Cruising the Northwest Caribbean 
Head Southeast to get to the Northwest

By Barbara Theisen 

A cruiser’s plans are always subject to change. That’s rule #1 when it comes to cruising. Aboard Out of Bounds it seems to be our only constant. 

Too many cruisers feel tied to a schedule, to a route, to deadlines. We feel the joy of cruising comes from being flexible, being able to change plans to accommodate new friends and from knowing that we never absolutely have to be somewhere by a specific date. This knowledge also means we can wait for favorable weather and favorable winds. It makes cruising safer and infinitely more enjoyable. 

“The Rio Dulce sounds fantastic,” I casually mentioned one day. Tom and I have been “casually mentioning” things since we met twenty years ago. I remember one of the first times we skied together. We were at the then just developing Beaver Creek Ski Resort in Colorado on a day off from ski instructing in Vail. “That looks like a great run,” Tom casually mentioned while motioning to a bunch of trees on a slope as steep as a cow’s face. “I don’t think that’s actually a ski run,” I said with a smile. I guess that was our first adventure together. How could I not fall in love with someone who would actually carry me out of the backcountry upside down – skis still attached – after I could no longer negotiate the up-to-my-chin snow. How could Tom not fall in love with a nut who not only loved every minute of our adventure skiing, but keeps on jumping into another adventure with him. 

Kate Theisen scuba diving in the Bahamas.

Not all of our casual remarks develop into all-out adventures. But part of the fun is that you never know which ideas will take off. 

“Yea, the Rio Dulce sounds great. We could head to Cuba first,” Tom responded. Out came the atlas. I knew an adventure was in the making. 

Most cruisers heading from the southeast US to the Rio Dulce of Guatemala take off from Key West, Florida. They head either to Isla Mujeres on the Yucatan Coast of Mexico or to Marina Hemingway near Havana, Cuba then west along the north coast of Cuba and jump across to Isla Mujeres. From there they hop down the coast of Mexico, through Belize and into the Rio Dulce. That was our original plan too. 

“Can we stop in the Bahamas on our way to the Rio?” Kate asked me one day. She knew a lot of her friends would be wintering in the Exumas in the southern Bahamas. Hmmm. We did love the Bahamas. Out came the atlas. 
By the time we heard Tom heading back home in the dinghy that day we had a new plan in mind. “How about heading to the Rio Dulce by way of the Windward Passage? I casually remarked before Tom was even aboard. “OK,” he said. 

So our new route to the Northwest Caribbean took us southeast through the Bahamas. This ended up being a great way to go as we had very favorable winds and never had a sail of more than 32 hours without a possible stop. 
We hoped to leave North Carolina in early October, heading either just off the coast or down the ICW to Florida, depending on the weather. We knew we would have to stay flexible, as it would still be hurricane season. But we thought perhaps we could make our way south to the Exumas by early November. 

Snowbirds heading south on the Intracoastal Waterway.

Well, Mother Nature had other things in mind. In September we were directly hit by three hurricanes. The rain and flooding brought delays to work commitments that Tom had. Hurricane preparations and three evacuations put delays in our personal schedule. A bit of damage to the boat put us in the boatyard for a couple of weeks. We finally left North Carolina in November. 

But departure day did arrive! We pulled up the hook at our Oriental, NC anchorage at sunrise on a glorious morning and headed out across the Neuse River. The weather kept us inside and on the ICW for the first few days where we had plenty of snowbird company. Everyone was sailing south. 

On our fourth day out we headed out the Cape Fear River into the Atlantic with a rather boisterous north wind shooting us down the coast of South Carolina. 

“Two days till your birthday Kenna. What would you like to do?” I asked our youngest daughter as Out of Bounds danced south. 

A snug anchorage on the ICW.

She replied that she’d like to go out for pizza. So we took a right turn the next morning into Charleston Harbor, one of the most beautiful cities on the ICW, and proceeded down the ICW towards Beaufort, SC and pizza. We’ve always tried to make birthdays and holidays special days for our kids. 

