Kauai, Maui or St. Lucia
 

My boyfriend and I are planning a almost last-minute getaway for mid-late Feb. We live in Chicago and consequently want to go somewhere warm and scenic. I'd done some research and was pretty settled on St. Lucia but happened to check flight prices to HI and was surprised that they were only marginally more expensive for our dates. As such, I'm now confused about where to go!

Our priorities are mainly aesthetic -- I just want somewhere warm and gorgeous with a mix of beach and green mountains, ideally (hence striking out several other Caribbean spots). We are primarily in search of a relaxation vacation, though at least a few extra activitiy options would be nice. We both love food and wine. I do not like huge super-touristy, ultra-commercialized areas with 15 super hotels on one strip; we both prefer more tranquil settings, though close enough to other resorts or towns that we could have variety in our meals, get a drink, etc.

If we went to St. Lucia we'd probably do 3 nights at Jalouise Plantation and 2 at Ladera.
Kauai we'd probably do the St. Regis for the full time.
Maui probably couple nights at Hana Travassa and a couple on the west side by Wailea.

I've been to Maui when I was a kid and loved it (though it was a little too commercial in the exact area I was in); I also went to St Maarten as a teenager and did not care for that much (again, in super touristy area) though from what I've read SM and SL are completely different animals.

Anyway! With all of that, any recommendations are appreciated! I'd be curious to know:
A) what people think is the most beautiful of these options
B) which overall one would do
C) ideal length of time in each (i'm currently thinking 5 is enough in St Lucia, but maybe a full week in Hawaii given the jet lag).

Thank you!

I forgot to add that my boyfriend has never been to any type of island/tropical setting. He is leaving me in charge of planning the trip, but this is the primary reason for my indecision. He has expressed a lot of interest in Kauai in the past but I think he would love any of these. If it were up to me I'd probably lean toward St. Lucia just because I've been to Hawaii but think he might enjoy Hawaii more as a first timer to islands? Unsure!

It's very late to be booking for the week after President's Day in any place.

Hawaii is lovely, but without a budget it is impossible to recommend something that might fit your request. In Hawaii, especially, rental cars may be very expensive at that time of year.

I wouldn't recommend Hawaii unless you are going for a full week.

Develop a nightly accomodation budget.

You can't go wrong with Kauai - gorgeous, lush, fabulous beaches and views and hiking. You should know, however, since you picked the St. Regis, that while it's (I'm sure, although I haven't been in it) a fabulous hotel, it's within the Princeville area - lots of people like this, but I don't. Basically you drive in to a "development" of golf courses, hotels, condominiums and private homes (but unlike where you stayed in Maui, which was very likely Kaanapali Beach, there is only one other hotel, I think - the Westin).

I've been to both. While I love Hawaii, it is very touristy in most areas. I love St. Lucia (have been there 3 times). I will be there in a little over a week. Jalousie Beach is laid back and beautiful.

Why would you spend 5 nights in 2 diff hotels in St Lucia? Same for Maui- it is easy enough to rent a car and drive around Maui to see and enjoy different aspects of the island.

What is the flight time? How many different flights to each location? Flight schedule? These might also make a difference on your decision.

BarbAnn, just curious whether you've been to "most areas" in Hawaii, specifically Kauai? Waikiki and Kaanapali Beach/Lahaina are for sure touristy, but most of Kauai is anything but.

I love Kauai (like Maui also) but that time of year I would stay south at the Grand Hyatt, North Shore can get rain in the winter.

Maui would be good for the whales, but reports on TA indicate people are seeing tons of them this year right from shore in Kauai as well.

Thanks for the thoughts everyone! I really appreciate it.

A few responses:
1) We both have nontraditional jobs/schedules, that make it next to impossible to book travel more than 3 months out tops, and we also just happen to like more spontaneous/last-minute trips. :) We both had a chunk of time open next month so we are thinking to go, and have actually had no trouble finding great rates.
2) Budget is "flexible" I would say. I don't want to be excessive (no Jade Mountain for us) but we have some room and these locations all seemed to be about the same in price once everything was added up.
3) It's of course a longer flight to HI but not a huge concern for us.
4) I love (Love) unique hotels, and Ladera is more or less on my bucket list for hotel experiences. That said, I think a night or two would be great to get the experience but the convenience of JM right on the beach and with the more traditional layout seemed like it would be a better fit for us for the longer stay. They seem to be two almost completely different experiences so the idea of mixing it up appeals to me. Same idea with Maui though not to the same extent, and we could easily stay in one location, you're right.
5) Thanks for the thoughts on Kauai. I appreciate the thoughts on princeville, too, as that definitely does not sound like my ideal sort of vibe. That said, the St. Regis is 50% off for Starwood members so that is pretty appealing!!

