The HANDS DOWN Best Way to See The Caribbean

Let me just preface this post by saying HOW THE HELL DID I NOT KNOW ABOUT THIS KIND OF TRAVEL BEFORE?! If I had known that you could hop on a beautiful boat with a comfy bed and a working bathroom that also had a staff that operated the boat and cooked the meals while traveling from island to island…well I would have been traveling this way years ago. Ok, you can breathe now. For the longest time, my husband and I have been trying to think of long term goals like having a vacation home somewhere we love when we are older, but after going on this trip, I think I’ve changed my mind. Being able to travel by sea to different countries within a few days is 1 million times more enjoyable than by flight or car. Luckily, I now know about TradeWinds and plan on doing more of these types of trips in the future! Why explore just one country when there is so much more out there to see?!

Anywho before I get into all of it, I want to explain how I even found out about TradeWinds while also warning you that there will be MANY photos throughout this post. I warned ya! Ok, so I honestly got invited on this trip out of pure luck (well, for me). My friend Vanessa did this same trip with TradeWinds last year through the Caribbean and when they were on the trip, they booked another one for the next year. Well, a couple had to back out so Vanessa asked me! I instantly said yes and practically through my wallet at her to book it because I wanted to be locked into that spot before someone else was lucky enough to take it. Of course, I asked my husband to go with me but he couldn’t take a total of 9 days off so I asked my sister-in-law instead. If I can’t take my husband, why not take the next best thing! Amirightoramiright?! So we went into this trip knowing absolutely nothing. Since we were pulled into the group of 10 last minute, we didn’t really know what the itinerary or experience would look like. All I knew that the boat was somewhat of a timeshare or club that someone in our group was part of and they are able to bring some of their friends (or strangers like us) with. But I’ll get into all those deets later.

After taking the redeye out and spending one night at the Westin St Maarten, everyone met up at the marina where we finished paying for the trip and handed over our passports for them to keep in a dry bag for entering customs in different countries. Within minutes, we were on our cruising class boat being welcomed by Captain Jordan and his 1st Mate Ryan. We were given beautiful cocktails and delicious snacks and we left the marina to go to Marigot Bay for dinner and settling into our rooms. I seriously had no idea what to expect with the rooms or even how big the boat would be. All I had anything to compare it to were the houseboats I’ve stayed on while in Lake Powell. And luckily, the rooms and the boat itself exceeded expectations. We had plenty of room to store our items and a bed that overlooked the water. Even the beds are pretty dang comfortable! And the boat uses a generator at night so the rooms were always cool and comfortable and you could control the exact temperature yourself. Which is a miracle since my body temperature when I sleep is about 4000 degrees. Check out this view outside of our window that we got to wake up to everything morning!

When you’re on a TradeWinds trip, almost all of your meals and snacks are part of the all-inclusive fee, so you don’t have to worry much about what you’re going to eat. As soon as we parked in Marigot Bay, we were served a beautiful dinner and offered wine with our meals. And not only do you get delicious meals throughout your trip, but you also get dessert after every dinner. Was that my favorite part? Yes, yes it was. Wine? Nah man, I’m here for the edible sugar. We spent the evening eating ginger carrot soup, fresh fish with potatoes and salad and a delicious custard for dessert then sipping on drinks in the net of the front of the boat! I swear I won’t list off every meal that I ate like I want to do, but I just want to paint a picture of how delicious each meal was.

Every morning on our boat would start off the same – I would wake up at a God awful hour before everyone else, I would start the coffee pot (Ryan gave me permission since my internal clock is the devil), then have my morning coffee, do a workout on the beach or on the boat, then we would have breakfast together where Jordan would tell us where we were going that day and what we could do at each island. Then we would set sail and begin our island hopping. Each day consisted of floating behind the boat, snorkeling, fishing, kayaking, hiking, scuba diving, shopping and checking out some of the towns, drinking on the beach, and worsening the dark spots on my forehead. My esthetician is gonna be hella pissed.

Our trip was suppose to include St Kits and Nevis but a huge storm was brewing and I don’t know if you know anything about sailing, but storm = bad news bears. So our itinerary changed a bit along the way as storm patterns changed. In the 7 full days that we were on the boat, we had 12 stops along the way. That’s pretty rad huh? These are all the spots we had the opportunity to check out!

1. Marigot Bay
2. Creole Rock
3. Colombier Bay in St Barths
4. Gustavia in St Barths
5. Ile Fourchue
6. Grand Case
7. Dog Island
8. Road Bay
9. Sandy Island
10. Prickly Pear Island
11. Meads Bay
12. Rendezvous Bay
    

Without listing every single detail of every day like I want to, I’ll give you the quick rundown.

