Note: This post is the first installment of a multi-part series on the two weeks I spent cruising the Caribbean with my little brother. In this chapter, I give you a glimpse of what life is like aboard the luxury cruise line Windstar Cruises. I also delve into the first three land days we had in The Grenadines, Saint Lucia, and Guadalupe.
The story begins in the autumn of 2018; I was looking for the best and most efficient way to see as many of the Caribbean nations and territories in one go. You see, there is plenty to see in this seemingly small part of the world, but it’s not so easy to do it all at once.
You probably don’t know this, but the Caribbean archipelago encompasses more than 7,000 individual islands in a region of approximately 1 million square miles. It houses not only 13 sovereign island nations but also 12 dependent territories, with close political ties to Europe and the United States.
I actually haven’t visited all the nations or all territories yet. I have been to the Caribbean before and visited places like the Dominican Republic and Cuba. Today, however, I am still missing nations like Jamaica and Haiti. I was planning to cross more of the Caribbean this May, but alas, CORONA.
I am also missing some of the U.S. Virgin Islands and some Dutch territories like Bonaire, Eustatius, and Saba.
The inception of this journey
Back in 2018, I searched for the best possible way to see as much of the Caribbean and the Lesser Antilles in the most efficient way. My research indicated that a cruise was the way to go. Why not fly? Well, you can find some flights that go in between islands, but even then, they are hard to coordinate and book. It can’t just be done through a platform like Skyscanner or Kiwi.
Kiwi, by the way, is one of my preferred flight search engines. You can book over them directly, which has great perks, such as a flight connection guarantee for example. If your flight is canceled or there wasn’t enough time to make your connection, Kiwi will put you on a new flight for free. Booking with them is simply much easier and safe than with most online travel agencies.
Sadly, to book most of the flights between islands, you have to go through the small private airlines that run the flight; they tend to run on island time and don’t really have the best and most efficient procedures in place. In my opinion, it is too much of an effort and also quite expensive to coordinate several flights between the small islands in the Caribbean. Which is why, after weighing all my options, I booked a 2-week cruise through this region.
I found a top of the line cruise provider called Windstar Cruises; they operate a fleet of small luxury cruise ships. Its six yachts carry just 148 to 310 guests and cruise to 50 nations, calling at 150 ports throughout Europe, the South Pacific, the Caribbean, and Central America.
In May 2014, Windstar added to its sailing yachts by adding the Star Pride power yacht, followed by Star Breeze and Star Legend in May 2015. The additional capacity opened up new itineraries, such as voyages to Iceland, the Panama Canal, and Costa Rica, and Tahiti.
The cruise ship line has won awards for the “best cruise ship line,” and they are also well known for having 2 of the three largest sailing ships in the world currently operating as a cruise. They are sailing cruise ships with a capacity of around 200 passengers. It looks pretty mind-blowing.
Sadly, our trip wasn’t on those boats; instead, we traveled in what was basically a massive yacht. 😎Our ship was the Star Breeze, which, by the way, is a German-built cruise ship – not a sailing boat, a motor ship. A luxury liner that travels between the Caribbean, Europe, and Africa, and it has been rated the “best small cruise ship” by the reputable luxury and lifestyle magazine, Condé Nast.
It was terrific only having round 200 people on board with us. It was the perfect home for two weeks as we explored the Caribbean.
The backstory…
Initially, I was supposed to be with my ex-fling Diana. If you have been with me for a while, you remember this was a short-lived affair that took flame after one of the Nomad Cruises a few years back. I had a really nice vacation planned to the Maldives(link), staying in a stunning overwater villa. Typical honeymoon vacation, so naturally, I was looking for a girl to join.
Much to my surprise, Diana said she would come. To be completely honest, I didn’t expect her to say yes when I mentioned the vacation. After all, we had only been on one date before, and that had been almost half a year earlier. This kind of dating is pretty natural for my lifestyle, but not for many other people – so I was pleasantly surprised by this girl’s spontaneous nature.
