Caribbean Travel Guide: Overview

With 28 island nations, the region of the Caribbean is a dazzling combination of mountain peaks, astoundingly bustling reefs and a long, fraught colonial lineage. Yes, sandy beaches and rum-based drinks make up one part of the distinctly Caribbean charm, but dig a bit deeper and you’ll start to see the startlingly diverse cultures that infuse these islands. Whether you’re looking to explore colorful reefs or understand an island’s foundational history, the Caribbean invites you to dive in at every turn.

Caribbean Travel Guide Overview

In many ways, the history of the Caribbean is the history of the various colonial powers that sought to control the land. Long before these colonial ships ever set sail, however, people had already populated and settled the various islands. The earliest evidence of human settlement here dates back to the mid-sixth millennium BC in Trinidad. By the middle of the fifth millennium BC, inhabitants had expanded to Hispaniola and Cuba. Successive groups of invaders then arrived, replacing the previous groups and settlements. Eventually the Mayoid, or Caribs, arrived through Trinidad and remained dominant until Spanish invasion and conquest.

Christopher Columbus is the first European man credited with landing in the Caribbean, claiming parts of current-day Bahamas, Cuba and Hispaniola for Spain. Columbus returned to Spain with a handful of natives, who had small amounts of gold adorning their personal objects, such as masks and belts. Seeing the opportunity for wealth in the region, the Spaniards and Portuguese subsequently came to the islands, enslaved the natives, drove them to near extinction and then supplemented their labor pool with African slaves. During this period, the Spanish officially claimed Hispaniola, Puerto Rico, Jamaica, Cuba and Trinidad.

As the Spanish empire weakened, other European powers asserted their presence in the Caribbean, including the British, Dutch and French. War frequently affected the colonial-era Caribbean, and this was seen most notably during the Thirty Years’ War, the French and Indian War, the American Revolution, the French Revolution, the Spanish-American War and many more.

Slave uprisings and rebellions helped eventually contribute to Caribbean liberation, and in 1804, Haiti officially became the first Caribbean nation to enjoy independence. Even today, several islands remain under European and US dominion.

As sugar production waned in the 20th century, the Caribbean turned to other means of economic diversification. With increased political stability, tourism became a staple of the Caribbean livelihood. To this day, the area remains an idyllic, beautiful and historically unique region for visitors around the globe.


Highly influenced by a number of other regions and cultures, including African, European and Asian, Caribbean culture is a diverse tapestry that reflects the many waves of migration that came through and settled the islands.

In the 1800s, much of the art and literature coming from the Caribbean followed the lead of the European colonial nation, meaning there was a great deal of French, Spanish and English influence.

In the more modern era, Trinidadian writer Sir V. S. Naipaul won the Nobel Prize in Literature (2001), as well as the prestigious Man Booker Prize (1971) for In a Free State.

The Caribbean region has also had recent exposure through sport—particularly the Olympics. Jamaica has arguably made the biggest splash in this arena with the flashy and superhumanly fast Usain Bolt and the Jamaican national bobsled team, on which the film Cool Runnings is loosely based. Many notable baseball stars (Nelson Cruz, Robinson Cano, Albert Pujols, Bartolo Colon, Manny Machado and many more) also hail from various Caribbean islands.

Music is also one of the most notable ways Caribbean culture has gone mainstream. From one-hit wonders (Baha Men with “Who Let the Dogs Out?” and Haddaway with “What Is Love?”) to multiplatinum recording sensations (Barbadian singer Rihanna and Trinidad and Tobago–born Nicki Minaj), the Caribbean has produced a slew of international recording successes. Robert Nesta Marley, better known as Bob Marley, was not only a Jamaican-born reggae singer and songwriter, but he ascended to the status of cultural icon, bringing Rastafarianism into the cultural mainstream.

Born in Humacao, Puerto Rico, and best known as Anita in West Side Story, the Academy Award–winning actress, dancer and singer Rita Moreno is another notable cultural figure of this region.

