The Perfect Boating Vacation Destination


By Jim Favors

The title to this article alone will stir up more differing opinions than there are people watching the summer Olympics in London this year. For Lisa and I, the ideal winter boating and/or vacation destination is Key West, Florida. If you've been to the southernmost point in the continental United States or if you're a boater who appreciates tropical climates then you probably understand our sentiment. If you haven’t been and just don’t know much about Key West then you should know it’s an island all its own, literally and figuratively. There really is no other place quite the same as Key West – that is, in our very humble opinion.

Kismet relaunched and heading to KWYH – notice the mast and antenna have not been raised and the cockpit canvas not installed yet.

Approaching the entrance to KWYH, just off of Hawks Channel and the Atlantic Ocean.

Lisa and I trailered our boat to Key West this year from Marathon, a distance of only 40 miles. We had planned on cruising under the Seven Mile Bridge, at Marathon, out into Hawk Channel, and down to Key West however the weather had turned sour and foiled our “Plan A.” We are finding out, more and more, that one of the greatest advantages of having a trailerable boat is we have more options available to us when things don’t go as planned. In this case, we decided not to wait out the weather, but instead chose to load our Kismet onto its trailer and tow the boat down Route 1 and relaunch in Key West. We had an appointment to keep at a boat yard to haul the boat out to add bottom paint, so it's a good thing we had the option of a “Plan B” and chose to execute it. A week after we had long been settled into our marina and already enjoying our winter accommodations, we heard frustrating news from a few boaters we knew who were still docked in Marathon. They didn’t have a Plan B option, after seven plus days they were still waiting for a good weather window so they could leave Marathon to continue their cruise to Key West.

Our slip was just a short distance behind this Tiki hut, an open air boater’s lounge where we’d go many times in the morning to check that the sun was coming up on schedule!

So why do we choose Key West? First of all let me clear the air and begin by stating that Key West has many facets, not just a touristy, splashy side. Although it does have a main street called Duval which is much like Bourbon Street in New Orleans or Beale Street in Memphis, Duval has a reputation as a party street. For us Duval Street is worth experiencing but certainly not as a steady diet and if this is all you ever knew about Key West then you've missed the very best of what this town has to offer. Now, if you lean towards a more eclectic destination, one that offers sandy beaches, a large variety of musical entertainment, art galleries, scuba diving, snorkeling, deep sea fishing, offshore power boat racing, big-time sailing events, Ernest Hemingway history, diverse lifestyle choices, a large variety of cuisine including some of the best Cuban food anywhere, fresh lobster, shrimp and stone claw crab then Key West might be the place for you. We've all heard the saying, "if you can’t find something to do while in (fill in the blank), then you're just not trying", this aptly applies to Key West.

Here is Widget being teased by a school of fish just before she joined in the swim.

Part of the fun in coming to Key West by boat is arriving by way of the emerald blue waters of Hawk Channel, with the Atlantic Ocean to port and the Keys nestled up next to starboard side. Because we trailered down we missed that part of the adventure this time around, except for the short cruise from the boat ramp over to Key West Yacht Harbour. KWYH resides on the Ocean side of Stock Island,a few miles from the hustle and bustle of downtown Key West. We chose KWYH for our month-long stay because it more resembles a resort marina in the islands, with its clubhouse, restaurant /bar, swimming pool and to top it off it was less expensive than the downtown marinas. A short walk down from the end of our dock, maybe 100 feet, is a tiki hut boater’s lounge where we watched several sunrises with our dock neighbors. The tiki hut was also a great place for happy hour; we could relax to the sound of the ocean waves gently lapping on shore and cool breezes blowing in on a hot and humid afternoon. If we had only been staying in Key West for a few days it would have more practical to have stayed at one of the Key West Bight marinas, just steps from the heart of the city. Because we had our truck parked in the marina, we had the convenience of being able to drive into town on a whim, so the few miles separation was not a problem and therefore another advantage to being trailerable boaters.

This is a shot of the shrimp boat fleet docked behind Fishbusters, one of the fish markets we frequented.

