Hawaii - Hawaii Help Please

Considering a trip to Hawaii for Christmas. First time. Just myself and my pregnant, but athletic wife. Want a combination of beach sports, hiking and the like. I don't actually need the pampering of an ultra-lux hotel, but am doing it mostly on points and would consider one if there is real value from it (e.g., great grounds, water sports, large room, amazing pool, manicured beach, etc.). Trip will be about 9 days. Thinking 1 to 2 islands. Don't want to move more than once, so max of 2 hotels.

First question is which island(s). I don't see any benefit from being in a city, so is there a strong draw to Oahu other than Honolulu and night life? With the Big Island, I feel like I would spend the entire time in the car since it is so big? I have been leaning toward a combination of Maui and Kauai but can be convinced otherwise.

Based on availability and price, I am considering the following hotels (I am pretty much limited to these, so unless there is some Ritz charging $99 a night, please limit your recommendations to this pool):

Maui:
Marriott's Maui Ocean Club - believe I can get very cheap
Westin Maui Resort & Spa - I hear it is big with lots to do
Sheraton Maui Resort - I hear it is quiet with a great beach for snorkeling

Kauai:
St. Regis Princeville - convince me it is worth the money/points. Very expensive, but maybe worth it for a couple of nights?
Courtyard Kaua'i - in case I need to escape the St Regis :)

Big Island:
Waldorf Grand Wailea - would probably only be for a couple of nights due to the cost, but is it that special to be worth it?
Hilton Waikoloa Village - Waikoloa Village sounds interesting in the marketing materials
Sheraton Keauhou

Oahu:
Waikiki Beach (Various Hotels such as the Marriott, Courtyard, Hilton Village, Hilton, Doubletree, Embassy Suites) - basically, the question is to Waikiki or not?
Marriott's Ko Olina



THANK YOU!!!

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Obscure2k
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Luxury Hotels

Oahu is nit just the city. Waikiki does have some great beaches, but so do other parts of the island. Visit the Nirth Shore to see where the championships take place, swim in the waterfall at the audabon sanctuary, shrimp from the trucks, the Dole Plantation, Pearl Harbor.

Kauai is my favorite, but I prefer the less populated side. Princeville has some great snorkeling, but not sure during the winter. Water can get rough.
With both of these islands you can circle them a few times a day. (well, you can't circle Kauai as the eastern side has no roads)

Kauai is actually my least favorite, but I put it down to companions more than anything. I bet it is beautiful and green during the winter. We were there for 2 weeks and didn't get even half of our must see kist done. Some great hikes there.

Envious! Enjoy!

Hawaii is awesome during the holidays. Good choice. But please note, many of the hotels you mentioned are full or near capacity during the holidays. So you'll want to book soon! Oahu and Maui typically have the highest occupancy rates so if they are full definitely try Kauai and the Big Island.

Based on what you've described Kauai, Maui and the Big Island of Hawaii probably offer the best fit. Kauai and BI will feel more laid back. Maui will have a nice energy but not too chaotic. The great thing about Hawaii is each island is so different. Kauai, is considered the Garden Isle. It's lush and tropical with 3000 ft. razor thin mountains that drop down to the ocean. Maui, is a beach paradise with over over 80 beaches to choose from. The Big Island of Hawaii, while big, has so much diversity from volcanoes, to rainforests and alpine vistas. You can't go wrong with either of these islands. Chances are you'll fall in love and want to come back to visit another island.

I had a chance to visit the following properties you mentioned in April 2011.

Maui:
Marriott's Maui Ocean Club - It's a good location in Wailea at a better price than the Ritz, Four Seasons, Grand Wailea and Fairmont.

Westin Maui Resort & Spa - It's not big. It's located right near the Sheraton Maui. Nice property. If you like Westin this is a good choice.

Sheraton Maui Resort - This is my favorite property on Kaanapali beach because of the location. It's at the end of the beach with great snorkeling. It also has Black Rock which offers cliff jumping during the day and an interesting Hawaiian torch lighting ceremony and cliff dive at night.

Kauai:
St. Regis Princeville - If your budget permits, it's definitely worth it for a couple of nights. Very romantic with some of the best views in Hawaii overlooking Bali Hai from South Pacific. Worth the splurge.

