Beachin’ it at Boca! My Day with Jane

Sherri DeWolf- Island Jane Magazine
Beachin’ it at Boca!

For those of you who have been following my journey, my snowbirding experience here in Key West has certainly been an adventure. I have had the opportunity to watch the season change from winter (Really? Winter is a season here?) to spring, and fully witness the everyday happenings of island life, here in the Florida Keys.

One of the most exciting things has been to watch the FishMonster charter fleet grow, by one, in the Historic Seaport of Key West, with the addition of the Island Jane boat, the Reel Deal. A sister ship to the already famous Premium Time, this pretty “little” boat made her way from Stock Island Marina Village to A & B Marina on what was, most definitely, a much-anticipated day for all involved! Not only did I get to be a part of that initial voyage to the Reel Deal’s new slip behind The Commodore Waterfront Restaurant, I also got to play for the day aboard her maiden island adventure with some guests from back home.

Waking up with the roosters and taking an early morning (peacefully dark, I might add!) walk down to the dock for a 7 a.m. half-day charter is magical when this little rock is still asleep. But, even more magical, is watching the sunrise over the harbor as you leave port and head out for a “Sunday Funday” offshore of Key West. The Conch Republic is well known for its sunsets, but the early morning light and color show over this tiny island is equally as magnificent!

As we made our way offshore, I was lucky enough to catch a glimpse of a sea turtle from the flybridge with Capt. Marlin and watch flocks of birds in synchronicity, swoosh past the bow as we set out to sea. Capt. Marlin told me that it was not uncommon for dolphins to come and play in the wake and alongside the boat when venturing out, so I made sure to keep a look out for these wondrous creatures too. What an incredible way to wake up with the ocean!

Sherri DeWolf- Island Jane Magazine
Passing by Ballast Key

The first stop on our scenic tour brought us by Ballast Key– famous for the home that “Fast Buck Freddie” built (or perhaps your very own pockets, if you were an avid home décor shopper in Key West’s former famed department store on Duval). This house is a sight to see, even from a distance! And a distance we kept, since rumor has it, if you get too close, the groundskeeper will ward you off with his rifle!

Sherri DeWolf- Island Jane Magazine
I’ve got the Boca Grande Blues!

Next, we made our way out to Boca Grande Key. This beautifully breathtaking island is pretty much the stuff island dreams are made of (and watching Capt. Marlin beach a boat this large was exceptionally impressive too!). We were the first to arrive on shore that day, which meant that we were also the first to gather up and see some amazing treasures! Newly washed up seashells, sponges and coral, along with hermit crabs, nostalgic lobster traps, and even a freshly hatched sea turtle nest, were among our finds. Oh, the stories such a pristine place would tell if you were there to witness it all arrive ashore. Walking along the shoreline, and around the magnificent mangroves (this area is protected so you are unable to set foot further into the Key itself), the backdrop was something straight out of a Corona commercial with the incredible shades of blue that the water seemed to shimmer and show off just for us. We made sure to stop and get a picture near the lone palm tree that stands proudly untouched by mother nature, before we headed back to the boat.

Sherri DeWolf- Island Jane Magazine
What remains of a former Naval target practice. Let’s snorkel!

After our island exploration, we arrived back at the boat to enjoy our brunch and begin another adventure. The next sight to see was an old Navy ship that had been purposefully sunk to be used for target practice years ago. Parts of the ship still protrude up out of the water, so this makes for great sights both above and under the water. Cormorants lined what was left of the bow, while barracudas zoomed past the boat and a shark patrolled the area in the distance. This wreck makes for a great place to snorkel, but being as spoiled as we are down here, the water temperature, in the mid-70s, was still a little chilly for some of us!

Sherri DeWolf- Island Jane Magazine
A Day with (my beautiful friend) “Jane”

As we made our way back to the harbor, while more boats began to head out for the day, I began to think about how grateful I am for this experience I’ve been manifesting here in the Keys for so many years. One of my favorite parts of the trip was spending time with Dianne Scott–the “real” Island Jane. This incredible woman is not just any fish in the sea. She is the beautiful mind behind Island Jane Magazine and a very special woman. Even more special, is that I get to call her my friend. Throughout my time here in the Keys, she has become an important part of my journey and, for that, I am exceptionally blessed.

Sherri DeWolf- Island Jane Magazine
Sister ships the Premium Time and Real Deal sitting pretty in port! Reunited at last!

Arriving back to the dock before lunch, the harbor now fully alive with tourists and locals alike, it was clear everyone was glowing from our day on the water, and our island adventure. My “Day with Jane” was “chum-full” of sunshine, fun and friendship. And all of this in a mere 4 hours—imagine 6 or 8? Next time, maybe we’ll paddleboard through some mangroves, take a trip to another local marina for lunch, visit the Marquesas Keys, brave the waters for some snorkeling, take a sunset cruise or even plan an over-nighter aboard the Reel Deal to the Dry Tortugas. I’m not sure what the next island adventure will bring, but I do know, I can hardly wait!

What will your “Day with Jane” look like? 

Click here for more information on how you can treat yourself to “A Day with Jane” aboard the Reel Deal.

Teacher, writer, and passionate creative mind, Sherri calls Southern Ontario home, but has a special soul connection with the island life and a great love for the Southernmost Point of the US--Key West, FL. Her love for the water started at an early age, splashing in Lake St. Clair--the "Heart of the Great Lakes" and international boundary between the US (MI) and Canada (ON). Being on, in, or by the water via the beach, dock or pleasure craft are favorite pastimes. She loves traveling, ocean life (including mermaids!), and, of course, her "Sweetwater Sea" in the North. Sherri enjoys inspiring others and sharing the happenings of a "Meandering Mermaid" from this small, but big-hearted, body of water as part of the Island Jane International Team.


  1. Hi Sherri,
    What an incredible experience you have shared with us. We had the pleasure of meeting you in person at Harpoon Harrys. We fished on both the Premium Time with captain Marlin and 1st mate Moses as well as the Reel Deal with captain Tim and Tommy hooks. Both trips were incredible and we can’t wait to come down and do it again. Next time though we will do one day of island exploring like you did as I was not aware that this was available. I know that your time down there is drawing to a close and I personally know how sad t hat is. But you have amazing memories as well as I’m sure a treasure trove of pictures to remind you of your amazing adventure. Have a safe trip home and I hope we see you again soon!

    • Jimmy and Family!

      It was so wonderful to meet you all at Harpoon Harry’s. I’m so happy we ran into each other and to hear that you enjoyed your charters so much! An “Island Adventure” is a must! I am back up north now and missing the Keys, but do have such amazing memories and pictures that I am carrying with me in my heart. Thank you so much for the well wishes and I hope to see you next winter too! You can keep up with my adventures here and there on Facebook at! I’d love to have you along! 🙂

      P.S.–Cassie makes an awesome cover girl this month! 😉

  2. Sounds like such a pleasurable trip, Sherri.
    I do miss being down in the Keys, myself, and hope to get back one day, soon.

    You have re-ignited that spark in me, for the blue waters and laid back lifestyle, which keeps calling me back to my roots of the Florida Keys.

    Thanks for sharing your adventure with us.

    • Thanks so much Rick! I know you’ll get back to your roots there someday! Thanks for taking the time to read my article and share your thoughts too! 🙂

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