We spent Kenna’s birthday relaxing in the lovely old town of Beaufort. We baked a cake and – as is tradition in our family – everyone joined in on decorating the cake with whatever goodies we could find to transform an ordinary birthday cake into a work of art. We spent the afternoon opening presents in the warm sunshine, strolling around town and finished off the day with a delicious pizza. The next morning we once again headed out into the Atlantic where we had a fantastic sail down the Georgia and northern Florida coasts. 

Back on the ICW, we anchored in Titusville just ahead of a squall. It hadn’t been our planned stop that day but we were glad we had pulled in. Not only were we all battened down when the squall arrived; we also heard some great news. A rocket launch was planned for that night from nearby Cape Canaveral. It was spectacular! 
Our next stop was Miami, where we would wait for a weather window to cross the Gulf Stream to the Bahamas. We sailed into the entrance to Miami and had to decide if we should turn south and anchor near Biscayne Bay or north and anchor near South Beach. We choose to go the mile or so north and we found a snug little anchorage near South Beach. Great decision! We soon found good friends of ours anchored in the same anchorage. These were friends we had met over five years ago. We often would spend months together in the same area. What a great reunion we had, as we hadn’t seen each other in almost a year. After spending some enjoyable days with our friends we headed just a bit further south to Biscayne Bay. From there we would make our Gulf Stream crossing. 
Finally, a weather window appeared. Some boats had been gathered here waiting for an opportunity to cross to the Bahamas for weeks. It was a mass exodus the next morning. We had a rough but tolerable passage to Cat Cay where we cleared into the Bahamas.

A snug anchorage on the ICW.

A few days later and we were in the Exumas, a lovely chain of nearly 400 cays – most of which are uninhabited. We made stops at some of our favorite anchorages – Allen’s Cay to see the iguanas and scuba dive/snorkel, Norman’s Cay – always a good place to stop if you’re hungry for conch, and Staniel Cay – for a visit with the friendly pig at Pig Beach and more great snorkeling. 

Out of Bounds arrived in George Town a week before Christmas. We hadn’t finished anchoring when we heard kids shouting, “Kate, Kenna, HI!” An inflatable filled with friends of the girls pulled up beside us and our girls were whisked away to Volleyball Beach. 

A church in the southern Exumas in the Bahamas.

The next week was filled with activities - a moonlit climb to the top of the “monument,” bonfires on the beach where we sang Christmas carols, a lighted boat parade. We rang in the new millennium with fireworks. 
We were soon caught up in the daily life at Volleyball Beach – consisting mainly of our daily afternoons of volleyball. We knew it was way past time to be heading towards the Windward Passage but the weather kept us in George Town. But that was OK. It’s a hard place to leave. 

Finally, around the third week of January the weather started improving. It began to look like we’d be able to leave soon. We had been waiting for a weak norther to come down from the US, turning the normally strong easterlies to a more minimal west wind. We had to make easting on the next leg of our journey and this would be the only time that we would be going against the trade winds. 

With our water and fuel tanks full, we finally could put off departure no longer. Herb, who broadcasts the weather over our SSB radio on “Southbound II”, was telling us we had a window. We headed out of George Town and sailed east to Conception Island in company with newfound friends aboard the S/V Poppy. 

The sail east to Conception took us longer than anticipated and we put the hook down just before sunset. We had hoped to spend a day or two here. The diving and snorkeling are said to be remarkable. But Herb told us we would have to be on our way. The weather was changing. Conception doesn’t have a secure anchorage. Once again our plans would have to change. We’d have to come back to Conception Island another year to enjoy its pristine waters. 

A successful day of spearfishing. Tom and friends with spiny lobsters and grouper.

Poppy and Out of Bounds left Conception Island in tandem the next morning. With a strong headwind we made slow progress tacking down the island chain. The northwest winds that Herb had predicted never came. We slogged on. Our friends on Poppy were heading on to Santiago de Cuba as they had already checked out of the Bahamas. We needed to stop at Great Inagua to get our clearance papers. We had hoped to make Great Inagua in about 36 hours but at this pace it would take us twice as long. And this sail just wasn’t fun! We don’t like to beat to weather. 

So in keeping with our motto of “keep the sailing fun” we headed in at Clarence Town on Long Island to wait for better weather. Another great decision. The weather continued to deteriorate the next day. But we were snug at Clarence Town and enjoyed walking around this friendly little town. 

