Close Protection in the Caribbean Islands | CloseProtectionHire

The Caribbean encompasses some of the most divergent security environments in the western hemisphere within a relatively compact geographic area. Within a two-hour flight radius, you can move from one of the most violent cities in the world to islands with crime rates that rival Switzerland. The challenge for close protection planning is that these markets are frequently treated as a homogeneous region, and they are not.

This briefing covers the primary markets for business and executive travel: Jamaica, Trinidad and Tobago, Haiti, the Dominican Republic, Cuba, and the more stable financial-sector hubs of Barbados and the Cayman Islands.

Jamaica

Kingston sits in OSAC’s Level 3 category – the same tier as Mexico City and Lagos – and the city has carried some of the highest per capita murder rates in the western hemisphere across the past two decades. The FCDO advises heightened caution in Kingston and Montego Bay, with specific advisories against travel to garrison communities.

The risk picture for business visitors is more granular than the headline figures suggest. New Kingston, the primary commercial zone, and the resort strip in Montego Bay operate at a meaningfully lower threat level than the inner-city garrison areas where gang-related violence is concentrated. The Jamaica Constabulary Force (JCF) maintains a stronger visible presence in commercial and tourist zones.

For executive visitors, the primary threats are:

Kidnapping. Both planned abductions of high-value targets and opportunistic express kidnappings are documented. OSAC Jamaica 2024 identifies this as a primary risk for visible foreign nationals and business travellers.

Carjacking and armed robbery. Vehicle approaches at traffic stops, gas stations, and hotel entrances are the most common method. Vetted armoured vehicles with experienced local drivers are the appropriate response for high-value principals.

Airport approaches. Norman Manley International (Kingston) and Sangster International (Montego Bay) both see opportunistic crime approaches. Principals should be met airside where possible and should not wait in the arrivals hall without a CP escort.

Jamaica’s Private Security Regulation Authority (PSRA) licences close protection officers and security companies. Operator quality in the Jamaica market varies significantly; requesting PSRA licence numbers and conducting reference checks with previous clients is the minimum vetting standard. Armed CP is available and warranted for elevated-threat principals.

MEDEVAC: University Hospital of the West Indies (Kingston) has the highest surgical capability on the island but is consistently under-resourced. For any deployment, a MEDEVAC contract with Air Methods or STAT MedEvac should be confirmed before arrival.

Trinidad and Tobago

Port of Spain has seen sustained gang violence over the past decade, driven by narco-trafficking networks connecting South America to North America via the eastern Caribbean corridor. The Trinidad and Tobago Police Service (TTPS) has acknowledged capacity constraints, and response times in affected areas are unreliable.

Business visitors are primarily concentrated in Port of Spain (financial district, Westmoorings, and St. Clair) and in the Point Lisas industrial corridor (petrochemicals). The oil and gas sector brings the highest volume of executive visitors, and this sector has a documented profile as a kidnapping target given the financial resources assumed of those working in it.

Security considerations:

Pattern-of-life discipline. The Point Lisas industrial zone requires regular commuting on predictable routes. Varying departure times and using counter-surveillance-aware drivers is the primary mitigation.

Maritime risk. Trinidad’s position at the southern tip of the Caribbean means that vessels transiting between the island and the Venezuelan coast operate in a zone with documented piracy incidents. OSAC Trinidad 2024 notes this as a secondary concern for maritime logistics operations.

Tobago has a significantly lower threat profile than Trinidad and functions as a practical alternative base for regional operations with less commuting pressure.

Haiti

Haiti presents an operating environment that is categorically different from all other markets in this briefing. The FCDO advises against all travel (Level 4). The United States State Department has issued a Level 4 Do Not Travel advisory. The UN Integrated Office in Haiti (BINUH) documented in early 2025 that the Viv Ansanm gang coalition – an alliance of previously competing criminal organisations – controlled 60 to 80 percent of Port-au-Prince and was actively contesting territory in the Artibonite region.

The Haitian National Police (PNH) has been operationally overwhelmed in Port-au-Prince since 2021. The Kenya-led Multinational Security Support (MSS) mission, authorised by UN Security Council Resolution 2699 in October 2023, was deployed to provide support, but its operational reach as of 2025 remains limited relative to the scale of gang control.

