The Official Magazine of the Bluewater Cruising Association

Cruising Cayo Hueso (Key West): Land of Hemingway, Hurricanes and History!

Steve Nash

Waterline 47
March 12th, 2018

After spending a very pleasant March, 2016 at a funky, Caribbean-style marina in Isla Mujeres, on Mexico’s Yucatan coast (one of our favourite stops BTW), we continued our seasonal semi-circumnavigation of North and Central America, which has seen many stops and wonderful sea and land travels over six seasons in the US, Mexico, Guatemala, El Salvador, Costa Rica, Panama, Colombia, Honduras, Rio Dulce and Belize. We checked out of Mexico and headed our boat, Kuyima, a steel, 47 ft Waterline Cutter, northeast bound towards Florida and the United States.

Getting around Isla Mujeres

Since the boat had been away from North America for about six years, we were keen to return her to the land of abundant, high quality, easily obtainable and reasonably priced parts, supplies and labour. After six years away, it was time to get some much needed work done and replace many of the things that were on their last legs or completely worn out. However, though we were keen on these opportunities, we were not particularly keen on checking back into the US, especially in Key West. The in/out process in every country in Central America had been relatively painless, (albeit overly and informally “expensive” at times) whereas from our cruising research and experience with land travels, checking into the US these days was relatively inexpensive, but could be unpredictable. We had learned that effective January 1 2016, the use of the cruising license, which had been on the books for a long time but never really used or enforced with any regularity, was now going to be a strict requirement. Not really a problem, as it is a clear, straightforward process, especially for Canadians (see postscript below), but just added a bit more uncertainty. Anyway, we were on our way.

Isla Mujeres

From Isla Mujeres we headed out on our two day passage, bound for landfall in the Dry Tortugas and Key West (Cayo Hueso in Spanish) in the Florida Keys. Ahhhh!…fabled Key West and the Keys. Well known mainly as the long time family home of writer, marlin fisher, boater and all round legend, “Pappi” Hemingway.  But also known, in olden days of course, as a prime pirate refuge and hunting ground; as a great landing spot for rum runners from Cuba during prohibition, and more recently, as a destination for eccentrics and cruisers alike. In our minds we looked forward to cruising this eclectic, history rich, southernmost archipelago at the tip of Florida for a short time, before heading north to St Petersburg, where we intended to lay the boat up for the summer.

Heading from Mexico to western Florida by sea is always an interesting, and often challenging, journey. On the one hand, you generally have a good following boost from the Gulf Stream, that enormous body of water that flows up through the Yucatan channel, north into the Gulf of Mexico for a few hundred miles then curves back south and winds its way past Key West, eastbound through the Florida Straits then northward up the eastern seaboard finally heading over the Atlantic to hug the coastlines of Ireland and Scotland where it brings warm water temperatures and sometimes even palm trees! Often moving at 3-4 knots in the centre, the Gulf Stream is an immense and massive body of water, roughly 62 miles wide and around 4000’ deep; it carries more water than all the rivers in the world combined! And this has to all fit, first through the gap between Mexico and Cuba (the Yucatan Channel), and then through the gap between Florida and Cuba. Combined with this is the fact that the predictable trade winds normally blow northeasterly or easterly against the current; if the wind is blowing 25 knots plus, creating standing waves, it is not a fun time.

With all sails, including the trusty staysail, tightly set we pointed Kuyima northeast into about 15-20 knots of easterly wind and 1-2 meter seas and right away felt like we were in a washing machine. Winds were just off the nose and waves felt like they were coming from all directions. Crew were dropping like flies. Thankfully, weather forecasts were calling for the winds to diminish, which they did over the next 24 hours, and the Gulf Stream soon headed north for quite a bit before turning back east. So as we cleared the Yucatan Channel and rounded the top of Cuba, after about 15-18 hours of sailing, the seas and our stomachs settled, much to the relief of all. As we continued our journey to the Dry Tortugas and Key West, the Caribbean showed us her best face as the seas calmed, the winds settled, the air warmed and the moon came out making for a peaceful and very pleasant sail as we made our last few miles to Florida. Arriving early morning we anchored and looked forward to exploring fabled Key West.