It is believed that Long Island was the third island Columbus sailed to during his first voyage of discovery. Long Island is about 60 miles long but averages only 1-½ miles wide. The Tropic of Cancer divides the island. Loyalists from the Carolinas settled here in 1790 with their slaves. They built great plantations where they grew cotton but when the slaves were freed in 1834, the owners abandoned the plantations and left the island. But agriculture is still important here and the island is famous for its fresh fruits and vegetables that are shipped throughout the Bahamas. We took advantage and stocked Out of Bounds.

We spent three days holed up in Clarence Town and then the weather turned. We had a fantastic 24-hour sail to Great Inagua, the southernmost island of the Bahamas. We were now 325 miles southeast of Nassau.

Great Inagua is the third largest island in the Bahamas and is home to about 1,200 people, most of whom are employed by the Morton Salt Company. Salt ponds cover about 12,000 acres of land and produce about one million pounds of salt each year. The process is quite fascinating. Seawater is pumped into the interior of the island and held in dikes. As the water evaporates in the salt ponds it turns into heavy brine. The salt solidifies at night and melts during the heat of the day. Eventually a crystallized bed is formed at the bottom of the pond. Finally, any remaining water is drained. Then the salt is bulldozed into bleached white mountains and shipped around the world for processing. We could see these white mountains near the shipping docks.

The island is also a naturalist’s paradise. It is one of the largest nesting grounds for flamingos in the western hemisphere and is home to about 50,000 of these beautiful birds. Although we didn’t get to see the flamingos, we did see the rare Bahama Parrot. Wild hogs, horses, and donkeys also inhabit Great Inagua.

We anchored in the lee of the island northeast of Matthew Town. Matthew Town is the main town on the island but does not have a secure anchorage. We decided we would stay where we were anchored and then move down to Matthew Town to clear out of the Bahamas once we had a weather window for heading through the Windward Passage. 

Kate and Kenna at the top of the Great Inagua Lighthouse.

In the mean time, Great Inagua has excellent scuba diving and Tom and Kate jumped right in. We also enjoyed hiking around this island with its “wild west” atmosphere. 

Herb told us there was a weak front stalled right over the Windward Passage. But he predicted we would be able to leave in a couple of days. So the next day we headed over to Matthew Town in anticipation of our departure. 
The anchorage was a bit rolly and landing the dinghy on the beach a bit tricky. We took a hike out to the Matthew Town Lighthouse, which was built in 1870. We climbed to the top and looked across the Windward Passage towards Cuba. On a clear day, we were told the high mountains of Cuba were visible, but it was too overcast for us to see far. I guess Cuba was hidden behind the front that Herb was telling us about. Looking back across Great Inagua, we could see an expanse of flat land covered with salt ponds. 

Back on the boat, we talked about what was next for Out of Bounds. When we left the states, our cruising plan had us heading through the Exumas then south to Great Inagua then west through the Windward Passage, along the south coast of Cuba with a stop at Santiago de Cuba and then a few more stops at Cuban ports along the south coast.

 From there we’d head to the Bay Island of Honduras (perhaps via the Cayman Islands) then north to the Rio Dulce and then on to Belize, the Yucatan of Mexico and back to the states by May to get back to work again. 

We had given ourselves about seven months for this cruise. But we now found ourselves only a third of the way through our route. Time was going by way too quickly. How would we manage to finish our route in our remaining 3 months? 

We also heard over our SSB radio net that a Canadian cruising boat that had checked into Cuba at Santiago de Cuba was being held by a Cuban gunboat in a small town west of Santiago. What was going on? Was it safe for us to go to Cuba? Would we have to change our plans? 

We got a good forecast from Herb. Yes, tomorrow was our departure date. We’d be heading through the Windward Passage. But where were we going? 

Yes, a cruiser’s plans are always subject to change. That’s rule #1 when it comes to cruising. But even aboard Out of Bounds, shouldn’t we at least have a plan? 

Barbara Theisen has spent the past ten years living aboard Out of Bounds with her husband Tom and daughters, Kate and Kenna. For more information on cruising with kids visit the Theisen’s Website at