Hello Joe,
Welcome to the Caribbean, the islands are so close together, it is difficult to pass by seeing as much as the region as possible. I wish however that it wasn't so disjointed transportation wise to travel from island to island.
I'm not sure of your budget, or the length of time you may have to do this but because Caribbean cruises outside of those holiday liners such Carnival etc, don't offer much distance in cover more than one ilsnad usually a neighbouring island.
There is not much option of travel from Trinidad/Tobago via sea (except the ferry between Trinidad and Tobago {T&T}), without enlisting a fly and sail tour. However there are plenty of of flights by air to allow island hoping but this would be quite costly, and tedious much planning and spare time for catching flights etc..
So it may be worth it to explore fly and sail options, Perhaps flying from T&T to a destination that you can explore that also offers sail tours to the other islands, the closest one being Barbados, which makes the flight component of the trip low cost. As I'm not aware of sailing tours out of Grenada other than private yatch charters.
The most economical flight options from T&T to Barbados can be found on caribbean-airlines .com and you can also compare these fares to Liat(s) . com both are Caribbean carriers. You can also book online and get special low fares on either of these two sites.
For example, a Caribbean Airlines flight may cost US$ 198.00 for a 2 day round trip (leaving Piarco 4th returning to Trinidad on the 6th) or if you embark on the Caribbean islands tour at the ending of your trip and your flight back home is not of out Trinidad, it may mean a one way ticket to Barbados which could cost approximately US $105.00
Then once on Barbados, Chantours Barbados offers a variety of island excursions, even day trips. chantours . com /day excursions or google Chantours Barbados. They offer sailing trips from Barbados to Grenadines, St.Lucia, St.Barts, Grenada and around the island of Barbados if you want. Not sure of the cost however. The extent of these tours is based on the amount of time you have and budget.
Also keeping in mind that St.Maarten and Anguilla offer cruises between the two islands so there is the option of flying out to either one of them. However the airfare quite high from Trinidad.
I hope this can help a bit feel free to respond with any questions or information
Best wishes
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