The One With All The Island Hopping

Before we started The Great Loop this is the type of post I thought I’d be writing each week. Boating meant a coastal lifestyle, right? And surely we’d spend the majority of our time island hopping.

Alas, it hasn’t quite been as dreamy as I imagined.

We’ve spent months on inland rivers, in locks and away from tropical locations. Arriving in southwest Florida after crossing the Gulf (read more about that HERE), gave us the feeling that we’d finally “arrived.”

Whatever that means.

In addition to finally being in the location of our dreams, we were also without a schedule for the first time since starting our Loop back in June. We’d hit every deadline thrown our way: the Erie opening, being off the Great Lakes by October, running down the rivers before winter, crossing the Gulf with a group, etc.

With a wide open calendar, and a map we began to consider our December destinations.

After looking at many possibilities, we put together a route that included several stops with lots sand and sun. Not to mention, another major ocean crossing!

Here’s a rundown of our month-long Island hopping adventure…

Anna Maria Island

Prior to boating, AMI became a family-favorite vacation destination. Naturally, we wanted to take our boat there and spend a week soaking in the huge sandy beaches.

Staying in a marina on the island (Galati Yacht Basin) gave us a whole different experience than our typical vacations in a rental house. We were easily able to walk to all the good shops and restaurants.

And, of course, the beach!

However, a highlight of the week was renting a car and driving down to Longboat Key to eat at our favorite restaurant (Lazy Lobster.) We spent about an hour that night driving around looking at Christmas lights- something we’ve missed out on living on a boat.

Cabbage Key

Our island hopping adventure took us to Cabbage Key for a day, and we were charmed by this little spot in the Gulf.

The Island is only accessible by boat and is quite the resort community. People come, rent cabins, eat at the Island’s only restaurant, and enjoy a very private beach.

One memorable quirk is that the island seriously conserves fresh water. Although we paid for a spot on the dock with electricity, we had no water connection. The restaurant even charges for tap water!

Speaking of water, the watertower is something of a landmark on Cabbage Key. A highlight for our family was climbing the tower just before sunrise!

Key West

Key West is the most famous and touristy of all of our island hopping stops.

Admittedly we had an ulterior motive for visiting Key West. We had plans to meet up with two boat friends and go to the Dry Tortugas. Unfortunately, that didn’t happen (I’ll have to write a whole separate post on that saga!)

Our family spent Christmas in Key West. This meant a lot of time on our boat- enjoying some “normal” Christmas traditions like decorating cookies for Santa, and Christmas Eve church (virtually.)

We did enjoy a couple touristy things on Key West like visiting the Southermost Point, riding the Conch Train, eating Key Lime Pie from the original creator, and viewing sunset in Mallory Square.

Again, there’s more to the Key West story…but I’ll get into that in a future post.

Marco Island

So I’m including Marco Island on my list, but it’s a stretch to really say that we were there.

We never actually set foot on the island!

Our original plan involved anchoring back in this cute cove, and taking the dinghy to shore for dinner and to explore.

However, we arrived to our anchorage completely exhausted. No one wanted to do anything so we ended up cooking on the boat and doing a little fishing off the bow.

Keewaydin Island

This is a tiny island between Marco and Naples. And it’s only accessible by boat.

To visit Keewaydin we had to drop our anchor out in the Gulf (a first for us!) and dinghy to shore.

The beach was super private, and full of huge shells. The kids both tested out their brand new snorkel gear that Santa brought. Captain enjoyed a rare opportunity to run around off his leash.

Unfortunately, this was just a day trip. If there was a more protected spot to anchor, we would stay for weeks! Reluctantly we pulled our anchor ahead of sunset and went to Naples for the night.

Cayo Costa

I saved the best island for last (although this list is actually in the order we visited!)

Cayo Costa is a new family favorite! It’s located west of Fort Myers just above Captiva Island.

Since it’s a state park, there’s no real development on the Island. And that means, a ton of wildlife and gorgeous beaches!

This is another island only accessible by boat. We were able to anchor in a cove and then dinghy over to Cayo Costa every day.

Our family spent New Years on anchor here with about 100 other boats. It was very cool to hear (and join in) the boat horns and celebrations at midnight! Definitely a memory we won’t forget!

We spent our days on Cayo Costa snorkeling, walking some beautiful trails, and being total beach bums.

Overall, our month island hopping exceeded every expectation! We relaxed, got a little sunburned, and spent a lot of quality time as a family.

Incidentally, if you’re familiar with Southwest Florida you might notice that we doubled back on our route. Yes, it was intentional.

We had plans with friends to be in Key West for Christmas and we also had plans to be in Fort Myers in January. This meant we traveled south and then backtracked north.

Other than burning through a little extra fuel, the route made sense for us. There are SO many locations to explore in this area so we never stopped the same place twice!

As always, thanks for following along on our crazy adventures. You may also enjoy reading:

The One All About Our Boat, Light & Salty

The One With All Things Remote: Working, Learning and Living

Las Vegas With Kids: All The Things You Want To Know

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  1. […] crossing to Key West (if you haven’t checked out my Island Hopping post yet, you can see it HERE.) Most Loopers who go to the Keys stop in Marco or […]

  2. […] The One With All The Island Hopping […]

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