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Forums » General & Multi-Country » Best Self Guided Island Hopping in the Caribbean


Best Self Guided Island Hopping in the Caribbean

by /bio/mvarre »

Hi All,

I'm looking for location recommendations for Caribbean island hopping via rental of: kayak, a hobie catamaran, or a small motorized dinghy for my girlfriend and myself.

This is our first vacation in several years, so we're trying to make it count haha.

We're looking for a set of closely grouped tropical islands that we can self-navigate in between via multiple day trips from a base island location.  For the base location, I'm looking for a tropical bungalow/guest house with just basic provisions (with hopefully a hammock nearby) - so not a large resort.  Ideally we’re looking for a town with at least one hole in the wall bar that serves boozy tropical drinks and local seafood.

The idea would be to paddle/sail/motor between an island or two a day and stop in between and hangout on the beach(es) and snorkel at leisure.  Maybe even do a little fishing from the shore and some light hikes.  We're fine with snorkeling from kayaks, or parking the boat on a beach and snorkeling from the shore. We don't plan on camping overnight on the day trip islands to avoid lugging around camping equipment.

We prefer really low crowds, scenic/secluded type areas.  Also looking for great tropical beaches and great snorkeling.

Budget: looking at spending less than $120 a night for lodging, and less than $100 a day for gear rental (so relatively low budget).

Trip length: 5-7days.

Time of year: late spring-early summer


Location ideas so far:

-Turks and Caicos

-St. John (USVI)


-Belize cayes

-Bonaire (I hear this has great snorkeling, but not the best beaches)



-Virgin Gorda

**The plan is to not island hop between all the options above, but hopefully just one location that has several small islands relatively nearby.

Let me know what you think on the locations, and if you have any recommendations on hotels, as well as places to rent equipment from.


Thanks for your help!



RE: Best Self Guided Island Hopping in the Caribbean

by /bio/rabbitt9 »


I have been to many Caribbean islands and Turks & Caicos is my absolute favorite - heading down myself in a couple weeks.  

Incredible beaches and snorkeling.  However, I am not sure how accessible other islands are via your proposed mode of transportation.  There are many islands that make up the Turks & Caicos that can be explored via kayak, paddle boat etc.   And, the water is quite calm and easily accessible.

I am not quite sure about budget accomodations as I have stayed at a resort on the beach, but I suspect you can find different options.  Overall, I don't find the island to be overly expensive - especially compared to St. Barths and other locales.

Also, if helpful, I have found great hotel discounts from and Orbitz via the below website:

Good luck!





RE: Best Self Guided Island Hopping in the Caribbean

by /bio/mvarre »

Great, thanks for the feedback!  I'll give T&C a look.




RE: Best Self Guided Island Hopping in the Caribbean

by /bio/pauline-frommer »

The Grenadines are exquisite---in fact, they were used for the Pirates of the Caribbean movies. Many island hop there. The only downside are the costs which can be high, at hotels and restaurants.


RE: Best Self Guided Island Hopping in the Caribbean

by /bio/healthcarebilling »

This is really interesting.I too love to visit there.Once I visted there for my Health Care Billing service.Frome your description 1 love to visit there again.