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One Wild Year in the Caribbean: a Possible Sailing Itinerary

Credit: Wix

Imagine where you were on this day last year... What if in that whole year you had been sailing around the Caribbean? In the midst of all the recent excitement (which you should read about here and here) I have been inhaling books to further refine the dream of sailing around the world. "One ocean, one year" is what I've read as a possible cruising timetable for such a long-haul journey, and I don't particularly mind that.

I have developed a possible itinerary for the first year of the trip taking into consideration a Charleston, SC departure, the prevailing trade winds, currents, hurricane season, and each country's legal ports of entry. The aim is to end in Trinidad and Tobago near the end of the hurricane season so that I could start the next big leg of the journey: rounding Cape Horn in South America (more on that later).

In making this itinerary it should be noted I have assumed a 6-knot per hour average speed and sailing only 12 hours per day at sea. Obviously if my crew and I are willing to suck it up and sail at night, we could shorten the time between ports and have way more time for sightseeing and enjoying each destination. Though I tried to utilize the predicted favorable sailing conditions when selecting destinations, I tended to assume that my crew and I would willingly endure periods of sailing into the wind and against the current when necessary. The main considerations were fun and being out of the Greater and Lesser Antilles during hurricane season. Without further ado:

1. Charleston, SC, USA to Marsh Harbour, Bahamas

Anticipated Departure Date: November 1, 2020

Approx. Distance: 510nm

Anticipated Arrival Date: November 8, 2020

Sailing route from Charleston, SC to Marsh, Harbour, Bahamas

The official hurricane season in the Caribbean is typically June through November, with highest frequency of hurricanes between August to October (Jimmy Cornell, World Cruising Routes at 124). Conventional wisdom advises to sail the northern and eastern parts of the Caribbean during the winter months (which isn't altogether a bad idea anyways) and either head home or head south during the summer months. While a November 1 start date is still in the tail end of hurricane season, that is a risk I am willing to live with for more time exploring. Plus, during the month of November we'll still be relatively close to the U.S. if we need to make an emergency trip to hunker down.

Though I have never heard of Marsh Harbour, I chose it as a first destination because I love the Bahamas and because it is on an island in the Bahamas I've never been to. Since getting there would be my first week-long sailing trip as my own skipper, I wanted to make new experiences all around, and that's the point of sailing around the world!

2. Marsh Harbour, Bahamas to Nassau, Bahamas

Anticipated Departure Date: November 15, 2020

Approx. Distance: 100nm

Anticipated Arrival Date: November 17, 2020

Sailing Route from Marsh Harbour to Nassau

There is no doubt that Nassau is a touristy place, but it's for a reason. The island is beautiful! Given that my brother and I are doing this in part to enjoy life, a little time partying with locals and with tourists can't be all that bad! I planned for a week in Nassau, and I just hope that we are willing and able to leave after that.

Credit: YoTuT |

3. Nassau, Bahamas to Cockburn Town, Turks & Caicos

Anticipated Departure Date: November 24, 2020

Approx. Distance: 413nm

Anticipated Arrival Date: November 30, 2020

Cockburn Town, the capital city of Turks & Caicos, is the next big destination. I am particularly excited about having the opportunity to SCUBA dive out here; according to Noonsite, the waters around these islands are reputed to be one of the best diving sites in the world, bested only by the Great Barrier Reef and the Belize Reef.

With views like this I believe it! Not surprising, I've added learning how to SCUBA dive to my list of adventures this summer. There are about 40 islands and cays we will be able to explore in our two weeks in Turks and & Caicos!


4. Cockburn Town, Turks & Caicos to Labadie, Haiti

Anticipated Departure Date: December 14, 2020

Approx. Distance: 122nm

Anticipated Arrival Date: December 16, 2020

From there we head southwest towards Haiti. The thing that seems pretty great about the Caribbean is that all of these islands are relatively close to each other, so you're not spending weeks at sea between ports. The prevailing winds throughout the year in the Caribbean blow from the East or Northeast, so going eastbound generally will be somewhat difficult. However, from Turks and Caicos to Haiti you can expect to be sailing with the wind at your back, making for a fast run.

