A Caribbean Sea Circumnavigation

Tales abound of ships crossing the Atlantic and Pacific Oceans. These are great oceans with well-documented routes and a large body of knowledge describing everything from the best time to depart to tips on provisioning.

There is an ocean that is lesser known. A sea that is not often discussed. Yet, since the utter devastation wrought by super-hurricanes such as Irma and Maria, it is a sea that many now need to consider crossing.

Prior to the 2017 hurricane season, Grenada in the southern Caribbean and St Mary’s Inlet on the Florida/Georgia line were commonly the boundaries of the “safe zone” for hurricanes.

New Hurricane Danger Zone - Atlantic
The “no-go” zone for the Atlantic hurricane season (June to November) has expanded drastically north and south since the devastating storms of 2017.

Since 2017, cruisers are being sent further north and south to minimize named storm risk. For the 2021 hurricane season, our 62’ sloop named DOUBLESTAR had to be either north of Cape Hatteras or south of latitude 10°N to have “named storm cover.”

In short, to be insured against hurricane damage, we had to be so far north or south that the possibility of encountering a hurricane was ZERO. Insurance companies are happy to collect the higher premium associated with hurricane insurance, but after the financial losses suffered in 2017, they want to be damn sure there is no risk of ever having to pay out again.

That means we’re either required to sail a significant distance up and down the US East Coast every year which includes navigating Cape Hatteras—the “Graveyard of the Atlantic”—twice, or we needed to head down to Panama.

After spending the previous two years sailing between New York and St. Maarten, we knew we were not heading back north.

And that meant crossing the Caribbean Sea.

There are several options when considering this crossing. One could head west from the windward islands, with a scheduled stop in Bonaire, Curacao, or Aruba (The ABCs), or even all three. However, that leaves a stiff challenge: beating into weather and current around the north coast of Columbia to reach the eastern parts of Panama.

We were faced with this challenge, along with continued country closures or long quarantine periods prevailing in many of the Caribbean islands when we had to make a final decision on where to spend hurricane season for 2021.

We were in St. Maarten, a very attractive proposition during COVID with its excellent chandleries, duty-free shopping, magnificent provisioning, and a wide variety of on-land activities. After spending eight weeks in St. Maarten, and already well into the hurricane season, we had to find a suitable window to depart for Panama.

Docked in St Maarten
Docked at the fabulous Yacht Club Port de Plaisance in Dutch St. Maarten.

When we set sail out of St. Maarten, our destination was Bocas del Toro, close to the Costa Rica border with Panama. We ended up not quite making it in the way we originally intended, but we’re kind of used to that by now.

We published our log entries for the 8-day, 1,300 nautical mile passage. As is often the case with the sailing life, we got there in the end. Just not when and how we expect to.

Life in Panama was good—for the most part. It was so different from other parts of the Caribbean. Thinking back, the word that comes to mind first is: JUNGLE.

DOUBLESTAR | Blaufield Anchorage in Panama
The jungles of Panama are out of this world.

I mean real jungle. The kind of jungle you see in the movies. The kind of jungle you imagine the Amazon rainforest must be like. Stuff just grows everywhere, on everything, all the time. The amount of life that surrounds you is astounding.

I hope to do Panama some justice in a future, more detailed post. For now, suffice to say we explored the Caribbean coast of Panama from the San Blas in the east to Bocas in the west, and much of it in between.

We were even lucky enough to spend three magical days—the highlight of our time in Panama—anchored off Escudo de Veraguas. It was a surreal experience we will never forget.

Our favorite beach on Escudo de Varaguas
A bird’s-eye view of our secret beach on Escudo de Veraguas, a place we will never forget.

With hurricane season behind us, we were free to venture north of the 10th parallel yet again.

We initially thought we had options.

We could transit the Panama Canal, which was what we thought we would do while we were still in St. Maarten making future plans. From there we had the option of exploring north to the US West Coast and Alaska, or the South Pacific (as most boats do).

Or we could work our way up the coastlines of Costa Rica, Nicaragua, Honduras, and then Belize. This option was appealing. Belize in particular has some spectacular diving and an amazing reef system.

The one thing we were starting to realize was quite the shocker: we were sick of the sun, beach, and tropics.

Yes, I know, we’re crazy. But we’re human. And humans tend to want something different. At least we do. That’s why we live on a boat, and after two years in the Caribbean, soaking up the sun, sand, and salt, we needed a change of pace.

So Europe, here we come!

Before we could make any final decisions, a decision was unexpectedly made for us:

We had planned to fly back to the US for 10 days in November to take care of a few things. This would be our longest time off the boat since we started our adventures in August of 2019.

We flew from Panama to Atlanta and drove up to Chicago via Chattanooga and Nashville. We then flew to Fort Lauderdale from where we would return to Panama via Miami. This is where things got…interesting. 

We had our Maltese with us for the trip to the US. While we had previously entered Panama with her onboard without any issue, the rules and regulations for flying into Panama with a dog turned out to be very different.

