Cruising from the Greater to Lesser Antilles


Drone view of Culebra

Figuring out the names of Caribbean islands was as daunting as learning island groups of the South Pacific. First, there’s a whole lot of them! Pinterest Caribbean geograhy 101And then, where does one country end and the next begin? And could I please have a Venn diagram that shows regions and island groups and countries? At least most Caribbean place names have intuitive pronunciation for English speakers (first guesses at cruiser destinations like Kiribati, Papeete, Whangarei, Nadi, Pago Pago, etc. are usually not correct). Cruiser cred points for anyone who can correctly spell these phonetically in the comments!

Quick geography tangent: Antilles is a general term that refers to ALL Caribbean islands, based on the legend of a phantom island—Antillia—that a 15th century Italian-born historian placed in the Atlantic, far to the west from Europe. As boats sailed from Europe to the Americas and the region became better mapped, Antillia gradually disappeared but the general reference for islands to the far west remained.

“Antilles” is less frequently heard than the subset as they are divided into—Greater and Lesser—which are conveniently grouped geographically: Greater Antilles being larger islands to the north (Cuba, Hispaniola, Puerto Rico, Jamaica), and Lesser Antilles being the smaller balance scattered to the east and south. The Lesser Antilles are further divided into windward and leeward islands, which include French Antilles and Dutch Antilles, and then there’s the Lucayan archipelago, didja know the ABCs are an island group not just an alphabet, and… right, too easy to get confused!

Most of our travel through the Greater Antilles was a tease of changing plans as we sought safer waters for hurricane season. We may regret postponing a visit to Cuba, as it is increasingly difficult for a US-flagged boat to access. Passing over Hispaniola I truly regret, and acknowledge the crew of Uma for their generous, speedy, thoughtful, and realistic guidance for visiting Haiti. Where armchair sailors who have no Haitian experience pronounced our certain death if we visited, Kika was a voice of reason: sharing contacts from their months in Haiti, annotating maps, suggesting anchorages. Anchorages we looked forward to visiting, until an unexpected weather window for quicker easting opened. And with that window, we skipped across both Haiti and the Dominican Republic (which together comprise Hispaniola) with one lone (but very memorable) stop. Puerto Rico would be similarly abbreviated if it hadn’t been for the matter of urgent health care. When we moved east again, expected to fast track the remaining necessary stops until Grenada. Anyone who knows our speed is laughing right now…we don’t “fast track” anything very well!

Expecting to skip through Puerto Rico’s eastern island of Culebra as just a pit stop, weather dictated otherwise. With the excellent hurricane hole in Salinas a day sail behind it was worth watching to see what the latest wave from Africa would do.

At left, the "spaghetti model" for the low which eventually became hurricane Gert
At left, the “spaghetti model” for the low which eventually became hurricane Gert; at right, the NOAA outlook about a week and a half later

Weather system 99L eventually became hurricane Gert, happily stayed away, but the active picture illustrates reasons behind the frequent pauses…also known as the wonderful opportunity to spend time with people previously known through the interwebs. Sophie and family, who our kids played endless rounds of jump-off-the-bow-swim-back-climb-aboard-repeat.

kids jumping off sailboat

Long awaited was meeting with Sue and Rick of Orion. Sue and I have been corresponding for quite a few years. You can see the solemnity of the occasion when we finally met up.

meetup with Sue and Rick

Anchored more than a week next to Orion in the Dakity bay corner of Ensenada Honda, they shared “their” Culebra. Long time Puerto Rico residents, they know this area intimately and it was a privilege to experience it with their guidance—from visiting a small museum to exploring on the island.

