Tropical islands exist all around the world, but when you live in the United States, the most easily accessible are the Caribbean Islands. With 26 distinct island nations and over 700 islands, big and small, it’s an incredible region to explore.

So, if you’re seeking a destination for a Caribbean vacation or adventure, it’s going to be very difficult to narrow down which one you want to visit.

• Do you visit the stunning beaches of Aruba?
• Do you reef dive and chill with animals in Curacao?
• Do you experience the huge variety of one of the largest islands from the Dominican Republic?
• Do you soak in the unique and vibrant beauty of St. Lucia?
• Do you hike the volcanic rise of St. Kitts?

There’s just so much to choose from and so many options; it feels impossible to decide! You could easily spend months in the Caribbean and never see everything you want to.

Rather than try to pick a destination and make the most of it – and potentially leave with regrets – why not consider another option? The Caribbean is one of the world’s most well-traveled and interconnected archipelagos, which means you have a unique adventure available to you: island hopping.

What is island hopping? Is it the right kind of adventure for you? What do you need to know to plan and execute an island-hopping trip? Let’s talk about it!

What is Island Hopping in the Caribbean?

The concept of island hopping is pretty simple. You fly to some destination island in the Caribbean, but rather than spend your entire vacation in that one place, you hop from island to island before eventually returning home. You don’t need to return to your original island to leave; anywhere with a large enough airport can get you where you’re going. It turns a potentially stagnant single-island vacation into an adventure packed with decision-making, unique experiences, and varied destinations.

The Caribbean spans over a relatively large geographic area, and the islands range from very small to quite large. Some you can see in a day, while others can take a lot longer to explore. There’s also the culture to consider! With deep histories of colonization and settlement from all sorts of nations, and with distinct national cultures that have developed over the centuries, every island feels unique.

It’s no wonder even the official Caribbean website has a whole page dedicated to island-hopping!

Make no mistake, though; island-hopping throughout the Caribbean isn’t exactly easy for most people. Since all of the major islands are different countries, you end up going through a lot of customs checks, and there’s orders of magnitude more paperwork and planning that goes into this kind of adventure than you would have with a normal one or two-island trip. Even just booking hotels or resorts across half a dozen or more islands can be a challenge!

If you pull it off, though, it’s easily one of the most memorable experiences you can have in the Caribbean. The question is, is it right for you? And if so, how do you plan and execute your adventure successfully?

Why Should You Consider Island Hopping in the Caribbean?

There are a lot of potential benefits to an island-hopping adventure throughout the Caribbean islands.

You can have a wide variety of cultural, culinary, and touristy experiences. Different Caribbean islands are known for different things. Some have great scuba diving, some have pristine sand beaches, some have full-service resorts, some have incredible hiking, some have exciting historical landmarks, and some have completely unique experiences you can’t find anywhere else in the world. If you want to pack your adventure with as many varied experiences as possible, island-hopping is definitely the way to go.

You minimize the FOMO and regret of missing an island. For many people, an adventure in the Caribbean is a once-in-a-lifetime adventure. For others, it might only be possible once a decade. With these kinds of limitations, if you pick an island and end up regretting it, you just have to hold that. If you hop islands, you at least guarantee more and varied experiences.

You can have a lot of flexibility in your plan. Some people like a rigid schedule, but if you’re a go-with-the-flow traveler, you can pick and choose when you want to move on and plan your next destination just a few days in advance.

There are a ton of excellent experiences you can have throughout the Caribbean, so making the most of a trip is very compelling to many travelers.

Why You Might Not Want to Island Hop in the Caribbean

Island-hopping is decidedly not for everyone. If you love the idea of island time and just want to spend your vacation lounging on a beach, sipping cocktails, and watching the waves, you’re definitely going to be better off if you just pick one island to visit or maybe two and plan to chill out.

Additionally:

• Island hopping can get a lot more expensive. It’s similar to the normal vacation, except you also have travel bookings between islands over and over, which can add up fast.
• Your plans are extremely susceptible to disruption from weather or other events. You never know when a planned trip might be canceled or rescheduled, throwing your entire itinerary in disarray.
• You’ll be spending a lot of time dealing with customs. While island-hopping isn’t unusual, it’s not super common either, and the fact that just about every major island is its own country means you’ll be spending a lot of your vacation at border control.

And, really, if nothing else, it’s just a lot more work. You have to do a lot more research, contact a lot more hotels and resorts and travel companies and all the rest, and it tends to require a particular kind of aggressively proactive personality to make it all work. If you’re easily flustered by delays and mistakes, or if you don’t know how to handle disruptions or problems along the way, it will be a lot more stressful than relaxing.

