Sailing the Florida Keys The Wandering Kellers Way

After our Sailing class in St. Pete with Offshore Sailing School we wanted to charter a boat as preparation and practice for the BVI’s (Part 1 and Part 2). We were concerned also that if we waited too many months, our skills and know-how would wane and it may be a more challenging vacation after 6 months not sailing a catamaran. We decided to do a Dream Yachts charter out of Key West since it was a place we could get without the need for COVID testing and they had the same exact model of catamaran (Fountaine Pajot 40) that we had used in our Offshore Sailing School liveaboard Class.

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Day 1- Travel to Stock Island Marina

The flight down to Key West was direct and easy. From the airport we took a cab to the Stock Island Yacht Club and checked in at the Dream Yachts office. The boat wasn’t quite ready, so we took dropped off our bags and took a cab over to the Hog Fish Bar and Grill for some lunch and a drink.

Tip: We met a nice cab driver on our way from the airport and he gave us his card so we used his services all week to get from place to place.

We had some tasty fish tacos and shrimp and with our hunger satisfied we headed back over to the Marina. Once there, we hit the pool for some relaxation. When the boat was ready for us we loaded our bags on the boat and packed away the provisions that were delivered from the local Publix through Instacart.

The boat was owned by a Frenchman and had 220-volt setup and also did not have air-conditioning. It was a 4 bedroom/4 bath configuration where our boat for the learn to sail class had two baths which allowed for a separate shower area that was more spacious and did not require the use of a sink faucet to rinse off. No complaints, just something we loved on the FP40 we used for our class and will look for in the future. As there was no wind in the marina it became very buggy and stayed hot (over 80 degrees) all night. This made for a very sweaty and bite filled “sleep”. We will never make the mistake of not asking whether the boat has air conditioning, a Genset and American power again. None of this was anything we couldn’t overcome, but compared to the fully loaded boat we used for our class, this boat required us to adjust some of our expectations. This is the big take away from this vacation as we assumed (we all know what that gets us) that a $600,000 plus boat that was relatively new would have A/C, fridges and freezers that got very cold, and the ability to plug in your stuff without a converter, but alas, it did not. Luckily, we brought our travel power pad we use when traveling overseas so this helped immensely in finding places to plug all our devices in.

We have the older model of the BESTEK International Power Adapter 250W, 220V to 110V Step Down Travel Voltage Converter with 4-Port USB and although you can buy any one you want, having one of these is great for travel anywhere as it provides 4 USB ports and 3 outlets for charging devices. We’ve had ours for 7 years and it has come in handy nearly everywhere we travel.

That night we took the dinghy down, fired it up and took a little spin outside the marina. This let us make sure we knew how to get it in the water, start it up and also let us cool off a little in the breeze outside the marina.

Day 2- Stock Island to Newfound Harbor

We awoke at 8 am and filled our cooler with ice. The Dream Yacht folks had given us some ice the night before, but we wanted to top off the cooler since we knew this would be paramount to keeping our food fresh and our drinks cold. Our fridge and freezer didn’t stay/get very cold so keeping them shut as much as possible on this trip would be key. The marina had a nice ice maker and they let us borrow a 5-gallon bucket to fill up with.

Someone from Dream Yacht came out to the boat to orient us and run over our float plan. After a quick debrief and run through the boat, we were ready to go. The table had been damaged on a prior charter and it needed fixed. The Dream Yacht staff member was great and gave us some great suggestions about where to go and what to see. We had done a good bit of research, but this really helped us make a few decisions. Local knowledge trumps any guidebook. The maintenance person from Dream Yacht did what he could to fix the table, but I had to retighten it several times over the voyage.

We shoved off the dock and headed out the channel to the open and deeper water offshore. It was the beginning of lobster season so the traps were everywhere but there was still plenty of room to maneuver. We motored all day because our destinations were upwind. The boat did make good speed into the wind and we arrived at Looe key by lunch time.

Looe key is a shallow reef a few miles offshore surrounded by deeper water and mooring buoys. We grabbed a buoy and hit the water for some fantastic snorkeling. In my opinion, this was by far the best snorkeling in the Key West area. It was not crowded because it takes a boat to get there, and the variety of fish was great. My wife and son saw what they described as a 6-7 foot reef shark as they were coming in, but I was dubious.

