Fortnight Caribbean Cruise Part 3: Anguilla, Sint Maarten, Antigua and Montserrat

Note: This post is the third installment of a multi-part series about the two weeks I spent cruising the Caribbean with my little brother. This particular chapter includes the adventures from land days 7 through 10, as we anchored in Anguilla, Sint Maarten, Antigua, and Montserrat.

At this point, we had been aboard the Star Breeze for almost a week. If you haven’t already, you can ready about Part 1 and Part 2 first. The time had gone by really quickly, mostly because we had land days nearly every day. It was great, we had seen a lot, yet we still had just as much to discover.

The great thing is that we had gotten into a pretty good flow during the first week. This allowed a hectic week to feel still relaxing and rejuvenating. It went like this; we would either sleep in a little (on those days, I would also work before going on land). Or, we would get up early and head out to explore the new island ASAP. On land, we mostly rented a car or walked around exploring on our own. After being on land, we would end up back on the boat right around sunset, just in time to start getting ready for the evening programming.

Every night we had incredible food, regardless of whether it was a special dinner or a standard one, the food was always superb. Dinners always included the indulgence of a nice bottle of wine, which my brother and I would finish over food. After dinner, we would play chess over cocktails and then visit the casino or enjoy some live music at one of the bars.

Our time was well spent both on and off-board. So the first week of the cruise was about to come to an end, but first, we had one last land day in Anguilla.

Anguilla 101 🇦🇮

If you look at a map Anguilla is one of the most northerly of the Leeward Islands in the Lesser Antilles, we actually continued North from the BVI’s, directly north of Saint Martin to Anguilla to finish the northward trajectory of the first cruise. After this stop, we would turn around and begin to travel south on the second cruise, but we’ll talk about that later.

Right now, let’s briefly talk about Anguilla, politically. As mentioned in my previous post, Anguilla used to be part of St. Kitts and Nevis. The territory was called Saint Christopher-Nevis-Anguilla (or Saint Christopher, Nevis, and Anguilla), and it was a British colony in the West Indies from 1882 to 1983, consisting of the islands of Anguilla (until 1980), Nevis, and Saint Kitts.

From 1882 to 1951, and again in 1980, the colony was known simply as Saint Christopher and Nevis. Saint Christopher and Nevis gained independence in 1983 as the Federation of Saint Kitts and Nevis, while Anguilla would remain a British overseas territory.

In 1980, Anguilla was finally allowed to formally secede from Saint Kitts and Nevis and become a separate British Crown colony (now a British overseas territory). Since then, Anguilla has been politically stable and has seen significant growth in its tourism and offshore financing sectors.

Sadly, Anguilla has seen negative repercussions after Brexit, since the territory doesn’t have an airport. This means it’s dependent on the airports in the EU territories nearby, meaning the connections have been severed or impacted, bringing about a lot of issues for the region.

Geographically, Anguilla is made up of the main island, with the same name, and several much smaller islands and cays that don’t have an established population. The capital of this territory is called The Valley, and it has a total land area of 35 square miles and a population of just under 15k as of this year.

Anyways, that’s enough for now, let’s talk about our experience of the island!

Land day 7: Losing my brother in Anguilla

To be honest, we didn’t have much prepared for this land day. As you now know, Anguilla is a small island, so we didn’t plan to explore it too much. That morning, we slept a little longer than usual, and I got some work done while my brother left the boat earlier to start exploring on his own.

Anguilla today one of my favorite tax havens

I was meant to join him in the afternoon, but when I got off the boat and searched for him by the beach, I couldn’t find him. After looking for a little while, I decided to just walk along the shore, all the way to a salt lake located a little further inland.

The spot was quite beautiful, there were some flamingos in the water, and I ended up spending some time there. After exploring the surroundings and taking in the beautiful sights, I went back to the main beach and tendered to the boat.

Pretty but boring

By the time I got back on the boat, I was a bit worried about my brother. I didn’t know where he was or what he ended up doing. He wasn’t back on the boat, and I had no way to reach him. It kept getting later and later and no news from him. He was actually one of the last few people to board the boat that evening.

Since he’s here with me, let’s ask him what kept him that day?
CH: “What did you do that day, Daniel?”
DH: “I was lying at the beach, enjoying the sun all day – Nothing else.”

That is a lot less fun than I had expected. I can’t believe I didn’t find him if that’s the case, maybe I just didn’t see him, it was a big beach, a lovely beach – but other than that, I don’t remember too much.

Elvis’ Beach Bar in Anguilla

We had initially looked into possibly renting a car for this day, but the task proved to be difficult because it is such a small island. So we just anchored near the harbor and tendered to the beach and back. On the island, I just moved in a tiny radius, exploring simple sites nearby.