• Marigot Bay in St Maarten – This is the bay that the boat is anchored in and it has a ton of shops and restaurants to wander around in. It’s pretty close to the airport so it makes getting to the bay extra easy if you’re going straight from a flight onto your boat.
• Creole Rock in St Maarten – This beautiful area had amazing snorkeling where people saw a ton of different kinds of fish and stingrays. I did not partake in Creole Rock snorkeling because floating is a little bit more my style. Depending on my mood, I like to ignore all the creatures below me and act like they don’t exist because I may crap my pants if I don’t. Ignorance is bliss sometimes. Stop hating me.
• Colombier Bay in St Barths – One of my favorite stops of the whole trip. This bay is a secluded beach area that includes a hiking trail that leads to the other side of St. Barths. Not only did I get amazing workouts in on this beach, but I hiked and actually enjoyed myself for once on a hike. The trail is a winding dirt path that overlooks both sides of the island and is filled with wildlife. We saw goats, turtles (literally everywhere) that we had to be careful not to step on, lizards and a very fit man who passed us 57 times while running back and forth on the trail in his full length leggings and splattering his sweat on my each time he passed. Odd outfit choice. Men in leggings creep me out. We didn’t hike the entire trail just because we needed to get back before dark, but we saw a cute little swimming hole at the end that we all wanted to go to. Next time. The sunset was truly magical in this bay and I didn’t want to leave.
  
  
  

• Gustavia in St Barths – If you have the chance to go to Gustavia, you MUST. It’s amazing. It’s this beautiful French town filled with super fancy shopping like Gucci and really any high end brand you can think of. We spent the afternoon wandering around the entire town, having the most amazing healthy juices from Tom’s Juice Bar (that also had my favorite granola from Boulder – Purely Elizabeth) while using the wifi for a little work time. Then we had a delicious lunch at Bo Káo (where I had THE BEST ceviche) before heading back to the boat. The only part that sucked about Gustavia was when one of our friends from the boat rented a scooter and lost control and ran into a wall, breaking 3 ribs and straining her ankle. Talk about a buzz kill. The poor thing was in so much effing pain throughout the entire trip, had to go to the hospital twice while in St Barths and couldn’t swim AT ALL. It was so damn sad. But she’s alive so that’s all the matters, right? Right. And since she was stuck at the hospital all day and we couldn’t get anywhere, we got drunk for her. And paid for it the next morning. Thanks for the hangover, Rhonda. OH, also, I went snorkeling here and saw absolutely no fish but did end up getting surrounded by jellyfish, and a fisherman told us there were sharks. Cool. Ignorance is bliss, am I right!?!?
  

• Île Fourchue of  St Barths – This beautiful island was where A LOT of sickness went down. Not only was our friend and her boyfriend who was on the back of the scooter in a ton of pain and both dehyrdrated, but others had sea sickness and a little sunstroke going on. That sun will get you if you’re not paying attention to it. Especially if you don’t drink much water to begin with and you feed your body with poison (aka alcohol). So this island included seeing a lot of people puke. But I wasn’t puking so I ditched them and hiked alone. The trail was a little grown over so I made my own path. And stepped on a cactus. That’s what I get for ditching my friends. Luckily, the view was worth it. If you like hiking, this island is for you. So many spots to hike and step on cactus. I really did love it.

• Grand Case of St Maarten – This cute little town was the perfect stop for our dinner night out. During the trip, they have you eat out for a meal so they can clean the boat and change the linens so we anchored in Grand Case and ate at Calmos Cafe where I had some amazingly fresh Mahi Mahi and then some bomb ass gelato down just a couple doors down. I seriously have no idea what the gelato place is called and can’t find any info online, but I’ll keep looking for you! This area has a ton of restaurants, but they also have some really cute stores to shop in, as well!

• Dog Island of Anguilla – This was my FAVORITE island. I ran awkwardly throughout the island screaming I LOVE THIS ISLAND because it was so stunningly beautiful and the sand was so soft. But don’t get excited, it’s not covered with dogs like the name implies. Bastards. It’s an uninhabited island that is owned by Anguilla and home to a ton of birds that I know nothing about. You can read about it on the island but I just wanted to run on the sand and scream random words instead. There’s nothing to do on this island other than be blissfully happy. It was so rad.

• Road Bay in Anguilla – After Dog Island, we sailed to Road Bay where we swam to shore and got drunk by ourselves at Dad’s while everyone hung out on the boat. We thought everyone would follow us since short was about 15 meters away, but come to find out, people don’t love hanging out with loud drunk b*tches, so we drank extra sugary and got super annoying at Dad’s while curling our toes in the sand. This little “quiet” town is filled with sleepy bars and restaurants that literally play music ALL NIGHT LONG. Our Captain said it was a sleepy town, but I think he meant to say sleepless town. The music seriously never ended. Come on, Jordan, you lying son of a b!
  

