Which Itinerary to take?

This discussion is limited to itineraries in the Caribbean. On 7 day cruises or longer, you generally have your choice of the Western Caribbean - which takes on Jamacia, Cayman Islands, Cozumel, and similar areas, or the Eastern Caribbean - Puerto Rico, St. Thomas, St. Maarten, and sometimes the other "Leeward Islands", or the Southern Caribbean - which goes to the less visited Leeward Islands (St. Kitts, Antigua, etc), as well as the Windward Islands (Barbados, St Lucia, etc.). The Western and Eastern routes usually leave from Florida, but the Southern route is either from Puerto Rico if a 7 day cruise, or occasionally from Florida for 10 days or longer cruises. Shorter cruises out of Florida, 5 days or less, are generally restricted to the Bahamas, or possibly a quick trip to Cozumel and back.

Out of all of the islands, St. Maarten is our favorite, so we like the Eastern Caribbean. But the choice is yours, and if you end up liking the cruising experience, you'll certainly cruise again and take the other itineraries. Also, it seems the size of ship has some bearing on which islands you visit. The mega-ships are just too large to visit some of the islands, as their port facilities may not be adequate. For some islands, there are no docking facilities, tenders are used. It's just harder to get a lot of passengers on and off a larger ship with a tender, so a smaller ship might visit that island more frequently. So look through the cruise line's brochures or websites and pick out the islands you desire to visit, then select the cruise to match it.

But for some, the ship is the destination. There used to be a popular T-Shirt for sale that said "Same crap, different island". While that is not quite the truth, there is some similarity in many of the islands. However, there are different things to do in different islands, although some do not have a lot to offer once you have seen them a few times. On our third trip to Nassau, Bahamas, we just stayed aboard and enjoyed the pool to ourselves. We'd been there twice before, and when you have seen Nassau once or twice, there is not a lot else to see.