Islands of Florida: How to Vacation at Sea for Landlubbers

Dan and I recently got out and travelled. Well, it was a two day road trip to one of the islands of Florida. We rented a sailboat through Airbnb on Merritt Island, located on the Space Coast. This may sound glamourous to you if you have never been on a sailboat before. In reality it is really more like glamping. For those of you that don’t know the term, it means glamourous camping.

sunset from one of the islands of Florida

We are not into extreme vacations so this was our version of an adventure. Neither of us sail so the fact that we couldn’t take the boat out on the water was fine with us. It was enough to sip our morning coffee on deck while watching the sunrise. At night we drank wine while watching the sun set on the horizon as the colors turned from bright orange to deep blue. Then we watched clouds dance across the moon.

This is a great way to have a socially distanced vacation since we were the only people on the sailboat, and most everything else we did was outdoors. Here is our basic itinerary, and then I will give some tips you need to know before staying on a boat, in addition to other things to do in the area.

Islands of Florida: Merritt Island Itinerary

Day 1: Arrival Merritt Island of Florida

We arrived at the Harbortown Marina around 4pm. Parking was simple as we didn’t have an assigned space. We easily found the assigned dock and slip number. We checked in on line and brought our stuff onto the boat, just a duffel bag and cooler. After unpacking the cooler we tried the padlock for the cabin doors and headed out to check the code for the bathrooms. After that, our evening was free so we decided to check out the local marina bar.

front of the Hawksbill bar and grill at the marina in Merritt Island, one of the islands of Florida
The Bar & Grill at the Marina

Hawksbill Bar & Grill

The bar was fairly full, but the tables had a lot of space between them. We chose a booth off to the side. The place had a full bar with a wide selection of beers. Dan chose a Lagunitas, and I had a Bahama Mama. I usually don’t drink fruity drinks, but it was hot out and it was very refreshing. The menu had bar food and seafood dishes. As usual we chose several appetizers such as blacked fish bites, calamari, and the choice of the day: jalepeno poppers. The food wasn’t as spicy as we like, but the staff was very accommodating and brought us extra horseradish and wing sauce.

The bar was full of locals, and it was Thursday which meant Karaoke night. Apparently the same people sing every week, meaning most were quite good. The hostess had a list that she compiled based on past singers. The good singing gave me an appreciation of country music, although there was some blues and pop mixed in. I smiled at a little girl who was dancing while her grandmother and mother were singing. She came over to try to get me to go sing with them. That is one of my favorite things about traveling, participating in the local life.

view of clouds passing in front of the moon
Witches Moon

The evening ended with us drinking some wine on deck, enjoying the moonlight.

Here are some sponsored links we chose for products that may come in handy for a beach vacation:

Day 2: Off the Islands of Florida onto Cocoa Beach

boats at a marina on Merritt Island, one of the islands of Florida
Sun Rising Over the Marina

We got up early to watch the sunrise while drinking our morning coffee. Then we packed up our beach bag and headed 15 minutes away to Cocoa Beach. We have friends who recommended going to the Pier area. However, when putting that in Google maps a diner comes up. Its ok, we figured out afterward that it is at the pier.


Make sure to come early. We went on a Friday and got there around 10am. There are metered spots for $2.50 an hour with a maximum of $10 until midnight. After that there is a lot for $20 per day. When we left around 2:30 pm there were people driving around because there was no parking available. We did a good deed for the day and let the guy after us know that we had paid until midnight.

Cocoa Beach: One of the East Coast Beaches Florida

We set out our chairs, blanket, and umbrella and headed for the water. It was cold by Florida standards in late March, but comparing to NY ocean temperatures in June it was warm. This area is popular for surfers so we watched people riding the waves on their surf boards, wake surf boards, and boogie boards. Even with the decent waves, there was no undertow the day we went so I was able to cool off from the sun at least up to the waist until I got too cold. The beach has miles of smooth sand so it is great for taking a stroll. However, you have to watch out for fishing poles propped in the sand as the lines go out into the water.

Here are some affiliate links for more modern versions of useful beach gear we use:

The Pier

Cocoa Beach Pier sign off coast of Florida
Cocoa Beach Pier

We brought snacks but decided to check out the Pier because I had read one of the restaurants had alligator bites and Bloody Marys with shrimp. There were guards doing temperature checks at the beginning of the pier, and they only let people onto the pier who were going to eat at a restaurant. We had our masks and got the green light to go ahead. Souvenir shops were open displaying merchandise commemorating islands of Florida. We had to pass through Pelican’s Bar & Grill to get to Rikki Tiki Tavern at the end of the pier. However, we were informed that now there was only one menu for both restaurants.

We decided to sit at the outside bar instead of walking through to the end of the pier. Again, Dan ordered a beer, and I got a fruity drink, this time a rum runner. Delicious. The menu was a touch free scan code through your smart phone. No Bloody Mary or alligator bites. We settled for raw oysters. Good, but they could have been cleaned better as we got bits of shell or sand. For our next appetizer we asked for a recommendation from the bartender. We got the peel and eat shrimp which were large and delicious with just the right amount of Old Bay Seasoning. No horseradish, but the bartender easily got some for us. All servers here wore masks and gloves and constantly wiped surfaces with Clorox wipes.

