps. Living adventures through his words. Sitting beside him at Captain Tony’s. Standing beside him at the Southernmost Point. Staring across the Atlantic horizon, waves crashing, an overnight sail away from the Havana marina bearing his name.

Junkanoo-Sunset But after 8 days in the Conch Republic, a much welcomed weather window appeared and the time came to continue our own adventures. We sailed Randy’s boat, Attitude, out of Key West’s Northwest Channel into 2-3′ seas towards Fort Myers. As the sun set into the Gulf of Mexico, the full moon over Florida Bay lit the horizon on all points of the compass.

Crab buoys, while easy to dodge via moonlight, pocked the surface in rows extending every direction. The seas laid down overnight to a pond-like state. So much so that when I awoke for my 4am watch, my first thought was that we were anchored. It’s hard to imagine such a large body of water can be so calm.

Nearly 24 hours after leaving Key West we pulled into Fort Myers and had a reunion with some sailors Randy had met last year in Orange Beach. That’s one of the great things about the cruising community–friendships are forged quickly and can last a lifetime.

The next day we made the short run up the Gulf Intracoastal Waterway to Cabbage Key, a highlight of the trip that I hope to write more about soon enough.

After waking up and exploring the surrounding mangroves, we ventured back into the Gulf northwards to Clearwater. Another overnight jaunt that would prove to be as memorable of a sailing experience as I’ve ever known. Shortly after sunset the wind clocked around to starboard and the seas began growing.

By the time the waxing moon rose over the Florida mainland, Venus was setting in the west, casting a glare bright enough to illuminate the whitecaps along its path.

To this point, the trip from Key West had been a motorboat ride rather than a sailing trip, the white sheets used more for stabilization than propulsion.

Tonight was different.

Attitude-Gulf-Sailing We’d left Cabbage Key just after noon and cut through the unmarked “Swash Channel” at Boca Grande Pass, saving 8 or 10 miles of westing. Current was against us along the coast and we spent the first several hours motorsailing uphill at 4 knots. It felt like we’d never get to Clearwater; wind and waves both on our nose.

But at sunset, everything changed. The forecasted NE winds kicked in as a thunderstorm boomed over Sarasota to our east. By 1830 we’d shut down the engine and began riding the 15 knot breeze to 6 kts under a reefed mains’l and genoa. For the next 10 hours, we experienced the kind of night sail that most dream about.

Sailing a 35′ boat 8 miles per hour into the black night feels like you’re going 50. It’s exhilarating. 3-5′ waves were just large enough to feel like a Disney thrill ride without being overly frightening.

Staying awake during our watches was no problem; time spent telling years worth of stories, identifying new constellations, and scouring the horizon for shipping traffic aimed at Tampa Bay.

By noon we were tied up in Clearwater, my leg of this adventure coming to an end on such a high note that I’ll be dreaming of the next for months to come.


For the first time in the last 3 years, the next several months of my life are already planned out. After an incredible family Thanksgiving in California, I’ve moved back to Auburn to serve as the Interim Producer of Videoboard Operations.

auburn-sec-championshipIt’s the position I held before moving to Orange Beach 3 years ago and if you’re at all familiar with the college football scene, you can understand it’s a pretty exciting time to be there.

It appears that February and March will bring opportunities like I’ve never had before, and I can’t wait to share those with you when the time comes.

Additionally, I’m on the verge of making great progress towards the educational curriculum portion of my dream to sail around the world. You’ll be hearing more about this soon.

Wherever your travels take you this month, I wish you the best and hope you’ll do at least one thing that pulls you out of your comfort zone.

And, as always, Dream Big & Live It.


Bo is currently based in Orange Beach, Alabama working towards checking #31 off his bucket list. If you’d like to be a part of the adventure, consider sponsoring a mile. To get more info on the curriculum, sign up here.