Let the Caribbean Island Hopping Adventure Begin!

Route of my Caribbean Trip
Hello from the island of St. Thomas in the US Virgin Islands where I’m one week into my Caribbean island hopping adventure!

I have been excited about this trip for quite some time. I’ve always had a fascination with small countries and islands. When I began my travels in 2007 I started in the Pacific for exactly that reason. I wanted to visit the small places I had only seen as small dots on a map.

Since then I’ve gone out of my way to visit places like San Marino and Liechtenstein but have never bothered to visit many large countires like Russia and China. This trip is my chance to visit a part of the world I’ve so far ignored as well as scratching my itch for visiting tiny countries.

You can get a rough idea of my route in the map I created above. I’m basically working my way south through the Lesser Antilles. My transportation between the islands will be a combination of short flights (often very short flights) and public ferries.

In doing research for this trip, it was interesting to see where there are ferries and where there are none. From USVI to BVI there is a ferry, but from BVI to Anguilla, which is only 40 miles, you have to fly. Some of it has to do with distances, some of it has to do with the conditions of the seas between islands and some of it has to do with economics and how popular a route is.

Planning this trip was extremely difficult, which is why I left it to my manager Amy. Because the trip is sequential, a 1-day delay on one island will have a ripple effect through the rest of the schedule. Also, we are working with almost 20 different tourist boards was extremely challenging. Some are totally on top of things, others….not so much. The end result is a frankenstein trip which will be half backpacking and half luxury. That should be interesting in its own right.

My schedule is still a bit in flux, but I have the basic plan for where I’ll be and when.

  • Bahamas
  • USVI
  • BVI
  • Anguilla
  • St. Martin
  • St. Bart’s
  • Saba
  • Sint Eustatius
  • St. Kitts and Nevis
  • Antigua and Barbuda
  • Montserrat
  • Guadeloupe
  • Dominica
  • Martinique
  • St. Lucia
  • St. Vincent and the Grenadines
  • Barbados
  • Grenada
  • Trinidad and Tobago
  • Turks and Caicos

After Trinidad I also may spend some time in Suriname and Guyana if time permits.

I’m guessing I’ll be in Trinidad somewhere around the middle of August. As I have nowhere to be after this trip, I have plenty of flexibility in my schedule.

My goal for this trip is to try and learn what makes each island different. Many of these islands get lumped together in people’s minds. In someways they are similar (climate, geography and history) yet in other ways they are very different (Dutch vs French vs British colonies). I’ve already noticed some subtle differences in accents between the Bahamas and St. Thomas.

I also hope to come away with some great photos :)

Hopefully I’ll avoid hurricanes and make it through August without any major incidents.

If you know of any out of the way spots on any of the islands you think I should visit, please feel free to give me your suggestions.

21 Replies to “Let the Caribbean Island Hopping Adventure Begin!”

  1. Hi Gary, I just found this blog of yours! Are you back home yet?
    I am doing research for my internship in London (I am Dutch) regarding more budget-independent-island hopping travel in the Caribbean. Is it possible for you to answer some questions?

  2. Great plan! One day – hopefully sooner that later – I want to do something similar too. Once for the Caribbean and once for the Pacific island from New Zealand to the Easter island! :-)

  3. Hi Gary I just got back from doing a tour in St Lucia. I can connect you with the best tour you’ll experience while there “Joe Knows St Lucia” he’s my friend now and I’m sure he’d welcome you on his tour. Also do you have any properties that are hosting you? I’d recommend a few days at LaHaute “Best view of the Pitons on the island”. If you’d like for me to introduce you to the property owner and Joe via email inbox me [email protected]
    FYI it’s mango season so if you are a mango lover like myself you’ll be in heaven.

  4. Good deal Gary. I’ve visited many and lived in a few of those islands and still some to visit yet. You’ll have a blast. They are all different as you will see. They also call the same foods different names as well.

