The boat was ready and so was I! I had done as much book learning and YouTube training as I could, plus my time with Captain Clint helped me tie it together. There was nothing left to do except wait for a weather window and start the trial by fire.
May 24th was Day 1. I pulled away from the dock and I was on my way to my first stop at Wormley Marina in Wormley Creek, Virginia, about 5 hours away. The waves going out of Norfolk were BIG and hitting me straight on my bow. I felt like I was in the Perfect Storm movie. I realize it will probably be normal once I am a month in, but they were intimidating on my first day. Kali freaked out and was under my feet the whole time. After about an hour, the waves settled and I started hitting my stride. I turned on my stereo and the adrenaline pumped. I felt a wave of gratitude for the opportunity to take this amazing adventure. Pam, the dockmaster at Wormley, called me while I was on my way to give me directions and info on the marina. I told her that this was literally the first day I had driven my boat solo and asked for her easiest dock. I will forever be grateful to her because she gave me a T dock that could have fit a 60 foot yacht. Ha! It was like landing a Cessna at CVG. Shew! It took me two tries but only because I could not get the dang line looped around the dock cleat before the wind and my momentum moved me just far enough out of reach. I nailed it the second time. Boom.





That night I played around with my little dink. Now this is what Kali was waiting for! She was on before I knew it and we took a little ride around the neighborhood to test it out.
One day down and many more to go. Day 2 was Memorial Day and I traveled another 5 hours or so to Safe Harbor Stingray Point near Deltaville, Virginia. I gave Mary, the dockmaster there, the same beginner speech and this time, she even came out to help me get set up. Amazing! I was super thankful. I stayed for 2 nights at this one because I had a long workday that Tuesday. It was nice to take a mental break anyway. I was exhausted!
On Wednesday, May 27th, I left Stingray Point and thought I would try out anchoring. I spent way too many hours overthinking where to anchor and pored over all my Skipper Bob’s guides, Waterway Guides, and the Active Captain links in AquaMaps. I picked Fleet’s Bay because it was just around the corner from Stingray Point and I could “easily” get there during my lunch break that day. Piece of cake. Found it, dropped the hook, and settled in. Until…the tide went out just enough for my shallow water alarm to go off during a meeting. Luckily, I was on mute most of the time but it was quite nerve-wracking. The alarm is set to go off at 5 feet and my draft is 3.5 so I still had some room. My next meeting was with my very-understanding boss and I asked her if we could reschedule so that I could move to a little deeper water. I moved out 15 feet or so, dropped the anchor again, and reset my anchor alarm. Fine, problem solved. Had another client meeting with no issues. My Starlink works spectacularly, by the way. Next was my meeting with my also-very-understanding CEO. I was settled in for about 10 minutes when a pop-up thunderstorm came roaring through. The wind whipped my boat 90 degrees sideways which was outside my anchor alarm radius (because of an ID10T user error) so my anchor alarm AND my shallow water alarms screamed all at the same time, while the black clouds rolled over and poured rain down upon me. I said “I gotta go!” and called Captain Clint to ask him what tf to do! It was actually quite amazing because the problem was not the anchor, it was me not picking deep enough water in the first place and then setting the wrong anchor point on my alarm. I had 50 feet of chain out plus another 15 feet of rode (rope) so I was stuck tight. The storm passed through in about 20 minutes and then went perfectly calm. I watched the ospreys fish in the little bay and tried to calm my nerves and get a little sleep. This is what my anchor alarm path looked like. I don’t think my boat actually went up on land but I am not 100% sure.

When I woke up on Day 5, Kali and I were both ready for a marina again! She had been holding her pee and poop since noon the day before. As we were leaving our little anchorage spot, I was going as slow as possible (not even at the no-wake speed) because there were crab pots everywhere and I have heard horror stories about getting the lines wrapped in your prop. There was a particularly big patch of them so I could either navigate through, go right, or go left. I chose poorly. I missed the crab pots but I came to an unnatural stop. Shit! I ran aground. Well, now what. I was too embarrassed to call Captain Clint within 12 hours of my last emergency and this was not a safety issue like the storm might have been, so I just sat there for a minute or two and thought about my next step. As I was thinking about it, an immature bald eagle flew overhead laughing at me so I figured I might as well laugh at myself too. I hailed a couple of the crab pot fisherman who said “you can’t go that way” and yanked me out. The trial by fire continues. I was a little rattled so I made it a short day and ended up at the loveliest marina yet. I pulled into Ingram Bay Marina, a family-owned hurricane hole. The owners, Billy and Mary, both met me at the dock and helped me dock, re-fuel, pump out, and very generously shared their knowledge of the area and their boating experience. Plus, their little slice of heaven has a big field in the back where Kali ran and relieved her bowels. This was exactly what I needed after my most recent couple of lessons learned.



I was on my way to Solomon’s Island on Day 6 and my first yacht club. As a distinguished member of the Mount Adams Yacht Club, I get reciprocity with other yacht clubs and I was excited! An added little challenge thrown at me from the universe was a black screen of death on my ipad. Very funny, universe! There is a Best Buy near Solomon’s Island so the plan was to leave in the afternoon after I wrapped up my work week and get to the marina in time for a quick trip to Best Buy. Jim met me at the dock and guided me in. Another successful docking…check! He gave me my 2 free drink tickets at the yacht club pub and I went to make friends. It was very cool to see the Mount Adams Yacht Club burgee hanging in the pub (the blue one to the right in the picture below). While I was enjoying my free wine, I missed the cutoff for pub food and then I missed closing time for the pizza place right next door. Dangit! I snagged some free peanuts from the pub and figured it was going to be wine and pizza for dinner. However, Bartender Kim dug around in their kitchen and heated up some leftovers from a party that they had there the night before and she scored me some shrimp and rice. Jackpot. Free wine and free dinner!




I was hoping to make it to Annapolis the next day but woke up to heavy winds. Another day in adorable little Solomon’s island was not a bad thing. I took advantage of the Yacht Club’s free laundry and did some grocery shopping. The best part of the day was meeting new Looper friends and I met them for drinks at the Tiki Bar in town. It was the perfect end to a fantastic first week full of more ups than downs. I am ready for week 2!

If you have questions about anything loop-related, feel free to leave a comment and I will answer them in my next post!
“Life begins at the end of the comfort zone.” – Neil Donald Walsch
To support the adventure or to track The ‘Nati Nomad’s progress, visit greatloop.thenatinomad.com.



Wow! Us landlubbers assume that your joutney is kind of like your pontoon ride. Nothing further from the truth. You have, and will always handle it well. Progress! Thanks for the post!
Congrats on your first week Colleen! You are an amazing person that breaks the mold- love hearing about your adventures and I know you got this!
Thank you, Chris!!!
Sounds like you are being tested and passing them all with flying colors! Lots of trials and tribulations, but at least you’re learning quickly how to get through all these adversities! I love reading every word of Your adventure!
So nice to see your smile in the posts! Your zeal and perseverance are the wind beneath the sails so to speak!
Continued successes in each challenge friend!
Love Kalis part in this too;)
Tammy