Pod72

Yes, I know this is a VERY broad question. I want to take my first solo trip to the Caribbean over Christmas week. I know this is a highly traveled season, thus expensive. It will be the first vacation I've been on in 13 years!

I want to go somewhere in the Caribbean. I've been to Puerto Rico twice and loved it, but want to go somewhere else.

I'm traveling from Chicago.

I don't want nightlife. I want quiet. I want a safe place with a pool and a beach fairly close by. I want good food. I don't want to pay more than $2000 for the hotel and airfare together. I want to be able to walk around and explore the island by myself.

A tall order - I know. Any suggestions for which island and perhaps a hotel or bed and breakfast?

Thanks!

cmcfong

Because your budget is tight and you have chosen one if the most expensive weeks of the year to travel, I suggest you look at packages offered by airlines for St. John, Dominica, and the Out Islands of the Bahamas. If you are open to other options besides the Caribbean, Panama or Costa Rica might meet your requirements. Enjoy yourself. Thirteen years is a ling time to go without a holiday.

WWK

I feel terrible saying this since you've gone so long (!) without a vacation, but I think you're in for some serious sticker shock. It may be next to impossible to find what you're looking for Christmas week with that budget.

Can you go another time? We often travel in the shoulder season, November-December 20th. You can sometimes find very good packages or stand-alone hotel deals at that time. Airfares will be cheaper, too, although still expensive.

Good luck!

tch912

If you buy your ticket now you can get it for under $500 to San Juan. The Posada San Francisco is a hostel in the middle of Old San Juan that gets good reviews. The owners will pick you up from the airport. The price is in your budget.

Pod72

Thank you all! I'm going to check St. John, Dominica, and the Out Islands of the Bahamas, Panama and Costa Rica. I can always go to Puerto Rico again. It's still cheap to go there doing the holidays.

I'm in a position were I can now work from anywhere - so the year of travel is going to begin!

Thank you for all of your kind words.

Odin

I think Dominica was mentioned in error and probably meant Dominican Republic.

suze

Would you consider the Caribbean coast of Mexico ('mayan riviera')? You can get more bang for your buck there than in the Caribbean islands.

cmcfong

Actually I meant Dominica. http://www.dominica.dm/index.php/where-to-stay

blamona

Your budget is way slim, so your pickings will reflect that

Try Roatan Honduras, sounds like everything you're looking for, cheaper budget overall too

Odin

I thought Dominica was a bit of an odd suggestion for someone who wants to walk around and explore the island by themselves, who wants a hotel with a beach nearby and has a small budget. The flight will not be direct. That's why I thought it was a mistake but maybe there are inexpensive lodgings.

sharona

You can often find good deals with a package. Look at:

http://www.applevacations.com

http://www.cheapcaribbean.com

http://www.travelzoo.com

and even a large all-purpose travel agency like Liberty Travel.

Dominica isn't known for its' beaches. I believe the beaches there are few and far between. Dominican Republic is one of the more affordable destinations in the Caribbean, especially for all-inclusive resorts, and it has nice beaches.

Personally, I wouldn't chance the Bahama Out Islands in the winter. They are too far north to be assured of warm enough (for me) beach weather.

diann24

I agree with Suze. I would look into Mexico. You are choosing a difficult timeframe and your budget is somewhat low.

RoamsAround

Yes, only a few "dark sand" beaches on Dominica - Atlantic side beaches are rocky and usually too rough for swimming, Caribbean side beaches are just OK. You go Dominica for the hiking (it's an eco-tourist's delight) not the beaches.

Yes, there are some inexpensive lodging in Dominica but it's difficult to get around without driving. Since most activities center around "nature" it's not a great place to travel "alone" - better to go with a companion as you don't want to be hiking alone through the mountains and rain forests.

For someone traveling at peak of High Season with OP's limited budget the best destinations where he/she will get biggest bang for the buck are:

Dominican Republic
Jamaica
Mexico (Cancun, Playa del Carmen, etc.)
Roatan
Belize

suze

I still vote for Mexico, but Negril Jamaica could also work.

ishkribbl

Pod72,
It sounds as though your needs are relatively few and you are open to the idea of B & B's or guesthouses. I do think it is possible to find what you are looking for- it just takes some looking. On a quick search I found air from ORD to St. Thomas, USVI (STT) for $705. I also found the Bayview Vacation apartments on Virgin Gorda http://www.bayviewbvi.com/
for $774 for one week ($129 per night based on winter rates for one bedroom). I have been to VG (love it) but did not stay at this place; however, I know it is located right in Spanish Town where you would arrive on a ferry from STT (check schedules for BVI ferries- some routes go through Tortola, either RoadTown or West End but it is do-able- check price as it will factor into your budget). There are several place to eat within a short walk, a grocery store (Buck's is a couple of blocks away- you could use your apartment kitchen to fix breakfasts or picnic lunches to economize) , taxis you can get to beaches or you could rent a car and explore for a few days. Bayview's site says it has apt/car package prices- you might check those. I think VG would feel like a safe and friendly place, even traveling alone.
Keep looking- this is just an example.
Happy Travels!
PS Over your budget by a bit but the Hillcrest Guest HOuse on St. John is $1400 for a week if you want to look at stretching your budget just a bit. SJ would also be a good choice,

ishkribbl

I am really disappointed that there aren't any creative thinkers out there coming up with ideas for you so I am bumping this up for another try~~