Island hopping in the Caribbean seems like a great way of taking in lots of smaller destinations in one visit to the Caribbean.

On paper – or on a map – it looks like it should be pretty straight forward. All the islands look nice and close together so just pick three or four that you’d really like to see and then book flights or find ferries that run between them. 

In reality, however, this isn’t quite as practical as it at first looks.

Why it’s not so easy to hop between the Caribbean islands

The Caribbean is encompassed by the Caribbean Sea which is some 2.7 million km², so those islands that all look like they are practically touching each other actually have pretty substantial bodies of water separating them.

With the exception of islands which are close enough together that their mutual waters are protected by both islands, ferry crossings are generally impractical, involving navigating open seas. The other alternative is by air, but this can get expensive, not to mention resulting in a lot of down-time hanging around airports.

Unless you have a few weeks on your hands, the disproportionate amount of time spent traveling can quickly make the proposition unattractive.

However, that’s not to say that island hopping in the Caribbean is completely out of the question, the trick is to pick islands which make it a practical and enjoyable travel experience, giving you time to enjoy the laid-back pace of these tropical islands.

Rather than aiming for three or four big islands spread out across the Caribbean chain, a more fulfilling island hopping experience is to find groups of islands which are close enough together to make traveling between them easy and enjoyable.

Practical considerations for island-hopping in the Caribbean

There are a few things to bear in mind when planning an island hopping expedition in the Caribbean (or anywhere, for that matter).

Firstly, check whether the islands you are visiting are all part of the same country. If not, you’ll need individual visas for each of them.

Secondly, be prepared to pack light. If you’re going to be flying, you can seriously cut down your time hanging around in airports if you can travel with just a carry-on. Likewise, if you’re darting about on ferries, it’s no fun being loaded down with luggage.

If the thought of spending more than a day away from home with nothing more than you can squeeze into a carry-on bag is unbearable, consider using one island as a central jumping off point. Book accommodation there for the entire trip and do day trips or overnighters to other islands leaving the bulk of your luggage at your central hotel or a holiday villa.

Caribbean island hopping itinerary ideas

Here are a couple of recommendations to get started with island hopping in the Caribbean.

The Virgin Islands

The Virgin Islands is a collective name for an island group bordering the Caribbean Sea and the Atlantic Ocean.  

The Virgin Islands and separated into the US Virgin Islands of St. Croix, St.John and St. Thomas and the British Virgin Islands of Tortola, Virgin Gorda, Jost Van Dyke and Anegada. As they are respectively controlled by the United States and UK governments, they are very popular holiday destinations for US and British citizens and boast some beautiful nature reserves and historic sites for adventurous tourists.

St. Croix

St. Croix is the largest and most southerly of the Virgin Islands. However, it is some distance from the rest of the island group and it is probably easier to fly than to take a boat. The rest of the islands are all within easy ferry distance, making hopping between them very easy.

Indeed, as St. John doesn’t have an airport, ferry trips from St. Thomas to St. John are extremely common as the main means of accessing the island. The longest ferry crossing is from St. Thomas, in the south west of the main group of virgin islands to Anegada, the most north eastern island which takes around 2 hours.

The rest of the main islands are generally reachable in hops ranging from 30 minutes to 1hr 30min, making this a very accessible group of islands, with lots of smaller satellite islands to explore on day trips to boot.

The Bahamas

The Bahamas is another great opportunity to indulge in some Caribbean island hopping. Located southeast of Florida, over 3,000 islands belong to this single country, meaning all of your island hops will be domestic.

The Bahamas have a rich and exciting culture, both current and historic. Once a safe haven for pirates, it is now a vibrant and lively country, fantastic for outdoor pursuits such as diving, fishing and golf. Relaxing beaches, an intoxicating night-life and festivals and fascinating historical sites are scattered throughout this archipelago state.

The Bahamas Fast Ferry service connects the islands with regular roundtrip services, making island hopping a straight forward affair. The Bahamas Tourist Board has some pre-prepared island hopping excursions which mostly involve a mix of ferries, domestic flights and transfer via hotel’s private plane.

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