While Haiti is one of the poorest countries in the Western Hemisphere, it is also one of the safest for cruisers, having no reported attacks on cruisers since 2015 as of the date of this post (Source: Noonsite). Haiti is still recovering from the onslaught of natural disasters over the past decade, but it is still a vibrant society rich in culture and a gorgeous place to visit. Definitely looking forward to it and maybe even getting some volunteer time in!

Maniche, Haiti--a small village in the mountains

5. Labadie, Haiti to Punta Cana, Dominican Republic

Anticipated Departure Date: December 20, 2020

Approx. Distance: 593nm

Anticipated Arrival Date: December 28, 2020

I struggled a bit deciding on this route. I originally wanted to take the most direct route to Punta Cana (i.e. via the northern shore), but many of the cruising guides and websites I read recommend sailing eastbound on the southern side of Hispaniola due to a persistent Atlantic swell on the northern side. If everyone's recommending it, it must be a big deal, so I'll take their advice... this time.

I imagine the arrival at Punta Cana will be much sweeter given the few extra days at sea. Growing up I had a few Venezuelan friends who raved about Punta Cana as being the preferred vacation destination for young Venezuelan partygoers. I'm excited to find out why, and during New Years celebrations no less!

6. Punta Cana, Dominican Republic to San Juan, Puerto Rico

Anticipated Departure Date: January 11, 2021

Approx. Distance: 130nm

Anticipated Arrival Date: January 13, 2021

I'm not going to lie, after a week of partying and a day and a half of sailing, I have no doubt that spending some time back in a familiar US territory will be a welcome experience. I have a few friends who are from Puerto Rico, so I'm hoping when they find out I'll be there they'll fly down to show my brother and I around!

7. San Juan, Puerto Rico to Road Town, BVI

Anticipated Departure Date: January 18, 2021

Approx. Distance: 86nm

Anticipated Arrival Date: January 20, 2021

From Puerto Rico we start the journey into a group of Caribbean islands known as the Lesser Antilles, made up of three subgroups of islands: the Windward Islands, the Leeward Islands, and the Leeward Antilles. The first group of islands we'll encounter are the Leeward Islands. The British Virgin Islands (BVI) are considered the capital of the bareboat charter boat industry, so we can expect it to be quite crowded waters. The cruising guides I have read indicate that finding anchorages anywhere in there can be quite challenging.

Notwithstanding, the island of Tortola, where Road Town is located, is known to be absolutely stunning--my mom could not stop raving about it for years after she visited it. I think it would be worth it to spend the extra time to find a good anchorage. Here's a little snapshot of what to expect ;)

Blue sky, blue water beach in Tortola

8. Road Town, BVI to Cruz Bay, USVI

Anticipated Departure Date: February 3, 2021

Approx. Distance: 13nm

Anticipated Arrival Date: February 4, 2021

The Virgin Islands of the United States (USVI) is another crowded group of islands, but can be well worth the hassle of finding a good anchorage. The island of St. John, in particular, is one I have never been to but would really like to explore. Approximately 75% of the island is a national park under the supervision of the U.S. National Park Service, and is well-maintained. Nothing like a bit of eco-tourism sprinkled in to our sailing adventure!

9. Cruz Bay, USVI to Christiansted, USVI

Anticipated Departure Date: February 18, 2021

Approx. Distance: 36nm

Anticipated Arrival Date: February 19, 2021

A short southerly trip to the island of St. Croix, USVI will be a welcome respite from the hustle and bustle of the main BVI/USVI islands. Apparently St. Croix, while still a popular destination spot in the USVI is less crowded than the other islands since it is a bit out-of-the-way from the normal cruising routes.

10. Christiansted, USVI to Road Bay, Anguilla

Anticipated Departure Date: February 26, 2021

Approx. Distance: 97nm

Anticipated Arrival Date: February 28, 2021

Perhaps this is the reason St. Croix is not as busy: given the general NE prevailing winds in the area, sailing to Anguilla will probably be a bumpy ride, sailing in to the wind for the whole day. No guts, no glory they say. It's just a day, right?

