Mar 152014

How to travel independently in the Caribbean – Making the impossible possible!

I'm a big fan of the Caribbean. We spent quite a bit of time there, and recently did a 5 5 months island-hopping trip where we visited 22 different islands and 13 Caribbean countries. It is obviously impossible to visit all the islands in the Caribbean as there are more than 7000 islands, but with a little planning it should be possible to visit all the countries in the Caribbean (27) in one trip. For those people who have an unlimited amount of money it is very easy - just fly everywhere and stay in nice hotels, but for those of us on a budget it becomes more challenging. Obviously, this is not an article about package-holidays to the Caribbean as they normally tend do be straight forward, and they do not necessarily have to cost that much. This is advice for people who want to do a trip out of the ordinary. Backpackers(independent travellers) are more or less non-existent in the Caribbean. During 5 months in the Caribbean, we did not meet any other travelers (but we only stayed in a hostel 2 times) other than package tourists and cruise tourists.

All of the Caribbean

All of the Caribbean

How to travel from Europe to the Caribbean? Of course it depends where in the Caribbean you want to begin your trip. The airlines in the Caribbean have 3 main airports which they fly to the islands in the Caribbean from: Miami, San Jose in Puerto Rico and Barbados. If your plan is to go to Cuba it is better to fly there direct, or to fly to Cancun, Mexico and then take a cheap flight to Havana from there.

Fly to the Sun :)

Fly til solen 🙂

Several of the islands in the Caribbean have well-developed charter flight that independent travelers also can use. Search for last minute charter flights, meaning only the flight without the hotel. Do not focus only on Norway (or the country you live in). Search for charter flights to the Caribbean from all over Europe. Flights between countries in Europe are cheap. First find a flight from any country in Europe to Miami or an island in the Caribbean, and then look for cheap tickets to that European country. Check from London. Thomson and First Choice are well-established charter companies that have cheap flights to the Dominican Republic and Cuba and several other islands.

Fly cheap from London to Cuba, the Dominican Republic, Barbados, Aruba, or Mexico: Even if it's only charter travel you are looking for in the first place there can be a lot of potential to save money by traveling from England. The British LOVE charter trips and all-inclusive. Check the website and for cheap charter flights. We travelled to Cancun via Cuba for around 1600 Norwegian kroner(14$) ". I searched all over Europe and found a plane from Brussels with Jetairfly – They fly to Mexico and Miami. The plane and the service was horrible, but if you are willing to sacrifice comfort for cheap prices then you should be prepared for that. The most affordable planes with regular scheduled flights from Norway fly to Miami where it is possible to find a flight for around 2-3000 Norwegian kroner(14$) ".

How to get between islands in the Caribbean on a Budget?

There are in principle 5 ways to travel between the Caribbean island - scheduled flights, ferries, cruise ships, hitchhiking with sailboats (or commercial boats), or swim (not recommended due to strong currents, sharks, high chance of death and inconvenience with luggage).


There are a limited number of airlines operating between the Caribbean islands.

"privatflyet" inside !

“Our private "jet"” inside !

There is little demand from the locals to travel between the islands, and there are very few tourists who are not on a cruise ship or have their own sailboat. If you are doing a round-the-world trip and buy a round-the-world ticket then flights between islands in the Caribbean are not included. Traveling in the Caribbean is something you have to organize yourself. The prices have gone up a lot in recent years. According to the airlines this is due to gasoline prices. The biggest airline in the Caribbean is LIAT ( . They operate throughout the Caribbean. Previously they offered an option where you could buy a multi-travel ticket that included a certain number of flights, or was valid in a certain time period, but they have stopped doing that. There are often various offers on their website which is worth noting if you are flexible and willing to take "last minute" tickets. In the Eastern Caribbean, there is also a company called East Caribbean airlines which usually is cheaper than Liat in this area. From Trinidad and Tobago, and from the Netherlands Antilles there are various other smaller airlines flying between the islands and South America.

Here's the best overview of all the small airlines around the Caribbean;

This list does not cover all the companies. Within the Caribbean, it is possible to find smaller airlines with very limited departures and routes. Several of these do not even have websites or updated contact details.