We had a bite to eat and headed up to Newfound harbor almost directly north. We tucked ourselves around the corner between Spottswood Island and Little Torch Key for the night. We grilled some shrimp and made some rice and had a relaxing evening watching the sun come down surrounded by other charter boats. The youngest noticed that our mooring light was out so we turned on the navigation light and sent a message to the Dream Yacht staff who arranged to meet us the next day to give us a temporary light. It was much cooler out on the water and far less buggy since we were so far from shore.

Day 3-  Newfound Harbor to Bahia Honda

The next morning, we were up with the sun and off for another snorkel at Looe Key. This time it was earlier when we got there and sunny. I can indeed confirm there is a 6-7 foot reef shark that patrols these waters so I had some apologizing to do for my dismissive attitude when originally told about the shark. The fish were even more vibrant in the morning sun. After a good swim we raised the sails for a few hour long sail and headed to Bahia Honda state park and its protected anchorage beyond the derelict train bridge. The old bridge has a section removed that allows sail boats with tall masts to pass in to the harbor between it and the new bridge.

There is a story about this old bridge. The old Bahia Honda railroad bridge was built and opened in 1912 connecting Miami and Key West. The Labor Day Hurricane of 1935 destroyed much of the line and the bridge was sold to the state of Florida and converted for highway use in 1938. A new four-lane bridge was built and opened in 1972, a few hundred yards north of the old bridge. Many lives were lost including many on an 11-car rescue train trying to make its way north from Key West. (My wife had recently read the book The Last Train to Key West by Chanel Cleeton, so she particularly enjoyed seeing the bridge).

 We dropped anchor as the holding was good and headed into the state park for some exploring and snorkeling off the beach. There were only 3 other boats in the anchorage so it made for a cozy spot. We blew up the SUP and let the kids float around while I affixed the temporary mooring light to the spinnaker halyard before raising it up.

I had tied a rope to get the halyard back down as the new light wasn’t heavy enough to lower it but the winds later in the vacation managed to untie my knot. Another lesson learned– I should have tied a bowline to a bowline to make sure they didn’t slip free. Well, the temporary light was up there until someone got it back down. I had screwed the table down at least 5 times already so I guess I earned a little forgiveness.

Dinner was steak and shrimp on the grill and a few glasses of wine for the adults. We were settling into the new routine and enjoying the great weather we were having.

Day 4-Newfound Harbor to Boca Grande

We awoke to blue skies again and 12 knot winds going just the right direction for us so today would make sailing part of our 30 nm trip to Boca Grande. When raising the anchor it got wedged in the fiberglass on its way up and I could not loosen it from on the boat. This boat did not have a metal sleeve where the anchor sat and I had not imagined the anchor might not right itself properly when sliding home. A metal sleeve over the fiberglass likely would have prevented this, but alas live and learn. It was almost in the hole so we decided to journey out into clear waters for me to try and pull it free with a winch where we were not drifting towards shore and other boats.

We slid out into the deeper waters and found some room. I boarded the stand up paddle board and went around to the front to tie a line to the anchor so that we could use a winch to pull the anchor free. With family teamwork, we were successful and I didn’t float away so, all in all, a successful mission. After that, we raised the sails and made our way down past Key West and civilization to Boca Grande Key.

Boca Grande Key is an uninhabited island within the boundaries of the Key West National Wildlife Refuge. It is a beautiful and protected anchorage where one can SUP, snorkel, walk the beach, and enjoy the wildlife. The one thing to be careful of is approaching this Key through the right channel. It can get pretty shallow in some areas (as it does frequently around many of the Keys). It as not a problem so long as you kept your eyes peeled on the water and the depth finder.

We spent a beautiful night there as a family – walking the beach, taking a dinghy ride around parts of the key and jumping off the front of the boat. As the sun set we fired up the grill for our last meal aboard the boat.

