Thinking About Vacation

For the past two years, we've taken our "big" vacation each January. We're trying to take fun and exciting trips with our kids while they are still home, before college kicks in and they scatter to one place or another.

For reference, we took a 10-day Caribbean cruise in 2012 and a 12-day one in 2013 (which was preceded by two days in New York City). In January 2014 we did not take a big trip for several reasons:

• We were just getting settled in our new home and didn't really have the time.
• The winters in Oklahoma seem so nice/warm compared to those in Michigan, why did we need to leave? It was great here!

That said, we're already getting used to the warmth and have even caught ourselves complaining it's "too cold" when it gets down to 50. :)

So with that said, we're thinking of taking a vacation next January and the top candidate so far is...Hawaii!

My parents love Hawaii (they may go with us), I have never been, and now just seems like the right time to go. But I have a gazillion questions! This is where I thought you all might help.

Here are a few questions I have about Hawaii:

• What island(s) should we visit? (I'm thinking two islands at the most)
• What attractions are must-sees?
• Where should we stay? (I'm thinking of renting a house, but maybe there's a better option. I do have almost 200,000 Hilton points I could use.)
• When should we go? (Is January a good time to be there?)
• Is there anything I should really think about but I may have missed?

I do have a Hawaii travel guide, but I want to hear from those of you who have been there -- the real people with real experiences.

Any advice on a trip to Hawaii?

Comments

[AJ]

I just went to Hawaii for my honeymoon. It was AMAZING. I used a travel agent who operates on a referral basis. If you would like I can refer her to you -- everything she told me about Hawaii was spot on.

(She didn't charge a fee).

-- AJ

[John]

Pride of America from Norwegian Cruise Lines. The ship takes you to many of the islands and lets you sample a taste of the Hawaii way of life. I did it last year and have been mesmerized by the experience ever since. The itinerary is port intensive with a couple of overnight stays. This is not your typical cruise experience since the crew, by law, is from the US and unionized. We had a great time.

[Adam G]

I'm going for my honeymoon in a few days. I will be in Maui for all 10 days because I was told there is so much to do and see there and it's so beautiful. I want to lay around a lot, eat some good meals, and do a few fun activities as well.

I'm staying in Wailea for half the time and Kapalua for half but with a family I'd say renting a house makes the most sense. I've been told to rent a convertible because driving at night in Maui is just amazing.

I have more tips and things to share but I'll have more to report after my trip.

[jdgjdg]

What do you like to do on vacation? How long?

Traditional sights -- Oahu (Diamond Head, Pearl Harbor, Honolulu, plantations, touristy luaus), Hawaii (volcanoes)

Relax & pamper -- Resorts and beaches are all over, but especially Oahu, Lanai, Kauai

Shop -- Oahu (Honolulu)

Outdoors adventure -- Hawaii (esp. volcanoes), and anywhere else away from people

[FMF]

jdgjdg --

I would say we like to be more relaxed than active, though we do like to sightsee a bit.

We LOVE the water and if we go for 10 days we'd want to be in it for 7 or 8 of those.

[DM]

We've been to Hawaii a few times - the first time we went to Oahu, the next time we went to Hawaii, and the last two times we went to Maui. Oahu felt busier than the other islands, but has many attractions that are worth seeing. Hawaii offered adventures like horseback riding through canyons to gorgeous waterfalls and a helicopter tour to waterfalls and volcanoes. We stayed at the Hilton Waikaloa Village, and that was a fun resort experience. Maui has definitely been the most relaxing - we stayed in different condos each time. We stayed on the west side of the island near Lahaina - once at Kapalua and once at Kaanapali. The golf courses are beautiful, and the drive up the western loop of the island is a fun way to see the scenery. Whaler's Village and Lahaina offer good restaurants and shops, and breakfast at the plantation offers a great view and sometimes some whale sightings. Black rock is also in this area, which offers some great snorkeling.

[TW]

I have been to three islands (Kauai, Oahu, and Hawaii). My favorite one is by far Kauai!! (FYI - I'm 26 years-old).

Why Kauai is the best of these three?

- Less touristy
- Great for hiking, kayaking, surfing, snorkeling, and exploring
- It's one of the older islands so it is more lush and green
- Puka Dog (best hotdog ever)

My second choice would be Hawaii just because the volcanoes are neat. Kauai = for the outdoors lovers; Maui = most relaxing, some of the best beaches; Hawaii = cool volcanoes; Oahu = more touristy shopping.

However all places I hear have great outdoor activities, so if you want that you will be able to find it anywhere.