Good to Know

When traveling in the Caribbean, keep some of the following in mind:


Multiple currencies are used throughout the Caribbean, depending on the island. In all, eight countries and territories use the East Caribbean dollar, five use the US dollar, and four use the euro.

To encourage US tourism, many islands will accept US dollars. Even in these locations, however, it’s always a good idea to have at least some cash in the local currency for smaller purchases, tips and the like. Always make sure to research the specific islands where you’ll be traveling, though, as some categorically don’t accept US dollars. Cuba, for example, requires currency exchange, and beyond that, US-issued credit cards and debit cards don’t work here.

If you do need to take out cash, ATMs are generally available in well-traveled regions of the islands. In areas where US dollars are generally accepted, the ATM will often ask if you want cash in the local currency or US dollars. As in most places, avoid exchanging money at hotels or commercial exchange bureaus, where you’ll be hit with the highest fees and/or worst exchange rates.


As with many tourist-centric destinations, tipping is common in the Caribbean. Also expect to encounter various service charges and industry-specific taxes. For example, a 7.5 percent government tax will typically be added to hotel bills, as well as a 10 to 15 percent service charge. If you notice these extra fees, tipping is less expected. If you don’t see the fees, a $1 or $2 tip per bag is typical for bell hops, and cleaning staff usually expect about $2 per day for their service. If you’re in an all-inclusive resort, tipping is sometimes expressly discouraged as it’s already included in your rate.

It’s common to tip taxi drivers throughout the Caribbean. A $1 or $2 tip for an in-town trip is usually sufficient, but consider giving more if it’s Sunday, a holiday or very late.

Caribbean restaurants tend to include a 10 percent gratuity automatically on all bills. Tipping, therefore, is not expected, but if you received great service, an additional tip would be appreciated. If you notice your bill doesn’t include a gratuity, go ahead and leave a 10 to 15 percent tip.


The Caribbean is famously known as a laid-back environment, but that doesn’t mean there aren’t rules for public conduct.

Be friendly and sociable with your greetings, and make sure to show extra deference and respect to the elderly. Don’t be offended if you’re asked a particularly direct question. This is common throughout the Caribbean. If you’re very uncomfortable answering a given question, a smile and polite denial should suffice.

When it comes to dressing, beachwear is best left to the beach. Some banks and government offices even have explicit dress codes written on their doors, and these should be respected.

Lastly, “island time” might be appropriate for your vacation, but if you’re meant to meet a local at a specific place and time, try to honor that.


Depending on the island you’re visiting, you’ll encounter either 120 or 230 voltage, and you’ll also encounter a variety of plug styles.

Especially if your travels are going to take you to multiple island destinations, make sure you’ve packed a universal converter and adapter. If you’re sticking to one island, research that voltage and plug type before jetting off.


The availability, type and hygiene level of public bathrooms will vary from island to island—and even from location to location on a specific island. In general, however, restrooms will be readily available in hotels, restaurants and most public buildings.

Some restrooms will require you to pay a nominal fee for use, so always have a bit of spare change, just in case. If you notice a waste basket in the facility with you, that’s often for used toilet paper. (The plumbing on some islands is too narrow to accommodate waste paper.) If you’re ever unsure about whether you can flush toilet paper or not, simply look for instructional signs.

Especially at beaches and other public areas, bathrooms might not be fully stocked, so come prepared with a roll of toilet paper and a bottle of hand sanitizer.


It’s safe to drink tap water in most Caribbean islands, but there are exceptions, including Cuba, Dominican Republic and others. Do research about the specific destinations you’ll be visiting, and if you’re ever unsure, err on the side of caution. In those cases, opt for bottled, filtered or sterilized water.

When to Visit

While it varies somewhat between the island subgroups, in general it’s best to visit the Caribbean from December to May. This window of time avoids hurricane season and other severe seasonal storms.

If you’re interested in specific activities, such as bird watching, turtle watching or hiking, do a bit of research before settling on your travel dates to ensure you’re in an ideal window.