All in all, It was a very chill day, as you know by now, life on board in the evenings was always pretty standard, but we wouldn’t have it any other way. We were enjoying delectable dinners over a nice bottle of wine and some great conversation with my little brother and after dinner, playing some chess while sipping on some excellent cocktails. Some nights there were other events organized by the crew. At one of these events, my brother even made friends with some older ladies who seemed to really enjoy his company. Our evenings on the boat were always enjoyable.

End of cruise 1 – Docking in Sint Maarten

The first cruise ended in Sint Maarten; at this point, some people left the boat, and some new people joined. Lots of people stayed on board as we did, even though we almost missed boarding back on for the second part of the cruise.

I will get into that story in a second, but first, let’s talk a little about Sint Maarten.

Sint Maarten 101 🇸🇽

Sint Maarten is a constituent country of the Kingdom of the Netherlands. As of last year, it’s known to have a population of around 40k inhabitants. The territory covers an area of 13 sq mi.

It encompasses the southern 40% of the divided island of Saint Martin, while the northern 60% of the island constitutes the French overseas collectivity of Saint-Martin.

The capital of St. Maarten is Philipsburg. This island, along with the other Dutch islands in the region, are often called the Dutch Caribbean. Before 10 October 2010, Sint Maarten was known as the Island Territory of Sint Maarten and was one of six island territories that constituted the Netherlands Antilles (along with Saba, Bonaire, Aruba, Curacao, and St. Eustatius).

After 2010 Sint Maarten became a constituent country within the Kingdom of the Netherlands, making it a constitutional equal partner with Aruba, Curaçao, and the Netherlands proper. Sint Maarten has the status of an overseas country and territory and is not part of the EU.

On 6 and 7 September 2017, the island was hit by Category 5+ Hurricane Irma, which caused widespread and significant damage to buildings and infrastructure. The aftermath of this hurricane is still felt and seeing across the island.

Land day 8: Almost missing reembarkation in Sint Maarten

While in Sint Maarten, we decided to rent a car. This time we opted for a nicer car, a Ford Mustang – not a Camaro like the road trip in Key West, but still, a nice convertible to explore the island on a beautiful day.

Today a small island shared by two countries. Sint Maarten

This time we anchored at the port, first time actually docking at a port in a little while. From the harbor, we took a taxi straight to the rental car company, got our convertible, and off we went.

We set off to discover the whole island; we wanted to see both the Dutch and the French part. Drove all around, first checking out the capital, then to some beaches – basically checking out all the main sites.

We made a stop at Maho Beach – it is a beach on the Dutch side of the island of Saint Martin, in the territory of Sint Maarten. It is famous for being next to the Princess Juliana International Airport, making it a popular site for tourists and plane watchers. There is a lot of people who visit the beach to watch aircraft on the final approach as they are landing at the airport. The thrill comes from the airplanes passing a short distance above your head.

Maho Bay – At the famous planespotter beach. This is rather small and up, but an A320 from New York is due to arrive in 20min

I have been on beaches like these before, and it’s pretty impressive to lay on the sand and seeing airplanes take off and land right over you. Albeit, this beach wasn’t as remarkable as I imagined it would be, but it was still pretty cool. I think my expectations have been set too high after visiting the more exciting airport beach in Somalia.

After Maho, we made our way to the French part of the island to check out the beaches there. This was when things took a change for the worse.


Car troubles and almost missing reembarkation

The event happened at the beach. As you know, we were driving our convertible around, we passed some lakes with some flamingos, and driving to this lovely beach through a really sandy road. I mean, up until now, we had already been driving through sand, and it was all working out fine until it wasn’t.

This Sunday convertible drive went wrong. We are stuck in the sand for 2h now. Called the towing service after nothing else worked 😉

It happened when we decided to try driving all the way to the beach. So, we drove further into the sand, and all of a sudden, our tires lost grip, and we got stuck. We couldn’t go forward, so we tried going back; we moved a little and then got even more stuck.

By the time we got fully stuck at this beach, we had about 4 hours to make our way back to our ship. For the first two of those hours, we tried to dig the tires out by hand – that didn’t really work at all. Next, we tried to use wooden sticks we found lying around as leavers – that also didn’t work.

There are worst places to get stuck at.

Some people who were going by stopped and tried to help us to dig it out, but nothing worked. After two hours unsuccessfully trying to do it our selves, we decided to get other help. A guy came by and wanted to get us out with his car, but that also didn’t work. Actually, he almost got stuck himself, so he didn’t keep going and continued on.

