Caribbean, Bahamas, Bermuda, Panama Canal, and Mexican Riviera cruises have all been grouped together, as they all share warm weather as a common denominator. Lounging on deck chairs in the sun, using the pool, and being outside in warm weather, is what makes all of these cruises similar. Sunshine combined with steady cooling ocean breezes and stunning colours, make the days at sea relaxing and enjoyable. The differences are in embarkation point, duration, and ports of call. Those looking for a 3, 4,or 5 day short duration cruise, can choose between those leaving from Florida (Miami, Fort Lauderdale, Port Canaveral, and Tampa) into the Bahamas or Western Caribbean. Bahamas cruises typically call on Nassau, and perhaps Freeport or a "private island". Western sailings often call on Key West, Grand Cayman, and Playa Del Carmen, although some call on New Orleans. Some limited Southern cruises leave from San Juan for short durations in the lower Caribbean, but air can be awkward for such a short cruise. Los Angeles sees short cruises to Los Cabos or Cabo San Lucas in the Baha California, as well as stops on Catalina Island.

Caribbean cruises can be subdivided into three main categories: Eastern, Western, and Southern. Eastern and Western itineraries primarily begin and end in Florida, which makes them convenient and a little less expensive for air connections. The months of December and early January can be cool in Florida on embarkation, but warmer weather is more likely once the ship sails further south. Eastern itineraries often call on the "shopping ports" such as St. Thomas, St. Maarten, Nassau, and San Juan. Western itineraries often call on the "snorkelling and watersports" ports of Grand Cayman, Cozumel, Playa Del Carmen, and Ocho Rios. Southern Caribbean cruises typically leave from San Juan, although some smaller ships may use another port. Airfare is usually approximately $200 more expensive, and often involves a connection, unless charter flights are possible, or departure is from a major US hub. Southern cruises are usually a bit more port intensive, visiting a port every day but one. These can be a little less relaxing, especially if you feel the need to see everything, but are great for those who want to take it all in. Average age on board most seven day Caribbean cruises is approximately mid-forties, with good representation in ages between mid twenties and mid sixties.

Mexican Riviera Cruises typically depart from Los Angeles, and call on Cabo San Lucas, Puerto Vallarta, Mazatlan, and perhaps Acapulco. Sound familiar? It’s the old Love Boat itinerary, but you’re not likely to see Captain Stubing, Julie, Isaac, Doc, Gopher, and a cast of has-been actors! Visitors are typically from the Western US and Canada.

Panama Canal cruises are longer, often ten and eleven days in duration. The traditional full-transit cruise leaves from San Juan and ends in Acapulco, or another Mexican Port, however there is an increasing variety of cruises that do "partial transit", which means that the ship does not actually go through the Panama Canal. Partial transit cruises enter a few locks and turn around on the interior lake, heading back to their port of embarkation. These cruises are often seven days in length, or they operate round-trip from Florida. The longer duration, more expensive airfare, and general appeal of the Panama Canal, tends to skew the average passenger age into the mid-fifties, with many fewer people in their twenties through thirties noticably absent. This makes for a quieter on board experience, particularly at night.

Bermuda cruises begin in May, and usually end in early October, as embarkation is from the colder ports of New York and Boston. These cruises are quite relaxing, as once the Atlantic voyage to Bermuda is complete, the ship basically anchors in port for several days before heading back. The pace is leisurely, as Bermuda is a daytime port of call, offering upscale shopping, golf, and quiet beaches. Given the coast of hotels and food in Bermuda, cruising is an excellent and affordable way of seeing Bermuda. Bermuda attracts a little older and more sophisticated clientele than most Caribbean Cruises, and the higher cost keeps many young people away.