Copilot i Karibien

Co-pilot in the Caribbean

When we were in St.Croix we had a problem finding transport to St.Kitts and Nevis, and on to Dominica because Liat was too expensive, but apparently the only option. I talked to local people in St.Croix and heard about a company called "Coastal air». It consisted of a man named Mike and his ancient 70's Cessna plane. I did not find any website or email-address, only a phone number. I called him 10 twice daily for 4 days, desperate for a ticket. There was no response, only an answering machine. When I had almost given up trying to contact Mike, he called back and asked if "we wanted to join him on a little flight». I ended up organising a special agreement with him where he dropped us off at Nevis and came back to pick us up 4 days later and took us to Dominica. It is the first time a plane has landed at an airport just to pick us up, and it was cheaper than doing the same journey with Liat. I even got to be co-pilot on one of the trips. It was a pretty fun experience, and a typical example of how flexible you have to be to be able to island-hop in the Caribbean.

The best way to get to South America without flying is from Trinidad to Venezuela by boat.


The Western Caribbean islands: There are no ferries between the countries (except the boat from the Dominican Republic to Puerto Rico). It may be an option to try to find fishing boats or commercial boats/mail boats for transport between the individual islands, but it is very difficult and impractical to organize. We went to Jamaica with plans to go to the pier in Montego Bay to find a boat to Haiti. There is sporadic information about boats that go to Haiti and Cuba from Jamaica, but it can not be arranged on the web. The problem that then arose was that customs officials in Jamaica requires seeing a flight out of the country to let you into the country. Of course you can easily make a fake e-ticket, or buy an expensive flexible ticket which you then cancel and get all your money back, but that requires some extra work. It is also very uncertain whether you actually manage to find a boat at the right time. There can be weeks between each time a boat goes in the right direction. Another thing to consider is your gender. If you are female it's generally not a good idea to isolate yourself on a boat with a bunch of dubious Caribbean sailors. See the next section for hitchhiking with sailboats, which is a little more convenient way to travel. It is possible to take an overnight ferry from Dominican Republic to Puerto Rico, but I found out that the plane (Iberia Air) was both cheaper and easier. It is also possible to take ferries between the islands of Puerto Rico. They go from the main island to Vieques and Cunto. From Vieques there are small planes on to St Croix (Cape air – cheap).

East-Caribbean: There are more options of transport between countries here, and between islands within each country. There is a ferry company operating between Guadeloupe, Martinique og Dominica – . There are no ferries between Dominica and St.Lucia and St.Vincent, which can create problems for onward travel. We chose to skip St.Lucia and travel straight to St.Vincent and the Grenadines, but we still had to make a transit in Barbados for a stopover. From St.Vincent the rest of the journey is fairly straight forward!

Ferry from St.Vincent

Ferry from St.Vincent

I definitely recommend island hopping in the grenadines. They are some of the most beautiful islands in the world, and except the yacht/sailboat-owners they are almost totally devoid of tourists. The only downside is that it is relatively expensive to stay there, and the people there are some of the grumpiest people we met on the entire trip around the world. There are scheduled ferries between Kingstown-Bequia-Canouan Mayreau-Union-island and all the way south to Carriacou (another country) and on to Grenada. From Grenada it is relatively cheap to fly to Trinidad and Tobago. There is of course a ferry between Trinidad and Tobago (, but if you have limited time I recommend booking flights directly to Tobago and skip Trinidad. The flights cost about the same as the ferry, and is definitely the best option if you already know you're going to be at the airport in Trinidad. Trinidad has very little charm, and Port of Spain has a reputation of being one of the most dangerous cities in the world. Tobago is more like a typical Caribbean tropical paradise, however, they have their problems too.

Hitchhike with sailboat This is definitely one of the more exciting and adventurous options. It is not necessarily the easiest option, but could potentially be the cheapest, most social and most convenient way to travel. If you find a sailboat that can take you, you become part of the crew. That means you need to help where you can. If you only want to pay for someone to take you from A to B then it is probably cheaper to fly. The advantage of being part of a crew is that the boat serves as transport between the islands, as a hotel and a restaurant - all-in-one !

Sailing in the Caribbean :)

Seiling i Karibien 🙂

To do this you must necessarily be a social and outgoing person, be flexible and willing to sleep a little cramped and rough and be open to new experiences. There is 3 ways to organize such an experience; check the internet for sailboat-owners looking for crew to share costs and work with, go to a popular sailboat-port and get to know people on the street, the pub and sailboat-club (requires you to use your social skills) or hang up notes in various harbors and pubs in the hope that a captain will contact you. If you hang up notes you should be prepared to wait 1-2 weeks at the same location. Tortola in the British Virgin Islands is definitely the biggest sailboat harbor in the Caribbean, and the place with the best chance to find someone. St.Croix is ​​also a good place. In Eastern Caribbean, Bequia is quite popular among sailboat fanatics.