How to Get from Island to Island in the Caribbean

If you think island hopping is for you, one of the big decisions you need to make is how you plan to do the hopping. While the Caribbean is relatively packed with islands for an archipelago in the tropics, it’s certainly not something you can swim.

Generally speaking, there are three options.

The first option is to take a cruise. Cruise ships are, by definition, island hopping, but they don’t have the same vibe. The center of the trip is really more about the ship than the islands, and you end up spending most of your time on the boat, and the few stops you make at the islands tend to be hurried and crowded. Cruises can certainly be fun in their own right, but if you want to go island hopping, you’re usually more interested in something that’s not a cruise.

The second option is short-hop flights. Pretty much all of the major islands have airports, and while you aren’t flying into most of them from Florida or California or wherever you start, the inter-island short-hop flights are common and effective. This is usually your fastest and most reliable option.

The third option is to charter a boat. There are plenty of boats that go between islands, much smaller than cruise ships but large enough to be more comfortable for the trip. These are slower, and they’re definitely not the right choice if you get seasick easily, but if you want to enjoy time on the open waves, doing it while you’re traveling from island to island can be a good choice.

These island-hopping boats range from private speedboats to small yachts, though ferries and catamarans are popular as well. You have a lot of choices.

How to Plan a Caribbean Island Hopping Adventure

If you want to island hop, how do you go about planning the trip? In general, you can break it down and fill in the blanks.

Pick a Region

First up, you want to decide what region of the Caribbean you want to visit. Since the Caribbean is so large, you need at least a month or two if you want to see it all, and probably more.

Usually, it’s best to pick one of the major regions:

• The Lucayan Archipelago is closest to Florida and encompasses the Bahamas, as well as Turks and Caicos. It’s also close to the Greater Antilles, so it’s often grouped together with their larger cousins.
• The Greater Antilles are the largest islands in the chain and encompass Cuba, Puerto Rico, Jamaica, the Caymans, and more. This is the starting point for a lot of island hopping, and some people never leave this region.
• The Lesser Antilles is the whole swoop of islands from the edge of the Greater Antilles all the way down to the coast of South America. It’s broadly divided into the Leeward Islands, the Leeward Antilles, and the Windward Islands, all of which are very small locations. A lot of the easiest island hopping happens here because it’s easy to spend 1-3 days on an island and see just about all there is to see.

You don’t have to limit yourself to one region, but the more you try to do, the longer you should take to experience it all. Otherwise, you’re basically showing up, unpacking, napping, packing, and leaving, with little time in between.

Pick a Place to Start and End

Your next step is to pick a place to start and a place to end your journey. This could be the same place if you wanted to do a big loop, or it could be different locations.

There’s no wrong answer here; just pick a couple of islands you want to see that have others in between them, and figure that’s the broad outline of your trip.

Pick Critical Destinations Along the Way

You don’t have to hit every island along the way, especially if you’re flying from island to island. Boat stops might be less inclined to skip islands, though it depends on the boat, of course.

You can refer to our posts linked all the way at the top of this page for some ideas of places you can visit and the things you can do on those islands. Remember, though, that those represent overviews; there’s a lot you can do on most islands, and you’ll want to prioritize the biggest attractions along your route.

Pick a Timeline

How long are you going to take? Figure out a start date and an end date, and determine how long it leaves you to spend on each island.

Don’t forget that travel takes time, so don’t crowd your schedule so much you end up spending all your time checking in and out of things.

Make Important Bookings

The most important bookings should be made in advance so you aren’t left scrambling.

We mean things like the more in-demand resorts, the bigger flights, and so on. The earlier you book, the more you can save, and the smoother things can go.

Tips and Tricks for Island Hopping in the Caribbean

To round things out, here are a few of our tips if you want to go island hopping in the Caribbean.

Don’t pack your schedule too tight. The more you want to cram into your schedule, the harder it will be to manage, and the more stressful it will be, especially since most of these islands don’t operate on strict schedules and punctuality. Make sure you have flexibility in your scheduling to alleviate the most risk of cascading failures.

Don’t pack your suitcases too tight. Since island hopping involves a lot of traveling, the less you bring with you, the better off you’ll be. Travel light, but make sure you have the essentials.

Consider renting a car at each destination. Private drivers are expensive, public transit is rare, and the islands are often a little too big to comfortably walk everywhere. Renting a car (or a scooter) is the simplest and fastest way around.

Don’t be too rigid in your plans. We can’t stress this enough: the more you make a schedule and strict itinerary, the more you set yourself up for failure. Flexibility is the name of the game with island hopping.

What do you think? Is island hopping appealing to you, or does it just sound like too much stress? Let us know!