Our cute Maltese
While we had no problem sailing into Panama with our Maltese, once we flew back to the US with her, we could not get back into Panama by air without the unacceptable risk of a long quarantine period.

The upshot was that we could not fly back to Panama with our dog. So we made arrangements to have her stay with our son, and we flew back to the boat sans Maltese.

This put a fire in our belly to get the boat out of Panama and to a location where we could fly out to the US again and back in with our Maltese.

That meant Estados Unidos Mexicanos.

Since we were planning to get to Mexico eventually anyway, we decided to skip out the rest of Central America and make a beeline for Cancún. 

Except the wind had other ideas.

We were at Shelter Bay Marina at the mouth of the Panama Canal, and the available wind direction meant we had to go east first to get a better angle for the run to the northwest.

We set off on a rhumb line for Cartagena, the capital of Columbia.  We made an F-1 style pitstop in Linton Bay Marina to fuel up. It was here that it dawned on us: we had come full circle! Linton Bay was the same marina we limped into four months earlier when we were running on fuel vapor as we entered Panama after crossing the Caribbean Sea from St. Maarten.

From Linton Bay we kept heading to Cartagena, and around 30 miles from this iconic city, the wind finally filled in. We made a 90° turn to port (that’s a hard left for your landlubbers), and set a course for the land of margaritas and cerveza.


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This was the longest tack ever. We had to run almost all the way to Cartagena in Colombia before we had a good wind angle for the trip to Cancún.

As small but noteworthy detail I left out: our air-conditioning system decided to stop working the day before we departed Shelter Bay Marina. So we had no climate control, and it was hot. I mean…it was HOT. And humid.

For the next six nights and seven days, we lived in the cockpit. We kept watch, ate, and slept in the cockpit. The afternoons were the worst, when the sun would beat down and the humidity would be at its highest. 

Thankfully the evenings were cooler and more bearable. On the plus side, DOUBLESTAR was absolutely flying. With a great, consistent 20 knot wind just aft of the beam, a clean bottom, and a helping current, we were doing a consistent 11+ knots. We had three 200+ mile days, and one day of 195 miles covered midnight to midnight.

Crossing the Caribbean Sea
Despite the lack of climate control on board, we had our best run yet with several 200+ nautical mile days.

It was the best sailing we’ve ever had for such a long period of time. Despite the rush of suddenly being under pressure to get somewhere, the stress of leaving the dog behind, the discomfort of melting in the tropics, and the tired-to-the-bone weariness of short handed sailing, we were having a blast.

We finally pulled into Cancún on 29 November, 2021. Cancún was an adventure in itself—which, again, we will cover in another post.

We enjoyed a fabulous Christmas in Cancún where Chef Engineer made up for the fact that Thanksgiving was spent at sea dodging pirates somewhere off the coast of Nicaragua. Our Christmas meal and boat decorations were both stunning. Feliz Navidad!

The highlights of our travels are usually created in the galley. Christmas table for 2021 in Cancún, Mexico.

By now we had crystalized our future plans. We would spend the early part of the summer in New England. By June we would make our way into Canada, and then depart for the Azores from St. John in Newfoundland.

This meant the time had come to cast off and head northeast to Florida. We slipped the lines on 28 December and headed toward the welcoming shores of the United States once again. 

Sailing along the mysteriously inaccessible north shore of Cuba, we marveled at the glow across the horizon that we knew was Havana.

So tantalizingly close!

Our first unofficial stop was a few nights spent on anchor in the Dry Tortugas National Park, waiting for suitable weather. We came face to face with Tommy (a Goliath Grouper that we so named because he is about as long as Tom Cruise is tall!) and explored Fort Jefferson. We were also reminded how much we missed the glorious East Coast sunsets.

Sunset in the Dry Tortugas
A glorious sunset behind DOUBLESTAR off Dry Tortugas National Park

Two days after we celebrated the promise of a new year, we made the day-sail to Key West, finally tying up to the Perry Hotel and Marina on Stock Island. 

We were home. Back in the US. And it felt great!

Here is a summary of our Caribbean circumnavigation.

  • Departed St. Augustine, Florida on 29 January, 2021.
  • Visited 8 countries and territories including Bahamas, Turks and Caicos, Puerto Rico, USVI, St. Maarten/St. Martin, Panama, and Mexico.
  • Dropped the hook or tied up in 69 separate locations.
  • Sailed 6,133 nautical miles.
  • Arrived back in Key West, Florida on 2 January, 2022.

We are absolutely loving being back in the US.

So is Amazon.

The boat is in great shape! We’re preparing for out Atlantic crossing later in the year, and we are researching the fabulous destinations in Scandinavia and beyond that we plan on venturing to.

If you wish to join the adventure, sign up and follow along.

One thought on “A Caribbean Sea Circumnavigation

  1. Ronel Wright says:

    Greetings from Plettenberg Bay, SA. Although I am fortunate to be in contact with my BFF, chef engineer, it was fascinating to read all the details. Well done Captain and crew, I am envious of this fantastic adventure that you are experiencing.

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