So she somehow made her way to the Maldives, and we had a nice 7-day vacation in the Maldives. We were in love for a short while after; it was then that I booked the cruise for us; but by January, the flame had started to burn low, and by march, it was entirely out. So that was the end of our planned cruise together. Which is sad, because I was looking forward to seeing her again on the cruise and spending romantic weeks in the Caribbean, but it wasn’t so.
I didn’t want to cancel the cruise, after all, the primary purpose of the trip was seeing new countries; so instead, I invited my little brother to join along.
In retrospect, I am thrilled that it worked out the way it did, mostly because I got to spend some really nice, quality time with him. I am proud to say he has now de-registered from Germany (since last October) and is pursuing a much nicer path in life. I can confidently say it’s mostly from all the conversations we got to have during this cruise.
It was truly wonderful to have him as my travel companion during this adventure. Actually, I am in Sweden with him right now. We’re having a nice little road trip through this beautiful country – can’t wait to tell you all about it after it’s done, so stay tuned for tales of these adventures.
From Panama to Barbados
The cruise would depart from Barbados, and I was flying into the island from Panama. I was in Chile and Bolivia prior, and the best way to get to the Caribbean from Chile was to fly first to Panama, which is one of the main gateways into Latin America and the Caribbean.
I flew from Santiago de Chile to Panama and had one night in the city. Come to think of it, that was the last time I spent a full day (more than just transit time) in Panama. It makes me sad to think it was already over a year ago.
That night I had a presentation about my lifestyle and Panama at a German restaurant; that was pretty cool. After the restaurant, I went with a few of my close friends and business partners to party a bit around Casco Viejo and downtown. We actually had a fantastic night. Little did I know back then, that it would be so long before I would revisit the country.
The next day I took a direct flight from PTY to BDS (Bridgetown, Barbados). The cruise was starting from Barbados and sailing to Sint Maarten. Making stops in various islands in between over the first week. On the way back to Barbados, it was taking a different route, docking in totally different islands.
To do this, I had to book two separate cruises, seven days cruising to St. Maarten, and seven days traveling back. Since they were different routes, we only had one stop that overlapped on both journeys. We docked in Saint Lucia twice but in totally different parts of the island.
Each time we got to see something, and none of the activities we had planned overlapped. Windstar does an excellent job of providing an itinerary that encourages people to book a more extended stay and seamlessly take back-to-back cruises.
So, after landing in BDS, I took a cab straight to the cruise port. My brother was already there, waiting for me. He had arrived the day before, flying from Frankfurt to Toronto, spending a day there, and then taking a direct flight to Barbados.
When we met, I could see he had a little sun, and he told me about the beautiful day he had at the beach the day before. We checked in at the terminal and were guided to our small, beautiful ship. It looked particularly fancy and small, surrounded by all the bigger, bulkier vessels in the harbor.
Life aboard the Star Breeze
When we got on the boat, we immediately went to our cabin. Even though the Star Breeze is a smaller boat, it still has beautiful, state of the art amenities, almost like a big boat. Especially the cabins, which are all suites. Meaning, there are no standard cabins on this ship, all the suites have a sun-deck balcony and lots of space.
Space is also very conveniently thought out and nicely designed. Of course, some cabins are obviously more significant, and you get them if you pay more – we still have the cheapest cabin on the boat, but even the most affordable room is on par or higher than the standard of suites in other cruise lines. We had a very comfortable set up, with stunning views along the way.
So when I say the boat is smaller, I mean much smaller than the boats I’ve been on with Carnival or the Nomad Cruise. Regardless of its size, it still offered many things to do while onboard. It has a spa with great offerings, a screening room for movie nights, and a well-stocked fitness center, a really lovely sun-deck with a pool and a hot tub.
looks more like a big luxury yacht rather than a small cruise ship.
Probably the best thing about the boat was the food. It has a few restaurants that offer lunch and dinner, and they also host special outdoor dinners with delicious steak seafood. Windstar is actually famous for its food, offering location inspired world-class dining aboard their ships. They partnered with a highly awarded and recognized chef to make delectable menus for each destination.