Does anyone know of any more romantic or boutiquey hotels in Kauai (I suppose preferably south given some of the comments above)? I have been surprised by the lack of other options besides huge chain resorts or timeshare/condo type of places? I think if we could find somewhere a little more unique or special that would push Kauai over the top for me.

Check out Koa Kea on the south shore of Kauai - definitely the vibe you're looking for!

http://www.koakea.com/

In February, the north shore of Kauai is more rainy and the water is much rougher than the south shore.

The St. Regis has an incredible setting, but it is a big overglitzed hotel that seems very out of place for the laid-back north shore. I'd chose a south shore accomodation. Better get that car rental reservation as soon as you make your plane reservations.

I've been to Maui, Kauai, and only St. Martin & St.Barts in the Caribbean.

I love Kauai - it has everything, especially warm tropical weather. The North Shore of the island is lush, tropical, mountains with rainbows, beautiful beaches, and the South Shore is dry, nice beaches as well. The island is small so you can drive from N to S in a short amt of time too.
I think Kauai reminds me of what Hawaii was a hundred years ago. I think Maui is too "mainland" for my tastes.

I also love the spirit of Aloha that you get in the islands as well.

Well, the south shore of Kauai is certainly dri-ER than the north shore, but I wouldn't call it dry!

:) true sf!
I would rent a car and if she stays on the south shore, I would recommend driving up to the North Shore to take the Napali Coast boat tour, eat at Bubba's Burgers, walk around the cute town of Hanalei (one of the most lush spots in the world IMHO).

If she stays on the North Shore I would also drive down to the South Shore. My point is not to settle in to one end or the other. And as pointed out the surf on the North Shore can be rougher in the winter time.

Just checked - Princeville's average annual rainfall is 78", Poipu's is 34". By contrast, in a "normal" year, San Francisco gets about 22" (although almost all of it falls between November and March).

I'm currently in bliss -- aka Kauai's "rainy" North Shore. I had the most glorious walk this morning at Hanalei Bay--in bright sunshine. Have had about twenty minutes of rain in the past three days. Look at the Acc-Weather forecast for Princeville. It's showing a couple of days with a mix of clouds and sun; highs around 80 degrees--followed by four days of sunshine.

No matter how many times I return, I can hardly believe the beauty. I spend a month here every winter, and while it certainly gets more rain than the South Shore, much of the rain comes during the night--or in short showers. For me, there's no comparison. South Shore is very pretty; but it's "generic" beach. The North Shore takes my breath away, with it's dramatic, jagged peaks and lush scenery.

The St. Regis is spectacular -- but it's definitely a very high-end, glitzy property. The restaurants there are outrageously expensive -- but you can always drive ten minutes to Hanalei for a wide variety of choices.

Even if you hated Princeville (and I happen to love it), I wouldn't let the fact that you'd be driving on a road that goes through Princeville stop you from staying at the St. Regis--if your budget allows.

As others have said, you can drive from North to South in about an hour. Enjoy--whatever you decide.

Songsoc, envious as usual!

Didn't get to St. Lucia - but friends on Antigua loved it.

Having said that - have been all over Hawaii many times since '77 - and we love the luscious North Shore of Kauai and if you can get into the St. Regis for half price - jump on it. You might consider staying up there 3 or 4 days and the rest down at sunny Poipu on the south side - only an hour or so beautiful drive (Unless you hit rush hour in Kapaa :) Really! Add 10 more minutes. )

And I love when it rains on the Garden Island - as afterwards - there are many rainfalls flowing down the Bali Hai mountains ringing the Hanalei/Princeville area. Unless you are smack in the middle of a huge winter storm, the rain comes and goes and you can still enjoy going to the beach.

Check out the classical WWII musical/love story/Academy Award winner - South Pacific by Rogers and Hammerstein - for an idea of Bali Hai (filed there - and the dock is stil in Hanalei Bay) - and actress Mitzi Gaynor "washes that man right out of her hair" - at the very scenic Lumahai Beach. That's about half way to the end of the road - over 7 one lane bridges - and the Ke beach at the end/Haena - is protected by a reef and great for swimming/snorkeling/watching the sunset - and hoping to catch the green flash!!

And great trip report Sondoc. Wish we were there to appreciate it - and maybe go into Hanalei town for lunch or dinner - to say - the Blue Dolphin? :)

http://www.hanaleidolphin.com/dolphi...rant-kauai.htm

Be sure to check these pics of the famous Taro fields and also the dock in Hanalei Harborn - again - shown in the movie South Pacific - 1958 - which was filmed there.

http://www.hanaleidolphin.com/hanale...n-location.htm