Read our When to Visit The Caribbean article for more info.
Fun Facts
  • The Caribbean is composed of over 7,000 different islands, but only a small percentage are actually inhabited.
  • The Caribbean has served as the backdrop for many famous films, including (not surprisingly) the Pirates of the Caribbean series.
  • The world’s shortest runway (about 1,300 feet long) is located on Saba, a Caribbean island.
  • Per square mile, Jamaica has more churches than any other nation in the world.
  • There’s an uninhabited island in the Bahamas known as “Pig Beach.” A colony of feral pigs populate the island and can often be seen swimming its many shallows.

Full Article Coming Soon!

Regions and Cities

Often associated with the slands of the Caribbean, nearby Bermuda is renowned for pink-sand beaches (yes, pink) and vibrant blue waters, Bermuda is what most people imagine when they think of a tropical paradise. Scuba dive or snorkel in crystal-clear waters, visit the Crystal Caves, or just lounge poolside and relax.

St. George's: The first permanent English settlement on the island, the town enjoys status as a UNESCO World Heritage Site. Students of the American Revolution will also be interested to learn about the Bermudians’ role in aiding the American rebels.

Hamilton: A vital economic center, Hamilton has the distinction of being one of the smallest capital cities in the world. With its green parks and humid subtropical climate, Hamilton is an always-popular stop for anyone traveling to Bermuda.


Cuba is a multiethnic boiling pot of diverse influences, from Spanish colonialism and its aboriginal peoples to African slaves and close Soviet Union ties. It’s a delight of dance, food and complicated history.

Havana: The beating heart and capital, Havana is an important economic, social and cultural part of Cuba. The imprint of Spanish colonialism can still be seen prominently in the city’s architecture, but to get the most complete picture, travelers should make sure to visit all three distinct regions: Old Havana, Vedado and the more modern suburban districts.

Jaruco: Protected as a park, Jaruco most prominently features the Escaleras (Stairs), which emerge from the plains and provide sweeping views.

Las Terrazas: This small community is designated as a nature reserve and features incredible flora and fauna. Make sure to explore the area’s many waterfalls, rivers and lakes.

San Diego de los Baños: While the town might be somewhat nondescript, it’s a mecca for spa seekers. The sulfurous waters are said to revitalize and heal, and a permanent spa location has been here since 1891.

Matanzas: Home to poets, vibrant culture and distinctly Afro-Cuban folklore, the “city of bridges” has, at various times, been referred to as the Venice of Cuba and the Athens of Cuba.

Varadero: One of the largest resorts anywhere in the Caribbean, Varadero offers a nature reserve, virgin forests and idyllic white-sand beaches.

Dominican Republic

A sovereign state within Hispaniola, the Dominican Republic is the most visited place in the Caribbean. From Pico Duarte, the tallest peak in the Caribbean, to year-round golf courses to internationally famous baseball players, the Dominican Republic offers much to its visitors.

Santo Domingo: With its roots in European settlement, Santo Domingo is a historically significant and culturally, financially and commercially vital part of the Dominican Republic.

Puerto Rico

From Christopher Columbus claiming the land in the name of Spain in 1493 to 2017’s Hurricane Maria, Puerto Rico has endured much in its history. However, the ever-resilient island (now an unincorporated US territory) remains as culturally vibrant and scenically beautiful as ever.

San Juan: A vital seaport and the island’s most populous municipality, San Juan is a major tourist hub and center for finance and culture. From modern downtown to ancient defensive forts, San Juan is a constant blending of the old and new.

Nevis & St. Kitts

Located in the West Indies, this island was among the first Caribbean locations to be settled by Europeans. It’s a mixture of lush tropical rain forests, uninhabited peaks and flat coastal land. Keep a special eye out for the national bird, the brown pelican.