Sunset behind Totem...
Sunset behind Totem…


...sunrise in front of Orion.
…sunrise in front of Orion.
Walking in Culebra with Sue & Rick
Walking in Culebra with Sue & Rick

girls and cactus

Coaching clients taking a few weeks on their Dean 44 catamaran joined in. This turned into several fun nights of sundowners (and beyond: would that be moonrisers?), playing at the beautiful little island of Culebrita, and some of the best tacos I’ve had in years. For all those memories, somehow I only ended up with pictures of the tacos… and a cucumber-jalapeno margarita, which was even better than you think. Mimzy crew, that was a lot of fun – we’d like a repeat in the South Pacific!


pork belly, beef tongue, and a truly spicy margarita
pork belly, beef tongue, and a truly spicy margarita

After a schedule centered around doctors’ appointments it was nice to fall back into a more normal family routine. Setting up dinner in the solar oven. Cribbage in the cockpit when the afternoon cools off. Jamie and I were on swimming restriction while our stitches healed, but the kids weren’t, and drawing them to the reef for a closer peek was Miss Dakity. That’s the name Sue gave a young flamingo that blew into Culebra earlier in the year and seems to have set up (solo) shop. Fuzzy pic… attempting with a zoom lens from simply way too far away, from a moving platform!

7c setting up dinner cribbage in the cockpit 7a kids swim out 7b Miss Dakity

The unplanned month in Puerto Rico was more pleasant than anticipated, medical stuff notwithstanding. More than that, it zoomed PR way up on the list of “places we could see living someday.” There is a vibe that I’m not sure how to describe: maybe it’s why year after year, Puerto Ricans are listed on a long-term study by the University of Michigan as among the happiest people in the world. There is a friendliness here that’s well over the bar of most. The gregariousness of “Puerto Rican Navy” (affectionate name for weekend powerboaters) dancing on the beach in Culebrita (and leaving no sign of their presence behind). The warmth and care and HOUSECALL by Dr Villa. The smile that greeted meager Spanish, helpful instead of patronizing. Even if it weren’t for the beautiful landscape and history to soak in, we’d be sold.

_DSC8570 5e birds in town _DSC8587





13 Responses

    1. Meghann, I thought of you as I watched the twinkling lights of Saba slide by during a night watch last week, when we sailed from the BVIs to Guadeloupe. I wish we could have stopped, I’d have enjoyed meeting you!

      1. Oh, missed you again. I’m glad you got to see the island lights though! It’s a special little place.
        Although I’ve never been, I hear Bequia is lovely! It may be a nice stop on your way to Grenada.
        And, in case you meet Patrick from FireFox II, please say hello! He took us to the BVI on his boat in April.
        Happy sailing!

  1. Hello Behan. Nice to hear your update. Just curious – what is your sailing plan for the next few months?. Are you planning to return to US mainland or continue south or cross the Panama?

    1. Hi Peter- our plans have a tendency to change, but the current intention is to spend time in Grenada, then head west via Curacao/Bonaire to Colombia (Cartagena for Christmas maybe?), enjoy the San Blas and aim for the Panama canal in early 2018. Sailing Totem back to the USA was never really in our consideration set, but I’ll fly back to Annapolis for the boat show in October.

  2. Behan, funny you mention “living” in PR someday as a possibility. If you were to move there as a homeport and Live there 6 months out of the year then you can take advantage of the tax laws there. Under US IRS law, you pay no income tax. It is not complicated, you just have to be there 6 months out of the year. There are several upscale communities to live in too. just a thought.

    1. This is definitely another one of the appealing features of PR! Thanks for mentioning it Carney. It’s a really good point.

  3. I jus started planning an ASAP vacay in PR (baraboat sailing and land-based) yesterday, because we need a freakin’ break from reality without leaving the US. Between seeing Hurricane Irma forecasts pointing right at PR, Vieques and Culebra, and coming across this lovely post, I feel like I have emotional whiplash. Thank you, Carney Hall, for posting that tax article. As highly-taxed California residents considering retirement living, PR is on our radar.

  4. I know Nan-di, Pango-Pango, Kir-ee-bas and Pa-pee-ay-tay, but not Whangerei. Where can I pick up my partial cruiser cred points?

    1. Well done– yes!! And hat tip to Helen for rounding off Whangerei. Points will be made available under the palm log at the western edge of anchorage motu, Suwarrow.

  5. Hello Behan,

    Wonderful read and great insight into Greater Antilles vs. Lesser Antilles. We havent considered Hispaniola on our route, would you be able to share more on how safely it can be done?
    We will be sailing into the Caribbean at the end of the year and we’ll be spending a considerable amount of time there and would be great to share resources along the way



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