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Wait. There is something different about this summary. With 13 independent island nations, god knows how many separate islands (over 7000!) and many more dependent [overseas territories] it just isn't practical to list country all countries with full summaries.
So we have split
this section by regions as much
as we could since each region is pretty similar - the regions are explained
to the right. There is one overview and summaries for the two
biggest and most interesting countries (Cuba and Jamaica).
There is also something different about the Caribbean too, in that travelling freely and independently (certainly on a budget) just isn't possible in the same way as in Asia, the Americas or Europe. As a region, despite the fact it is tough to get around, short on 'attractions' and expensive it is, in places, sensationally beautiful and impossible not to fall in love with.
As always if you decide these are some of the countries you want to visit and need more planning information then you are strongly recommended to complement what you find here with a planning guide. Trust us it will make life much easier. If you are set on going and need a guidebook or reading material please see a list of recommended guides/books here (go on, have a look). All guides/books can be viewed in more detail and click-through purchased with Amazon in the UK, US or Canada. Plus shopping through the site is a big thank you (if you have been helped out), to see why click here.
It is worth looking, if you have not already, at the example layout to see the guidelines each section of information is based on - or for other travel advice and site home head for www.travelindependent.info
It is important to start with a little geography
as 'the Caribbean' can be a pretty open term in which some include parts
of Central and Latin America under. For the record we only
Caribbean Islands here, which have four distinct regions: (working
West to East and then South to North) - The
Greater Antilles, that's Cuba, Jamaica and Hispaniola (Hispaniola
being the island that is split between Haiti and Dominican Republic).
After Puerto Rico (an American territory) as you hit the British and America Virgin Islands, you come to a large group of small islands known as the Leeward Islands (note, the Leeward Antilles are something else off Venezuela (the ABC islands not covered here). Here you'll find most of the small islands - a mecca for yachts - such as Saint Kitts and Nevis, Antigua and Montserrat.
Then heading South towards South America you find the Windward Islands or Less Antilles - Dominica, Martinique Saint Lucia Saint Vincent and the Grenadines and Grenada. The last in the chain, really part of South America, is Trinidad and Tobago.
The Bahamas and Turks and Caicos Islands are considered part of North America and because not so budget independent traveller friendly are more or less excluded from this page. The Leeward and windward are of course loose terms from an age long since passed and there are many examples of islands some consider in one or the other group. We just keep things simple here!
The answer is both yes and no, depending on your expectations. Yes, in that as much
as 'of course it is', you can travel virtually anywhere on the globe and there
are some great destinations within the region. And no in that don't expect to
hop from island to island freely and cheaply. In fact if you have any expectations
of cheap travel, island hopping and a network of facilities (such as hostels)
geared to budget travellers (such as in South East Asia) you are going to be
sorely disappointed. With a few exceptions in the Lee and Windward Islands,
island hopping across the whole region just isn't possible [on the whole]
by ferry (and inter-island airfares are expensive). Equally any travel
without a return/onward ticket can be problematic.
The other issue is cost. The Caribbean is no more expensive than Europe or North America, but finding cheap places to stay can be tough (US$40-100 for a double needs to be considered an average for a private double (outside Cuba, where US$15-30 is more normal)) and the same goes for cheap eats. Transport is not too pricey, but public transport can be patchy and a pain on Sundays or late in the day. So you will need to use local taxis at some point. Thus getting the best out of many countries requires a hire car which will likely be slightly more expensive than in North America/Europe.
The key consideration for most of the Caribbean (greater Antilles aside) is the countries/islands are tiny with generally little to see/do (apart from hang-out, the appeal for many) and with small populations. Where there are no direct flights from North America or Europe (Saint Vincent, Dominica, etc.) the number of tourists is also tiny. Small islands, small populations and few tourist make islands idyllic, but can also limit you to no/little transport, no/little choice to stay and the urge (if time pressured and unable to find a nice place within your budget to kick back) to want to move on - when perhaps the next ferry is only in several days' time. That's a down-side, the language, people, music, clear water, scenery, rum, occasional sense of isolation and leaving 'it all behind' do go a long, long way to compensate.