BasseterreThe capital city of St. Kitts and Nevis, Basseterre is a small town surrounded by mountains and lush hills, and it offers a tropical rain forest climate. As such, don’t expect a dry season. Despite constant year-round temperatures around 80 degrees (Fahrenheit), every month experiences, on average, over 60 mm of rain.

CharlestownThe capital of Nevis, Charlestown has particular significance for US history buffs as it’s the birthplace and childhood home of Alexander Hamilton.

Worth a Visit
Bob Marley Museum (Kingston, Jamaica)

One of the most iconic musical figures, Bob Marley is essentially synonymous with distinctive Jamaican reggae. The museum in his honor is a must-see for any musical aficionado.

Castillo San Cristóbal (San Juan, Puerto Rico)

The largest Spanish fort constructed in the New World, this imposing citadel (built 1783) features thick walls, heavy fortification and a healthy dose of history.

Che Guevara Mausoleum (Santa Clara, Cuba)

Along with the site’s cultural significance, take in the 22-foot statue of the revolutionary, the tiled plaza and the sweeping view of Santa Clara.

Dolphin Cove (Ocho Rios, Jamaica)

Have you ever wanted to swim with dolphins? Snorkel among stingrays? Feed sharks? You can do it all in this picturesque Jamaican cove.

Things to See and Do

Full Article Coming Soon!

How to Get There

Most Caribbean islands don’t require US citizens to possess a visa for entry, so long as the stay is less than 30, 60 or 90 days. Some islands will have fees associated with travel, such as the departure tax in Saint Kitts and Nevis. Payment is often required in cash, so be prepared for this.

Some islands, such as Puerto Rico and the US Virgin Islands, are actually US territories, meaning entry to these areas for US citizens is, by and large, no different than simply crossing a state line.

At the other end of the bureaucratic spectrum, US tourists will find visiting Cuba much more difficult. After President Barack Obama eased travel restrictions, the current administration has since instituted a policy rollback. This means there are now only 12 authorized reasons for a visit to Cuba. According to the US Embassy website, these include, “family visits; official business of the U.S. government, foreign governments, and certain intergovernmental organizations; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic and other competitions, and exhibitions; support for the Cuban people; humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or informational materials; and certain authorized export transactions.”

Before you leave for your trip, always check the specific restrictions and potential entry or departure fees for every location you intend to visit.


Most people entering a Caribbean island will do so by air, and most Caribbean islands have at least one international airport as a potential port of entry.

The five busiest international Caribbean airports include the following:

  • Luis Muñoz Marin International Airport: San Juan, Puerto Rico
  • Punta Cana International Airport: Punta Cana, Dominican Republic
  • José Martí International Airport: Havana, Cuba
  • Sangster International Airport: Montego Bay, Jamaica

 Las Americas International Airport: Santo Domingo, Dominican Republic

Getting Around - Transportation
Public Transportation

If you’re attempting to get quickly from destination to destination, flying is your best bet. Especially on popular tourist islands (Jamaica, for example), it’s easy to find hoppers to other islands. The price can quickly add up, but if you’re short on time, the time savings might be worth it to you.

If price is truly no object, there are many ways to sail from island to island. Chartering a private boat, hiring a skippered boat or enlisting a fully crewed yacht are all possible.

Perhaps the most popular way to see multiple Caribbean islands is through a cruise, which goes from port to port over a multiday journey. Cruises range from having relatively low-key amenities to touting outright luxury. Ferries are also a popular option to get from island to island or to enjoy a scenic view around a given island.

Taxis are a very common way to get around a given island’s mainland. Hail a car yourself, or have your concierge call you one. Note, taxis are certainly convenient and readily available, but they can be pricey.

Buses are consistently the cheapest mode of transport, but they often only run from major cities to major attractions, meaning getting off the beaten path can be tricky on a bus. You’ll almost always need to pay for a bus with cash, so always be prepared for this with small bills.

Independent Transport

If you’re looking to hire a car, it’s a pretty straightforward process on many of the islands. In most cases, you’ll need to be 25 with a valid driver’s license.