I found the food to indeed be excellent; in those two weeks, I definitely gained some weight. #sorrynotsorry – This [mostly] all-inclusive boat did not include alcoholic beverages, but all of the fantastic food was included. You could also get an all-inclusive alcohol package, but that was way more expensive.
We decided to buy alcohol ourselves whenever we wanted to treat ourselves. We mostly invested in a bottle of wine at dinner and some cocktails throughout the night. This was definitely not a cheap cruise, but it was still affordable.
We paid around 4k for a two-week cruise, including food and soft drinks. We also didn’t partake in most activities provided by the cruise company while onshore, like jet skis, paddle boarding, and such, and we still felt like a good value for our money. During land days, we mostly rented a car and drove around, exploring by ourselves.
I should mention that we are not part of the typical Windstar audience. The boat was filled mostly with middle-aged Canadians and Americans, with a few Europeans and Australians, but predominantly a North American population.
We were also not the right age group. It was mostly coupled in the 40s-60, not entirely a pensioners ship, but definitely not for people in their mid-twenties the early thirties. My brother was amongst the youngest on the boat and the same thing with me. There were a couple of 15-20-year-olds with their families, but that was it as far as contemporaries. We mostly got to know older men on the ship, enjoying excellent talks over a few drinks at the bar.
Aside from that, the ship offered plenty of activities to keep yourself busy. All cruise offer activities, but these were a bit more interesting than the norm. There were exciting talks about the destinations we were visiting, telling you about the culture, history, and even the nature of each place. They had other meetings about geeky things and a movie night. I would say this cruise offered a more enriching program rather than purely entertainment.
Of course, there was beautiful live music at dinner, and at the bars, there is still a place to dance, and it even has a small casino – sadly, no roulette, but we still had a couple of goes at the poker and blackjack tables. Oh, and of course, in the evenings, my brother and I also enjoyed playing chess – a lot.
Oh, another cool thing about this ship is that it has an open Bridge policy. So whenever you want to, you can visit the Bridge, where the Captain and officers are delighted to share charts, routes, and views with you.
Now let’s begin telling you the stories of the destinations we visited – our first land day was in the Grenadines.
St. Vincent and The Grenadines 101 🇻🇨
Our first land day would be in Saint Vincent and the Grenadines. It is an island nation in the Caribbean, north of Trinidad and Tobago. The main island of Saint Vincent has most of the land area and population of just over 100,000. The many small islands and islets of the Grenadines trail south in a curve spanning more than 60km. The southernmost part of the Grenadines is part of Grenada – hence their name.
On this stop, we actually wouldn’t dock in St. Vincent. The Star Breeze threw anchor in Bequia, the largest island in the Grenadines. The beautiful thing about the Star Breeze is that because it is so small, it doesn’t need to dock at most cruise ports, it can anchor apart from busy harbors.
Basically, it is large enough to pamper and entertain you, yet small enough to navigate into delightful tiny harbors and hidden coves that other cruise ships can’t access.
This was also one of the main reasons I really loved the cruise. Not docking in ports meant anchoring at sea. Waking up on the cruise the first morning after leaving Barbados, stepping out into the balcony, and seeing the beautiful scenery and landscape of the Grenadines right before my eyes was really nice.
Land day 1: Snorkeling and touring in Bequia
On our first land day, we didn’t anchor at a harbor, so we had to take tender boats to get on land and also back on the boat. With only around 200 passengers aboard, and many small, high-speed boats, getting back and forth was no issue. That morning we slept in, not too late, just half an hour after the boats started running, and we had no trouble making it on land quickly and swiftly.
As mentioned before, we weren’t on Saint Vincent proper, that island was a bit bigger than Bequia. Bequia is the first island south of St. Vincent. This island is actually famous for being one of the most beautiful islands in all the Grenadines.
For the first part of the morning, we had a snorkel trip booked with Windstar. We took a smaller boat and went to a few different snorkel sights and to see some landscapes of Bequia from the water.
We got to see this one hotel looking villa, which is built into the rocks on the side of the cliff, it actually looks pretty cool. We visited two snorkel sights, but nothing really stands out from those memories. It was your standard beautiful day in paradise. It was nice to see different sides of the island and snorkeling in stunning waters is always nice.