Highlights: Jamaica, its vibe and beauty. Cuba its equally special vibe and sheer uniqueness (no where else in the world quite like it).
Carnival in Port of Spain, Trinidad and Santiago de Cuba. It goes without saying it is impossible not to love the language/slang, rum, dominos, sunsets, music and friendly faces. And of course for anyone lucky enough to see the region on a small boat/yacht.
Lowlights: It's not cheap and many [smaller] islands have limited attractions along with major hassle/cost in moving onwards to find more to do/see. Food in many parts is not only expensive, but uninspiring (Jamaica aside).
Cruise ships and the periodic crowds they bring are also a downside if they affect your plans due to the sudden influx of temporary visitors.
The Bahamas, although stunning away from major entry points is the most heavily developed, expensive and American influenced.
Onward travel and naturally the crime and violence that unfortunately affect many urban areas (although playing dominos in a small town on a small island it won't be further from your mind -nevertheless you do need to take care especially after dark).
Getting Around: For ferry options, see right. The regional airline is Leeward Islands Air Transport or LIAT (Luggage In Another Town or Leave Island Any Time, which say it all for the reputation). Caribbean Air is a second option with a smaller network focused on Jamaica covering only the major islands. As part of Air Jamaica there are good connections with Air Jamaica into Jamaica from North America and the UK. Getting into the region from Europe the UK and Paris are the best/cheapest hubs.
Apart from Cuba, where you need a 'Tourist Card' the region is pretty much visa free, but getting around a few countries on a loop on one-way tickets can be problematic.
So what to do? Well booking ferry tickets in advance
outside of the region/country is near on impossible and booking
onward plane tickets for a long journey removes any flexibility
which is the joy of travel. In situations where you plan to move
onwards using private transportation (such as a charter or yacht)
it is even more difficult. So if you are transiting/travelling through
countries that you don't have a fixed booking to leave from, you
are strongly advised to have evidence at hand showing onward transport
- even if you have created it yourself. We have handled this previously
by simply editing the text on a previous/old flight booking confirmation
to read as if we have a booking to leave on a later date.
We have also been advised that a letter from a yacht charter company (put together yourself) or similar that you will join xyz vessel on a certain date is another option. To someone selling you a ferry ticket, a print out of a flight confirmation is an easy simple option to get a one-way ticket and no way will it be checked (as long as it is realistic). The same goes with a flight-check in (obviously with a different airline than the one you are checking-in for). We have put such a confirmation/reservation in front of many with no issues and in the event there was - you could simply plead ignorance or that your travel agent screwed up. The other option is the purchase of a return ferry/plane tickets for every leg - an expensive option.
Money: There are plenty of ATMs in the Caribbean
and you can use credit cards in many situations. The USD is king (many
of the regions currencies are pegged to it). Many of the smaller
islands (Anguilla, Antigua/Barbuda, Dominica, Grenada, Montserrat,
Nevis, St. Lucia, St. Kitts, St. Vincent and the Grenadines), have
a shared currency in the form of the Eastern Caribbean Dollars (or
EC for short). This and most of the local currencies are referred
to as 'dollars' (e.g. Jamaican Dollar, Barbadian Dollar, Trinidad
and Tobago Dollar, Bahamian dollar).
In these cases and with EC when you are quoted a price (and certainly near cruise ship ports) make sure it is for the local currency rather than US dollars. The French Islands (Guadeloupe, Martinique, St. Barts, St. Martin) use Euros and Puerto Rico, Bonaire the British Virgin Islands (BVIs) and the US VIs use USD. In Cuba both USDs and Euros are perfect, but there is a small transaction tax on USDs so if you get the choice, Euros are better.
