Caribbean
While hurricane season officially lasts from June through November, the months of August, September and October are the most common months for tropical cyclones here. Mid-September is the peak of the season. However, you are more likely to encounter the affects of a hurricane in the southernmost Caribbean in October than in August or September. Aruba, Bonaire and Curacao are rarely hit as hurricanes move north of them, but they can get heavy rain from trailing rain bands.
You will typically have significant advance warning if a hurricane is coming since most of them come from the east or southeast and can be tracked well before they impact the area. They typically affect the east, southeast and northeast sides of islands hardest, although rainfall is usually highest up in mountainous terrain. A rarer late season hurricane can move from west to east, making the west side of islands more vulnerable. Storms and hurricanes affecting the region usually are moving quickly enough so that the event itself tends to last one day or less.
U.S. Gulf & East Coasts
Tropical activity is possible from June through November, but the peak is mid-September. There are year-to-year variations of the number of storms and hurricanes that affect the U.S. and where. The long term average is 2-3 per year somewhere along U.S. coast, but exceptional years like 2005 saw 8 affect the U.S. South Florida and the Outer Bans of North Carolina are most frequently hit, followed by the Florida Panhandle, Louisiana and Texas coastlines. Northeastern-most Florida is rarely directly hit from the east by hurricanes, but bypassing impacts and weakening storms from the southwest do affect his area from time to time. Outer Long Island is much more likely to be directly hit by a storm than is western Long Island and New York. Storms and hurricanes in the northeast U.S. usually move quickly and hence are a 1/2 day event.
Mexico/Central American
Hurricane season runs from June through November and peaks from June through November and peaks in late August to early September on the west coast of Mexico and Central America. There is a large year-to-year variation in both the number and the track of hurricanes in the Eastern Pacific. Because of this, hurricane landfalls are rare in some years, but more common in others. Predicting these year-to-year variations in advance is currently not possible. Landfalls are historically more common earlier and later in the season (early July and October) than during the peak of the season. Flooding rains and mudslides can occur even with weak tropical systems along the mountainous west coasts.
Along the east coast of Mexico and Central America, the hurricane season peaks in mid-September; however, hurricane landfalls here tend to b e more common (relative to the number that form) in June and October than during the remainder of hurricane season. Storms and hurricanes in Central America and the western Caribbean Sea tend to move slower and therefore last longer in the locations they affect. Flash flooding and mudslides are also a threat in mountainous areas from systems which come in from the Caribbean and Gulf of Mexico, especially slow-moving ones.
Hawaii
The islands called "paradise" are rarely struck by a hurricane. In this region's season (July-October), hurricanes that form east of the Hawaiian Islands and move west toward them are usually weakened by strong upper-level winds. The remnants of these systems can at times result in brief rainy weather, gusty trade winds up to 30mph, and dangerous waves on exposed beaches facing northeast, east and southeast. Most never make it to Hawaii but instead dissipate south of the Big Island and steer harmlessly west pas the Hawaiian Islands; the Big Island and steer harmlessly west pas the Hawaiian Islands; however, high surf from these can b e hazardous to swimmers.
Roughly every seven years, an El Nino develops in the tropical Pacific and hurricanes can form southwest of Hawaii. It is during these years that some strong hurricanes have affected Hawaii from the southwest. In the past 30 years nearly all that have affected the region have impacted the island of Kauai most, while Oahu and Maui have experienced the least impacts the past 50 years. In general, don't worry ab out a hurricane fouling up your plans in Hawaii.
South Pacific
In the South Pacific, tropical activity peaks in late February and early March. There are large year-to-year changes in where tropical cyclones form within the South Pacific; when they develop nearer to land they obviously have greater impacts. On average, about 10 tropical cyclones obviously have greater impacts. On average, about 10 tropical cyclones form here each year (including those close to the northeast coast of Australia). Most land areas in this region are small islands and island chains; it would be relatively unlikely to have the worst portion of a tropical cyclone over the one island your are visiting. Hence the likelihood of a big event during your wedding/honeymoon would be very rare, but peripheral impacts from a bypassing cyclone are a little more frequent during the peak of the season. Watch out for the possibility of large waves crashing ashore from a tropical cyclone far away from your dream beach!