We get this question from our friends and family all the time, “So what’s your favorite island in the Caribbean?” We’ll be sitting around the coffee table or standing in someone’s kitchen, performing our Q&A session with our curious audience. I love sharing our stories, so I’m usually rambling on and on about some long crossing, how we choose weather windows, navigation systems, marine engines, and trying to explain how it can possibly take an entire afternoon to fill our water and diesel tanks. What do you eat? Have you ever been in bad weather? Do you get scared? What’s the longest you’ve been at sea? These are all questions I can answer easily, but when someone wants to know which island they should visit for their next vacation, a big empty pause stops my rambling. Romain and I look at each other in hopes the other has a well prepared answer. Sadly, we both stare blankly. Not knowing what to say, but not wanting to disappoint our waiting audience, we typically respond with a, “Uumm… it depends?” This was not what people wanted to hear. It seemed everyone expected us to have a definitive answer and our unsure hesitation was killing the dream. I’ve thought long and hard about this question ever since, and while I still stick to my initial, “It depends,” response, I’ve also realized the best parts of our trip haven’t been the islands themselves, but the time we took to get there.
Up until now the most memorable moments were the ones when we were going from one place to the next. Like that time when we were sailing along the coast of Florida, under a super moon. The night was so bright, I truly felt I could reach out and almost grab the moon. Or that time when three dolphins were swimming in the front of our bow, leading our way through the Turks and Caicos banks. It was watching nearly a dozen shooting stars while crossing the Gulf Stream, the countless gorgeous sunsets, and waking up to humpback whales passing by our boat. It was all of these magical moments that I never would have been able to experience if we weren’t traveling in our floating home. However, I realize not everyone can, or would even want to, travel by boat. It’s definitely much easier to hop on a plane and arrive in paradise. So, to expand a bit further on the “it depends” response, here’s a brief rundown of our favorite places in the Caribbean so far.
There are 700 islands in the Bahamas, with some of the best, clearest waters we’ve seen. If you like water activities, then you’ll be in paradise. You can spend your days snorkeling, diving, fishing, or just lying on the beach. Obviously we haven’t been to every island in the Bahamas, but one of our favorite places is Compass Cay. It’s a tiny island in the Exuma chain, only two-miles long, and it’s the kind of place you go when you want to disappear from the world. There’s one marina, a few cottages available for rent, and an “airport,” which is actually just a strip of sand that floods when it rains. You can swim in the marina and spend your afternoon snorkeling with angelfish, spotted eagle rays, and even nurse sharks. The marina feeds the nurse sharks every day and at high tide they swim onto the dock.
The beach at Compass Cay is stunning, with some of the best sand we’ve seen. Romain and I have compared a lot of beaches and their quality of the sand, and we always seem to remember the sand at Compass Cay as one of our favorites. The only downside, in our experience, is the lack of food. I like to call the Bahamas a food desert. Not much grows there and everything is imported from the U.S. So if you’re wanting a food holiday this is not the place for you.
Go for: Beach, seclusion, marine life, water activities
Turks and Caicos
We spent most of our time on the main island of Providenciales, or Provo as it’s known locally. The north shore is lined with hotels and villas, with Grace Bay being the main vacation beach. Incredible snorkeling, scuba diving, and plenty of amazing restaurants to choose from, it’s the perfect place to go for a week holiday if you want all the luxuries of home. However, Provo is no secret so you’ll probably see a good amount of people during the peak season. For us, after being off the grid for nearly two months in the Bahamas we were excited to see so much civilization. The south side of Provo is bit calmer and we found the water and beaches to be much nicer compared to Grace Bay. Even though the island has many hotels and is well catered to tourists it still feels quiet and calm. If you’re looking for a relaxed, beautiful getaway, then take a look at Providenciales.
Go for: Luxury, foodies, beach, water activities
By island standards, the Dominican Republic is massive. It’s also home to the tallest mountains in the entire Caribbean chain, appropriately referred to as the Caribbean Alps. The DR was everything we pictured the islands to be; lush, green, and finally for the first time, it felt like the tropics. Most vacationers go for the beaches and all-inclusive hotels, but I would skip all of that. The most beautiful views are from the mountains, so here’s what I’d recommend. Rent a car, make sure to get liability insurance because the driving is an experience in itself, and head to Jarabacoa. There you’ll discover fantastic hiking, gorgeous waterfalls, and less of the tourist crowd. Depending on which airport your fly into you can spend a day exploring the old town in Santo Domingo or stop by the cigar factory just outside Santiago. Both are a nice stop, but we especially enjoyed the Dominican cigars. There is also something special about the people in the Dominican Republic. You instantly feel the warmth and energy, and we very much appreciated their patience as we stumbled our way in Spanish. Don’t hesitate, just go.
Go for: Adventure, hiking, waterfalls, budget, low-key
If you didn’t know this already, Puerto Ricans love to have a good time. It seemed like everywhere we went and every weekend the beaches were filled with families, barbecues, and of course, music. It’s a lively island and you won’t find friendlier people anywhere else. We spent one month sailing along the coasts of Puerto Rico and even though we enjoyed each stop along the way, our top place without a doubt would have to be a little island off the east coast of mainland Puerto Rico called Culebra. The pace is slow, and although the island gets a fair amount of visitors, you’ll feel like you’ve discovered your own little hidden gem. It’s a great island to explore by bicycle and you’ll truly be able to get on island time. Make sure to stop by the Culebra Museum to learn about the history of the island and its people.
Go for: Beach, low-key, island time
U.S. Virgin Islands
St. Thomas is the main island in the U.S. Virgin Islands and it has a big port for the cruise ships, which seem to come in every couple of days. For that reason, I would skip it all together and head straight for St. John instead. About 75% of the island is a national park and there are some beautiful hikes along the coast. There’s not too much to do except to enjoy the beach, relax, and sip painkillers all day. There are a few public buses on the island so you can get around without having to rent a car. I’m a little biased, but the best views of the island are from a boat. If you do decide to go on a day charter, make sure to stop by the other island next door, Great St. James. There, in Christmas Cove, you’ll find Pizza Pi, a floating pizzeria. Order yourself a pizza and your second (okay, maybe third) painkiller of the day, and then hop in the water to snorkel while you wait. You won’t be disappointed.
Go for: Island hopping, water, beach, low-key
St. Martin has been our home base for the summer while we’ve flown back and forth between the U.S. and Europe, so we’ve gotten to know it fairly well. It’s definitely catered towards the “yachtie” crowd, meaning you’ll find tons of boat people. Cruisers like us, racers, crew members, mega yacht owners, they all come down here at least once a year. The island has a reputation for its party scene, particularly during the winter season when all the yachties are in town, but right now most of the marinas are empty because it’s the hurricane season and the island feels a little sleepy. For some of you, this may be the best time to visit. The beaches are a lot less crowded and there are so many of them to visit, 37 to be exact. We’ve been on the island for over a month and we still haven’t seen them all. So if you’re looking to have a good time, maybe admire a few mega yachts, and meet people from all over, then you’ll definitely enjoy St. Martin. And if by chance you get bored of beach hopping, you can catch a quick ferry ride to Saba, Anguilla, or St. Barts.
Go for: Beach, party, boat scene