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Cruise the Caribbean


Outside traveling in the U.S. and its territories, the Caribbean is one of the most accessible regions for American travelers to explore and is filled with beautiful beaches and crystal clear waters. Unfortunately airfare and the expensive resorts at these little gems often negate the accessibility of trips there, making them typically honeymoon destinations. However, there are occasionally excellent discount rates for cruises to visit several of the islands with room and board included making the price nearly impossible to beat!

For nearly two years I checked on and off for cruises that would work, but none seemed to fit the right timeline or the most desirable destinations until finally one popped up that aligned with my month of travel around South America. After sharing the itinerary and showing what a steal the package was, I convinced my mom to fly down to Puerto Rico and meet up with me to sail around. So far about $450 per person we spent seven days cruising around the Caribbean and visiting five additional islands. Here are a few of the trip highlights that are a must when visiting the Caribbean!

Snorkeling in Barbados

Snorkeling opens the underwater world to all the aspiring mermaids. With several shallow shipwrecks and an abundance of underwater marine life, Barbados is an excellent destination to go snorkeling. I convinced my mom to take her first spin at it and we got to see several a massive variety of fish and several sea turtles (meanwhile I was scolded for following one too close). However, the real treat of the snorkel trip was getting to explore two of the local wrecks. The boats were only 25ft underwater making them easy to fin around and explore. The endless schools of fish happily accompanied us as we kicked around and peeked inside the rusty hull. While there are plenty of snorkeling packages available through the cruise line, it is substantially cheaper to do a few minutes of research and find a tour. We did a Viator tour, but at most of the cruise ports there are several companies that arrange transportation and even provide welcome drinks for their snorkel excursions.

The Piton Mountains

Tucked away on the side of a mountain up a narrow and bumpy road, is the incredible Jade Mountain Resort. The luxury hotel offers 32 private sanctuaries where complete solitude is provided and any service that is required, can be delivered directly to the comfort of your room. Each sanctuary is unique with special colored glass tiles and matching interior details throughout the room. The lavish rooms include their own private infinity pool and lounge chairs for sun tanning in the open air as the exterior wall does not exist. The pools in each room offer stunning views of the Piton Mountains, probably the best on St. Lucia. Also the resort enforces a strict no-drone policy for obvious reasons, so in these pools it is a personal preference for swim attire or lack thereof. One of these exclusive sanctuaries with a private infinity pool will set you back around $2k a night, but certainly earn their spot as a bucket list vacation resort.

Local Rum Tasting

There is something about the taste of rum that just completes the feeling of a beach vacation. Mix it in a glass of cola, serve it in a fruity cocktail, or take a shot of it to get any trip off to a good start, especially in its place of origin in the Caribbean. With Bacardi the world's largest rum exporter, originating in Puerto Rico, it is no surprise that many of the Caribbean islands follow suit and have their own homemade liquors. While I have done wine tastings at vineyards around the world and tried numerous flights of beer at breweries and pubs, St. Lucia was the first place I have been offering a full rum sampling.

Single (generous) shots of any rum on the table cost $2, two shots for $3, or as many samples as possible for $5. Obviously being the frugal alcohol enthusiast that I am, the unlimited choice was one of the easiest decisions I made the whole cruise. However, with only a 15 minute stop I had no time to spare and quickly drank my way across at least ten of the rum varieties. I am not sure if the server was more impressed or concerned as I quickly finished each shot he served and selected the next flavor, but I certainly got my monies worth! At that point I would have happily purchased several of the homemade delicious bottles, but alas the cruise did not let us take them back on board, which was probably in everyones best interest.

Day drinking in Sint Maarten

Pretty clearly I place the importance of a good cocktail pretty high on the to do list during beach vacations. When a scuba diving trip fell through in Sint Maarten due to the inbound Hurricane Irma, we decided to spend an afternoon relaxing on the beach and soaking up some rays. While mom was not quite up for the famous nudist beach Orient Bay on the French side, she happily enjoyed for a few rounds of rum punch and making new friends on the Dutch side.

See Where the Atlantic Meets the Caribbean

St. Kitts

On St. Kitts and Nevis there are numerous small open air shuttles that take visitors to some of the top destinations on island including the old British Fort Brimstone Hill, Mount Liamuiga, and South Friars Beach. The scenic drive passed the lush rainforest and stopped at several of the famous beaches for us to go for a quick swim. However, the top of St. Anthony's Hill was the highlight of the tour as it provided the best view of the island where the Atlantic ocean on the left meets with the Caribbean on the right. This is definitely an excellent viewpoint to see in all directions from this small West Indies slice of paradise!

Hike to Magen's Beach

Magens Bay

Let me be honest first and admit that hiking to Magen's Bay from the cruise ship port is a pretty awful idea. In my defense when I planned the afternoon there was no way I could have known that the sidewalks in St. Thomas would just disappeared half-way up the mountain. Actually I am sure there are plenty of places that explain that, but I never found them and instead thought I had a lovely little hike with viewpoints and through a nature park before reaching the Magen's Bay.

While the park and the viewpoints were lovely, there are large portions of the road that have no sidewalks and it is rather steep the entire way. Mom was a champ though and quietly sweated her way to the top of the mountain. Eventually we made it down to the soft sandy beach on the other side with crystal clear water where we took a well deserved swim to cool off. On the way back we opted for a small open air shuttle that transports visitors anywhere on the island for only a few dollars. Back at the port we passed a bar surrounded by swings and stopped for a fruity drink before heading back on the boat. After explaining our days adventure, the bartender incredulously asked why I had made my mother do that hike and was greatly impressed that she made it. He rewarded her with another delicious round of Pina Coladas so it was a win all the way around!

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