On our way out we saw a huge line just to get into the Pier. However, for those that didn’t want to wait there was a hot dog stand at the entrance.

Leaving the Beach

After we grabbed our beach gear and left we stopped about a block away at Ron Jon’s surf shop and Key Lime Pie Company. Ron Jon’s is a great place for buying beach gear such as surfboards etc. Even if you aren’t planning to buy, it is always a great place to browse around and get out of the heat. At the Key Lime Pie Company we tasted some local wines and purchased a coconut infused wine. They also had homemade ice cream with unique flavors such as Earl Grey Tea. With items such as jalepeno jam, locally made fudge, salt water taffy, jellie candies, and of course Key Lime Pie this is a must see.

Store front of Ron Jon's Surf Shop off  Islands of Florida
Ron Jon Surf Shop
Store front for Key Lime Pie off the islands of Florida
Key Lime Pie Store

Then it was time to head back to the marina. After showering and a nap we made up some sandwiches and sat on deck to enjoy the remainder of the evening sun. After that we finished our evening sharing some wine until the air got too chilly and we had to go below deck.

Day 3: Time to Leave the Islands of Florida

On our last day, I woke up early to take some photos of the dock lit up in the dark. Then we enjoyed watching the sunrise while drinking our morning coffee one last time. We packed up our stuff and loaded our car. However, we did stop in at the local flea market held each weekend morning before we left the marina. Although it was mostly fishing equipment we did find some kitschy signs and some beautiful outdoor deck furniture. Then we said good-bye to the islands of Florida and headed inland.

Tips for Staying on a Boat

view down the steps into the cabin of a sailboat on one of the islands of Florida
Steps into the Cabin
view of a sailboat bed docked at one of the islands of Florida
Bed Takes up the whole Stateroom
sailboat docked on one of the islands of Florida
Steps to Climb into the Sailboat
  • Take seasickness medicine at least an hour prior to going on a boat. Even if you normally don’t get seasick, being in the closed space of the cabin will mess with your equilibrium.
  • Make sure you are physically fit. This isn’t a cruise ship with a gang plank. You most likely will have to hoist yourself onto the boat from the dock. Also, you will have to go up and down steep narrow steps to get in and out of the cabin. And you will have to lift your belongings up and into the boat.
  • Don’t plan a boat stay if you have stomach issues. Boat toilets generally need to store the waste in a holding container or use a processing system. Either way, you want to mostly use the marina facilities to avoid backups and bad smells on the boat.
  • A galley fridge basically means a built in cooler. It is not a refrigerator with shelves for storage. Don’t bring food items that easily spill or that don’t seal properly.
  • Make sure your belongings are not too wide. We barely fit our cooler through the doorway.

Places to Visit Near Merritt Island of Florida

There are several nearby towns to visit if you are taking a longer trip. Either on islands of Florida or mainland, there is plenty to do.

Daytona Beach

Less than an hour and a half north is Daytona Beach. Spend a day at the races at Daytona International Speedway. Or experience the thrill yourself at the Richard Petty Driving Experience. As an alternative, just relax on the beach and stroll the boardwalk with its famous midway.

Kennedy Space Center

About an hour north on one of the islands of Florida sits the Kennedy Space Center. Learn about the history of space exploration through the Heroes and Legends exhibit along with the Astronaut Hall of Fame. View the iconic Rocket Garden and Space Mirror Memorial. Visit Race to the Moon to explore artifacts and history of the moon landing. Several simulators are available for you to experience what it is like to actually train as an astronaut. Space themed play areas are also available for ages 2-12. Check ahead to time your visit with an actual rocket launch.

Saint Augustine

Just 2 hours away is the oldest continuously inhabited city in the USA. See the historic lighthouse. Wander the fort at Castillo de San Marcos National Monument. Enjoy the beauty of Spanish architecture at Flagler College. Learn about the areas pirate days at the Saint Augustine Pirate and Treasure Museum. Get locked up in the Old Jail. See the treasures in the Lightner Museum. And no trip here is complete without Ponce de Leon’s Fountain of Youth Archaeological Park.

Here are some sponsored links through Get Your Guide or you can check Trip Advisor for additional activities:

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4 thoughts on “Islands of Florida: How to Vacation at Sea for Landlubbers

  1. I love sailing, and it’s one of the best ways to get away from it all. Very relaxing and to stop at small harbour towns and places makes it even more amazing.

  2. Staying in a boat sounds interesting although not that interesting with the toilet situation. And I want to stop at the Key Lime Pie shop. I would like to try some of their unique flavor ice cream.

  3. This definitely sounds like a glamcamping, and an experience to relish forever. Your post made me realize that during covid times, this can be a better way to travel. Book the whole yacht, caravan at least you are safe without much public interaction and involvement. I am bookmarking your post for future reference, when I will be traveling to that side.

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