Bahamas - daily ferries (in season) from Fort
Lauderdale, Florida. No regular public onward transport via water to
other island nations.
Greater Antilles: Jamaica, Haiti/Dominican Republic or Cuba - fly in/out only. All have regular flights from Europe and North America (apart from Cuba which is best accessed from Canada or Mexico) and regionally, with Jamaica being the best connected locally.
Leeward Islands: The following island group is connect by ferry - Puerto Rico, USVI, BVI / St. Martin, Anguilla, Saba, St. Bart's, St Eustatius / St. Kitts, Nevis / Antigua, Barbuda, Montserrat. To get between this group to another you need to fly (or have a yacht) or there is a once a week ferry between Nevis and Montserrat - but double check it is still running when you read this (M.V. Caribe Sun). It should be noted that Antigua is the air hub for the regain for LAIT airline. Puerto Rico has the cheapest flights from the USA and a main cruise ship boarding point. For Guadeloupe, see below.
Windward Islands: Barbados and Trinidad/Tobago are fly in/out only (although between Trinidad/Tobago there are good/regular ferries). From Guadeloupe a good chain of possible island hopping ferries starts where you have connections via Express des Iles from Guadeloupe to Dominica to Martinique to Saint Lucia. From Saint Lucia you need a flight to the neighbouring island of Saint Vincent (or Barbados to the far East). From Saint Vincent you have the possibility of a daily (M/V Bequia Express) service to Bequia. Then from Bequia (or Saint Vincent) you'll find a less regular ferry all the way down the Grenadines (M/V Gem Star - other services come and go). When you hit the last island (Union Island) of the Grenadines you can wait for a public ferry if available or find a local to take you the short hop to Carriacou the first island in Grenada (this won't be cheap at between 100-200 USD for the whole boat depending on your negotiation skills and fuel prices) or take the twice weekly ferry to Carriacou. From Carriacou you have a good ferry to St. George in Grenada (the main island) from where you then need a flight to move onward from.
So..... the three main hubs (starting points) to 'explore' from via ferry are from Antigua and around (least recommended group due to island size and costs - best suited for those with their own boats), Guadeloupe/Martinique (one of the best apart from the fact the 'French Islands' are pricey and touristy) and Grenada/Saint Vincent/Grenadines (the least touristy, but most remote, experience). If you want to see as much as possible and cover the region overland - fly between the Greater Antilles (or visit separately) and/or from Antigua with only three small flights you can get to Port of Spain in Trinidad. Or with only one flight from Guadeloupe/Martinique all the way to St. George in Grenada. Either way, as you see, it is not easy, ferries are no bargain and getting into/out of countries without providing some evidence of onward travel can be painful. Flying (LIAT is unfortunately the only realistic option for the most part) can get you just about any significant island.
Through out the Caribbean you will see these massive vessels off shore and in dock. There are a few countries where these vessels cannot dock anywhere, but on the whole they visit every territory (apart from St Vincent and the Grenadines, Cuba and the smallest islands).
On one hand they provide a nice tour of the region with no discomfort and a snap shot of many islands for their guests. From a practical point of view for those not on board, the area directly around the typical docking port will have a different flavour and will be crawling with tourists and touts on days when a vessel is docked. On these days every conceivable attraction, natural or otherwise will be totally over-run by - typically badly dressed - tourists who on the most part seem to want nothing more than to get back on their boat. Waterfalls in the likes of Dominica and Jamaica that can be a deserted oasis of peace and calm on one day will be total zoos the next. Just the way it is.
Get your bearings... show/hide map of the region
There is one thing beyond all doubt, Jamaica is stunning and one of those select few places in the world where natural beauty is abundant. As you would expect many of the beaches are pretty good too. Long
of golden sand on crystal blue waters with many little hidden beaches where a clear rivers runs into the sea from a virgin forest or cane field.