At some point, they treated us to some really ‘delicious’ rum. When I say delicious, I mean strong – it was basically straight alcohol, something like 99% proof. After one drink, everyone was definitely feeling it. This was after we were done snorkeling, so it was all good.
This excursion only lasted a few hours, and we still had over 3 hours on the port. We went back to the boat for lunch and enjoyed a nice meal outside with nice views of the island.
After lunch, we made our way back to land. The tender boat dropped us off at a small, secluded beach, and we made our way to Port Elizabeth (the main port in the capital of Bequia). From the port, we took a taxi tour of the main y sights of the island.
First, we went to the Old Hegg Turtle Sanctuary, a conservation effort for hawksbill turtles on the island. The sanctuary is one of the top things to do in Bequia for visitors.
There are a lot of turtles being protected in the facility until they are strong and old enough to make it own their own. They have mainly hawksbill turtles but also some different species. It was really nice to see the little babies and also some bigger turtles at the sanctuary.
After the sanctuary, the driver took us to Mount Pleasant viewing point and Hamilton Fort. This location boasts the highest accessible point in Bequia, offering unobstructed views of Admiralty Bay (where our ship was anchored) and the southern Grenadines. From here, you can see the island in all it’s beauty, the lush green mountains, and the turquoise waters truly make it picture perfect.
The remains of Hamilton Fort have similar views over Admiralty Bay towards Port Elizabeth and Princess Margaret Beach. The old fort lies to the north of Admiralty Bay and was built in the late 18th Century by the French, who fortified the site to protect the harbor approach from the English.
There is little that remains of the original gun battery except for a few French and English cannons, which have been re-mounted. The cannons are among many guns salvaged from the waters around Bequia. In truth, there is not much to see of the 18th Century fort; however, it is all made worthwhile by the amazing views.
We stayed at the viewpoint for a little and eventually ventured back to town, making our way to the beach to catch the tender boat back to the ship. The walk to the beach was really nice; we just had to follow this wooden dock that trails along a massive cliff with some more stunning views of the landscape. It was a really nice way to end our first day on the island.
Back on the ship, we had a relaxed and enjoyable, typical cruise evening, dined on amazing food, enjoyed delectable wine and participated in great conversation… oh yeah – and chess. While we enjoyed our dinner, our boat sailed past Saint Vincent arriving in Saint Lucia for our second land day.
Saint Lucia 101 🇱🇨
Saint Lucia is a British Commonwealth country (island), located off the coast of Central America. It lies between the Caribbean Sea and North Atlantic Ocean, just north of Trinidad and Tobago. We docked in Castris, the largest city and capital of St. Lucia.
Castries is in a flood gut (prone to floods), and it houses the seat of government and the head offices of many foreign and local businesses. The city’s design is in a grid pattern, and I really appreciate that it has a pretty great infrastructure, especially for an island.
Its sheltered harbor receives cargo vessels, ferry boats, and cruise ships, duty-free shopping at Pointe Seraphine and La Place Carenage. We had pretty much a full day in Castris and decided to rent a car for ourselves and drive around discovering the island.
Land day 2: Exploring St. Lucia (for the first time)
In the morning, when we left the boat, we weren’t brought to the cruise port, we were anchored on a smaller bay, which was a bit further away than we expected. We still managed to find a taxi that brought us to the car rental place by the cruise port.
We got our car and proceeded to explore the island. St. Lucia is actually famous for having these incredible rock formations, the twin Pitons (Gros Piton and Petit Piton). They are striking cone-shaped, monolith-like peaks found on the island, and they are one of the scenic natural highlights of the Caribbean, and we were looking forward to seeing them in person.
To get there, we drove there past some sugar cane plantations and just enjoyed the very tropical mountainous landscape. Saint Lucia is a beautiful island, and we took a whole lot of pictures. Even though it was raining a little, we still managed to take some good photos after it passed.
We stopped by some stunning beaches in the small town near the Pitons; it was actually quite the adventure to navigate the car there. After the twin Pitons, we drove all the way south towards Vieux Fort through some really winding roads – it was a really lovely drive with beautiful landscapes.
