The 1899 San Ciríaco hurricane, also known as the 1899 Puerto Rico Hurricane or The Great Bahamas Hurricane of 1899, was the longest-lived Atlantic hurricane on record, and the second-longest-lived tropical cyclone globally on record after 1994's Hurricane John in the Pacific. It was also one of the deadliest Atlantic hurricanes in recorded history, with an estimated 3,800 fatalities. The third tropical cyclone and first major hurricane of the season, this storm was first observed southwest of Cape Verde on August 3. It slowly strengthened while heading steadily west-northwestward across the Atlantic Ocean and reached hurricane status by late on August 5. During the following 48 hours, it deepened further, reaching Category 4 on the modern day Saffir–Simpson hurricane wind scale (SSHWS) before crossing the Leeward Islands on August 7. Later that day, the storm peaked with winds of 150 mph (240 km/h). The storm weakened slightly before making landfall in Guayama, Puerto Rico with winds of 140 mph (220 km/h) on August 8. Several hours later, it emerged into the southwestern Atlantic as a Category 3 hurricane. The system paralleled the north coast of Dominican Republic and then crossed the Bahamas, striking several islands. Thereafter, it began heading northward on August 14, while centered east of Florida. Early on the following day, the storm re-curved northeastward and appeared to be heading out to sea. However, by August 17, it turned back to the northwest and made landfall near Hatteras, North Carolina early on the following day. No stronger hurricane has made landfall on the Outer Banks since the San Ciriaco hurricane.

The Okeechobee hurricane of 1928, also known as the San Felipe Segundo hurricane, was one of the deadliest hurricanes in the recorded history of the North Atlantic basin, and the third deadliest hurricane in the United States, only behind the 1900 Galveston hurricane and Hurricane Maria. The hurricane killed an estimated 2,500 people in the United States; most of the fatalities occurred in the state of Florida, particularly in Lake Okeechobee. It was the fourth tropical cyclone, third hurricane, and only major hurricane of the year's hurricane season. It developed off the west coast of Africa on September 6 as a tropical depression, but it strengthened into a tropical storm later that day, shortly before passing south of the Cape Verde islands. Further intensification was slow and halted late on September 7. About 48 hours later, the storm strengthened and became a Category 1 hurricane on the Saffir–Simpson hurricane wind scale. Still moving westward, the system reached Category 4 intensity before striking Guadeloupe on September 12, where it brought great destruction and resulted in 1,200 deaths. The islands of Martinique, Montserrat, and Nevis also reported damage and fatalities, but not nearly as severe as in Guadeloupe.

Hurricane Allen was a rare and extremely powerful Cape Verde hurricane that struck the Caribbean, eastern and northern Mexico, and southern Texas in August 1980. The first named storm and second tropical cyclone of the 1980 Atlantic hurricane season, it was the fifth most intense Atlantic hurricane on record in terms of barometric pressure, behind Hurricane Rita, the 1935 Labor Day hurricane, Hurricane Gilbert, and Hurricane Wilma. It was one of the few hurricanes to reach Category 5 status on the Saffir–Simpson Hurricane Scale on three occasions, and spent more time as a Category 5 than all but two other Atlantic hurricanes. Allen is the only hurricane in the recorded history of the Atlantic basin to achieve sustained winds of 190 mph (330 km/h), thus making it the strongest Atlantic hurricane by wind speed. Until Hurricane Patricia in 2015, these were also the highest sustained winds in the Western Hemisphere.
Hurricane Betsy, known as Hurricane Santa Clara in Puerto Rico, was the first North Atlantic hurricane to make landfall in Puerto Rico in 24 years. The third tropical cyclone of the 1956 Atlantic hurricane season, Betsy developed from a tropical wave on August 9 to the east of the Lesser Antilles. It rapidly developed into a 120 mph (195 km/h) major hurricane before striking Guadeloupe. There, Betsy heavily damaged 1000 houses and left severe crop destruction, and there were 18 deaths in the territory. As Betsy continued into the northeastern Caribbean, it capsized a ship, killing its crew of two.

Hurricane Cleo was the strongest tropical cyclone of the 1964 Atlantic hurricane season. It was the third named storm, first hurricane, and first major hurricane of the season. Cleo was one of the longest-lived storms of the season. This compact yet powerful hurricane travelled through the Caribbean Sea and later hit Florida before moving offshore Georgia into the Carolinas, killing 156 people and causing roughly $187 million in damage. Major damage was seen as far north as east-central Florida, with the heaviest rains falling along the immediate coast of the Southeast United States into southeast Virginia.