I struggled adding Anguilla to the list. Although known as being one of the most beautiful of the Caribbean islands for its crystal clear waters and pristine ecosystem, the cost of keeping the island so gorgeous translates to higher costs and restrictions to boaters. The island has certain designated anchorage sites, and the cruising permits are both expensive and restrictive. I have read that anchoring anywhere other than Road Bay can cost you upwards of $100 USD per night! Notwithstanding, since presumably we are only doing the Caribbean once, I couldn't take it off the list--if we have to pay $100 one or two nights, so be it. It looks to be worth it:

The fruits of sailing around the world: sunset in Anguilla

11. Road Bay, Anguilla to Marigot, St. Martin

Anticipated Departure Date: March 13, 2021

Approx. Distance: 14nm

Anticipated Arrival Date: March 13, 2021

Growing up I was fortunate enough to be able to visit St. Martin a couple times, and I can honestly tell you back then it was one of my favorite tropical destinations. Naturally, I couldn't pass up including it on the list. Like most of these islands so far, the sands are white, the people friendly, and the life relaxing. This is one week I am particularly looking forward to, and it should be interesting being able to stay overnight this time around.

12. Marigot, St. Martin to Basseterre, St. Kitts & Nevis

Anticipated Departure Date: March 20, 2021

Approx. Distance: 67nm

Anticipated Arrival Date: March 21, 2021

Apparently St. Kitts and Nevis is off-the-beaten-path as compared to Antigua, mostly because of a difficult current to navigate. Again we will have to put on our YOLO hats and make it happen. Though less scenic than the other islands, the history of St. Kitts and Nevis is quite fascinating (more on that in a future post). I think it's worth a day of rough sailing.

14. Basseterre, St. Kitts & Nevis to English Harbour, Antigua & Barbuda

Anticipated Departure Date: April 4, 2021

Approx. Distance: 62nm

Anticipated Arrival Date: April 5, 2021

As the itinerary gets closer and closer to hurricane season in June, sadly we'll be forced to skip some other awesome islands on the journey southward. Barbuda is one of them. The island is currently being rebuilt following the devastation of Hurricane Irma in September 2017, and though I would really love to see it, I think we're going to have to pass. Antigua is not a bad substitute, however, and English Harbour is supposed to be absolutely gorgeous, having one facility in particular, Nelsons Dockyard, designated as a UNESCO World Heritage Site.

15. English Harbour, Antigua & Barbuda to Little Bay, Montserrat

Anticipated Departure Date: April 19, 2021

Approx. Distance: 30nm

Anticipated Arrival Date: April 19, 2021

I have Montserrat slotted for one week, but depending on how the situation actually is once we are out there, we may have to depart early. The island has no natural harbors, and I have read that anchoring can be quite wavy in the wintertime. The island itself is mostly scenic as a volcanic eruption in 1995 wiped out two-thirds of the island, including the capital of Plymouth. Given the rustic nature of the place, I would be very excited to do some hiking though (and see the volcano if we're allowed to)!

Soufriere Hills Volcano

16. Little Bay, Montserrat to Trois Ilets, Martinique

Anticipated Departure Date: April 26, 2021

Approx. Distance: 158nm

Anticipated Arrival Date: April 28, 2021

With Martinique we skip down into the Windward Islands and experience a bit of French culture. Martinique is said to have numerous calm anchorages, great food, and good hiking. Given that Martinique also has a reputation of having high-quality yacht facilities, this may be a convenient place to give the boat a thorough review and repair anything that needs to be repaired.

17. Trois Ilets, Martinique to Bridgetown, Barbados

Anticipated Departure Date: May 5, 2021

Approx. Distance: 132nm

Anticipated Arrival Date: May 7, 2021

Again, another difficult decision. Barbados is the most visited island in the Caribbean and is the most developed island in the region. I think it would make a pretty great stop before we head closer to South America, but we will be restricted to anchoring on the southern side of the island due to the Atlantic waves. I'm not experienced enough to know what a night sleeping in that water would be like, but everyone seems to keep commenting on it in the material I am reading, so it must not be pleasant. Nevertheless, we can't leave the Caribbean without at least spending a few nights at its most popular island!

18. Bridgetown, Barbados to St. George's, Grenada

Anticipated Departure Date: May 14, 2021

Approx. Distance: 148nm

Anticipated Arrival Date: May 16, 2021

The most southern of the Windward Islands, Grenada is reputed to be a favorite of many sailors who sail the Caribbean. For the fans of interesting random facts, Grenada is one of the world's largest exporters of nutmeg and mace, giving it the nickname the "Island of Spice."