Hemingway House, Key West

Alas, the Keys and Key West are still magical in many respects, but of course things have changed. Pappi Hemingway still dominates as one of the prime local tourist attractions; the house he and his family lived in is very interesting, very well maintained, and very busy, but the key word here is tourists and tourism. Discovered by mass tourism in the last 10 years or so, like many popular places (cruise ships arrive at the rate sometimes of 2-3 per day), this makes it a very busy and, most recently, a very expensive place. Combined with a relative lack of marinas and the odd hurricane, this has had a negative effect on cruisers and the cruising community.

Marina Key West

For the first time ever, we were faced with fees of $3USD a foot (plus, plus) to go into a marina, albeit in downtown Key West. In Southern and Central Florida, at least, the practice is to charge a very high “transient rate” (in Miami $10 a foot per day is not uncommon), but a more reasonable monthly rate (there are very few weekly options). However, even when we returned to Key West for a visit in January and decided to stay a month in Stock Island (a cheaper alternative), which is about 6 miles outside of Key West, the rate was about $42USD per foot per month, plus tax and electricity (for a 47 foot boat, you do the math…ouch!). So, with limited longer term anchoring options due to very shallow depths and often high winds and northers, especially in January/February, Key West could only warrant a short visit.

Having said all that, if you can hold your nose at the cost for a bit, Key West and the Keys are overflowing with character and generally are a great place to visit and cruise. Notwithstanding the tourism, the town is still very quaint in many ways, with lazy looking streets, beautiful “Key West”style homes (verandas and fans), nice beaches and friendly people. The downtown is alive every night and there is an abundance of great restaurants, bars and music spots. In fact, the live music scene is amazing and extremely diverse. We spent New Year’s Eve in Key West and it was the perfect choice.

Key West marker indicating southernmost point, continental USA

For cruisers, once the weather settles, you have generally very nice (but shallow) cruising grounds, with many anchorages. Though not overly protected from prevailing easterlies, there’s great fishing, and the option of an easy overnight to Cuba and all that beautiful island has to offer. We particularly liked the cruising area between the Keys and Tampa Bay. You are in the lee of Florida, so the seas are smoother and the sailing is great and there are many wonderful places to visit along the way. St Pete was a great place to leave the boat for the summer, although we had a scare from Hurricane Irma.

After leaving Key West and the Keys, we sailed up to Miami and then to Fort Lauderdale, where we are now at anchor. We will be in South Florida until the end of March, when we head to the Bahamas for the start of another adventure!

Key West

Postscript: Notwithstanding our slight concern at checking back into the US at Key West, I have to say that the process was very straightforward and we were pleased and impressed in all respects. I do not know if this is the case in other states, but in Florida there is a 1-800 number that goes to the central small vessel reporting center. For Canadians, once you are anchored or alongside in Key West, you simply call this number and advise that you have entered the country and answer the usual questions: people on-board, passports etc. The officer then gives you a number and advises that all must report within 24 hours to the local CBP office. We were at anchor, so the next morning the three of us went ashore to the CBP office downtown, where each of us spoke to a CBP officer, showed our passports and boat docs and “cleared in”.

During the process, the officer, who was very professional and helpful, asked if we wanted to obtain a cruising license (applicable throughout the US). Cruisers do not have to obtain a license, but if you do not, you are required to check out and then check in to each CBP district to which you travel. This usually involves a special trip and payment of a $20 navigation fee at each place, which is a real pain. With a cruising license, an official document signed and stamped with a number special to you, you simply call the 1-800 number and report when you have arrived at a new district. The officer on the phone may ask you one or two questions, but normally simply takes the info and gives you a reference number, which we log as proof. The cruising license is valid for one year, then it expires. To obtain a new cruising license for a further year, the boat MUST leave the US for at least 15 days (most people here go to the Bahamas or Cuba). Upon returning to the US, you can apply for a new cruising license. If you are leaving before the year is up, you can also “surrender” your cruising license, so that when you return after 15 days, you will be eligible for a new one. If you do not surrender, you may return under your previous cruising license, but subject to the original expiration date. Any questions on this, please do contact me.



  1. Russell Mead says:


    You are following our path is o many ways!!

    If you make it to Nova Scotia, look us up we could trade stories…

    RUss and Heidi Mead

    Tillicum 1 Schooner
    Upper laHave RIver NS
    2009-2010 Vancouver to NYC and beyond..

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