Secret option number 4 is to simply buy your own sailboat. If you are comfortable sailing you can gather up 4 friends (or search for crew on the web) and go to Miami and buy a boat. It's amazing how cheap sailboats are in Florida. I heard about large sailboats with 6 beds for less than 25 000 dollars. After you finish your Caribbean-journey you can probably sell it for close to the same price (unless you crash the boat). If you choose this option then please contact me, I already volunteer as crew, your guide to the Caribbean and robotdancer (as required). Here are some websites that are good to look for vessels that require "crew"; , , . There are also many other resources to find sailboats.

Cruise If you are considering this option there is no reason to read this article,Cruise i Karibien

as it is for independent travelers who do not appreciate the sheep-herd way of travelling. Most cruise ships leave from Miami and take a little trip to a few of the islands. On each island, you are guaranteed to be greeted by hundreds of locals who make their living selling stuff and crap to cruiseship tourists. Throughout my journey in the Caribbean, I did my best to avoid the cities and ports where the cruiseships docked.. Once in Dominica, I found myself in the middle of the spill from one of the cruiseships. It was not a pretty sight. Hundreds of American senior citizens with small pink sun-hats invaded my little tourist-free paradise. I can understand that even independent backpackers need to relax once in a while, so cruiseships can be an option as a little vacation from your vacation, a small travel-break to relax on a cruiseship.

Swimming This is not an option I would recommend, as previously mentioned. It is very inconvenient with respect to luggage, and there are relatively many dangers associated with swimming in the Caribbean. If a shark does not eat you, there are strong currents and bad weather in the Caribbean that can kill you. I can understand the temptation because you can sometimes see the next island, but still have to pay $300 to fly there, and you sometimes have to fly through 3 other islands first. If you are considering this option I would recommend Full immersion courses, and many training classes in a pool and in safe seas.

Swimming after a boat

Swimming after a boat


How to arrange cheap accommodation in the Caribbean?

It depends very much on which island and which country you are in. I Cuba, the Dominican Republic, Mexico and to a certain extent Dominica, Trinidad and Tobago and Grenada, it is possible to find reasonably affordable guesthouses, especially if you are 2 traveling together. A single room and a double room usually costs exactly the same. Somewhat reasonable on these islands is something like 30-50$ per night for one room. Sometimes you can be lucky and find guesthouses on hostelbookers, hostelworld or , but many of the cheapest places have no website. You may be lucky and find useful information by searching on google, and see what guesthouses people on various forums have found. Before we were going to Roseau in Dominica, I found nothing better than 60-70$ for a room. I checked on google earth and found a few names of guesthouses that were not listed elsewhere. We went there without a reservation and were lucky enough to find a rasta-nest/guesthouse at 30$. It is one of the saddest rooms I've ever seen, but it was cheap. Often the only way to find a cheap room is to actually go to the island. Sometimes when people see you on the street they invite you to stay with them for a small sum of money, a kind of homestay. We did that a couple of places in the Grenadines as most of the options there are horribly expensive. If you're looking for someone who does homestay the best way is to ask random locals on the street. These islands are so small that everyone knows everyone, and any random person can probably steer you in the right direction. We arrived to a very small island called Mayreau, and I found a place to live before I had gotten off the boat. The boatman's sister coincidentally had a reasonable ground-floor flat!

Our trip through the Caribbean would have been very difficult to complete without couchsurfing – Many times we planned the whole trip around the country and the island where we could find people who could host us. The two economic factors that governed the journey were; where can we find fairly inexpensive flights, and do we have anyone to stay with?

Couchsurfing i Grenada

Couchsurfing i Grenada

In St.Croix, St.Kitts and Carriacou the cheapest hotels were very expensive (150$), and not even an option. They were amazing islands, and I'm happy we went there, but could not have done it without couchsurfing. If this is your plan, it helps to host people in Norway (or your home country) first so that you can create a good profile with many references.

Camping - Some of the islands in the Caribbean have campsites where you can pitch your tent, and have access to showers and electricity. They can be relatively expensive, up to $30 per night, but it depends on where you are. Few of the islands in the Caribbean allows pitching a tent on a random beach. It is a possibility, but may result in penalties.

Hotels – Usually quite expensive in the Caribbean.

Some other good articles:

 Posted by at 4:17 pm

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