Big Island:
Waldorf Grand Wailea - This property is actually on Maui. Very nice. Great pools. They have an elevator in the pool that is powered by water!

Hilton Waikoloa Village - Very large property and no beach. You get around by tram or boat. But they have a network of saltwater lagoons to swim and snorkel in which are cool. The dolphins on property are also a joy to watch.

Sheraton Keauhou - Good value but not on a beach. Also located about 30-45 minutes from the main resorts. But closer to Kona and the volcano.

Since you mentioned the Marriott on Maui, the Marriott Waikaloa is actually my favorite Marriott in Hawaii. Great property on a swimable beach.

Hope this helps. Have a great trip!

Good luck finding award space during that time, especially Maui. Even harder for air. Let us know if you do find something though.

Great advice Hawaii Guide, but a couple opposing points.

Marriott's Maui Ocean Club - It's a good location in Wailea at a better price than the Ritz, Four Seasons, Grand Wailea and Fairmont.
Marriott Maui Ocean Club is the timeshare on Kaanapali Beach. The Wailea Beach Marriott Resort fronts the rocky coastline just north of Wailea Beach (walkable). Great option if available.

Westin Maui Resort & Spa - It's not big. It's located right near the Sheraton Maui. Nice property. If you like Westin this is a good choice.
Westin is notorious for being incredibly busy/crowded. Prepare for a parking lot view on an award stay. Other than Westin loyalists (which there are many) the consensus is Sheraton, especially on points. Shame the Westin Villas went up 8K/night this year.

St. Regis Princeville - If your budget permits, it's definitely worth it for a couple of nights. Very romantic with some of the best views in Hawaii overlooking Bali Hai from South Pacific. Worth the splurge.
Two possible problems, on points you wouldn't be guaranteed the (killer!) view. 20K SPG is pretty high for a garden view. And generally, winter on the North Shore makes the beaches viewing-only.

We usually stay next door to the Kapaa Courtyard, at the Kauai Coast Resort. It's a great area for exploring the island. Unremarkable otherwise, the hotel is just a standard Courtyard, on a non-swimmable beach. Do your math though, as the hotel can usually be had for ~$100/night through various channels.

You may want to consider the Big Island on the Kona Coast as it is the driest of all of the islands at that time of year. Check availability on the Kona Coast.

You're booking *really* late for this Christmas, so if that's what you're set on, I'd suggest looking at the deal you can live with and not worrying so much about which island. Many of the places you mention will have already closed their wait lists.

My comments in bold.


Maui:
Marriott's Maui Ocean Club - believe I can get very cheap Never stayed here
Westin Maui Resort & Spa - I hear it is big with lots to do It's a very large resort that feels a bit cramped, but the pools are very nice. Not on the best part of the beach
Sheraton Maui Resort - I hear it is quiet with a great beach for snorkeling Great beach, awful pool. We were able to spot a few giant honu swimming around a few times. If you can get a room perched atop Black Rock, it does feel like it's just you and the Pacific Ocean

Kauai:
St. Regis Princeville - convince me it is worth the money/points. Very expensive, but maybe worth it for a couple of nights? Got back from this resort last weekend. Very nice, but you're mostly paying for the view. I must admit, Hanalei Bay is one of the most relaxing places to look at from the comforts of your own room. Attentive service as well.
Courtyard Kaua'i - in case I need to escape the St Regis :) After the St. Regis, this will feel like a let down. Can you also consider the Hyatt Kauai? Don't believe the beach fronting the Courtyard is swimmable.

Big Island:
Waldorf Grand Wailea - would probably only be for a couple of nights due to the cost, but is it that special to be worth it? This hotel is on Maui. Great pools, but tired rooms.
Hilton Waikoloa Village - Waikoloa Village sounds interesting in the marketing materials It's the Disneyland of the Big Island. Has fun pools and monorails and boats to take you to/from your room. Waikoloa Village is just an bunch of upscale shopping areas thrown in together with hotels and timeshares. No true beach at the HWV, but nearby Marriott is behind A-Bay, another good place for snorkeling.
Sheraton Keauhou I'm really not a big fan of this hotel. It's dated, feels like a concrete prison, has dark hallways to match, and is cursed. My one night stay here last year was enough. No beach here too.

