Bermuda, being farther north, is in the 80's from June to September and dips to the high 60's in winter, good weather for golf and tennis. The Bahamas are comfortably warm all year, with occasional cool days in January. Hurricane season runs from April to December, peaking in September. Distances are great in the Caribbean, and bad weather in one place has no influence on islands many miles away. The islands of the Caribbean offer families long sandy beaches to walk on, crystal clear water to snorkel in, different cultures and historical places to experience, and different foods to eat and music to listen to, all just a few hours from home.
Kids love the Caribbean.
Adults always need picture proof of identity to travel, and that is sufficient for travel to the U.S. Virgin Islands and Puerto Rico. All other islands require proof of citizenship and picture proof of identity. Proof of citizenship can be a passport, or green card, or a birth certificate issued by a government agency with a raised seal. Margarita and Belize require passports. In general, no.