Shortly after getting settled into an outer basin assigned slip, located literally a stones throw from the ocean, separated only by a row of mangroves, we noticed a small dog swimming frantically around the bow of a neighboring boat. My first thought was that this dog was in trouble and could not get back onto his boat or land, I could not have been more wrong. Apparently, Widget loves to swim with fish and does so every day, for hours at a time, ever since he was a puppy. We learned that he grew up onboard with his owners, who have been live boards for 18 years – he just loves the water and his fish friends. He'll sit on the bow of the boat or the edge of the dock scouting the water for a school of fish all day long. Once he finds one, he’ll bark a while to get their attention then he’ll jump in and swim around with the fish that are only inches below his continuously moving paws. Widget does not do this just once per day but several times each and every day and one day we saw him accompany a manatee for an hour or so swim around our boats. It seems the fish like his company as well and do not dart away when he's in the water with them. It probably does not hurt that Charles, Widget’s master, feeds the school of fish a couple of times a day. This is one lean and fit dog, maybe we should all swim several hours a day with fish!

Here is a typical conch style house in the Old Town section of Key West.

Our typical day in Key West would be to wake up and immediately start enjoying the tranquility around the marina while having coffee and letting the day naturally unfold. We'd often go for a walk in the morning either in Key West or around Stock Island, before, or after, our chores were finished. On our walks we'd pass the fishing docks of the Stock Island Lobster Company or Fishbusters. Most days we'd hear the rumble of the fishing fleet depart for a day of fishing at or slightly before sunrise. On the days we sat under the protective shade of the tiki hut at happy hour, we'd catch the same fleet returning to port after a 12 to 14 hour day out on the water. With fresh fish so readily available we'd stop at least once a week to pick up reasonably priced lobster, crab claws, tuna, or shrimp. The only way we could have gotten anything fresher would have been to catch it ourselves. In the afternoons, especially when it was fairly hot, Lisa and I would venture over to the pool for a dip and before we knew it the day had just zipped on by.

Up close and personal with the setting sun, shown at this waterside sunset celebration bar just next to Mallory Square.

Every few days we'd venture into the heart of Key West, park our big truck on the narrow streets of Old Town and explore the city on foot. Old Town is considered the historic district; it’s located on the western side of the island and butts up to Key West Bight seaport. Often our only mission was to walk aimlessly around the tree lined neighborhood streets of Margaret, Olivia, Southard, Simonton and others to take in the sights of Victorian and Bahamian, Conch Style houses while getting some exercise in. Most of these houses are around a hundred years old, are wood sided and were built with raised and covered front porches. Back in the late 19th century, Key West was the largest and wealthiest city in Florida; because of this there are many stately houses in Old Town. I'm not certain but I think we found them all in our many walks around the island during our month-long stay.

Lisa and I would time our excursions into town around mid to late afternoon to coincide with sundown. Sunsets are more of a celebration in Key West. Thousands of people gather at various locations, Mallory Square being the most popular, to watch the sun set into the western waters of the Gulf. To keep the revelers busy while waiting for the sun to make its daily journey on the horizon, visitors are entertained by sword swallowers, cat and/or dog shows, balancing acts, jugglers of swords, fire batons and more. It's a sight to see and every visitor to Key West should participate in a Mallory Square sunset celebration at least once, but after a few times it's also nice to find a more relaxed environment to take in the spectacular descent of the sun.

Dinner with friends Jeff and Denise (our hosts Gary and Jean along with Lisa are inside putting the finishing touched on dinner) on a typical raised front porch in Old Town.

There are many restaurants lining Key West Bight and some have rooftop bars, this is where we prefer to take roost for the sun's departing show. The added benefit of coming downtown in the late afternoon is that most restaurants offer a food and beverage happy hour during the twilight time, so it turns into a win-win all the way around. During one of our rooftop happy hour meals, I mentioned to Lisa that we should make plans to visit the flats, Marquesas Keys and Dry Tortuga during our stay in Key West. As the sun settled into the horizon we heard hoots and hollers from the throngs of happy hour revelers, conch shells moaned and we heard various pitches from many boat horns honking loudly in the harbor. As we relaxed and basked in the afterglow of the sunlit sky, still up on the rooftop enjoying good food, we contemplated how magnificent it would be to experience the same event anchored out on the unattached westerly keys of Marquesas or Dry Tortugas a short 20 to 60 miles away.