For organisations with unavoidable operational requirements in Haiti – typically humanitarian organisations, mining operations, or media – the operating model is:

• Minimum footprint deployments with pre-planned extraction routes
• Accommodation in hardened compounds, not commercial hotels
• Armed local security with vetted, experienced operators who maintain current intelligence
• Regular check-ins with a crisis management firm
• MEDEVAC via helicopter to the Dominican Republic (Santo Domingo or Santiago) as the nearest viable surgical facility

No commercial CP operator based outside Haiti can operate effectively in Port-au-Prince without active local intelligence partnerships. Deployments without this capability are high-risk and not recommended.

The Dominican Republic

The Dominican Republic occupies the eastern portion of Hispaniola and has a fundamentally different security environment from Haiti, with a functioning state, active tourism industry, and conventional commercial activity.

Punta Cana, La Romana, and the north coast resort zones present a manageable security environment for business visitors who are not engaged in activities that attract elevated threat. Santo Domingo, the capital, has elevated street crime, petty theft, and a drug trafficking-adjacent criminal ecosystem that occasionally generates violent incidents.

The Direccion Nacional de Control de Drogas (DNCD) – the narcotics enforcement agency – conducts operations that create localised disruption in Santo Domingo. Awareness of DNCD operation zones (provided by vetted drivers and operators) is a practical precaution.

For executive visitors, standard precautions apply: vetted vehicles, accommodation in known-standard hotels (Marriott Santo Domingo, InterContinental), and avoidance of displaying visible wealth outside secured venues.

MEDEVAC: Clinica Abreu (Santo Domingo) and Centro Medico UCE are the primary surgical facilities for serious trauma. Regional MEDEVAC to Miami or Bogota is available through AirMed International and Global Rescue for cases beyond local capability.

Cuba

Cuba presents an almost entirely inverted risk profile relative to the rest of this briefing. Street crime in Havana is low by Caribbean standards, and violent crime against foreign nationals is rare. The primary security concern is authoritarian surveillance.

The MININT (Ministerio del Interior) maintains pervasive intelligence collection capability against foreign nationals. Hotels used by business visitors are a specific surveillance environment – room access by intelligence officers, technical installation in meeting rooms, and monitoring of digital communications are all documented.

For executives conducting sensitive meetings or due diligence work in Cuba, the operating protocols are:

• Clean devices: no personal credentials, no sensitive client data, no confidential communications on devices entering Cuba
• No sensitive meetings in fixed hotel locations
• ETECSA (the state telecommunications monopoly) controls all internet access – assume all traffic is monitored
• No independent commercial CP operators function in Cuba – there is no close protection option available

The economic situation in Cuba has deteriorated significantly since 2020, and the combination of US sanctions, reduced Venezuelan oil supply, and COVID-19 has created fuel shortages and periodic civil unrest. FCDO currently advises normal precautions but monitors the situation closely.

Barbados and the Cayman Islands

These two jurisdictions represent the regional hubs for financial sector and HNW operations and are the appropriate staging points for Caribbean regional deployments.

Barbados. British overseas territory (Commonwealth realm) with a functioning legal system, Grantley Adams International Airport with direct British Airways connections to London Gatwick, and manageable crime primarily in urban Bridgetown rather than the business districts. The FCDO advises normal precautions. Barbados functions as the eastern Caribbean headquarters for multiple international financial institutions and professional services firms.

Cayman Islands. A British Overseas Territory with the lowest crime rate in the Caribbean by most metrics. The Cayman Islands is the registered domicile for a significant proportion of global hedge fund and private equity vehicle structures, and the legal and financial infrastructure is accordingly sophisticated. Direct connections to Miami, New York, and London. For executives conducting fund administration, compliance, or asset management work in the region, the Cayman Islands offers a low-risk base with strong connectivity to higher-risk markets accessible for day deployments.

Both jurisdictions have functioning emergency medical services and hospital capability adequate for standard medical events. For serious trauma or specialist surgical requirements, air transfer to Miami (Jackson Memorial or Mount Sinai) is the standard evacuation destination.

MEDEVAC Summary for the Caribbean Region

Operator Selection Across the Region

The Caribbean close protection market is fragmented and quality is inconsistent. The following criteria apply when selecting operators across the region:

1. Confirmed PSRA licensing in Jamaica; TTPS registration in Trinidad; formal registry in the relevant jurisdiction
2. Demonstrated local intelligence network – not just a security guarding background
3. Current country knowledge with named contacts in police and emergency services
4. MEDEVAC coordination capability – the ability to activate an evacuation with a pre-arranged provider, not just contact a general number
5. References from previous clients in the same country, verifiable by direct contact

For a broader overview of security in the wider South American region that feeds into Caribbean threat dynamics, see our guidance on executive security in Latin America and close protection in South America.