How To Spend 3 Days in Sunny South Florida

The first picture I took at my new home in Florida - a spork in the road

The first picture I took at my new home in Florida.

I hadn’t been at my new home for 2 hours when a friend of mine texted and asked when he could visit. Truthfully, he could have flown in the next day because I hadn’t been around people for a week, and was ready to be surrounded by laughter again. Instead, I asked him to give me 2 weeks to settle in. By breakfast the following day, his trip was booked for Labor Day weekend. In all his travels, he had never been to Florida before, and I was newly transplanted. It seemed somehow fitting that we’d explore a bit of my new home together. Here’s how we spent Bobby’s 3-day vacation.

Day .25

Bobby arrived Thursday evening around 6. I made dinner reservations for the two of us, plus my roommate and his girlfriend at 15th Street Fisheries, for 8 P.M.. I adore this restaurant, situated on the waterfront in one of the many marinas that fill Fort Lauderdale. The first time I visited, I had the best cioppino I’ve ever tasted, and that was really what drove me to pick this restaurant as a “Welcome To/Back” for Bobby and me. We ate upstairs, even though there’s an option to eat dockside, because the view of the canal and Port Lauderdale bridge is spectacular. On my first visit, it was near the Christmas holiday, so the palm trees and resort across the canal were lit up in a way that made you think Gatsby himself was partying over there. This time, it was decidedly less lit.

I can’t remember what I ate. I didn’t take pictures. I – for once – just enjoyed the company and the flavors. Besides, I was set to document the rest of the trip.

Day 1 – Friday

The Maple & The Patio at The Grind Coffee Project

The Maple & The Patio at The Grind Coffee Project

We decided to drive to Key West for the night, so Bobby booked an AirBNB night on a sailboat, and we set out to my local (and favorite) coffee shop – The Grind Coffee Project – to caffeinate before the 4-hour drive. We had to be at the marina where we were meeting our boat captain, John Yates, by 2 P.M., and were pushing the limit by leaving my house at 9:30 A.M. (considering possible weekend traffic).

The Grind Coffee Project is a few blocks from my home, and anything within walking distance that has great service is aces in my book. CJ and crew at The Grind are very friendly and knowledgeable, and the shop itself is always clean and smells of fresh-ground coffee, as you might expect. There’s a separate room for working, if you need quiet, and I think you can rent it for a conference if you need to. The Grind also has patio seating, entirely in the shade, though that doesn’t provide much relief in South Florida over the summer.  I ordered a maple coffee, Bobby ordered a warm chickpea wrap, and we decided we also wanted what the other was having. As always, the maple was divine, and the warm chickpea wrap was surprisingly delicious. Soon after finishing our coffee, we were off to Publix to buy the required beef jerky and bag-o-nuts to keep us from starving on our 4-hour road trip.

Big Betsy - The Giant Lobster on Islamorada - A Spork in the Road

Bobby seems stoked. I’m trying to figure out how much butter I get to eat.

We decided to take the Turnpike to The Keys, instead of Highway 95, because it is a toll road, and ostensibly less busy. It was packed, and I think it took us longer driving the Turnpike than it would have just driving the 95 to Highway 1; it definitely added a few miles.

Before we left, my roommate’s girlfriend told us about a gigantic lobster on the side of the road on one of the keys. We thought it would be a great idea to stop, but we were already running late, so we hopped out, snapped a pic, and hustled out to Key West…almost. We made it to Marathon Key before we were hungry again, despite the bags of beef and nuts, and so we stopped at [undisclosed fast food chain] for some really disgusting [greasy fried food] and my favorite Dr. Pepper.

We met Captain John at 1:56 P.M., barely having time to spare. What I didn’t know until we were on the dinghy out to the boat was that we would be sailing to Sand Key and snorkeling the coral reef. We met John’s amazing girlfriend Lori, who welcomed us aboard. John helped stow our bags, poured us beverages, and released the mooring so we could set sail. As Lori steered us out of the bay, John offered to teach us to sail, and we were ecstatic to learn. Bobby used to have a boat, but not a sailboat, and I’ve been on sail, motor, and pontoon boats, but haven’t ever done anything but lifeguard or ski behind.

The first thing we learned was how and when to raise the mainsail. Instead of a skinny Jib, we had a Genoa – or Genny (Jenny) – which is just a jib that overlaps the mainsail. We furled and unfurled while

From left: Captain John, Lori, and Bobby at the helm.

From left: Captain John, Lori, and Bobby at the helm. I can’t find Captain John Yates’ AirBnB link. If you find it, he comes HIGHLY recommended by Bobby and I.


Lori tacked and the boat was heeling on the starboard side. It’s a little scary for the boat to lean so far over in the water, if you’ve never experienced it. The keel makes it almost impossible for the boat to tip over while heeling. After we were out of the protected bay, and on our way to Sand Key, we heeled less, and could stand on the bow safely. I could. Bobby, the lucky duck that he is, got to stand at the helm and take us all the way out.

Sand Key is little more than a lighthouse, though I’m told the sand does occasionally build up and make an island. This appeared to have been an operating reef for quite some time. The water temperature was in the 90s, and as I found out after flopping in, much saltier than I expected. Sure, the ocean is salty, but this water was so salty it was burning my skin. I was also unusually buoyant. Still, I couldn’t get the snorkel mask to stay put because it was too big, and I had to wear someone else’s water shoes in my fins because they were too big. It felt like I was reentering Clown College, and headed for a fail.