Hurricane David was an extremely deadly hurricane which caused massive loss of life in the Dominican Republic in August 1979, and was the most intense hurricane to make landfall in the country in recorded history. A Cape Verde hurricane that reached Category 5 hurricane status on the Saffir-Simpson Hurricane Scale, David was the fourth named tropical cyclone, second hurricane, and first major hurricane of the 1979 Atlantic hurricane season, traversing through the Leeward Islands, Greater Antilles, and East Coast of the United States during late August and early September. David was the first hurricane to affect the Lesser Antilles since Hurricane Inez in 1966. With winds of 175 mph (280 km/h), David was the only storm of Category 5 intensity to make landfall on the Dominican Republic in the 20th century and the deadliest since the 1930 Dominican Republic Hurricane, San Zenon, killing over 2,000 people in its path. In addition, David was the deadliest Dominican tropical cyclone since the 1834 Padre Ruíz hurricane, which killed over 200 people.

Hurricane Dean was the strongest tropical cyclone of the 2007 Atlantic hurricane season. It was the most intense North Atlantic hurricane since Hurricane Wilma of 2005, tying for eighth overall. Additionally, it made the fourth most intense Atlantic hurricane landfall. A Cape Verde hurricane that formed on August 13, 2007, Dean took a west-northwest path from the eastern Atlantic Ocean through the Saint Lucia Channel and into the Caribbean. It strengthened into a major hurricane, reaching Category 5 status on the Saffir–Simpson hurricane wind scale before passing just south of Jamaica on August 20. The storm made landfall on the Yucatán Peninsula on August 21 at peak intensity. It crossed the peninsula and emerged into the Bay of Campeche weakened, but still remained a hurricane. It strengthened briefly before making a second landfall near Tecolutla in the Mexican state of Veracruz on August 22. Dean drifted to the northwest, weakening into a remnant low which dissipated uneventfully over the southwestern United States. Dean was the second-most intense tropical cyclone worldwide of 2007 in terms of pressure, only behind Cyclone George in the Australian region, and tied with Felix as the most intense worldwide in terms of 1-minute sustained winds.

Hurricane Hortense was the first tropical cyclone to make landfall in Guadeloupe and Puerto Rico since Hurricane Hugo in 1989, and the second most intense hurricane during the 1996 Atlantic hurricane season. The eighth tropical cyclone, eighth named storm, and sixth hurricane of the season. Hortense developed on September 3 from a tropical wave in the central Atlantic Ocean.

Hurricane Hugo was a powerful Cape Verde tropical cyclone that inflicted widespread damage across the northeastern Caribbean and the Southeastern United States in September 1989. Across its track, Hugo affected approximately 2 million people. Its direct effects killed 67 people and inflicted $11 billion in damage. The damage wrought by the storm was more costly than any Atlantic hurricane preceding it. At its peak strength east of the Lesser Antilles, Hugo was classified as a Category 5 hurricane—the highest rating on the Saffir–Simpson scale. Over the course of five days, Hugo made landfalls on Guadeloupe, Saint Croix, Puerto Rico, and South Carolina, bringing major hurricane conditions to these and surrounding areas. Lesser effects were felt along the periphery of the hurricane's path in the Lesser Antilles and across the Eastern United States into Eastern Canada. The scale of Hugo's impacts led to the retirement of the name Hugo from Atlantic hurricane names.

Hurricane Inez was a powerful major hurricane that affected the Caribbean, Bahamas, Florida, and Mexico in 1966. It was the first storm on record to affect all of those areas. It originated from a tropical wave over Africa, and became a tropical depression by September 21. It moved slowly westward, initially failing to intensify much; it was upgraded to Tropical Storm Inez on September 24. The storm strengthened into a hurricane and was quickly intensifying when it struck the French overseas region of Guadeloupe on September 27. Inez severely damaged the island's banana and sugar crops, and thousands of homes were damaged, leaving 10,000 people homeless. Damage on Guadeloupe was estimated at $50 million, and there were 40 deaths. After entering the Caribbean, Inez briefly weakened before restrengthening, attaining peak sustained winds of 150 mph (240 km/h) on September 28. That day a hurricane hunters flight reported a gust of 197 mph (317 km/h), which was the highest recorded at the time.