Backroads Pro Tip

The one big exception to easy, seamless car hire is in Bermuda. Local regulations state no foreigner can drive on the island. Buses also don’t allow travelers with luggage, so you’ll largely have to rely on taxis and minivans to get from place to place.


Scooters are also quite common on many of the islands, and renting one is usually relatively cheap and straightforward. For many, this makes for the ideal way to self-tour for the day.


The most prevalent languages throughout the Caribbean are English, Spanish, Dutch, Haitian Creole and Papiamento (A Portuguese-influenced creole language). Because so much of the Caribbean is a tourist hub, English is very common (either as a first or second language). Generally speaking, most travelers who only know English will not encounter much of a language barrier in this region.

If you have a base knowledge of a romance language, you’ll likely notice links between languages, such as Haitian Creole and French. Here are just a few example phrases to illustrate:

  • Welcome: Byen venu
  • Hello: Bonjou
  • Where are you from: Ki kote ou sòti?
  • Good evening: Bonswa
  • Yes: Wi
  • No: non
  • Do you speak English?: Eske ou pale angle?
Food and Drink

Caribbean cuisine is a unique and highly distinct fusion of many culinary and cultural influences, including African, Creole, European, South Asian, Arab and more.

The most common ingredients you’ll encounter are:

  • rice,
  • plantains,
  • beans,
  • bell peppers,
  • tomatoes,
  • coconut
  • and locally available meats (fish, pork, poultry or beef).

Generalization across the region is difficult, though, as every island has a distinct food tradition. While goat stew is a signature dish from St. Kitts and Nevis, ackee and salt fish is unique to Jamaican cuisine. On special occasions, you might also come across Black Cake (the Caribbean take on English Christmas pudding).

Wherever you are, don’t forget to try the fresh seafood, the distinct jerk seasoning (on chicken or other meat), callaloo and more.

Of course, no Caribbean travel guide would be complete without mentioning rum. This region makes some of the world’s most distinguished—and delicious—rums available.

Food in the Caribbean: What to Know and to Eat—Full Article Coming Soon!

Safety Tips

In general, Caribbean travel is safe for tourists. The United Nations Office on Drugs and Crime lists the safest islands as Martinique, Anguilla, Antigua and Barbuda, Guadeloupe and the British Virgin Islands.

Most crime on the various Caribbean islands involves locals rather than travelers, but common sense precautions should always be taken. For example, women should avoid traveling alone at night and never accept drinks from strangers, and all tourists should be aware of the potential for petty theft. Always keep an eye on your passport, cash, credit cards, camera and other valuables.

While marijuana use has a place in the Jamaican-based Rastafarian culture and religion, marijuana is illegal throughout this region. To avoid problems, it’s best to abstain, no matter where you are in the Caribbean.

Most safety concerns here actually revolve around the natural environment. When swimming at beaches, for example, always be aware that surf can be rough, and waves can be deceptively strong. Even if you’re at a resort or populated area, avoid swimming alone. If you have small children, only opt for swimming areas with qualified lifeguards on duty. Also note that the sun can be quite intense. Always wear adequate sun protection to avoid an unpleasant and potentially vacation-ruining sunburn.

If your travel dates line up with hurricane season, be particularly cautious—especially if your destination lies within the “hurricane belt.”

If you need to contact emergency services, every island has its own emergency number (or numbers). Make sure to look up the relevant numbers for each location you’ll be visiting. To show this disparity, here are just a few examples:

  • Antigua and Barbuda: 999; 911
  • Aruba: 911
  • British Virgin Islands: 999
  • Cuba: 26811
  • Jamaica: 110 (ambulance or fire); 119 (police)
What is Backroads

Established in 1979, Backroads is a pioneer in active, immersive and off-the-beaten-path travel. Now operating adventure tours in over 50 countries, our passion for discovery and our desire to experience the world in original ways continue to inspire our pursuit of new adventures. Explore all our Caribbean tours here, and we hope this guide will be enlightening as you plan your next great adventure!

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