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Spring Break Family Sailing Trip

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Spring Break ’21 Sailing Trip

grandparents with grandson in cockpit of sailboat


Sailing with our kids (now adults) and grandchildren aboard always brings an extra dose of joy and highlights to our boat trips. During spring break 2021, Kendra and their two youngest sons, Isaac and Titus, were eager to come for their trip on Terrapin. Their dad and older brothers, Ethan and Judah, had come on their boat trip before Covid. Now, after a long delay due to Covid, it was finally the younger brother’s turn!


daughter and two grandsons on the bow of our sailboat

Covid and Boats

Not only was the time of quarantine and travel restrictions difficult for many people, it was also hard on our boat! After a year on the hard due to Covid, we launched Terrapin in March 2021, a few weeks before Kendra’s trip. We thought we allowed enough time to address boat maintenance before they arrived, but every day we found more and more things on board that didn’t work and needed fixing.

Rather than postpone their trip, the boys learned first-hand how being flexible and going with plan B is a big part of our boating life. It is a good skill for land life too!

Plan B

Plan B: Using a Car

Part of our plan B for their trip was an attitude adjustment to use our car. Once we leave the boatyard, we normally rely on walking, biking, or taking a bus or trolley to get wherever we need to go on land. It’s part of our boating lifestyle. But, having our car available to shuttle to and from the airport, get supplies for repairs, and explore further than walking distance made sense for this trip. So, we took a Lyft from Punta Gorda to our boatyard to pick up our car and have it with us for the week. It was a smart move so we could visit Englewood Beach and Boca Grande beach by car until our boat the needed boat repairs were done and we were ready to sail to Cayo Costa State Park.

Boca Grande offered more than a day at the beach, we also visited the lighthouse to learn some history of Boca Grande and pick up a few souvenirs at the gift shop. And the boys were very excited to see a large iguana basking in the sun on top of a fence.

Boca Grande iguana and grandma, mom, boys visit to lighthouse

Plan B: Menu Planning

Another part of our plan B for having family visit us while still working on needed repairs was to eat out more often than normal for the first few days. Busy with boat projects, I had not prepared a menu plan or purchased provisions yet. The boys thought one of the sandwiches from a nearby deli (club sandwich on a croissant) was so delicious that we put the ingredients on my grocery list so we could have it again in the coming days. Another food highlight from eating out was trying new things like gator bites and conch fritters.

boys trying gator bites and conch fritters

Plan B: Multiple Beaches

Titus jumping the waves at the beach
boys, mom, and grandpa playing in the sand making castles and trenches at the beach


Our original plan was to go to Cayo Costa and stay there for their whole trip. Since we weren’t ready to go to Cayo Costa right away, we drove our car to different area beaches. Being spring break, the popular and easy-to-access beaches were very crowded. Englewood beach was the busiest and Boca Grande a little less busy.

Once we got to Cayo Costa, Kendra exclaimed “now this is my kind of beach!”. Fewer people and lots of room for the boys to build in the sand, swim, run and jump. From the docks at Cayo Costa, you can take a tram across the island to the beach or walk. We did a combination of both. On one of our walks, the boys struck a pose of being lost and stranded in the jungle.

taking tram and walking across Cayo Costa state park to the beach, boys pose as stranded on island.

Punta Gorda

bagpipe band playing in a park in Punta Gorda

We started and ended our trip with Kendra & the boys anchored off Fisherman’s Village in Punta Gorda. Punta Gorda is one of our favorite spots to stop when heading to or from our boatyard. There’s a dinghy dock at the sailing club, beautiful walking paths along the water, and interesting murals painted throughout the town. The town always seems to have something going on. While Keng and the boys were there, we saw an old car show and heard a bagpipe group play in the park.

murals in Punta Gorda, FL; books stacked by library, swimming turtle, row boat in water with grandson swimming
Do you see Titus in one of these murals?

Dinghy Rides

Preparing Titus for his upcoming trip, I mentioned on the phone that we would pick them up in our dinghy to bring them to Terrapin. He asked, “what is a dinghy?”. Oh yeah, on his last sailing trip he was two years old and probably didn’t remember all the nautical terms.

Speaking of dinghy rides, we forgot to mention to Kendra that we were anchored quite a ways out for sufficient depth. So when we brought the boys out to the boat first while Kendra stood on the dinghy dock, in the dark, for what seemed to her like a long time, we felt bad we had forgotten to mention that detail. From the dock, the anchorage isn’t visible so once we rounded the bend, she didn’t have any visual reference point for where we were.

Kendra's back side all wet after dinghy ride

That wasn’t the only memorable moment for Kendra concerning a dinghy ride. When we weren’t transporting duffel bags or groceries in the dinghy, we preferred to overload our dinghy a tad so we could all go in and out from shore in one trip. Oh, and the weather was mostly 15-25 knot winds every day. With the wind comes the waves, waves that often splash over the side of the dinghy. Wet dinghy rides became the norm. Kendra definitely won the award for the wettest ride with her whole backside drenched as if she just took a swim!

There were a few moments of calmer waters (and dry dinghy rides) such as exploring Pelican Bay at Cayo Costa State Park. We were off to find the manatees that frequent the area. What a highlight to see manatee noses peek above the water and their massive bodies gracefully swimming just under the surface.

grandma, mom, boys on a dinghy ride to see manatee, shadow of manatee in water

Military Heritage Museum

Isaac & Tony were interested in seeing the Military Heritage Museum and were in for a nice surprise. When they paid for admission, the cashier noticed Isaac’s birthday was “close enough” for him to use the flight simulator. What a special treat for both of them to learn to fly a plane using the flight simulator!

pics from military heritage museum of flight simulator and by a jeep

Activity and Relaxing Onboard

While under sail, there’s usually a varied mix of contributing as crew along with moments to relax and reflect. As part of our crew, Kendra and the boys took turns at the tiller. Titus wore a specific crew member outfit, a Chewbacca costume. Captain Chewbacca Titus!

boys at the tiller, Titus in a Cheebacca costume
daughter sailing in high winds, waves on side of sailboat, wind meter showing 25 knots

As a teen, Kendra liked sailing when it was sunny and had no wind. Imagine how impressed we were as she sailed Terrapin in 25-knot winds, way to go!

To relax after handling an exhilarating high wind sail, Kendra might read a book or paint her toenails. Too bad the toenail polish wore off quickly while standing on the beach where the waves crash over your feet. If you don’t want to use nail polish remover, just go stand in the beach surf for a while.

mom relaxing by painting toenails and reading a book in cockpit of sailboat

Shared Adventure

Whether our sailing trips are filled with mishaps and repairs, fun outings and activities, or move at a relaxed pace, they always end up bringing special memories of an adventure shared together!

collage of picnic at beach, grandparents and grandsons in large tree, grandpa and grandsons playing uno
picture of happy mom and boys at beach, bird on cayo costa beach

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5 thoughts on “Spring Break Family Sailing Trip”

  1. Wonderful post! But I must say all the pictures of beaches and 🌞 sunshine makes it seem even colder up here in nova scotia 🥶😭

    1. Looking through our past “fun on the beach” photos has been helpful to keep us motivated while we work on boat projects in the boatyard. Soon we’ll be back on the water and visiting beaches again!

  2. Awesome pictures and narrative! Easy to see that all we’re having a great adventure. Wonderful family memories formulated as you sailed the waters!

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