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Kallie Rollenhagen Photography

Northfield & Minneapolis, Minnesota Photographer
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This sailboat was our home for four days. Brother Trevor captured this with his drone.

Florida Keys Sailing Adventure

Kallie Rollenhagen January 13, 2024

We usually don’t have New Year’s Eve plans beyond sitting in front of our fire and staying warm. However, my brother Trevor was turning 40, and he’s a New Year’s Eve baby. His girlfriend planned a 4-day, 3-night sailing trip to the Florida Keys and they graciously invited us along. We couldn’t say no!

We flew into Tampa, then drove with them from St. Pete to Miami early in the morning, where we met our captains: Rodrigo, from Chile, and Cezary, from Poland of Destino Charters. Our sailboat was bigger than I expected! Two bedrooms, two bathrooms, a dining and living space, a galley kitchen. The captains slept above deck, which is where we spent most of our non-sleeping time.

The first two days were overcast, but we had some wind — an essential sailing factor, we’d come to appreciate. We read, ate Rodrigo’s incredible cooking, and went snorkeling at Christ of the Deep. As we sailed out of Miami, we were essentially part of the Orange Bowl, a competitive regatta race. So fun to see the colorful spinakkers come out. We spent the first night anchored in the shadow of Pumpkin Island, just off Key Largo, and the second at a marina where we got dinner and took a hot shower.

The sun came out for the second two days, but we lost the wind. This wouldn’t have been an issue, except our motor broke on day three, after the most incredible snorkeling at Carysfort. So, we decided to head out to the Gulf Stream on New Year’s Eve to pick up some momentum from the current. I'll never forget Rodrigo grilling flank steak on the back of the boat for Trevor’s birthday dinner as Cezary expertly captained the sailboat through the huge waves and luminescent neon green fish lit up in the waters around us. A huge orange moon rose on the horizon and we saw fireworks dotting the entire horizon. As we tried to buoy in the middle of the ocean in the middle of the night, thousands of flying fish were sailing through the air.

Captains Rod and Cez sailed us through the night, into 2024. We woke up with Miami back in view and had mimosas and one last round of chorizo scrambled eggs and French press coffee. While the harbor was in view the entire last day, it took us several hours to go a few miles given the complete lack of wind. It was such a memorable trip, and I was thankful I only needed motion sickness pills once!

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Captain Rodrigo took this photo of Christ of the Deep at our first snorkeling stop

Another Captain Rodrigo photo. Our second snorkeling stop had lots of jelly fish and was home to this amazing sea turtle

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For our second night, we pulled into the marina right at sunset.

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