One recurring theme that stands out in your post is your desire for: "cheap entry points", "eat cheap" which suggests you are on a tight budget.

While you certainly can hop to the islands on your list you may find airfares will be a bit pricey and you cannot get between any of them by ferry as they are all too far apart from one another for boat travel. You have to go by air. Also, with the exception of Puerto rico it is difficult to get from Jamaica to any of the other islands on your list without going through Puerto Rico as there are no direct flights.

If you want to visit Puerto Rico, St. Matin, St. Kitts and Antigua your best bet will be to fly into San Juan. From there you can fly to any of the islands on your list in any order that works with your schedule. You'll have to check fares and schedules with the following airlines: American Eagle or LIAT out of San Juan and LIAT or Winair between the islands of St. Martin, St. Kitts and Antigua.

Lastly, you may have to fly back from one of those islands to San Juan for your trip back to Canada in order to avail yourself of the "cheap entry point" fare you got into Puerto Rico as flying back to Canada from one of the other islands may result in a surcharge.

You can save money and travel times by flying into San Juan then taking ferries to the "Spanish Virgins" of Vieques ad Culebra which are just off the coast of Puerto Rico. This will be the easiest and least costly way for you to island hop but you won't be going to any of the slants you mentioned.

Money isn't a problem. We are both working professionals. When i say cheap entry point i mean the difference between $450 to San Juan v $1,000+ to get to any of the island directly.

We have heard that San Juan is a great fun city to visit so it sounded like a good place to fly in.

Thanks for your reply. When i say cheap eats i am referring to eating local food. Basically i am looking for a varied food scene.

Roams around, you didn't notice the doing it in 10 days part?

Beyond ambitious! Maybe 2 places at most, you loose travel time and won't see anything. Unlike Europe where countries are together, most easier to get to islands still take up your day getting there. And Liat is never on time, it's best to have " free time " travel days.

From San Juan, you can probably one other island on you list for 10 days. Actually you'll have 7, you loose the first and last days in San Juan, and you'll loose a connecting day. So really you have 3 days at 2 destinations, and Puerto Rico is big!

The best easiest way to see multiple islands in 10 days is a cruise. Even with a cruise you loose some travel days, but it will get you a taste of different islands.

Hi Blamona,

Maybe we need to add some days

My boyfriend would never go on a cruise.

What do you think of just Puerto Rica and St Martins?

We read that you can tqake ferries from St martins so maybe we could day trip an island or two.

Thanks a lot for your post.

That sounds like a good split

From St. Martin you can ferry day trip to either Anguilla or St. Barth. St Martin will also fill the restaurant requirement, best in Caribbean, including the local eats.

But if you want to day trip, you do need to add more days. You won't see much of St Martin and combine with another day trip to another island in 3 days. I say, minimum of 5 full days with 1 day trip to Anguilla. Have a minimum of 4 full days in Puerto Rico, it's a big island!

It sounds like you're trying to crame in as many islands as you can. In the Caribbean it's really hard to do, no ferry systems between many islands, tons of open water. Terrible local airlines and only a limited to islands too. People don't realize the logistics aren't there to island hop without a lot of time, a lot of patience.

You can easily fly from San Juan to St. Martin (no "s") on American Eagle or LIAt (about a 40 minute flight). From St. Martin you can go by ferry to Anguilla (25 minutes) or St. Bart's (about 1 hour) so they make good destinations for day trips.

Okay so i need to add some days

If we went mid July do you think it would be too hot?

Mid-July temps in the Caribbean will be in the high 80's F. with occasional forays into the low 90's F. Humidity will be on the high side. That combined with the strong sun might make it seem warmer. You'll have to decide if that is "too hot".

For me, summer feels better in Caribbean than on East Coast beaches, don't know if it's just better to put up with because the scenery is so awesome? Or because the humidity on the East Coast is more brutal than at the beach?

I almost didn't click on this post as you tagged it Trinidad & Tobago, which I know nothing about.

I also can't help you with Puerto Rico as we only fly through. But it's a large island so you can more than likely find what you're looking for.

I think St. Martin is a good choice. You can take the public ferry (about 25 minutes) to Anguilla for a day trip. Head to Shoal Bay East for the day. It's a beautiful beach with some local restaurants (Gwen's, Uncle Ernie's, Elodia's) and beach chair rentals available. Just make sure you check the ferry schedule to find out the last departure time and plan accordingly. You can get a taxi at the ferry dock (you'll need to go through immigration both on arrival in Anguilla and on arrival back to St. Martin) and arrange a time with the taxi driver to pick you up from the beach and return you to the ferry dock. There's some okay snorkeling at Shoal Bay.

Another day trip from St. Martin is to St. Barts. The passage can be a bit rough, however, so if money isn't a problem why not arrange a day-long private charter. I'm a bit prone to sea-sickness and I find if I'm going fast I don't have as much problem as I do if I'm on a slower ferry boat. You can take a private charter right to St. Jean Beach, which has the most tourist facilities on the island. Gorgeous beach, wonderful food and fabulous people watching. On your charter you can also stop by Pinel and Tintamarre, two small islands off the northeast coast of St. Martin. Make sure your charter captain lets you try a mud bath. You won't believe how smooth your skin feels afterward.

Another area for you to consider (sorry for adding more confusion!) if you want to day-trip, is either the US Virgin Islands or the British Virgin Islands. You can easily get ferries between some of those islands and the scenery through that region is stunning. There are some wonderful beaches and very good snorkeling. Probably your best bet would be to fly into St. Thomas or perhaps Tortola.

It will definitely be hot and humid in July.