Oahu:
Waikiki Beach (Various Hotels such as the Marriott, Courtyard, Hilton Village, Hilton, Doubletree, Embassy Suites) - basically, the question is to Waikiki or not? Waikiki = crowded, urban jungle but great nightlife. Beaches are subpar, but you can always drive to others. If you're looking for an active nightlife, this is your best bet in the Islands. If you're looking for "paradise," probably not
Marriott's Ko Olina Nice resort with nice lagoons, but just a simple pool. We have picked this place to get married.

Marriott's Ko Olina is beautiful and restful, but a long way from anything but resorts. The traffic on Oahu is so bad, that a simple trip to Honolulu (30 minutes) can be a nightmare at the wrong time of day.

Sheraton Keauhou I'm really not a big fan of this hotel. It's dated, feels like a concrete prison, has dark hallways to match....

It's not just the hallways. I had a very painful fall going from the room to the lanai. No lights whatsoever on the lanai, no indication that there are two steps down from the room to the lanai. Don't know if they've fixed the problem or not, but the illumination throughout the hotel is chintzy.

My comments in bold. Marriott's Ko Olina Nice resort with nice lagoons, but just a simple pool. We have picked this place to get married.

Congratulations! ^^^

It's not just the hallways. I had a very painful fall going from the room to the lanai. No lights whatsoever on the lanai, no indication that there are two steps down from the room to the lanai. Don't know if they've fixed the problem or not, but the illumination throughout the hotel is chintzy.
Was there for a wedding a few months ago--same as always.
Congratulations! ^^^
Thanks. :)

You may want to consider the Big Island on the Kona Coast as it is the driest of all of the islands at that time of year. Check availability on the Kona Coast.

IIRC its the Kohala Coast on the Big Island that is the driest.. although Kona would almost be at the tip of it I think..

Considering a trip to Hawaii for Christmas. First time. Just myself and my pregnant, but athletic wife. Want a combination of beach sports, hiking and the like. I don't actually need the pampering of an ultra-lux hotel, but am doing it mostly on points and would consider one if there is real value from it (e.g., great grounds, water sports, large room, amazing pool, manicured beach, etc.). Trip will be about 9 days. Thinking 1 to 2 islands. Don't want to move more than once, so max of 2 hotels.

First question is which island(s). I don't see any benefit from being in a city, so is there a strong draw to Oahu other than Honolulu and night life? With the Big Island, I feel like I would spend the entire time in the car since it is so big? I have been leaning toward a combination of Maui and Kauai but can be convinced otherwise.

Based on availability and price, I am considering the following hotels (I am pretty much limited to these, so unless there is some Ritz charging $99 a night, please limit your recommendations to this pool):

Maui:
Marriott's Maui Ocean Club - believe I can get very cheap
Westin Maui Resort & Spa - I hear it is big with lots to do
Sheraton Maui Resort - I hear it is quiet with a great beach for snorkeling

Kauai:
St. Regis Princeville - convince me it is worth the money/points. Very expensive, but maybe worth it for a couple of nights?
Courtyard Kaua'i - in case I need to escape the St Regis :)

Big Island:
Waldorf Grand Wailea - would probably only be for a couple of nights due to the cost, but is it that special to be worth it?
Hilton Waikoloa Village - Waikoloa Village sounds interesting in the marketing materials
Sheraton Keauhou

Oahu:
Waikiki Beach (Various Hotels such as the Marriott, Courtyard, Hilton Village, Hilton, Doubletree, Embassy Suites) - basically, the question is to Waikiki or not?
Marriott's Ko Olina



THANK YOU!!!

Initial note.. Waldorf Grand Wailea is in Wailea, Maui.. a fantastic kids water park is there.. if you've got the points, and you will need alot of points, then this is the hotel I would try for.. imo Wailea, Maui is the most beautiful location to vacation in all of the islands.. We usually stay at the Fairmont Kea Lani in Wailea, and we did walk through the Grand Wailea grounds this past spring break..

Big Island Hilton Waikoloa Village.. a massive resort like the Grand Wailea with dolphins, boat and train transfer, many restaurants.. Both this hotel and Grand Wailea is Vegas meets Hawaii.. be prepared for some action..

Marriott's Maui Ocean Club - Not bad middle of the road.. in Kaanapali..
Westin Maui Resort & Spa - Higher end resort.. in Kaanapali

Ko Olina Resort.. I would book VRBO neighbor resort villas with the private owners.. more bang for the buck.. a new development.. in fact, this next spring break we'll be trying the Villas at Koolina out.. Near Aulani, the new Disney hotel..