• Sandy Island of Anguilla – Ok so I need you to picture something. You know that Corona commercial they play around Christmas time where a palm tree that looks like it’s on a deserted island in the middle of no where lights up with Christmas lights? Do you know what I’m even talking about? No? Whatever. That’s what Sandy Island reminds me of. It’s this beautiful tiny island in the middle of the ocean that has a single bar and a ton of white sand and comfy day beds. It’s adorbs. The bar opens at 11am and I definitely recommend getting there early or right on time to enjoy the island before it gets busy. It definitely picked up pretty quickly and got crowded in minutes since it’s so small and so popular.
  

• Prickly Pear Island of Anguilla – This island wasn’t too far from Sandy Island, but it was just as adorable and extra quiet. The entire time we were on this island, we only saw one other couple just hanging out in the water. The island has a bar and restaurant but it didn’t look open when we were there. We did notice why it was probably called Prickly Pear…because we kept getting little prickers in our feet while we walked the beach. Half this island is beautiful white sand beaches and the rest is coral that looks and feels like you’re walking on Mars (since I know what that looks and feels like, ya know) so it feels like you’re exploring two completely different islands while you’re there. Just beware of the prickers!
  

• Meads Bay in Anguilla – We stopped in Mead’s Bay because the festival Carnival in the Caribbean was playing there that night. Sadly, I wasn’t super impressed. I went to shore ready for a dance party since all I could hear was bass when we were on the boat, and NOBODY was dancing. No one! They all just stared at the stage while standing completely still. It was so strange. And I wasn’t drinking which made me feel even more strange. BUT I did get an amazing workout in on their long stretch of beach. We had our boat anchored about 50 meters out so I swam to shore to workout on the beach and was able to see some the ocean floor covered in starfish and sand dollars.

• Rendezvous Bay in Anguilla – This area was AWESOME, except for the crazy amount of seaweed sweeping ashore. It makes floating in the ocean a little less fun. But when you go to Rendezvous Bay, you’re welcomed by the coolest bar that the famous singer Banxie Banx opened called Dune Preserve. I had never heard of this singer before, but this guy has built this beautiful never-ending treehouse where you can get food, drink, and hang out right on the beach while listening to music. And we were lucky enough to get our own show while we were there. First, the 1st Mate of our boat Ryan performed since he is an amazing singer then Banxie Banx got on stage and serenaded us. His voice is pure magic. Look him up because it really is incredible. And the food was awesome, too. Expensive, but awesome. Get the jerk chicken and plantains. So bomb.

Now let’s talk about some of my favorite experiences from the trip. Honestly, every day was awesome. I mean, you’re on a boat in paradise with a drink in hand most of the time so it’s pretty hard to have a bad day. But here were my favorites.

• Captain Jordan catching a fish…for the second time. When we are sailing, they have two fishing lines cast out. At one point, we hear FISH ON and see Jordan run over and work his ass off to pull in a fish. He gets it onto the boat, it slips out of his hands and the line breaks. I’ve never seen a more defeated man. Luckily, this happens again (with a different kind of fish) and he got it this time. And that same day, they caught a lobster, as well. They actually caught two lobsters but when they pulled the second one out of the trap, it fought like a son of a b and Jordan noticed that it was pregnant so of course he set it back out to sea. But within the hour of catching the fish and lobster, we had the tuna sashimi style and the lobster freshly cooked. So good!

• 1st Mate Ryan playing his guitar – This guy loves music as much as I love food and he played his guitar whenever we asked him to! On the boat, oceanside, wherever. His voice was beautiful and it made evenings on top of the boat even more enjoyable!
• Seeing Banxie Banx play – Seriously, look this guy up. His voice is the sound of sweet baby angel wings.
• Getting cold brew drink from Tom’s Juice Bar – If you’re ever in Gustavia, go straight to this juice bar. Not only do they have wifi (which was a savior for me and getting some work done) but they have amazing products and items on their menu. I got a coffee drink with cold brew, cacao, dates and other amazing stuff. My biggest regret of the entire trip was not getting a large. Then being too hungover the second day to go back into town to get another one.
• The meals – Everything we ate on the boat was fresh and delicious! We had a prosciutto salad, a tuna steak salad, an amazing pineapple chicken salad, a fabulous frittata, and the best ever flourless molten cake. Luckily my sister-in-law doesn’t like dessert so I got to eat hers every night…and pay for it this week. I requested for gluten free meals and I had absolutely no issue on the boat!

