How NOT to island hop

When I found out I was going to be heading to Jamaica for a few days for a workshop, I knew I didn't want to fly all the way to the Caribbean JUST for 4 days & fly all the way back.  Then, shortly thereafter I was offered two free nights on St. Barth's if I could get myself there.  Now, I am certainly not an expert on the Caribbean, but I'm also not a geographic idiot, and so before I did anything I looked at maps and flights.  Yes, the two islands are a bit on opposite sides of the Caribbean Sea, but there was a direct flight from Jamaica to St. Martin, and two free nights on the glamorous French island of St. Barth! So easy, right?? I went for it.

Well, the closer I got to the actual day of travel between the two islands, the more I realized I may have gotten myself into a mess.  Firstly, that direct flight landed on St. Martin fairly late in the afternoon, and it was the only one.  That meant that I only had one ferry option, and that boat wouldn't get me to St. Barth until about 8pm.  Oh well, no big deal, right? 

Well, then I came to the realization that the direct lovely Jamaica-St. Martin flight left from Kingston, on the far side of the island.  Now, if I had been smarter and/or more determined, I could have booked myself a room on that side of the island for my last night on Jamaica - the Blue Mountains, for example, do have resorts that aren't far from Kingston.  But, again, I had the chance to stay with my friends for one final free night over in Montego Bay- so of course I decided to take that!  (And we had a great time together that day/evening too!!). So- there are a few ways to get from The Montego Bay Area over to Kingston... Obviously I could have driven or gotten a private transfer, but even with a new road being completed recently, that was going to be at least a four hour drive (if not more).  The other option was obvious: fly!  Well, there is just one scheduled flight from MBJ (Montego Bay) to KIN (Kingston).  And it leaves each day at 7:30am.  I did briefly look at a helicopter flight, but they're only charters possible and, well, cost WAY more than I was willing to spend.  When you then factor in the costs associated with a private transfer vs. a hopper flight, and the fact that I'd have to leave early in the morning no matter which option I chose, I went with the cheaper option: the flight.  That's why a simple "island hop" ended up taking me over 14 hours door to door, even though the actual transport time was only about 4 hours (or less).  Yes- I left my hotel at 6am, sat in a horrible empty room for an hour or so, then waited in the departure hall in Kingston (reading & napping) for a few hours before I could check in and enter the comfy lounge with free drinks & snacks (yay for lunch!).  Then, once I got to St. Martin it was time for a cab and a beer or two before I got to actually ferry over (in the dark) to my final destination.  Luckily, what greeted me was fabulous, but day certainly wasn't - here are a few pics from each stage: 

Ridiculous!  Do not make my same mistake!  If you DO want to see multiple islands in the Caribbean on one trip- don't force it.  Pick neighboring islands with frequent ferries between them (eg: St. Martin/St. Barth's/Anguilla would work, or the classic St. John's/St. Thomas of course), and really research connection times.  And remember that schedules are subject to "island time".  I actually had scheduled my ferry & flight connection for my trip home perfectly, but my mid-day ferry apparently never runs, so I was forced to leave St. Barth's about 4 hours earlier than I'd hoped.  With all that in mind, honestly, I believe the BEST way to island hop is to do it via boat.  And I'm not talking about the giant cruise ships (which often can't get to the cool little islands anyway)- I'm talking about a small little boat with 6-10 of your best friends.  There are all sorts of options for that- from bare bones budget to super luxe, and you can often completely customize your itinerary.  I know when I go back to the Caribbean, I'll either just pick ONE island for a relaxing stay, or I'll pick a boat to hop around in.  Lesson learned!  Doesn't this look better anyway???