As great beaches and natural beauty are not something lacking from the
Caribbean as a whole, what really sets Jamaica apart is it shows them all off with its crowing features: the vast
mountains in its interior and a vibrant culture.
So undeniably Jamaica looks great - and the food and music are awesome too - but clearly the down-side is the crowds that flock to it and who are comprised almost totally of package tourists or cruise ship passengers. Those exploring independently are few and far between and as such facilities for backpackers are not plentiful - especially if on any sort of a budget. It seems the concept of someone without pre-booked accommodation for every night of their stay is an enigma in Jamaica and don't try to explain it to immigration or tourist officials. Equally the 3-4,000 cruise ship passengers, most getting off the boat for only the day, - (over 1.3 million a year, on top of over 2 million long-stay visitors) in a country where the majority of the population scrapes a living - clutching hard currency will have an inevitable effect on how visitors are treated/greeted in parts (there is a lot of hassle in major ports and resorts) and how busy some attractions get.
So to get the best from Jamaica you need to get well away from the major resorts and cruise ship ports (located mainly around Montego Bay), have a reasonable budget, explore the interior away from the beaches (for this you really need your own transport) and find your own little corner of paradise in the more budget orientated and independent hide-always such as Treasure Beach and many places in the East of the island.
Crime and violence is certainly a widely reported issue and you need to take care anywhere after dark and certainly after dark in urban areas (as in Africa, Latin America and parts of Asia), but most of Jamaica's astronomical crime/murder rates is not aimed at or concerned with tourists, and on the whole Jamaicans are some of the loveliest bunch of people you may care to meet (that is well away from a major resort or cruise ship ports). In compensation you have an island easy to self-drive and explore by car, with best in class food (vegetarians and vegans will enjoy it in particular), music, beaches and scenery. The core issue is someone spending one week in a Montego Bay resort is likely to have a low opinion of Jamaica, the same person taking in more of the country well away from the best beaches and major air/sea ports will feel totally different. The fact remains along with the likes of India there is so much to like and dislike about Jamaica that your ultimate opinion will depend on what you can see/do and moreover manage not to see/do.
The jury is out on: Negril - although cruise ships don't call and there is no lack of bars and fun, along with a sunset/beach to die for, Negril, the original backpacker/hippie corner/resort of Jamaica is clearly over-developed and with a probability (depending on the season, bar and where you stay) of a crowd you might not want so many of around. The hippie feel still exists and is reflected by a collection of neat places to stay and the odd place with 'special' ingredients to some dishes. It all comes at a price and is clearly on the package tour industry map.
Highlights: The more remote areas where small scale independent places to stay and restaurants have sprung up. Examples are Treasure Beach, Strawberry Field, many parts of the Eastern part of the island, plus many more. The scenery, the rum, the dominos, the locals, the views in North Eastern Coast and the language. The local food/music and getting off the beaten track to interact with the locals.
Lowlights: The prices - Jamaica is [like most of the region] not cheap (when compared against most of Asia or Central America). Unfortunately there are many private beaches and large areas of prime coastal land not accessible. Getting around without a car, lack of cheap places to stay or simply independent places to stay outside the resort or large hotel model. Crowds at attractions on days cruise ships call.
Some persistent hassle around main resorts (although it is much better now than in years gone and you can't blame the locals from trying to make a living in a tough environment). And lastly coming across a group straight off a cruise ship or package resort that leaves a lot to be desired in their behaviour/attitude to the locals, culture and environment.
Visa strategy: US, Canadian, Australian, and EU passport holders do not need a visa.
Typical tourist trail: Very few travellers to Jamaica actually go very far. The key resorts are on the northern coast near Montego Bay and Negril. Some visitors will make tours from their hotel resort to places such as Nine Mile and the Blue Lagoon. Those independent travels who do visit will typically make a beeline to Treasure Beach, but when on public transport won't go/get too far. Those with a car will typically follow a loop around the island perhaps focusing on the Northern and East coast the most.