• Sitting in the dolphin seat of the boat – The boat has these awesome seats that stick out on the front that you can sit in while sailing. And when then the water is super rough, you get a ton of splash back to cool you down, but you also feel like you’re on a rollercoaster. It’s the best.
• Sitting in the hammock of the boat – My second biggest regret from the trip was not sitting in this hammock more. The captain would sleep most nights in the hammock then take it down during the day but I asked him if he would leave it up the last day and I sat in it for a good hour while we were sailing…BEST TIME EVER. You flop around like a little rag doll and have the best view on the boat. It was so damn fun.

If you have never been on a trip like this, like me, here are some things to pack with you that make the trip just a tad more enjoyable.

• Cash for tips, restaurants and shops. I brought $500 cash with me and blew through that pretty quickly then had to end up going to an ATM (which sucks since there are probably fees from both countries for using it). So bring more than you think you’ll need so you don’t have to stress out about that or worry about your CC info getting stolen when using it in places you’ve never been.
• Floats. You can see the ones we brought with in the photo above. You can find them on amazon for pretty cheap and the roll up to a slightly less awkward size. Jordan tied them to the net of our boat and we drank our cocktails there while we sailed. Then we could all hook together when we were floating behind the boat.
• LOTS of conditioner + leave in conditioner – I lost probably 1/2 my hair while on that boat (Jordan and Ryan would agree after cleaning it). The sun, salt and wind make it a nightmare to brush. So definitely bring more leave conditioner than you think you’ll need.
• Sneakers for hiking – I forgot to bring any because I’m a dumbass, but you definitely need them since you get to hike a good amount on different islands. We had to go on a mad taxi run around town trying to find some and all I could find in my size were these flimsy little Ked style shoes which different really help me out when I battled a cactus.
• So much sunscreen – You run through this stuff so fast. I recommend bringing cream sunscreen. Everyone who used the spray had weird sunburns everywhere. So bring cream and put it on in every spot before you even put your swimsuit on. Because if you miss a spot, the sun will find it and tell you who’s boss.
• A water bottle that doesn’t sweat and keeps ice for a good amount of time – Ice melts so damn fast in the Caribbean and then you don’t drink as much water because it’s warm. So bring a big water bottle that keeps ice frozen and you won’t get dehydrated and get sunstroke.
• Lots of sunglasses, cover-ups and comfy shorts and tanks – You really don’t need much attire for this trip
• Dramamine if you get seasick – I’ve never experienced seasickness, so I don’t know what it’s like, but a handful did on our boat. You can get pills at the store, but a guy on our boat got prescribed patches that you put behind your ear that helped even more.

Now you’re probably wondering how you can even book a trip like this and I’m still learning since I had never heard about TradeWinds until I stepped foot on the boat. So I’ll do my best to explain, but you can always just go to their website to find out more answers. Here’s the quick rundown:

1. They have 3 different kinds of boats – each one a little more expensive than the other and offer different things on the boat. They also all go to certain areas.
   • Cruising Class – This was the boat we were on
   • Flagship Class
   • Luxury Class
2. They sail all over the place and continue to add new destinations. Right now they have the Caribbean, South Pacific, Central America, and Mediterranean. High on my list to go to someday includes the French Polynesia, Grenadines, BVIs, and Greece!
3. When you’re on the boat, it’s almost like being at an all-inclusive resort. You get all your meals and snacks prepared for you and work with you depending on your dietary needs, they make drinks for you (we would often make our own, too) and then you get to do any of the outdoor activities you want – like snorkeling, swimming, paddle boarding, hiking, floating….drinking and floating. Whatever suits your fancy.
4. For this type of trip, you can either book a room on a boat with a ton of strangers or book the entire boat then invite the friends you want and have them pay you back. That’s what the friends on the trip I went on did. One person booked their trip a year out then they all paid him for the cabin. So when I joined, I paid $1800 for my cabin (for 2 people) then when we got to the marina, we paid $995/person for the all-inclusive fee for food and drink through the week. Plus flight to get there and cash for tips and whatever else – just helping you get a number in your own head with figuring the trip out yourself. We also paid for a hotel the night before and the night after. The next time I do this trip, I will get a hotel the night before getting on the boat (just in case a flight is cancelled or delayed – wouldn’t want to miss the sail time) but I wouldn’t get a hotel after we got off the boat, I would just get a flight straight home. If you click here, you can play around with dates, private vs shared charter and different classes of boats to find the right fit for you.

Ok, I think that covers all of it but I could be completely wrong…because I still have vacation brain. Sorry for the crazy long post…if you even made it this far…but I wanted you to get the full experience of the 7 days. It was truly one of the coolest international trips I’ve ever been on. I’m not sure how I’ll be able to go back to just one hotel for a week after experiencing 12 stops in one week. It was a relaxing, exciting, beautiful, fantastic trip that I hope to do again someday! If you have any questions, feel free to leave them below and I’ll answer them the best I can!

Shop My Looks From The Trip