I like the Fairmont Orchid on the Big Island.. this resort as well as the Fairmont Kea Lani is where we stayed this past spring break..

...St. Regis Princeville - If your budget permits, it's definitely worth it for a couple of nights. Very romantic with some of the best views in Hawaii overlooking Bali Hai from South Pacific. Worth the splurge.... Having stayed at this property five times in the past two years, I'd completely agree.

...Two possible problems, on points you wouldn't be guaranteed the (killer!) view. 20K SPG is pretty high for a garden view... It is possible (or at least it was as recently as May 2011) to book an ocean view room for just a few thousand more points (IIRC it was 22.5k instead of 20k for the mountain/garden view). But even the mountain views should be gorgeous at this property.
We usually stay next door to the Kapaa Courtyard, at the Kauai Coast Resort. It's a great area for exploring the island. Unremarkable otherwise, the hotel is just a standard Courtyard, on a non-swimmable beach. Do your math though, as the hotel can usually be had for ~$100/night through various channels. I wouldn't consider it a "standard Courtyard." It's not yet up to brand standard and still undergoing renovation, but worked for a night (in our case it was late arrival and relatively early departure the next morning - so pretty much a crash pad) for us a couple weeks ago. My comments in bold... St. Regis Princeville - convince me it is worth the money/points. Very expensive, but maybe worth it for a couple of nights? Got back from this resort last weekend. Very nice, but you're mostly paying for the view. I must admit, Hanalei Bay is one of the most relaxing places to look at from the comforts of your own room. Attentive service as well. Completely agree with slippahs' comments regarding the property & service level. One of my favorite SPG properties anywhere, and not because of the "hard product."
Courtyard Kaua'i - in case I need to escape the St Regis After the St. Regis, this will feel like a let down. Can you also consider the Hyatt Kauai? Don't believe the beach fronting the Courtyard is swimmable.It would be a let down if the property was up to brand standards, but unfortunately (as mentioned above) it's not there yet. The beach in front of the Courtyard is not swimmable but still affords a nice view, especially of the sunrise. Recommend the OP check the FT master threads of all the properties queried about for relatively recent reviews & comments.

Wow, lots of great intel. Thank you all!

So I was getting ready to pull the trigger but left the car till the end. Seems like they are going for ~$150/day+ on autoslash. That is certainly cramping the concept of an almost free vacation. I was going to center the trip around the Sheraton Maui (based on all your advice) including biking down the volcano, driving the road to hana and a few at the beach. Sounds like it would be semi-difficult with public transit. Anyone ever try? Maybe just rent a car for a day for Hana? Though it seems like everyone but Hertz in the Lahaina area is sold out, so may be risky?

I resigned myself to using double airline miles since if you want to go weekend to weekend at anypoint through the winter, you have to get pretty lucky to not use double miles so the plane ticket costs the same christmas week. There is enough hotel availability on points (surprisingly enough) that that isn't much of an issue either. It is just the damn rental car that is 3 times the cost of what it would be the next week. Any ideas?

Wow, lots of great intel. Thank you all!

So I was getting ready to pull the trigger but left the car till the end. Seems like they are going for ~$150/day+ on autoslash. That is certainly cramping the concept of an almost free vacation. I was going to center the trip around the Sheraton Maui (based on all your advice) including biking down the volcano, driving the road to hana and a few at the beach. Sounds like it would be semi-difficult with public transit. Anyone ever try? Maybe just rent a car for a day for Hana? Though it seems like everyone but Hertz in the Lahaina area is sold out, so may be risky?

I resigned myself to using double airline miles since if you want to go weekend to weekend at anypoint through the winter, you have to get pretty lucky to not use double miles so the plane ticket costs the same christmas week. There is enough hotel availability on points (surprisingly enough) that that isn't much of an issue either. It is just the damn rental car that is 3 times the cost of what it would be the next week. Any ideas?

Christmas week rentals are crazy..

I booked my parents for Christmas week on Maui one year, and lucked out on their rental.. getting an extra low off season week for a December 25 to January 1st rental.. condo rate at Maui Sunset in Kihei was low season.. and the flight on a charter was super low last minute fare firesale..