Before he left us, however, he gave us the number of a friend who had a towing service. We called him, and the guy came pretty quick and tried to toe us out. Again, another futile attempt, even with his much larger car he couldn’t get us out, he was actually getting stuck as well. He ended up leaving, and we were left stuck and alone once again.

At this point, we tried to call every towing service available on the island. It was a Saturday in the Caribbean, so not many people were working. Luckily, we found one company that was open and could come and help – This was after almost 4 hours of waiting and dealing with this thing.

As you can imagine, my brother was already pretty stressed out by this point. To make things worse, we had no water, and it was the hottest time of day.

Thankfully, the towing service arrived quickly, and he had no problem getting our car out of the sand. It also didn’t cost that much; I think around 100 euros or something like that. By the time we got out, we were already very late to catch the boat, so we had to rush straight back to the car rental place.

In the end, we managed it and just got back to the ship 45 min late. Just 100$ each for towing and cleaning. Could have been worse 😉

We wanted to see some other sights of Sint Maarten – which is actually a gorgeous island – despite having been devastated by the hurricanes that frequently pass by. During our visit, most of the trees were eradicated, and the landscape was noticeably affected.

Either way, we were sad to have to hurry back to the town but still managed to enjoy some excellent views from the car along the way. We couldn’t go straight to the harbor; we first had to give our car back in Phillipsburg.

After the ordeal, our car was full of sand, and the rental company made a huge deal about it. They wanted 100 euros for cleaning costs, and because we didn’t have time to clean the car ourselves, we just paid and left a bit upset about the whole thing.

We took a taxi to the harbor, and people from Windstar were already searching for us at the port. A woman was running up to us, saying she had been searching for us. Apparently, we were the last passengers to get on the boat, just as the ship was about to leave.

In fact, we found out that the ship was about to leave 1.5 hours earlier, but we had some great luck while being also unlucky. It turns out that since it was the day that old passengers left and new passengers boarded for the second part of the cruise, the ship had to make the mandatory security briefing. This time it took a little longer than usual. That’s why the boat was there 1-2 hours longer than it should have been.

Thankfully, it gave us enough time to get back on board… and the best part of it all: we didn’t even have to do the security briefing again. Since we had already done it on the first leg, they were ok with the fact that we missed it this time around.

Shortly after we boarded, the ship set sail to our next destination, Antigua and Barbuda. On this cruise we didn’t go to Barbuda, we just visited the island of Antigua.


Antigua 101 🇦🇬

Antigua is the larger of the two main islands that make up Antigua and Barbuda. It is part of the West Indies, and it is one of the Leeward Islands as well. The nation was granted independence from the UK in 1981, and Antigua has since built itself up as a tourist hotspot rivaling surrounding islands in the Caribbean.

Over 32,000 people live in the capital city, St. John’s. The capital is situated in the north-west and has a deep harbor that can accommodate large cruise ships. On 6 September 2017, the Category 5 Hurricane Irma destroyed 90 percent of the buildings on the island of Barbuda, and the entire population was evacuated to Antigua.


Land day 9: Walking through Antigua

Last moments in Antigua

This land day we didn’t really do much, mainly because we didn’t have much time. I think we only had 6 hours in port, and we slept in late. I also had some consulting to do in the morning, so we basically left the ship in the afternoon and did a quick tour of St. John’s.

Today Antigua and Barbuda

We simply walked from the boat to the center of the capital and roamed the streets for about an hour. We walked by a beautiful church, St. John’s Cathedral, an Anglican church perched on a hilltop in the capital.

St. Johns Cathedral – Another passport nation with 150 countries visa free. It’s 100k donation plus around 30k fees or 400k real estate investment plus 50k processing fee. The Antigua government recently announced Bitcoin as donation option.

The present cathedral was built on a fossilized reef, in 1845, and is now in its third incarnation, as earthquakes in 1683 and in 1745 destroyed the previous structures.

We also saw some beautiful beaches from afar, but we didn’t get to discover them properly. In conclusion, we didn’t really see too much of Antigua, but just enough for me to cross it off my list. 😉

The uninhabited micronation of Redonda (officially part of Antigua and Barbuda)

After our quick tour of Antigua, we were back on the boat and enjoying a chill evening as we anxiously awaited our next stop: The island of Montserrat.

St. Johns Actually saw that sign never ever before in the world… 😀


Montserrat 101 🇲🇸

Montserrat is a volcanic island in the Caribbean, whose former capital city of Plymouth was turned into a “modern-day Pompeii” by the Soufriere Hills volcano in 1995. Since then, only the northern third of the island has been inhabitable.

