I am assuming you don’t want an all inclusive, so my suggestions are keeping that in mind.

For the Caribbean, I would look into Barbados. It is an expensive island, but it can be done on a budget. To give you an idea, we are going in March (which is high season) and we are paying less than $600 per person and that includes the flight and the vacation rental. If you don’t mind staying in a rental or a bed and breakfast, you can save tons of money. We basically had the same requirements as you, and chose Barbados based on those requirements. Warm, nice beaches, safe enough to go out and explore on our own, great (cheap) public transportation, plenty of restaurant and dining options for people of all budgets.

Outside of the Caribbean I would look at Costa Rica, especially if you are interested in the options of having a city/jungle/beach. There is a lot to explore in Costa Rica, so it would be better for a longer vacation (where you could easily do Barbados for a shorter getaway). It’s also fairly safe and you could definitely find plenty economical lodging options. Costa Rica does not have the clear blue, calm beaches of the Caribbean though, so keep that in mind if that is important.

Dontcallmecass, Hi. That sounds like a real deal. Where are you flying from for that price? We are going from the East Coast to St Kitts in a couple of weeks and tickets alone are over $600.00. Perhaps we should have choosen a different island, or is it our departure point?
Thanks.

I would not call Barbados off the beaten track, lovely island though it is.

If you truly want something off the beaten track & unique, consider either Guadeloupe or Martinique, if you can get there. For example:-

http://www.aujardindescolibris.com/uk/index.html

There is an abundance of inexpensive accommodation, called gites on both islands. These islands have everything you asked for, even an interesting city in Martinique called St Pierre, destroyed by a volcanic eruption and you can walk around the ruins, around the colourful market and boutiques. For those on a budget, the French supermarkets and bakeries are great and there is street food too. Around Grand Anse beach (Guadeloupe), there are (or were) trucks selling pizza or couscous dishes and local dishes.

The botanical gardens on these islands are wonderful and so are the plantation houses/rum distilleries open to the public.

Where are you departing from? Most of the above suggestions are not really considered "moderately priced to inexpensive". The airfare alone will probably be fairly expensive as some Islands are fairly difficult to actually get to.

April is still considered high season, so rates will be more expensive than some other times of the year. If you can push it to about the 2nd or 3rd week of May you will find much better prices.

Look at the Riveria Maya area of Mexico. Great beaches and tons of things to see and do off property that can be considered "jungle" and "off the beaten path". Also will fit into your ""moderately priced to inexpensive" budget.

dontcallmecass, I would also love to know how you got that price. We can only fly AA to Barbados from our departure airport and can't get air for 2 people less than about $1,600 - to $1,800 much less adding in accomendations. We've been wanting to go for a couple of years now, but the prices are outragous. I can't see paying $5,000 - $6,000 for a weeks stay when they are so many other destinations for 1/2 that.

Sassafrass – we are leaving from NYC. The flight was less than $400.00 and it is non stop. My friends are actually driving from Northern Virginia to leave with us because the flight from NYC is so much cheaper than airports near them. The airport closest to them had a flight around $650.00 and it had two stops. Since we are so close to NYC we are spoiled when it comes to finding good fares.

KVR – that fare is absolutely insane. There is no way I would pay that much for a flight.

How much is a flight from your starting point to NYC? Maybe it would be more economical for you to fly to NYC and then go to Barbados from there? When we booked I believe the flight was $410.00. A couple days ago the flight from NYC to BGI was only $350.00 and that was non stop! I’m closest to Newark but we usually fly out of NYC because they have the BEST priced flights to the Caribbean.

JetBlue is giving American a run for their money to many Caribbean destinations, including Barbados. Just looked at January fares from Boston: $500RT, going through New York.

AA fly from San Juan to Martinique daily and AF fly from Miami to Martinique and Guadeloupe. Expensive it might be, since Easter is end of March, but difficult, that would depend on the starting point, which we don't know.