It was interesting to see both English and French names all over the island. St. Lucia basically went back and forth between the English and the French for a long time. Actually, the island has a vibrant history, let me give you a quick rundown.
Saint Lucia History 101
Saint Lucia’s first known inhabitants were believed to have come from northern South America around 200-400CE. Numerous archaeological sites on the island have produced evidence from these times.
Europeans first landed on the island during Spain’s early exploration of the Caribbean. The British failed in their first attempts at colonization in the early 17th Century. The island was first settled by the French, who signed a treaty with the locals in 1660.
Like the British and Dutch, the French began to develop the island for the cultivation of sugar cane on extensive plantations. Caribbean conditions were hard, and many slaves died before they lived long enough to have children.
The French (and later British) continued to import slaves until the latter nation abolished the trade, and then the legal institution. By that time, people of ethnic African descent greatly outnumbered those of European ethnic background.
For a long time, Saint Lucia was disputed by the two European powers until the British secured it in 1814. It joined the West Indies Federation (1958–62) when the colony was dissolved. In 1967, Saint Lucia became one of the six members of the West Indies Associated States, with internal self-government. In 1979 it gained full independence. Pretty interesting, huh?
Visiting the south part of the island
When we arrived in the south, we made our way to visit Moule Chique, a spot with spectacular views, located at the southernmost tip of the island. There is a lighthouse building, which is pretty interesting to see, it has been left rusting and abandoned as a piece of industrial and maritime history.
From there, you have marvelous views from the top of much of the southern part of the island; on a clear day, you can even see the airport. After spending some time at the fort, we went back to Castries along the east coast, basically completing a circle around the whole island in the 5 hours we had with the rental car.
We made it back to the town with enough time to walk around the capital for a little bit before going back on the boat, just in time for departure.
This was the first of two stops we would make in St. Lucia, and we really enjoyed our time. So much so, that we were actually looking forward to coming back to the island on our way back to Barbados. When we come back, we’ll spend more time on the northern part of the island, but you can read about that later on the later chapters of this cruise voyage.
For now, I’ll just say that I really enjoyed St. Lucia, it’s a beautiful island with excellent beaches, a really nice infrastructure, albeit with very winding roads, but with really astonishing landscapes.
That evening, the cruise set sail to our next destination: Îles des Saintes (“Islands of the Saints”), also known as Les Saintes. It is a group of tiny islands in the archipelago of Guadeloupe, an overseas department of France.
Guadalupe 101 🇫🇷
Guadeloupe is an archipelago forming an overseas region of France in the Caribbean. It consists of six inhabited islands, Basse-Terre, Grande-Terre, Marie-Galante, La Désirade, and the Îles des Saintes, as well as many uninhabited islands. To get there, we passed Dominica and Martinique, Martinique is the one island we didn’t touch at all in this circuit, so I made plans to go there this year on my own. But I’ll let you guess what happened to those plans. 🤷♂️🤦♂️
I was actually supposed to be there right now. A few days ago, I should have boarded a flight from Paris to French Guyana and from there to Martinique. In a parallel universe, I am beachside instead of road tripping through Sweden with my little brother (basically making lemonade out of lemons).
On the cruise back to Barbados, we actually stopped in Dominica, so it was ok to miss it on the way up. However, I was sad to miss Guadalupe main island; instead, we just made a stop at Îles des Saintes, the small group of islands that are really close to each other, south of Guadalupe. I should probably mention that the archipelago of Les Saintes actually belongs to the Guadeloupe FWI (French West Indies).
Les Saintes is a volcanic archipelago fully encircled by shallow reefs. Its location lies precisely at the heart of the arc of the Lesser Antilles, and it is composed of two very mountainous inhabited islands, Terre-de-Haut Island and Terre-de-Bas Island. Grand-Îlet is an uninhabited protected area. There are six other uninhabited îslets.
These isles are french speaking and a part of the EU. The inhabited islands have excellent infrastructure and are really, really small. This applied to the island we anchored at Terre-de-Haut; for this reason, we didn’t book a tour or a car. Instead, we decided just to visit yet another old fort and the nearby beaches.
