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Caribbean Island Hopping: 5 Very Comfortable Boats You Probably Didn’t Know About

Caribbean Island Hopping: 5 Very Comfortable Boats You Probably Didn't Know About

The Caribbean is a popular holiday destination that offers many exciting places to visit and things to do, but the best way to explore it all? By going island hopping! If you’re looking for a way to get around the Caribbean without relying on public transportation like buses or ferries, take a look at this article for suggestions on some of the best boats at your disposal.

Best boats for the Caribbean

If you’re planning a Caribbean island-hopping adventure, comfort should be one of your top priorities. Here are some of the best boats for the Caribbean that will make your trip as comfortable as possible:

  1. The Luxury Catamaran: This luxurious catamaran has everything you need for a comfortable island-hopping experience, including spacious cabins, a large sundeck, and a hot tub.

  2. The Sailboat: A sailboat is the perfect option if you’re looking for a more traditional island-hopping experience. You can relax on the deck while enjoying the beautiful views of the Caribbean Sea.

  3. The Powerboat: A powerboat is a great option if you’re looking for speed and convenience. You can get to your destination quickly and easily with a powerboat.

  4. The Yacht: A yacht is the ultimate in luxury and comfort. It’s perfect for those who want to enjoy the finer things in life while island-hopping in the Caribbean.

Boats I like – Sawyer, Robalo Edge 130, Bayliner 195 Bowrider, Key West 239 Coastal Cruiser
Caribbean Island Hopping: 5 Very Comfortable Boats You Probably Didn't Know About

There are many different types of boats that can be used for Caribbean island hopping, but some are more comfortable than others. The Sawyer is a small boat that is perfect for those who want to explore the islands without having to worry about space. The Robalo Edge 130 is a larger boat that is perfect for families or groups of friends. The Bayliner 195 Bowrider is a great option for those who want to have a little more space and comfort while they are on the water. Lastly, the Key West 239 Coastal Cruiser is the perfect choice for those who want to cruise around the islands in style.

What is my opinion?

After years of adventuring throughout the Caribbean on various charter boats, I’ve come to have a solid understanding of what makes for a comfortable yacht. It’s not just about the size or amenities of the vessel, but also how the boat is crewed and operated. Here are five points that I believe contribute to a comfortable yacht experience:

  1. The vessel should be well-maintained and clean.

  2. There should be a sufficient number of crew members to attend to guests’ needs without being intrusive.

  3. The food onboard should be fresh and plentiful, with options to suit different dietary needs.

  4. The itinerary should be flexible, allowing for some down time as well as opportunities for excursions and exploration.

  5. The vessel should have a relaxed atmosphere onboard, with music and conversation flowing easily.

How to be Comfortable on a Boat
Caribbean Island Hopping: 5 Very Comfortable Boats You Probably Didn't Know About

  1. How to be Comfortable on a Boat

Sailing can be a very comfortable experience, but it’s important to be prepared before setting sail. Here are a few tips on how to make your time on the water as enjoyable as possible:

-Wear comfortable clothing that you can move around in easily.

-Bring sunscreen and hats to protect yourself from the sun.

-Pack snacks and drinks to keep yourself hydrated and fueled throughout the day.

-If you get seasick, there are over-the-counter medications that can help alleviate symptoms.

 Boats You Might Not Know About

There are many different types of boats that can be found in the Caribbean, ranging from small personal vessels to large commercial ships. While most people are familiar with the more common types of boats, there are actually a wide variety of boats that can be found in the region. Here are just a few of the many different types of boats that you might not know about:

  1. Catamarans: These boat types are actually two connected hulls, which makes them much wider than your average vessel. Because of this, they provide a very stable ride and are perfect for island hopping. Many catamarans also come equipped with large covered areas, making them ideal for relaxing in the shade.

  2. Sailboats: While sailboats are not as common as they once were, they can still be found throughout the Caribbean. These boats rely on wind power to move, so they are perfect for gentle cruising around the islands.

  3. Yachts: Yachts are luxury vessels that come in all different sizes. They often have multiple levels and decks, and are usually equipped with a wide range of amenities. Yachts are typically used for leisure travel and cruising, but can also be chartered for fishing or diving adventures.

What size boat do you need to sail the Caribbean?

The first thing you need to consider when island hopping in the Caribbean is what size boat you need. There are many variables to consider such as the size of your crew, the type of islands you want to visit, and the type of sailing you want to do. 

For example, if you are a solo sailor or have a small crew, you might be able to get away with a smaller boat like a 30-footer. But if you have a large crew or want to visit bigger islands, you’ll need a larger boat like a 50-footer. The type of sailing you want to do will also dictate the size of boat you need. If you plan on doing mostly day sails with the occasional overnight stay, a smaller boat will suffice. But if you plan on island hopping for extended periods of time or doing long-distance sailing, you’ll need a larger and more comfortable boat. 


There are many great boats available for island hopping in the Caribbean. Below are some of our favorites:

  • Beneteau Oceanis 381 – A great option for couples or small crews, this 38-foot sailboat is perfect for day sails and overnight stays.

  • Bavaria 42 Match – An excellent choice for families or groups, this 42-footer has plenty of space for everyone on board.

  • Jeanneau Sunshine 38 – Another great option for solo sailors or small crews, this 38-footer is  perfect for island hopping and coastal sailing.

  • Hunter 45 Deck Saloon – A large and comfortable option for extended island stays or long-distance sailing, this 45-footer has plenty of space and amenities for a crew of up to six.

Island Hopping Comfort

When you island hop in the Caribbean, there are a few different ways to get from one island to another. You can fly, take a ferry, or take a boat. Taking a boat is often the most comfortable option, and there are a few different types of boats that you can choose from. Here are some of the most comfortable boats for island hopping in the Caribbean:

  1. Catamaran: A catamaran is a type of boat that has two hulls connected by a platform. This makes them stable and comfortable, even in rough waters. They also have large decks that are perfect for lounging and enjoying the views.

  2. Yacht: Yachts are luxurious boats that come in all different sizes. They typically have multiple levels, including a sundeck where you can relax and enjoy the views. Some even have swimming pools!

  3. Houseboat: As the name suggests, houseboats are like floating homes. They usually have several rooms and all the amenities you need to live comfortably onboard (kitchen, bathroom, etc.). Houseboats are great if you want to spend extended periods of time on the water.

So, next time you’re planning an island hopping trip in the Caribbean, consider taking one of these comfortable boats instead of flying or taking a ferry.

What You Want in Your Island Hopper

The first thing you want in your island hopper is a comfortable boat. You don’t want to be cramped up on a small boat with no room to move around. You also want a boat that is stable and won’t rock back and forth all the time.

The second thing you want in your island hopper is a good captain. You want someone who knows the area well and can get you to your destination safely. You also want someone who is friendly and informative, so you can learn about the area as you travel.

The third thing you want in your island hopper is a good crew. You want people who are competent and experienced in operating the vessel. You also want people who are friendly and accommodating, so you can feel at ease during your journey.


There are plenty of amazing places to visit in the Caribbean, and island hopping is a great way to see as many as possible. But comfort is important, too, which is why we’ve put together this list of five boats that will make your island-hopping experience as comfortable as possible. From sleek catamarans to luxury motor yachts, there’s sure to be a boat on this list that’s perfect for your needs. So what are you waiting for? Start planning your next Caribbean vacation today!



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