    I have a friend in Trinidad, so let me know when you will be there and I can have you connect with him. He’ll tel you how to get some buss up shut (its a meal) :-).

    I’m disappointed that you are not visiting the best of them all, Jamaica :-D.

  5. In the best of intentions, I’m jealous of you Gary Arndt! hehehe Beautiful route you did! Just missed the pictures in the post, you did photographic record?

    Very good post.

    Thanks for sharing with us.


    Renan Ferrerssage

  6. What a cool mission and I am really glad (sorry) that you won’t be sitting in the lap of luxury the entire time and doing some backpacking as well. That’s one thing that bummed me out when I was just in St. Lucia, it didn’t seem to be a place I could explore on my own. Locals were warning me the entire time about using public transportation to get from Marigot Bay to Castries like I had wanted because they said it was dangerous so I just didn’t in the end. Of course maybe they had some interest in me using a private taxi instead, but I can honestly say that I did feel a little uncomfortable when we made a stop on a side street in Soufriere to get some groceries one day. Even with 10 other people and a local guide standing next to me.

    With that said, be careful if you do try to make it to out of the way places all on your lonesome. Will you be driving yourself around at all? Be careful with that too. Some of the craziest driving I have ever seen!!

    Now here is the good news. St. Lucia is positively stunning. I can’t speak with too much authority as I haven’t been to most of the other islands, but it’s scenery is something else. Very lush and much more mountainous than a vast majority of the Lesser Antilles. It also has a really interesting history having been passed back and forth a few times between Great Britain and France. I’m sure you’ll read all about it.

    Climb The Pitons, of course! Also very cool is Pigeon Island and climbing up to Fort Rodney. Get over to Marigot Bay and take the short ferry over to Dr. Dolittle’s for a Coco Loco on the beach- best icey tropical beverage I think I’ve ever had. Marigot Bay is where the original Dr. Dolittle was filmed. We didn’t get to do the famous fish fry they do on Friday’s, but had we, we would have gone to Anse la Rey because we heard it’s less touristy and more mellow.

    Can’t wait to read about your experience. Safe travels and enjoy!

  7. Wow… That’s an amazing opportunity! I’ll wait for your photos and your stories about the islands that you’re going to visit. :)

  8. brings back happy memories… (used be a Caribbean specialist in a former life)…. St Barths is stunning but EXPENSIVE, Montserrat is wickedly cool and undeveloped (only other place in the world where St Patricks Day is an official holiday)… The Grenadines are breathtaking and one to include on a future trip is Curacao …. enjoy

  9. My Dad lives over in the BVIs (he charters his yatch) and after reading your post I suggest you visit anegada in the British Virgin Islands, it’s remote, completely flat and has amazing beaches and snorkling which are deserted by the end of the season. Watch the sunset and have dinner at the only restaurant there!
    Also virgin gorda has so much to offer, the baths and jumbies are a must do! Enjoy and I can’t wait to read how your trip goes, traveling over there is hetic to say the least so good luck!

  10. If at all possible when you go to Guyana, try to fly into Canaima and see Angel Falls. We used to run tours for women there, but the airline and political situation changed in Venezuela. Worth a try anyway and there is a lodge which was very nice back then.

  11. Wow Gary, what a dream to not only go to the Caribbean, but to see SO much of it! I would love to aspire to do this trip one day, I’m looking forward to reading updates on your future posts, Bannie.

  12. My dream trip…I will definitely be following you throughout your journey! Anywhere on St. John in the USVI will be out of the way, try The Shipwreck Landing Restaurant for some nice island ambiance. Good luck and I hope you have pleasant weather throughout your trip.

  13. I am not visiting the islands of the Greater Antilles on this trip. That includes the Dominican Republic, Haiti, Jamaica and Cuba.

    They are all rather large islands so I am going to visit them at a later time.

  14. I’ve been wanting to do this same trip for a while, except in the opposite direction. A one way flight to trinidad and tobago, and then island hopping north before returning home to Florida. Looks like a fantastic trip, enjoy!

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