Day 5- Boca Grande Key to Stock Island

We awoke to a 15 knot wind blowing just the right direction and rode the wind around Boca Grande Key to Cottrell Key to grab a mooring ball and do some snorkeling. There are several sets of mooring balls, but the best area to the north and east was full so we tucked into an area off the western edge. The water was full of large moon jellyfish and was pretty cloudy. There were a number of large fish but really no colorful fish or beautiful reef plants so after 30 minutes we headed back to the boat to see if we could jockey into a better position. After waiting around for 20 minutes or so we decided to make our way back toward Key West, and of course, once we were a half mile away, two spots opened up. Murphy’s Law in full effect.  We had intended to spend our last night at anchor between Wisteria Island and Key West, then take the dinghy in to Key West to eat and explore. When we arrived, the channel was busy and there were many boats abandoned. In addition, the anchorage was tight and the hold not great. Knowing I wouldn’t sleep, we made the decision to grab some gas and head back into Stock Island Yacht Club.

The moment of truth for most captains had arrived. Backing your borrowed boat into the slip at the marina with everyone watching. We had a practice run of sorts at the fuel dock in nearby Stock Island Marina at the fuel dock. They have great hours and a nice large area to pull your boat up so it’s a great place to grab fuel if you’re in the area. When we got to the Yacht Club it was busy with boats coming and going but I just channeled our teacher Kelly from Offshore Sailing School and backed the boat in without any issues. I was anxious, but gained enormous confidence after accomplishing what for most of us is the most stressful part of boating.

None of us were looking forward to spending another hot, sweaty night on the boat, so as we were coming in, mom booked us a night at the Barbary Beach Hotel (now owned by Margaritaville). We packed up our stuff and some extra provisions and gave a ring to our taxi and were off out of the heat to the hotel. We were greeted with welcome drinks and a smile. The room was beautiful, the resort full of amenities, and most importantly air-conditioned. The kids had a large set of bunkbeds and the wife and I had our own area with a beautiful bathroom. There was a small kitchenette to keep our provisions cold and a beautiful beach across the road with Hobie cats and other toys to play with.

Day 6-The Long Trip Home

We awoke well rested to find that our flight home was cancelled. There were no flights out from Key West that day on any airline with availability. I had to get home to get to work and managed to get a flight from Miami and a car to drive me there. The kids grabbed breakfast and played at the pool while we officially checked out of the boat. We then headed across the road for some fun in the sand and took out a Hobie cat for 40 minutes or so to let the kids practice their skills on a slightly less intimidating boat.

After that it was time for me to grab my car for the 3 hour ride to Miami and the long flight back home. I arrived home late as per the usual Wanderingkeller fashion of squeezing all the juice out of the vacation. The rest of the family spent another night in the hotel and flew home direct from Key West the next day. As a bonus day of vacation, the kids got to parasail for the first time. They were both nervous at first, but ended up really loving it and the company they went out with was fantastic!

All in all, it was an excellent vacation full of fun, relaxation, and plenty of learning moments. We all came away with great stories and lessons that we will hold with us the rest of our lives.

We will definitely sail in the Keys again and definitely want to explore further north as we only made it as far as Bahia Honda. Some charter companies will let you pick up the boat in Marathon and that allows you faster access to the eastern area of the Keys which we would like to explore next time we are down.

What did we learn on this trip?

  1. Make sure your boat has A/C if sailing in warm weather climates especially in the summer.
  2. Some of our boating legs, especially from Bahia Honda to Boca Grande were too long and we decided to avoid such long stretches in the future as we did when planning our BVI trip. 15-20nm is probably a good leg for vacation especially if you’re not stopping for a few hours to break it up.
  3. A boat with 2 bathrooms is more spacious and better served for a family vacationing alone. We opted for a 3 bedroom and 2 bath configuration on the Lagoon 40 we used in the BVI’s based on this experience.

9 thoughts on “Sailing the Florida Keys The Wandering Kellers Way

  1. Sailing around the Florida Keys sounds like a dream to me! Being able to visit uninhabited islands and snorkel in areas that aren’t overly crowded seem like definite perks. The lack of AC and mosquito bites at night don’t sound fun though. Definitely a good tip to check for AC before renting a boat!


    1. It definitely was amazing to be able to go places others couldn’t get to. The no ac definitely was a challenge. The best part for us was the accomplishment that came along with the adventure. Thanks for reading.


  2. What an adventure! It was interesting to read your experience and the places you visited. Thanks for sharing.


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