We are looking for a luxury island vacation in Jan with the shortest travel time. Last year we went to Anguilla and had to change planes and take a boat which was too much. We also went to Barbados the year before and really enjoyed both vacations, w/ the exception of the painful travel. Any suggestions?

I thinks because of it's location, finding direct flights to most of these islands from Chicago is difficult. At least besides Puerto Rico, Bahamas and Jamaica. We are even having a hard time getting direct flight from Chicago to Puerto Rico for the March 22. Leaving on a cruise on 03/22, have even tried for 03/21 but still not reasonable direct flights. They are all upwards of $900. Wemt on a cruise out of PR in August, and was able to get flights for $300

Can you say what was painful about the travel to Barbados? Do you mean just switching planes was painful? If so, let us know where you're flying from so that we can recommend islands with nonstop flights from your departure gateway.

If you do not mind changing planes once, on American Airlines you can get to just about any island in the Caribbean with a connection in either Miami or San Juan.

The islands with the most non-stop flights from various gateway cities in the US would include Puerto Rico, St. Thomas, St. Maarten/Martin, Jamaica, Aruba and Grand Cayman. Without knowing more about where you're flying from, I'd suggest looking at these destinations.

In terms of luxury, what is your nightly price range for accommodation? There are Ritz Carltons on Puerto Rico, St. THomas and Grand Cayman. Elsewhere on Puerto RIco, if you like you resorts you could check out the El San Juan or El Conquistador, or if you prefer smaller luxury places, check out Horned Dorset Primavera. On St. Thomas, the RC is really the only luxury game in town. On Jamaica you could check out Jamaica Inn.

<doh> Okay, I just realized that you put Chicago in your post. Sorry for not seeing it! But I think the islands I just mentioned in my previous post are possibly all nonstop from ORD. The nonstop to Grand Cayman is not on American but on Cayman Air.

The only 5* resort in the Caribbean is The Four Seasons, Nevis which takes two planes and a boat from ORD. Your criteria might work for the Ritz Carleton or El San Juan Resort, San Juan, Puerto Rico. Make reservations soon - it's high season and January may already be booked up at the popular destinations.

No advice beats those who have 'been there and done that'. The problem really is your location. We fly out of Mpls. and have the same issues every winter. Plus, the places that are the closest i.e. the Bahamas aren't very warm in January. We just made up our mind years ago that we know we are ging to leave on a 6am flight and waste an entire day flying, pay for a night on whichever island just to sleep and start on our vacation when we wake up. Buy yourself a nice piece of jewelry while you are there that will serve as a reminder of what a great vacation it really was. After a few years, it's not so painful anymore.

air jamaica has a has a non-stop to montego bay. i've never been but others could direct you to nice resorts there.
you can also fly to st. thomas or grand cayman in under 6 hours using american or delta.
both islands have a ritz. can't speak for the one on gc but the st. thomas ritz is very very nice.
if you wanted to go back to barbados you can fly in approx 71/4 hrs. i have been looking at sandy lane and think it looks pretty much 5*.

As already noted, "zero to 80" (degrees fahrenheit!) in four hours from Chicago to Grand Cayman.

Non-stop service on Cayman Airways, warm weather (tucked into the NW Caribbean, not exposed to the Atlantic like Bahamas or Turks).

Pretty much any accommodation in Cayman is "high end", you have lots of choices.

Knowing-
Us Mpls people must be on the same page. We have resigned ourselves to the very same thing. Besides, the best islands seem to be the ones that are more challenging to get to. We are headed to Anguilla on Friday. I am digging your jewelry idea. I'll have to give that one a try.

Hi Anguillagirl,
I haven't discovered many of us MN people in the Caribbean because it is such a difficult destination, but the Caribbean fits our definition of "vacation". I suspect from your name that you must visit Anguilla with some regularity. You leave Friday? Have a great adventure!

Have you considered Provo in Turks & Caicos? You can fly on American and connect thru Miami. The Palms is very upscale and several other very nice condo developments.

Thanks to everyone for the replies. "Painful" meant switching planes, running through the San Juan airport carrying luggage to clear customs, taking another plane, then taking a boat to Barbados; same for Anguilla. I see where the MN people are coming from - you resign yourself for a full day of travel. Unfortunately my traveling partner does not see it that way So I want to compromise....I am finding Puerto Rico and the Caymans as our best non-stop options that are warm in Jan. Cabos is also being suggested, but doesn't belong in the Caribbean Islands forum. So...does anyone know about the Ritz in PR? I assume it is beautiful. Any Cayman suggestions?
THANKS!
PS - we loved Anguilla - to those that are going, enjoy!