Barbados has a rich traditional use of medicinal plants, especially among the older population who may have a chronic noncommunicable disease. This study aims to identify possible drug-herb interactions between popular herbal remedies used to manage elevated blood pressure and conventional antihypertensive drugs. In this study, in silico molecular docking experiments with AutoDock Vina (Scripps Research Institute, La Jolla, CA), a part of Yasara Structure software, version 20.12.24, were used to screen 30 potential phytochemicals for drug interactions from 11 popular plants in Barbados that are used for high blood pressure and could influence the pharmacology of the most prescribed antihypertensive drugs in Barbados. Thiazide and thiazide-like diuretics, calcium channel blockers (CCBs), angiotensin-converting enzyme inhibitors (ACE-I), and angiotensin receptor blockers (ARBs) are the most prescribed antihypertensive drugs. Twenty-seven phytochemicals show dissociation constants (K d) < 10 μM with pharmacological drug targets. Catharanthus roseus (L.) G. Don, Phyllanthus niruri L., Petroselinum crispum (Mill.) Fuss, and Lantana involucrata L. contain various compounds that show high binding affinities in all experiments. Possible interactions could affect renal excretion (thiazide-like diuretics), CYP metabolism (CCBs), absorption (ACE-I), hepatic CYP, and phase II metabolism (ARB). Oleanolic acid shows high binding affinities to almost all protein targets. This study also reveals potential candidates for the drug targets: T-type Cav3.3 (psychiatric diseases), PEPT1/2 (influencing bioavailability), and BK channel (epilepsy). Twenty-seven of 30 phytochemicals from C. roseus (L.) G. Don (Madagascar periwinkle), P. niruri L. (Seed under leaf), P. crispum Mill. Fuss (Parsley), and L. involucrata L. (Rock sage) have potential binding affinities with pharmacological targets of frequently prescribed antihypertensive drugs in Barbados and are likely to cause drug interactions. Compounds that are similar to naringin (e.g., astragalin, rutin, and quercitrin) and compounds that bind to OATP1, PEPT1/2, and enzymes involved in the metabolism of CCBs may be clinically relevant for further research. There should be greater awareness of potential drug-herb interactions, and further in vitro and in vivo studies are needed to unravel the exact effects on the pharmacology.