Also quite interesting, in the early 80s the government of Grenada was in turmoil following its independence from the UK in 1974. A series of power struggles ensued, ending in a preliminary military government that had executed the former Prime Minister of the island. The U.S. led an invasion of Grenada six days after the PM's execution, codenamed Operation Urgent Fury, which ultimately overthrew the military regime and reinstated democratic elections. Wow!

For such a small island, it boasts a fascinating history. I never knew about the US operation before researching Grenada, and I am particularly excited to learn more and visit this island first hand!

19. St. George's, Granada to Willemstad, Curacao

Anticipated Departure Date: May 30, 2021

Approx. Distance: 442nm

Anticipated Arrival Date: June 5, 2021

Leaving Grenada we travel to the Leeward Antilles just in time for the start of hurricane season. From here on out we are relaxing, killing time in the Southernmost parts of the Caribbean until it is safe(er) to head even further South towards Brazil and Argentina. Spending five months near South and Central America is definitely not a bad plan though!

I decided to skip Venezuela because I read that crime has been a little too frequent for my taste lately due to the ongoing political and humanitarian disaster in the country over the last few years. That's a bummer because I have some extended family that used to live out there, and it would have been nice to see where they grew up.

Curacao, however, should be pretty awesome in its own right. It's an autonomous country within the Kingdom of the Netherlands, and it shows (see below). I find it particularly spectacular to observe the impact European colonization has had on the culture of these islands!

Row of multi-colored buildings on the water

20. Willemstad, Curacao to Oranjestad, Aruba

Anticipated Departure Date: June 19, 2021

Approx. Distance: 70nm

Anticipated Arrival Date: June 20, 2021

Aruba, another autonomous country within the Kingdom of the Netherlands, has been high on my list of places to visit since I first heard about it back in high school from my then-girlfriend from Venezuela. Reading recently about people's experiences in Aruba has only made my desire to visit more intense. Not only can we expect white sands, clear waters, and beautiful sunsets, but the nightlife is supposed to be mind-blowing!

21. Oranjestad, Aruba to Barranquilla, Colombia

Anticipated Departure Date: July 4, 2021

Approx. Distance: 311nm

Anticipated Arrival Date: July 9, 2021

Colombia has a special place in my heart thanks to an amazing two weeks spent in Medellin a few years back with some of my closest friends. I have a few extremely kindhearted Colombian friends I met on that trip (at the airport no less), who I am very excited to visit. I even have recent confirmation from Bruce, one of my friends who came on that that two-week trip years ago, that he wants to be a part of the voyage from Aruba to Colombia to celebrate this adventure with me and my brother! We'll then spend a month in Barranquilla, a smaller port town, much less touristy than our next stop in Colombia: Cartagena. The more I think about Colombia, the more I itch to leave for this trip already. It is truly a paradise.

22. Barranquilla, Colombia to Cartagena, Colombia

Anticipated Departure Date: July 30, 2021

Approx. Distance: 67nm

Anticipated Arrival Date: July 31, 2021

Cartagena is a more touristy, popular place to be than Barranquilla I hear, but we'll have time, so I figured why not spend time at both? As one of the most important Spanish port cities during the colonial era, Cartagena has a rich and fascinating history. I haven't stayed two months in any one foreign country for almost a decade, but I am really looking forward to spending a good deal of time in Colombia.

23. Cartagena, Colombia to Portobelo, Panama

Anticipated Departure Date: August 21, 2021

Approx. Distance: 260nm

Anticipated Arrival Date: August 25, 2021

After a long stay in Colombia we head in to Central America to travel along the Spanish Main. Portobelo, Panama has ruins of a Spanish fortification that has been designated a UNESCO World Heritage Site that is in danger of destruction due to lack of maintenance and increasing urban growth in the area. In addition to checking out these ruins before they are totally destroyed, Panama is renowned for the beauty of its landscapes, and Portobelo is right on the edge of one of Panama's national parks. After spending months in the city it will probably be nice to do a little more hiking and eco-sightseeing.

