Where to go for winter break - best islands
 

HI all, I see many "another question about where to go," threads so I will try to give lots of info and appreciate your patience. Taking early retirement now and want to explore a few places I can visit for 2 or 3 weeks during the winter's cold over the coming years. Will be traveling with my sister, would prefer to know about hotels for first visits rather than AirBNB etc., till we are more familiar.

We are very quiet, not interested in a hugely loud and crazy nighttime club scene (OMG I am so OLD!) but would like to be able to walk around a medium sized town, explore restaurants with great food, buy some fun things, and see other people. Mostly we want to lie in the sun, walk on the beach, spend time walking around a town, or two read, hang out at an outside bar or restaurant and relax. We are not adventurous. (Egypt was very hard for me, although it was worse because the war started 5 days in).

I have read a lot about get-aways to some islands that involve flights, boat transfers, etc. Would like to make it as simple as possible for now. I totally admit this, and also apologize, we are a little spoiled. Not sure what cost to give you but I would say all in - maybe up to $1,000 a week per person? Plus travel, etc. We would also prefer to be in a warmer spot, rather than one that is cool in Jan/Feb. I would be very grateful or any suggestions. Thanks.!

Where is your home? Some islands are easier to get to from certain places.

"Not sure what cost to give you but I would say all in - maybe up to $1,000 a week per person?"

If you mean full board in a good hotel at a lovely place, things could get rather difficult. But according to the Island, you may find tons of not too expensive guesthouses and local restaurants.
May be you have a look at booking.com or expedia.com in order to get an idea about the prices.

Hi Susan,

Agree with Neckervd that 1000 $ is not a spacious budget. Given above information, I would consider Negril (Jamaica), Oistins (Barbados), Philipsburg (St. Maarten) and Rodney Bay (St. Lucia). Oistins and Philipsburg are under half an hour from the airport, as you seem to prefer. Negril some hours even. Budgetwise, in Negril, consider a stay in West End area - at sea though not on beach but not far from Seven Mile beach. In any regards , as Necker stated, look for smaller hotels given your budget. I can recommend Bay Gardens (shuttle to beach) in Rodney bay, Seaview in Philipsburg. Oistins might be pricier (I stayed further west so dont know)

Good morning! I live in Washington DC. And I saw a post that said that 1K a week per person was not a spacious budget. Since I really didn't know what to estimate, I think I should say (after that comment) that we can easily to $2500 a week each. Since I'll be traveling with my sister we can share one large hotel room. :)

Hi Caribbean Boy and thank you! Given your comments and also neckeryd's I opened up the budget to $2500 per person per week. I just had no idea how much things cost. Money is not the deciding factor here. :) Thanks again to both of you.

Hi, that budget should get you a long way Susan.
Then still, choice remains full amenities resort v smaller and intimate hotels.

Departing from one of the Washington, DC area airports you should be able to find non-stop flights to the following islands: Providenciales (in the Turks & Caicos), Puerto Rico, the Dominican Republic, Jamaica, Grand Cayman, St. Thomas, St. Martin, Aruba and possibly St. Lucia and Barbados. Your budget of $2,500 per person per week (not including air fare) will be more than adequate to have a very enjoyable vacation on any of those islands.

Based on the information you provide in your initial post I'd suggest you start by doing some basic research on Providenciales, Grand Cayman St. Thomas and St. Martin as they each offer everything on your wish list.

Do you want an all inclusive resort? Do you want adults only?
I know you want low key and quiet with a nice beach.

RoamsAround : See first post: Susan looks for easy travel and little transfers - does that apply to Puerto rico, and if so where? I fear cd be quite a transfer time. TCI good addition of yours, though bit $$$? In agreement re Barbados, St. Martin, St Lucia.

She also would like to stroll a town nearby - not sure where that would be in domrep

From DC she can fly nonstop to San Juan (about 3:45 flight time). There are plenty of hotels in varying price ranges within a 10 to 15 minute taxi ride from airport. Many of them are either beachfront or within a few blocks of Isla Verde beach and have shops and restaurants within walking distance. Old San Juan is a short taxi or bus ride away and offers a very safe area for tourists. The only drawback is it’s a city environment which may not appeal to a first time visitor to the Caribbean which I why I suggested the other destinations.

Hi everyone, and thank you so much for your thoughtful responses. You have given me a bunch of islands to research and read about and that is excellent!

So, I will be traveling with my sister, as I am single, therefore would rather avoid the "romantic couples resorts," but would be happy to look at both suggestions CaribbeanBoy. (full amenities vs.) What I am delighted about is that you guys have offered up some islands, and now I need to do a lot of reading.

I have been to the Bahamas (Lyford Cay, which was gorgeous, but private and for weathly people and spent a great deal of time on Grand Cayman as my friend lived . there for many years. Although the diving was excellent (I do not dive anymore) I found GC to be a scrubby and not really pretty island.

Thanks to all of you - I definitely have some fun work ahead. We will try a few places over the next few years, and now we really have some names to explore.

Ok good luck with the considerations.

Given your extra information on Bahamas experiences, I stick to advised lot - will be more genuine. Same with roamsaround suggestions, only Providenciales to me seems upscale and you might not want that.

Since you want WARM in Jan/Feb go to ABC islands - the further south the better - Aruba, Antigua, Anguilla, Barbados, Curaçao.

Aruba is more commercialized from what I hear. I’m going in 2 weeks for a quick 5 days. I’ve only gone to USVI, A couple Bahama islands, Jamaica, Turks & Caicos and Bermuda. All are nice but Bermuda is too cold then & kind of (not totally) shuts down in winter. Out islands of Bahamas are beautiful but may not have the shops you want and wouldn’t be as warm in Jan - Feb.

Look into Bonaire, not here on Fodor’s though, no one seems to know much about it

Bonaire is excellent for snorkelling, but not somuch for sandy beaches.
Aruba and Curacao have both la lot of good sandy beaches.
Venezuala would have some of he best destinations (Islas de Los Roques; Isla de Margerita, Islas North of Puerto La Cruz), but under the actual political and economical circumstances, it would be a very bad idea to try to visit them..

Trinidad and Tobago may not be the best alternatives, as criminality there is rather high.