Between 1995 and 2000, two-thirds of the island’s population was forced to flee, primarily to the United Kingdom, leaving fewer than 1,200 people on the island in 1997. Today, mild volcanic activity continues, mostly affecting the vicinity of Plymouth.

This includes its docking facilities and the eastern side of the island. Around the former W. H. Bramble Airport, the remnants of which were buried by flows from volcanic activity in 2010. Since then, the volcano remains active at varying levels. At times, this can make for a spectacular volcanic show from the Montserrat Volcano Observatory.

Politically, this island is also an overseas territory of the United Kingdom, forming part of the Leeward Islands, which is part of the chain known as the Lesser Antilles, in the West Indies – just like all the other islands on this post.

Geographically, Montserrat measures approximately ten mi in length and seven mi in width, and it has around 25 mi of coastline. Montserrat is nicknamed “The Emerald Isle of the Caribbean” both for its resemblance to coastal Ireland and for the Irish ancestry of many of its inhabitants.


Land day 10: Disaster tourism in Montserrat

For our day in Montserrat, there were lots we wanted to see. For this reason, this was one of the days were we actually booked a proper tour with a company.

Today one of the trip highlights. Visiting the modern-day ghost town capital of Plymouth buried below 3m ash of the 1995 volcano eruption

As you know, most land days, we did our own thing, rented a private car, and explored at our own pace. This time, however, we wanted to get a proper tour of the devastation from the volcano eruptions.

You usually can’t just walk into the area. Access to the ruins of Plymouth is severely restricted, depending on the level of volcano activity. To be allowed in officially, you could apply for a permit from the authorities or find a paid guide.

Especially during periods of less volcanic activity, if a tour guide accompanies you, you’ll find fewer restrictions on viewing/visiting the destroyed settlements of the south.

Montserrat is a UK overseas territory of just 5000 people after the devastating 1995 eruption making half the island inhabitable. It even celebrates St Patrick’s day due to the fact that most settlers originating there.

So we decided to opt for the tour, mainly because we wanted to see as much of the exclusion zone as possible. The restricted area encompasses the southern half of the island all the way to the far North.

What there is to see you may ask, well, as mentioned before, what you can see at any given time is pretty much at the mercy of the volcano. When it’s very active, volcano viewing can be dramatic, but then access to most zones closer to the base is totally restricted.

The only still official capital of a country which is a ghost town…

Thankfully, when we went, it was less active. When this happens, you won’t get the spectacular volcanic show, but you may be able to get closer to the prime attraction of the island: its former capital city Plymouth – and that is exactly what we did.

We rode a bus that took us all along the different interest points of the island. Montserrat is actually quite a beautiful island, might I add. The backdrop and landscape are pretty stunning, with the big volcano in the center, gently sloping down to the Caribbean sea.

Nature evolves. If we want or not. It’s hubris to think that humans can change that fact

On tour, we visited a viewpoint in Garibaldi Hill; there was an abandoned hotel and some really stunning views of the island and its surroundings.

Keep in mind that the former capital is now a ghost town covered in 30 to 40 feet of hardened ash and lahar mud. It’s one of the eeriest places of its kind. This makes Montserrat the prime destination for disaster tourism in all of the Caribbean at the moment.

Old government quarters in the abandoned town

During our visit, we went into different houses, the old parliament building, all of it was devastated by the eruption. It was super interesting to see the former capital of Montserrat buried under layers of hardened lava.

In fact, the town gets buried more and more every year. Some features seen on older footage, such as the top of the cathedral steeple still poking out of the grey wasteland, have by now disappeared completely, as successive layers of volcanic deposits grow in thickness.

Sulphur smell in the air and totally eerie feeling walking through this ghost town

Many houses still stick out – only what appears to be a two-story house is often a half-buried five-story house—super eerie feeling being in this place.

At some point, we stopped to have our packed lunch at a rest stop, and after we are, we visited a back sand beach that was nearby. We went down to the shore to take a look; the landscape on this island was completely unique from all the previous land days. We really enjoyed our visit.

After the beach, the bus took us straight back to our boat. I think this was probably one of the more noteworthy days of the cruise. Our visit to Montserrat was full of new experiences.

As a matter of fact, I even learned that the island is a British overseas territory. I always thought that because of the name, it was French, but no – it’s actually British, but not the typical tax haven you may imagine.

Our time in Montserrat was a great start to the second week on the cruise. We were now making our way back south to the Final destination of Barbados – back to where it all started.

In the next post, I tell you all about Dominica, St. Lucia (again), Grenada, and finally, Barbados. To continue reading about the final leg of this fortnight cruise trip, click here.