Land day 3: Îles des Saintes
The town has plenty to offer some nice walks, good views, and cool beaches. The whole day we had there, we just walked around, found a really lovely French restaurant that served delicious food, so we didn’t even go back to the boat for lunch. We just walked and enjoyed the vibes, nature, and the sights. Not too many specifics really, it was pretty much what you would expect from a lovely and chill day in a gorgeous, tiny island of the Caribbean.
Before lunch, we walked to Fort Napoleon, a tourist attraction located on the north-west part of Terre-de-Haut. It was initially named Fort Louis, and it was destroyed by British forces in 1809. It was then rebuilt in 1867 and named after Napoleon III, but never saw use in battle.
It was instead used as a penitentiary for most of its useful life. It has now been turned into a museum dedicated to the Saintes’ history, culture, and environment. It is also the home of the ‘Jardin exotique du Fort Napoléon’, a botanical garden dedicated to local succulent plants and iguanas.
The journey up to the fort was quite tiring; it is a long walk up a steep hill. Once you’re at the top, however, you’re rewarded with stunning views of the bay.
Sadly, by the time we got to the fort, the museum and gardens were already closed. It wasn’t too bad because we still managed to see some parts of the ruins and it’s beautiful surroundings.
After the fort, we went to the other side of the island to the Baie du Marigot. Marigot beach, which stretches over 100 meters of sand, is an almost private place, looking quite deserted, it has quite a charm.
From there, you can witness the classic pack of coconut groves and stunning crystalline water. It is a dream place to rest, escape from prying eyes, or a massive congregation of tourists. This is where we found the lovely french restaurant we had lunch at.
After lunch, we made our way back to the west coast of the island to go check out the landscape by the Pain de Sucre. The “Sugar Loaf” is a volcanic hill culminating at an altitude of 53 meters.
It is made of steep slopes that plunge into the Baie des Saintes. It occupies a small peninsula in the west of the island, between the Petite Anse Pain de Sucre and Anse Devant. It’s very similar to the sugar loaf in Rio and even the one in Fernando de Noronha, just slightly smaller. 😅
We walked down the west coast to get to the sugar loaf; once we got to the bay, we had a nice swim in the refreshing and beautiful waters with stunning views with the sugar loaf as a backdrop. From there, we walked back to the ship and made our way back on to the boat to relax before dinner and the evening itinerary.
Our day in Terre-de-Haut marked the end of our first three days on the boat. Having all land days made for busy days, yet the adventures we embarked on were chill enough to make for stress-free days and really enjoyable evenings aboard the Star Breeze.
Delightful evenings on the cruise
Evenings on the boat had a standard rhythm and flow. We would have a wonderful dinner with delicious food and then play chess at the bar over a few drinks and good conversation. During this cruise, I also had great internet, which was nice because I could even get a lot of work done.
That’s the beautiful thing about the Caribbean islands; they are so close together that I always had excellent network coverage and reception with my google fi. Sometimes in the night when we were too far out at sea, I lost my google fi, but the internet onboard would kick in, and it was also fast internet and for a reasonable price.
All in all, the set up on board was ideal and very conducive to good times, efficiency, and relaxation. I can really see myself spending an extended period of time on a boat like this again, simply to get work done. Maybe on a transatlantic cruise or something of the sort.
In the evenings, there were some events onboard such as live music or movie night; and every three nights, they had a party or a BBQ dinner at the top deck. Everyone gets dressed up to enjoy a beautiful dinner mingling under the stars, savoring good food, and lovely music.
Even when there wasn’t a special night on the program, we still enjoyed terrific 5-course dinners with a nice bottle of wine. My brother and I would finish the whole bottle over dinner, no wonder we had so many great conversations. Thinking back on all of this, I can really say that it truly was a really cool trip.
I’ll leave it at that for now, but stay tuned, up next I’ll be regaling you with details from some more Caribbean destinations such as Saint Kitts and Nevis, Sint Maarten and a few of the U.S. Virgin Islands. These are just a few of the many stops we had ahead of us, and each destination had its own magic and charm.