I am a strong swimmer, I’m trained in water rescue, and I suck at snorkeling. Bobby, on the other hand, took to it like a fish to water (heh) and took off across the reef with John. Lori stayed behind with me and the float I needed so that I could hold the mask on while I looked at the wildlife. Eventually,

Sand Key Lighthouse

Sand Key Lighthouse

I drank enough of the ocean while struggling with my mask, that I had to climb back in the boat. John and Bobby were back minutes after I climbed aboard, and we released the mooring and headed back for the bay.

The Captain served an after-snorkel snack of veggies and hummus, and Bobby saved my nauseated stomach with some chewable Pepto. I’m so grateful he had it, because I would’ve been reduced to tears and begging for land by the time we reached the bay. I don’t get seasick, and this turned out to be the result of my ocean cocktail. Thirty minutes after eating Pepto, I was ready to party again. Sidenote: I don’t advise anyone to willingly drink the ocean, even if you have a stomach remedy.

On our sail back to the bay, the clouds rolled in, and we didn’t get to see the sunset like we had hoped. Still, it was an unbelievable sight. We silently took in the crowds that were on Mallory Square, and watched the captain fly his drone with Lori at the helm and bringing us back to the moorings. There may or may not be video of us from a drone’s-eye view.

We got back after dark, which isn’t really something you want to do in a boat because water is dangerous without light; it’s difficult to see the lobster trap markers and the posts and poles that stick up out of the bay, and it’s hard to find the mooring balls. Luckily, we didn’t hit or catch anything, and were able to moor for the night. Captain John pulled the hammock up at my request, and then cooked us steaks and grilled vegetables, while we tried desperately to make our cameras not suck in the twilight.

Our dinner was delicious, and we were exhausted from furling and unfurling, and swimming in the sun. We slept well in the air-conditioned aft-cabin.

Day 2 – Saturday

exhausted sailors

Exhausted sailors. Photo by Bobby Borszich.

When we woke, it was still cloudy, and so we didn’t really get to see the sunrise, either. After a pre-breakfast snack of fresh pineapple, orange slices, and coffee – and an actual breakfast of Captain John’s famous breakfast scramble in a wrap, we dinghied back to the pier, and reluctantly headed for South Beach.

On the way out of Key West, we headed for the Southernmost Point Buoy, where you’re as far south as you can get in the United States. We also stopped to walk around White Street Pier, which is named something else now, and is the home to the AIDS memorial. The traffic heading out to The Keys was stop and stop, and we were glad that we went on a Friday and not Saturday.

Drained by the heat of the day, and the messier traffic near the mainland, we stopped on Marathon Key at Sweet Savannah’s for some delicious cake dough and whatever-Bobby-had ice cream and a cupcake that was more squished than eaten by weekend’s end. We did pop in to see Big Betsy, the gargantuan lobster, and explore the hidden treasures in The Rain Barrel Artisan Village on Islamorada.

Our next stop for Bobby’s final night in Florida was the Loews Miami Beach Hotel. South Beach was pure craziness, as expected, and it took quite a while to get the car valeted and get checked in, just because of how many people decided to check in at the same time. the staff were cheerful and pleasant. Our room wasn’t ready, so we had drinks and a Margherita pizza at Bar Collins inside the hotel. We really sat on the patio of the bar, and cooled off with delicious drinks: Bobby had a Zacapa Old Fashioned, and I enjoyed (immensely) a 50 Pounds & Tonic.

Loews Miami Beach - photo by Bobby Borszich

Loews Miami Beach – photo by Bobby Borszich.

We were ready for a nap, so we promptly dropped our bags in the room, changed to swim suits, and made it to the beach minutes before the staff dragged all the furniture in for the night. We spent an hour or so splashing around, and then headed for poolside drinks. We were disappointed to find that it was not a saltwater pool. The fact there were children present should have been a dead giveaway. It donned on us we were hungry, our drinks were empty, and we smelled like chlorine.

Quick showers, and off to walk South Beach. I didn’t realize we were walking a long way, so I wore stilettos. They came off as we hit the boardwalk, and went back on as we stopped to taste the appetizer menu at The Front Porch Café, where the food was slightly-over mediocre, but the conversation was spectacular. One of my favorite things about Bobby is the conversations we have. They run the gamut, from mundane catching up to ridiculous laughter and poking-fun. The best part of the entire trip was all the laughter.

We were back in the hotel room and asleep before midnight, as you might expect sun-drained tourists to be.

Day .75 – Sunday

Balans Burger and Huevos Rancheros

Balans Burger and Huevos Rancheros

We woke up late, too, and so it was brunch time when we headed out in search of food. We ended up at Balans Restaurant & Bar, after walking the entire City Center. I had a Balans Burger, and Bobby had the Huevos Rancheros. We talked and laughed some more, and then realized the time. Bobby had a plane to catch that evening, so we headed up Highway 1. I drove, so Bobby could take in the scenery and get some pictures of the gorgeous architecture.

It was a wonderful weekend, and I couldn’t have asked for a better companion. Since you (probably) can’t travel with Bobby, you should at least take in these sites and flavors.


***I’m still having a tough time reconciling the damage Hurricane Irma did to The Keys, only a week after we were there playing on the boats and swimming with jellyfish. South Beach is mostly destroyed, by many accounts. I will go back in the coming months, to see how its doing after the storm. ***

How To Spend 3 Days in Sunny South Florida - A Spork in the Road

About Terra Walker

Terra loves creating recipes, imparting wisdom, searching for an amazing cider, owning this website, and traveling the globe. You can catch up with Terra on the channels above, where she never uses third person, because she hates writing about herself that way.


  1. Very good travel journal! I really enjoyed the way you describe food!

What do you think?