Didn't think anything of it and got the bookings done.. now a member on FT, and find that we must have super lucked out on the bookings..

We used a promo code provided by Maui Sunset to secure Christmas Break car rental at low season rates..

.. including biking down the volcano, ..

not sure if this is particularly advisable during pregnancy...

as for car - there are options:
hotwire/priceline
play with various corporate etc codes
check if you can book with car points
book with miles (via AA portal for example)
book refundable for for $$$ and wait to see if prices drop - IME they normally do but holidays are harder to predict

overall - go for it - it will be a royal PITA for you to travel in the near future

including biking down the volcano
Including your pregnant wife? Absolutely not!

You can try contacting Discount Hawaii Car Rental. Avis and Budget sometimes offer fixed rate reservations, but when they're sold out, they're sold out. Definitely check out using AA miles as mentioned above. There can be drastic savings.

Also keep in mind top restaurant reservations might be tough to come by.

Including your pregnant wife? Absolutely not!

You can try contacting Discount Hawaii Car Rental. Avis and Budget sometimes offer fixed rate reservations, but when they're sold out, they're sold out. Also keep in mind top restaurant reservations might be tough to come by.

Sorry to scare you all. I would be flying solo on that. She's adventurous, but we aren't that crazy. We will need to keep our eye on the altitude for some of the bigger hikes.

Didn't think about the restaurants either, though I've never worried too much about that. If there is a special place I want to go, I'll deal with off hours and I'm hoping there are some local places or fast casual for other times.

For a car on any of the islands - www.aloharents.com is da kine - I've never had problems with them, though they are essentially middlemen, with renting at much cheaper rates (on the Big Island, I wind up with an Alamo rental, even if Alamo is officially out - through Aloha).

A car is crucial, IMO - I am on the (dry, albeit windy,) Kohala coast (near HWV) right now, and enjoy hiking to the various cultural and petroglyph sites, visiting less expensive (but perhaps better) restaurants, etc. HWV is "nice" (it's all marketing), but impersonal and impressively crowded, huge and betting they can sell you everything from activities packages to expensive food.

You are very late to be expecting any deals at all, and hopefully can get air, lodging and auto bookings during this very busy and high season.

It is just the damn rental car that is 3 times the cost of what it would be the next week. Any ideas?

This is also my experience of trying to plan holiday trips to Hawaii. Someone else might have a magic trick for this, but I have never found one. Ran into the same outrageous prices the last time we tried to go at that time of the year and I realized it was just hopeless unless I wanted to spend a lot of money. So we went to New Mexico instead and had a great time. I know that is not what you want, so good luck with the car and let us know if you figure anything out!

As I've said before, they transport in cars (at great expense) specifically for Christmas, so your options are, basically, suck it up or do without. You may find that booking tours covers most of your needs and cabs may cover the rest for less net outlay.

Probably your best bet for getting a decent price on a car during any holiday is using your company's corporate code - if they have one AND if you're allowed to use it for personal use. The car rental companies are contractually obligated to rent at a specified rate no matter what week of the year it is.

FWIW - you may need to speak with your travel manager if there's no specific policy noted. While most companies include the insurances, my company allows us to use their rate and specifically tells us the insurance will not be included.

I've managed to pay about $170-$180 a week for a midsize during the holidays.

Probably your best bet for getting a decent price on a car during any holiday is using your company's corporate code - if they have one AND if you're allowed to use it for personal use. The car rental companies are contractually obligated to rent at a specified rate no matter what week of the year it is.

FWIW - you may need to speak with your travel manager if there's no specific policy noted. While most companies include the insurances, my company allows us to use their rate and specifically tells us the insurance will not be included.

I've managed to pay about $170-$180 a week for a midsize during the holidays.

Thanks. I have a rate with avis, but unforgettably they have no cars on Maui until the 30th, I think. Maybe we do the road to hana our last day or something and just cab it the rest of the time, but that could be less than ideal. I will keep looking and hoping while checking out some alternatives.

The hard part is, with a pregnant wife, I don't want to get too adventurous or far from Western medicine, so my alternatives are limited.

I would hang on to whatever Avis rental you can get, and check to see if more days become available. You certainly don't have anything to lose.

I know that's what I generally do when the rates are high. I protect myself with the corp code and then keep shopping.