Getting around: As with Cuba, to get the best out of Jamaica you need to hire a car. The roads are good for the most and driving is easy. If you can afford it, a small 4WD is best for bumpy/poor rural roads. Car hire is slightly more than in the USA or Europe, but worth every penny. For those who cannot or won't drive there are frequent mini-vans along the built up areas of the coastal roads and long-distance buses across the country between major towns. The problem is these take you on the whole to and from the city centres which are the last place you want to be and always from the accommodation options and attractions which are normally well outside urban areas. Jamaica is totally possible and fun to get around on public transport, only you'll get to plenty more places, see more and save loads of time if you can club to together and share the cost of a hire car.
Costs: You'll need between US$50-80/day per person between two, with the average room normally costing between US$50-100 and the balance being spent on food/drinks and transport. If you want to stay in more upmarket places and take the odd tour you need to probably double this amount.
Money: Plenty of ATMs. Take USDs as a back-up.
Communications: Wi-Fi plentiful.
Guide book: Rough Guide read and worked the best in our test
Dangers: Gun crime and gun violence is an unfortunate reality within Jamaican society and it is worth note driving after sun set or being on the streets after dark with anything of value in areas not normally frequented by tourists. However whereas inner-city murder and gun crime rates are on a per capita level through the roof, much is political violence or drug-related and not target against tourists.
Locals: As with the likes of India you will find an extreme cross-section of locals from those who can be extremely aggressive, persistent and/or rude (normally around tourist areas) to the most beautiful friendly welcoming and peaceful people you can imagine, whether a Rasta running a beach cafe or a housewife in a rural area - although as you guessed you need you need to far away from the tourist hotspots to meet the best people.
Other travellers: Typically American and Canadians (although more Canadians do gravitate towards Cuba) along with a splash of Brits. Most will be on package tours and you can come across in the younger crowds some less than respectful behaviour. If a cruise ship is in port most of the visitors at any attraction are probably from it and again typically American. Independent travels are typically North American, European or ex-pat Jamaicans visiting their home country.
Hot water: Typically, but not always in the cheapest of places.
Average cost: It is possible to find rooms for US$20, but not probable outside certain areas/seasons. More likely is US$75-100/night for a double. There are no hostels or backpacker geared places outside Kingston. Although the standard is generally high for your money and cost/standard is in line with the rest of the [English/French speaking] Caribbean, prices are way, way more than in Central America or most of Southern and South East Asia.
Language: English spoken. If English is not your first language you may struggle with the accent.
Food: Jamaica has a great and distinctive cuisine and plenty of outdoor cooking. Most popular are patties and jerk is a style of cooking in which meat (normally chicken or pork, but often also fish and many other dishes - even tofu) is dry-rubbed or wet marinated with a very hot spice mixture called Jamaican jerk spice. Some dishes can be bland due to proportion of yam and other sweet potatoes used, but jerking adds a kick to the rest. The national fruit is the Ackee and is cooked with saltfish to form the national dish of Ackee and saltfish, which is superb.
Vegetarians: By virtual that the Rastafarian religion precludes eating of meat, there are great vegetation and vegan options available.
Hassle and annoyance factor: Some persistent hassle, notably around Montego Bay and Negril.
Women alone: Fine, but with caution if travelling widespread
Tourist factor: 8/10
Local poisons for the body: Bars are split clearly between those aimed at and used by tourists (live music - almost
certainly a Bob Marley track played - fancy decor,
cocktails, safely after dark and high prices) and those used exclusively by locals,
which are dark, not generally inviting and the main drink being consumed is 'overproof'
white rum (with overproof refereeing to an alcohol content of over 100% proof). To find the happy middle, you need to be
outside urban areas and somewhere more rural where you can enjoy a Red Strip or Rum
and Coke with a game of dominos
and watch Jamaicans interact with each other without blaring Dancehall music
or urban tension/youths. These you find more with ease in the more relaxed corners of the island.