Hurricane Iris was the first of three tropical cyclones to affect the Lesser Antilles in a three-week period, preceding the more destructive hurricanes Luis and Marilyn. The ninth named storm and fifth hurricane of the 1995 Atlantic hurricane season, Iris developed from a tropical wave to the east of the Lesser Antilles on August 22 and attained hurricane status within 30 hours. The hurricane weakened to a tropical storm before crossing the islands of the eastern Caribbean from August 26 through August 28. During that time, Iris became one of four active tropical storms in the Atlantic basin. Earlier it had interacted with Hurricane Humberto, and beginning on August 30, Iris interacted with Tropical Storm Karen. Iris re-intensified into a hurricane and attained peak sustained winds of 110 mph (175 km/h) while moving slowly across the central Atlantic. The hurricane accelerated to the north and absorbed a dissipating Karen on September 3. Iris weakened to a tropical storm and became extratropical on September 4, though its remnants reattained hurricane-force winds before affecting western Europe on September 7.

Hurricane Isaac was a deadly and destructive tropical cyclone that came ashore in the U.S. state of Louisiana during August 2012. The ninth named storm and fourth hurricane of the annual hurricane season, Isaac originated from a tropical wave that moved off the west coast of Africa on August 16. Tracking generally west, a broad area of low pressure developed along the wave axis the next day, and the disturbance developed into a tropical depression early on August 21 while several hundred miles east of the Lesser Antilles. The system intensified into a tropical storm shortly thereafter, but high wind shear initially prevented much change in strength.

Hurricane Luis was a very large, long-lived, powerful and very destructive Category 4 Cape Verde hurricane, as well as one of the strongest and most notable hurricanes of the 1995 Atlantic hurricane season. Luis was also the strongest hurricane to make landfall, and the third-most intense hurricane recorded during the extremely active season. It was the twelfth tropical storm, sixth hurricane, and second major hurricane of the season. At one point, the storm was one of four simultaneous tropical systems in the Atlantic basin, along with Humberto, Iris, and Karen. The storm lasted for 14 days as a tropical storm between late August and mid-September.

Hurricane Maria was a deadly Category 5 hurricane that devastated Dominica, St Croix, and Puerto Rico in September 2017. It is regarded as the worst natural disaster in recorded history to affect those islands and was also the deadliest Atlantic hurricane since Mitch in 1998. The tenth most intense Atlantic hurricane on record and the most intense tropical cyclone worldwide in 2017, Maria was the thirteenth named storm, eighth consecutive hurricane, fourth major hurricane, second Category 5 hurricane, and deadliest storm of the hyperactive 2017 Atlantic hurricane season. At its peak, the hurricane caused catastrophic destruction and numerous fatalities across the northeastern Caribbean, compounding recovery efforts in the areas of the Leeward Islands already struck by Hurricane Irma. Total losses from the hurricane are estimated at upwards of $91.61 billion, mostly in Puerto Rico, ranking it as the third-costliest tropical cyclone on record.

Hurricane Marilyn was the most powerful hurricane to strike the Virgin Islands since Hurricane Hugo of 1989, and the third such tropical cyclone in roughly a two-week time span to strike or impact the Leeward Islands, the others being Hurricane Iris and the much more powerful and destructive Hurricane Luis. The thirteenth named storm, seventh hurricane and third major hurricane of the extremely active 1995 Atlantic hurricane season, Marilyn formed on September 12 as a tropical depression from a tropical wave that moved off the coast of Africa on September 7. After formation, the storm quickly became a tropical storm, and steadily intensified into a hurricane by the time it struck the Lesser Antilles on September 14 at Category 1 strength. Entering the northeastern Caribbean Sea, rapid intensification ensued and it peaked on September 16 north of Puerto Rico as a Category 3 hurricane shortly after it had impacted the U.S. Virgin Islands. A Hurricane Hunter reconnaissance flight reported hail, which is unusual for tropical cyclones. After heading north past Bermuda, Marilyn weakened and became extratropical on September 22. The remnant circulation wandered the Atlantic Ocean from September 23 – October 1, just south of Nova Scotia.

Hurricane Rafael produced minor damage in the northeastern Caribbean Sea in mid-October 2012. The seventeenth named storm and ninth hurricane of the annual hurricane season, Rafael originated from a tropical wave roughly 230 mi (370 km) south-southeast of Saint Croix on October 12; because the system already contained tropical storm-force winds, it skipped tropical depression status. Though initially disorganized due to moderate wind shear, a subsequent decrease allowed for shower and thunderstorm activity to develop in earnest by October 14. While moving north-northwestward the following morning, Rafael intensified into a Category 1 hurricane. A cold front off the East Coast of the United States caused the system to turn northward and eventually northeastward by October 16, at which time Rafael attained its peak intensity with maximum sustained winds of 90 mph (150 km/h). As the cyclone entered a more stable atmosphere and tracked across increasingly cooler sea surface temperatures, it began extratropical transition, a process the system completed by the following afternoon.