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Anchoring is kinda like yoga class. Our first week on the Loop.

After checking most of our final must-do projects off the list, we turned the engine on for the first time by ourselves, unhooked the lines, and took off for our Great Loop Easter morning. Here are some highlights.

1. Broke a travel rule and stayed at likely the nicest marina on the Loop night 1.

April 5th was our 18 month wedding anniversary. When we were in the thick of boat projects and training, Tim said wherever we are on April 5th, we’re going to make it a day to celebrate us. We just so happened to be staying at the very nice marina, Longboat Key, which is associated with one of the nicest resorts in West Florida. (Marina hack—if you book a slip at a marina, sometimes you get their beach resort access without having to pay to stay at the actual resort, which in this case was $800/night.) So we treated ourselves to grouper sandwiches, a cocktail, and a nap on the beach. (We also gave up alcohol for lent, so was well enjoyed). While we're advised you should save the nicest places for the end of a trip, we have no regrets.

2. Home cooked meals taste even better after a day on the water.

Our first night of our trip, we were treated to a visit and homemade Easter dinner, from our friends, the Ulloms. They say when trying to meet up with someone on the Loop you can tell them where or when, but rarely both. Luckily the Ulloms lived close by in Sarasota, and were gracious to share their Easter dinner with us and to celebrate our maiden voyage. (They even hid Easter candy in our boat before they left so often when searching for a tool we get a little chocolate reward too). Thank you Ullom family for such a fun and special night.

3. Boating is like training for a parade.

The intracoastal waterway (ICW), at least what we have travelled so far, is kind of like a highway. There are “2 lanes” and everyone stays primarily in the channel—the space between the red and green markers (otherwise you’d hit bottom). Sometimes there are houses to gawk at or birds/dolphins passing by, but mostly the activity is passing other boaters, and have found it customary to give a small wave. When you are cruising on “the highway” for 4+ hours, that’s a lot of waving.

4. Anchoring is kinda like yoga class.

We anchored for the first time right outside Cayo Costa State Park, an island off the coast of West Florida. There were about 30-40 boats already anchored in the cove, and we had to find the right spot for us. Similar to rolling out your mat in yoga class, you want to give your neighbors enough space, but be in a good area yourself. But if you’re a little too close to one neighbor, it can make class feel awkward. Which, happened to us (it was 100% our fault, as we didn’t consider how much the wind/anchor chain length would move our boat), but luckily our neighbors were very forgiving. Also like yoga class, no matter how many people are there always seems to be space for one more (boat or yoga mat). Once settled, you also peak around at other boats to make sure yours is doing what the other boats are doing (facing same direction, anchor's not dragging, etc). Luckily, our anchor held and had a successful first night at anchor.

5. Our boat is relatively small.

When docking and passing fast speedboats on the ICW, our boat seems large and slow. We found a lot of it is just in your perspective, and more times than not, Sweet Day is really our little nugget on the water.

6. Dock C at Legacy Harbor is a special place.

We pulled into Legacy Harbour in Fort Myers, where we planned to spend a couple days to wait out a storm and finish some projects. We quickly found out it was Looper Central—where a lot of post-Loop loopers come to live on their boat after they’ve completed the Loop. We were welcomed with open arms. We attended our first docktails, (every night at 5 pm Dock C residents come together for BYOB drinks). Friday night it was Dee’s birthday and made grilled twinkees for everyone (yum!). Bruce, our new neighbor, within 5 minutes of meeting us, drove Tim to a follow up eye doctors appointment (Tim’s eyes are fine). We received countless offers to borrow cars or be driven on errands we needed to run, and infectious enthusiasm for us as we start our journey. Not to mention, the fun witnessing the activity of everyone helping out with each other’s boat projects on a Saturday afternoon. The community built here is real, and lucky to have experienced it.

7. Schedules are meant to be broken.

While on our first week, we received the unfortunate news that Tim’s grandfather, Donald G. Carney “Papa”, had passed away. He was a wonderful grandfather, always showing enthusiasm and support for any of his grandchildren’s accomplishments and pursuits. He will be greatly missed. So we packed our bags, and headed to MD for 2 days to see family and attend the funeral, before we return back to our life on water later this week. Grateful to have the opportunity to leave our boat in good hands and to celebrate a full life lived in the presence of loved ones.


David Henderson
David Henderson
Apr 19, 2021

It's Dave back at legacy sorry about your grandfather! Hope all is well and way nice to have you guys here!


Robert Conrad
Robert Conrad
Apr 14, 2021

Very sorry for your loss, TC. Safe travels on and off the water. -RC and Fam.


Apr 14, 2021

Our condolences on the loss of your grandfather Tim. So glad you two could come back for the funeral. Kate you are turning into a stellar story teller!! Enjoying your blog very much. Safe travels!

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