You may hear cocaine offered around resorts, but ultimately the drug of choice and fame in Jamaica is cannabis. Getting hold of some weed is not something that takes much effort and there are clear hot spots for its sale. Almost everywhere you will catch its scent and get hold of in the same way as you might ask for a spare cigarette. Despite the widespread smell of ganja emanating from every other set of dreadlocks and offers of plenty of trips to see 'me [sic] plantation', there is no real centre for it where its use by tourists is tolerated. In fact police are all too happy to 'stop and search' a car and shake you down for so much as a jumbo rolling paper and would in turn march you to the station (or look for a bribe) if they found anything actually illegal. So be warned and don't carry anything around in your car/person that might be found. It is one rule for the small-hold-farming Rastas in mountains and another for tourists. Decriminalisation is still a long way off in Jamaica.
Rating: 8/10 (with some spare cash)
Cuba is unique in the Caribbean and throughout the world, and there is much to like
in terms of a travel destination.
Things are changing fast, but essentially you have a two tier system within the country
- one for visitors and one for locals. It is this two tier system, the politics that created it and the prolonged period of isolation that makes Cuba so special.
To enter a country isolated from the rapid development the world has undergone in the last fifty years is
extraordinary, to see the still strong remains of a period [the 1950s] - when clocks, as it were, stopped in Cuba (the
revolution) - in the architecture, interiors, cars, decorations etc., is
astonishing. Above this all is also an island of stunning natural beauty and to top it off,
friendly, welcoming locals and cheap rum/seafood.
The dilemma in all this is it is clearly the politics and isolation that makes Cuba so special and has preserved it,
yet in those politics and
isolation is a situation that has (and still is) making life very tough for millions of
Politics aside, Cuba is very different to other countries in the region and around the world from a traveller's perspective and for that reason it is hard to know how to approach this summary. Given these unique particularities, there is already much written on the internet about the practicalities of Cuban travel (although less from a backpacker perspective), so this information is kept brief. Travel in Cuba is a little more expensive than you might at first think, but travel is easy and arriving on one of the many daily flights from Europe, Canada or Mexico, picking up a hire car, hitting the road and staying with locals is easy and something that should not be missed. Cuba is also the biggest (single country) island in the Caribbean and there is a lot to see. It is thus easy to bite off more than you can chew, especially with the 'big three' highlights of Varadero's extraordinary beach, colonial Trinidad and the capital Havana, having enough to suck up plenty of your time and tough to pull yourself away from.
Hiring a car is by far
the best way to go as driving is simple on near deserted roads. You'll have the pick of the country
opportunity to stop in more out of the way locations and meet the endless
streams of locals always
looking for a lift. If you can't afford to rent a car (it's not overly cheap)
or don't drive there is a good
efficient network of inter-city buses, but as a foreigner you are limited to specific
bus line(s), being locked into their timetable and the network does not allow for
spontaneous exploring. On shorter legs you will be at the mercy of taxis
that can become quite expensive.
The food can be a little bland, although with a little cash to splash out, the seafood is exceptional value for money, and the various rum cocktails and local cooking ingenuity more than make up for any limited choice suffered. Naturally, imported items are expensive and essentially only on sale for the tourists and Cubans with relatives abroad that can afford them. Other than this there really isn't much not to like. Cuba is changing fast, and for the better with restrictions on private business lifted, making independent travel much easier (such as locals providing food and lodging). It will keep on changing with further relaxation even attracting more foreign capital. The thoughts that every visitor is stuck with are how will these changes affect the country? And a guilty pleasure in seeing it 'before' any major change whatever 'before' or the change may be.
Highlights: Havana, Trinidad, Santiago. Partying like it is 1959. Exploring and getting to know towns slightly off the tourist trail such as Cienfuegos and really getting anywhere off the normal tourist trail. The people, self-driving, architecture and beaches.
Lowlights: Package tours and resorts, the cayes and high cost for of imported items.