Mexico has everything you ask for. Or Costa Rica. Or Belize.

dontcallmecass, we live in the middle of nowhere Texas, so I pay some of the highest airfares out there. We can only fly United or American, and United doesn't go to all Caribbean Islands including Barbados. I think they have a monopoly in this area.

We are also looking at flying to PR and starting a S. Caribbean cruise, but the airfare is more expensive then the actual cruise tickets. It would be cheaper for us to fly to Miami, spend the night and then start from there, but that is a hassle. What's funny is I can do an air/hotel package for 6 nights in PR for almost the same price that I can get 2 round trip tickets to to PR. Crazy.

Southwest is supposed to start flying from Houston Hobby to PR and other select Mexico/Caribbean destinations starting in April. I'm waiting to see what their fares will be. We flew to Seattle in 2011 for an Alaskan cruise and the tickets were $900 for 2, so I hoping less than $1,000. We actually used miles, so that helped. We'll see. Will probably have to put off Barbados again for another year.

For the OP. It's makes a huge difference where you are flying from, what time of year and what carriers you have available when pricing out a vacation. That is just one of the reasons why we have been going to Mexico consistantly over the past 12 years.

Thanks for the comment and suggestions, everyone.

We're departing from Chicago, so it's not too difficult to find flights to many places.

After much consideration, it looks like we'll be heading to Puerto Rico in April. As KVR said, Southwest starts flying there and fares were relatively inexpensive from Chicago the last time I checked (and I have plenty of points saved up, so we'd likely fly for free).

If anyone has suggestions about what to do in PR, where to go, etc. that'd be great. I have only just begun looking.

PR is a great choice. I actually went there back in the early 1980's, but that was so many years ago. I've only just started looking too, but have found a food tour and a bar hop tour. We've done those in various places and enjoyed them. Of course a tour to the El Yunque Rainforest. I still have a pic my mom took of me there. A City tour. Day trips to Culebra for snorkeling and Vieques for the Bioluminescent Bay tour. There is a Rum Factory tour.

For hotels, I'm looking at the El Covento. It's in the city and not on a beach, but shares privledges with their sister resort located on the beach. For a cruise stop that would be OK, but for a weeks stay the La Concha and the San Juan Water & Beach Club Hotel get good reviews. As well as the Marriott. I didn't want to be too far away from various dining options since there are no real AI's there or activities. Taxis can add up easily.

There are plenty of posts here for PR. I've read through them and got some good information. I'll be interested to read any other information regarding PR also. We're not going until November if everything pans out.

KVR - flights from Houston to NYC can be pretty decent. You might be able to reach a more expensive destination by flying to NYC first and then to the destination. You could easily get to barbados for around $1200.00 that way. It's still not cheap, but it might be something to consider if you really want to go to Barbados.

That's a round about way getting there and back. I have to fly to Houston or Dallas and then NYC, which may include another connection or 2. That's means 2 to 3 connections to get to NYC and then Barbados. At this point and time I refuse to ever get on another American Airline flight ever again, which means I may never get to Barbados unless on a cruise.

When we went to Curacao, I refused to go with AA and connect in Miami. We flew Continential to Houston and then Aruba and then took Insel Air to Curacao. I wonder if I can do that getting to Barbados. It won't be this year though. We've already made tentative plans for our winter trip this year. I'm also interested to see what Southwest does within the next few years.

I'd second the recommendation to Barbados and also suggest looking into St. Lucia.

I've been to both - and they're both really beautiful places and each have a different vibe. St. Lucia is a little more "off-the-beaten path" than Barbados .. but it really depends what your looking for in a vacation.

Also Jetblue has great prices & direct flights to both islands from NYC now.

Hope you have a great vacation!

I'd second the recommendation to Barbados and also suggest looking into St. Lucia.

I've been to both - and they're both really beautiful places and each have a different vibe. St. Lucia is a little more "off-the-beaten path" than Barbados .. but it really depends what your looking for in a vacation.

Also Jetblue has great prices & direct flights to both islands from NYC now.

Hope you have a great vacation!