24. Portobelo, Panama to Limon, Costa Rica

Anticipated Departure Date: September 1, 2021

Approx. Distance: 200nm

Anticipated Arrival Date: September 4, 2021

Another beautiful country on the list is Costa Rica, which I've been wanting to visit for years! Living in Colorado for the last couple years I have come to love and appreciate the natural beauties of our world. Costa Rica is a tremendously popular ecotourism destination, and I am particularly excited to walk around the Monteverde Cloud Forest. I have heard through the grapevine that Costa Rica is a popular home for retired US expats, and while we are there I will definitely take the opportunity to scout it out for the future :)

Bridge in Monteverde Cloud Forest

25. Limon, Costa Rica to Placencia, Belize

Anticipated Departure Date: September 18, 2021

Approx. Distance: 688nm

Anticipated Arrival Date: September 28, 2021

While I would love to visit Nicaragua again, if I do so I would like to visit my grandfather. He lives closer to the Pacific coast, so at this time we'll probably visit Nicaragua the following year. I have also heard conflicting reports about the safety of Honduras and Guatemala, so I thought it best to skip them. Instead, we head to Belize to experience more beautiful SCUBA diving spots. Belize is actually a fairly cheap flight from Denver... I'm not sure if I'll be able to wait to visit haha.

26. Placencia, Belize to Cozumel, Mexico

Anticipated Departure Date: October 12, 2021

Approx. Distance: 262nm

Anticipated Arrival Date: October 16, 2021

And from Belize we head back to another one of my favorite countries: Mexico. The last time I was in Cozumel was during a family vacation almost a decade ago, and I loved it. White sand beaches, great food, and great people. This will be a fun place to celebrate our one-year sailing anniversary and chill out for a month before we head down the South American coast. We'll probably have to keep an eye out for potential hurricanes while we are there since we'll still be in the heart of hurricane season. Cozumel is not immune, and actually the last time I was there the whole island was recovering from a major hurricane that passed through.

27. Cozumel, Mexico to George Town, Cayman Islands

Anticipated Departure Date: November 15, 2021

Approx. Distance: 335nm

Anticipated Arrival Date: November 20, 2021

Towards the end of hurricane season it will be time to race back towards Eastern edge of Venezuela to start the trip around South America. Along the way we'll be able to stop in the Cayman Islands and stay for a few days if necessary. The Caymans are pretty well-developed, and it will be a little bit of home after almost a year sailing! Depending on how the financial situation is at that time, we might have to book it out of there early--it can be quite expensive.

28. George Town, Cayman Islands to Montego Bay, Jamaica

Anticipated Departure Date: November 27, 2021

Approx. Distance: 219nm

Anticipated Arrival Date: November 30, 2021

Whatever time we lose in the Caymans we can certainly make it up in Jamaica. There is no getting around it--Jamaica will be about partying. Based on what I have read about rounding Cape Horn, we're going to need to stock up on good memories because at times we'll be going weeks without civilization. These last few islands will be our last times to enjoy the Caribbean, so we'll have to make them count!

29. Montego Bay, Jamaica to Oranjestad, Aruba

Anticipated Departure Date: December 7, 2021

Approx. Distance: 602nm

Anticipated Arrival Date: December 15, 2021

The second trip to Aruba will be fun for sure, but at this time we'll be somewhat in a hurry. The window to make it down to Cape Horn in time for the good weather will mean we'll be in somewhat of a time crunch. More on the South America trip in a later post :)

30. Oranjestad, Aruba to Scarborough, Trinidad & Tobago

Anticipated Departure Date: December 18, 2021

Approx. Distance: 560nm

Anticipated Arrival Date: December 26, 2021

From Aruba we head straight to Trinidad and Tobago. I have a couple old friends that are from there, and I think one of them is living there right now. If we time it right we should hopefully be arriving there during the holiday season, which will no doubt be epic given the pictures I have seen from my friends. Though we'll have already been sailing for more than a year at that point, celebrating New Years at the edge of Caribbean, right before we start the next big leg of our journey, will be a very powerful moment for sure.



So this is what the proposed Caribbean adventure looks like. All in all, I am very excited! I was a little upset about my decision not to include Cuba in there--I have always wanted to go and I have family I have never met that live there. However, after reading about how it can still be somewhat unsafe for cruisers, I decided it best to skip it this time around. Who knows, maybe we'll change our minds and make a stop there after Cozumel.

Though I tried to route this sailing itinerary as best I could using the materials I have read, I'll admit I have never been out there on the water. I'm well aware that even the best laid plans fail, and books are no substitute for on-the-water experience. If there is anyone reading this who spots any flaws with what I am suggesting, I would sincerely appreciate some constructive commentary! Otherwise, I'll keep on researching for the next big post: rounding Cape Horn!

- Anthony

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