Visa strategy: Most nationalities visit visa free, but you need a 'Tourist Card' or tarjeta de turista which you need to buy before arrival. Most package tourists have these sorted out for them, but for everyone else you need to buy one in advance. If there are flights to Cuba from the country you are in you will find one easy to pick-up from the embassy in person or by post. Costs vary, depending weather you go in person or not and where you are, but the process is simple and you'll pay about US$25-50. More often than not the airlines flying to Cuba sell them, so if you are a US visitor, buy your tourist card at the airline desk from your country of departure. Aside from the visa/tourist card, you are also required to have and prove you have travel/health insurance for the duration of your trip. There is a high chance your normal travel insurance won't cover you due to US sanctions, so get on the web and buy a short stay policy that does or buy the basic insurance from the airport when you arrive.
Typical tourist trail: Probably 90% of those visiting Cuba, take in only Havana and Varadero (the near-by impressive beach/resort) and to honest you could fill a week on these two alone. Those with more time and energy to make the journey will most likely take in Viñales (an area in the West with limestone karst mountains/hills which is slightly overrated) and the standout highlight on the south coast of Trinidad. Cienfuegos nearby is often included in a typical itinerary and there are many stops of interest between/around Havana and Trinidad that can be made. Package tourists often head to the Northern coast Cayes to purpose built resorts where great bridges connect the series of islands to the main land. And lastly those with time take in Santiago in the East.
Costs: Cuba is expensive to fly to. It is expensive for imported items and foods; fuel and car hire are not overly cheap - but not too bad. On the whole (for accommodation and local produce) Cuba is great value for money.
Money: There are two currencies in Cuba, the CUC (Convertible Cuban Peso) and the CUP (Cuban Peso). Much is written about these two 'systems',
but it almost doesn't make a difference to a visitor.
The essential difference is you (as the wealthy visitor with
access to hard currency - even the most cash strapped
backpackers are wildly rich compared to locals living within the
state system) have and spend convertible pesos. You will have CUCs and spend CUCs
which are pegged to the US dollar, no need to think about CUP,
you probably won't even see them and locals certainly won't want them
over CUCs - anywhere that takes CUP will take CUC at a rate everyone will know.
As a foreigner you are expected to pay for everything in
convertible Pesos (technically you can't change your money into CUP - nor would you really want to -, but can get hold of them if you really want) and this is no great hardship.
It is true that tourist are at times slightly over-charged using CUCs, but given the CUP state system is a low standard and the tiny wages most Cuban live on, losing a few dollars by overcharging here and there is not something anyone who can afford a plane ticket there should moan about.
Communications: Your mobile phone will work and you can get a data connection, but the network is state-owned with crazily high roaming costs. You are best advised to ensure all data roaming is turned off and you don't make/receive calls (use SMSs). Internet can be found in big/package hotels, but it is slow and expensive. Forget about Skype and leave your laptop at home.
Guide book: All the major travel guide publishers have good options.
Getting around: As with Jamaica, the best thing you can do is hire a car, the road system and major roads are good, plus there is very little traffic. Hire car costs are expensive compared to the USA and Europe and to pre-book a car you normally use an agent in Europe paying in Euros. If you can't or don't want to drive, then there is a good public transport system between the towns of major tourist interest (but you will miss out on the gems between the attractions along with the opportunity to get to know the endless tide of locals who hitchhike). As a foreigner you are restricted to one (and the best) bus company and since the local transport is very basic (along with the fact you are banned from it technically) getting short distances is impossible unless on foot/bus or in an often expensive taxi. Domestic flights are available from Havana to Santiago and Trinidad.
Locals: Cubans are on the whole friendly, welcoming and hospitable. However having good, basic in Spanish is essential in getting the best from locals and using your time with them to understand the country and its psyche.
Other travellers: Most package tourists are Canadian, most independent travellers are European (French, Italian, Spanish, German, British), there are naturally few Americans.
Visiting as an American: If you are a US citizen you are technically breaking US sanctions not by visiting, but by spending money (which in turn makes it impossible to visit). As an American in Cuban you will be welcomed with open arms and are free to visit without restriction (the restriction is on the US side). Many Americans visit Cuba each year trouble free, you just need to pick up your flight in Canada, Mexico or similar and keep your travel destination to yourself [from US authorities]. Restrictions have been lifted in recent years (even The Simpsons made it!) but even with Castro dead free access tourist travel (you need another reason) for Americans is some way off.
Accommodation: There is
plenty of accommodation in Cuba, split into three very clear categories.
State-run big resort hotels, often on the cayes or more remote areas of
coastline. These are expensive and not really setup for walk-in
business. Secondly, you have smaller state run hotels which can be great and a window to
the past, but can also be overpriced and with poor service/standards.
And thirdly the staple and one of the highlights of any trip to Cuba:
Casas Particulares. A Casa Particular
(Spanish for private house) are private homestays where (since 1997) is a
private household can rent a room or rooms to tourist. Sometimes these
rooms are in a separate building/annex, sometimes they are part of the
main house. Often they are run older Cubans (since children would have
left home, leaving more room). Typically speaking, the owners are
extremely hospitable and the interior of their homes are a window into
the past and to that of the lives of Cubans. Think of it as like a bed and breakfast.
Casas particulares can be recognised by a small sign on the door, with two blue triangles ('roofs') against a white background, which the owners obtain after paying a fixed per-room annual tax. It is hard not to be able to find a room in a Casa particular anywhere close to somewhere on the tourist circuit and if you can't find one, there is normally someone to show you the way. Equally all the owners seem to know each other and will normally recommend a place of a friend in the next town you visit. However the very best and most charismatic ones do fill up and if upon scanning your guidebook, which will list the ones of particular note, you see something that takes your fancy, a call/SMS ahead is worthwhile (if only calls and e-mail where easier/cheaper!). There are now however even booking websites, but unless you are going at peak time and have your heart set on one address, it is better to play it by ear on the ground.
Average cost: For a Casa Particular between 15-30CUC - 25CUC is a typical price quoted for better properties in better locations. Bargain hunters will be able to get lower prices and it always makes sense to ask for a discount in low season. Note that not all Casas Particulares are registered (with the blue and white sign plus tax payment to the government) occasionally you can be offered a room in one of these (which is illegal - but still possible) at a lower price.
Language: Not a huge amount of English spoken outside Havana. It really helps to have at least basic Spanish and the more you speak the more you will get out of your trip.
Food: Breakfast is typically included at a Casa Particular and dinner is normally offered for an extra fee (most are keen to offer). There are plenty of places for each in tourist destinations (less so when you get away from the tourist hotspots) and food is good/cheap (cheap by Caribbean not Asian standards) - but can be basic. Seafood is the exception where prices are lower and standards are high. However, if a foodstuff is not grown or produced on the island [and has to be imported] it will be expensive. A Paladar means a private restaurant that has been permitted since 1994. These are normally restaurant set into homes (or outside) with few places, perfect for home-cooked food. Some are commercialized and expensive, while others are hidden and cheap.
Vegetarians: No problem
Hassle and annoyance factor: None really
Women alone: No problem
Tourist factor: 4/10, clearly Cuba is not touristy with most visitors staying put in one of many resorts, but at some points/places it can be a little busy.
Local poisons for the body: Rum dominates Cuba and every kind of cocktail that can be made out of it. It is also dirt cheap. Naturally you will find cigars aplenty, although the best go for export.
Ratings: Overall - 8/10; When you are on a tight budget - 7/10; For something unique and stimulating - 10/10; For peace and an easy trip - 8/10
"How much does a person live, after all? Does he/she live a thousand days, or only one? For a week, or for several centuries? How long does a person spend dying? What does it mean to say 'for ever'?"