[Lisa Aberle]

I've been to Hawaii twice and I agree with TW's comments. Love Kauai! It's very lowkey and pretty. I liked Maui a lot, too. I went to the big island once, but only spent a couple of days there, so I don't really feel like I have a good grasp of that.
Oahu is my least favorite, because it is busier, but there are really cool things to see there, too.
You can't lose!
And one of my trips there was in January. Great time to go.

[B]

I agree with TW - Kauai is bar far my favorite Hawaiian island. I prefer the lush, tropical landscape and beaches. There are so many wonderful hikes and the kayaking along the Napali coast is just so peaceful and gorgeous. If you go to Kauai because you love beautiful scenery and outdoor adventures, rent a house on the North shore (anything near Tunnels beach or in Hanalei Bay is my favorite). If you stay on the South side, you're kind of missing the point (in my opinion). I wouldn't stay in a hotel when there are so many great vacation homes available there.

[Bill]

I'd highly recommend you take a tour to the top of Mauna Kea in the middle of the night for star gazing. I worked for a summer at a telescope there and the night sky seen at 14,000 feet from the middle of the Pacific Ocean is something you can't experience any where else.

[Old Limey]

B:
I agree, Kauai Is an excellent island on which to vacation and the Napali coast is an adventurous and unique place to hike. You need to be very careful along that coast. One time I stood on a good sized rock to take some pictures and not too long after that I was amazed to see that the rock was underwater. There are warnings to that affect but I hadn't noticed them at the time. It's definitely a hike that you need to use caution and to not get too close to the water, but it sure is a unique and memorable hike.

[Matt]

I have been to Oahu, Hawaii, Maui, and Kauai. I think everyone should go to Oahu and see the basic attractions. Spend a couple days between Waikiki beach and Pearl Harbor. Honolulu isn't the prettiest place and you'll want to switch islands for the island experience. Kauai is a beautiful Island, but laid back and very rainy during the winter. I'd recommend Maui. Beautiful Island. Plenty to do. Be as adventurous as you want or keep to the beach. You can't wrong. Kauai was beautiful, but much more of a local feel and not much to do if the weather isn't great which can be often that time of year.

[Tim]

Everyone should visit once – vacationed many times including twice last year on trips to South Pacific. January is a great time to visit except the north shore has stronger winds and more surf in winter which impacts snorkling.

Oahu - Stay in Waikiki Beech for action or North Shore for tranquility.
1-Drive to Hanauma Bay for snorkeling early in morning. Continue around island stopping at Polynesian Cultural Center, late lunch at Turtle Bay, and dessert at Dole Pineapple plantation (pineapple soft serve is fabulous).
2-Enjoy all the water activities on Waikiki and shopping. Lots of great restaurants.
3-After morning at Waikiki Beach, drive to Pearl Harbor in afternoon, and then Germaine’s Luau by 6pm and get front row seats before buses arrive (and great sunset photos).

Maui – Stay in Kaanapali or Kapalua for beaches or Makawao for quiet and access to nature.
1-Enjoy beaches and shopping in Lahaina.
2-Drive to North Shore to view surfing and then Haleakala National Park for great views at 10,000 ft.
3-Save drive road to Hana (not for feint hearted) for your next visit – have picnic lunch in Hana and stop at east side of Haleakala NP and hike Pipiwai Trail through bamboo forest.

Kauai and the Big Island (Hawaii) are great for nature lovers. Lots of good comments above.

[Mrs PoP @ Planting Our Pennies]

In 2012, we did Oahu and Maui. Of those, I would do Maui again and spend more time on the volcano hiking (bring cold weather clothes as it gets very cold up at that elevation!). I have also heard great things about Kauai.

January should be a great time to go as I think that's during both whale and the big wave surfing season, so you should get some nice shows going out in the water on day cruises.

[Ivy]

We have been to Maui and loved it. We rented a condo above Lahaina for half of the time and did Marriott in Wailea the other half. I liked the condo better as it was more relaxed and we could do our own food, but the hotel was nice too. We did the drive around the eastern side of the island (in one day), the snorkeling was spectacular especially on the black rocks. Highly recommend "Maui Revealed" as a travel guide, it had all kind of hidden treasures in there.

[JimD]

The bicycle ride down Haleakala (Maui)was great. The bike company takes you to the top of the mountain just before sunrise, you see the sun come up over the crater and then ride the bike down. I believe this type of thing is available on several of the islands.
Do it a day or two after arriving since your internal clock will wake you up early anyway.

The helicopter tour was also nice but a pricey.

[Deserat]

A fellow finance blogger lives there and just blogged about what to do in Hawaii - http://the-military-guide.com/2014/05/01/lifestyles-in-retirement-hawaii-vacation/ He has some great ideas.

My husband and I went snorkeling on the north side of Oahu, took surfing lessons from Doug at Plains Beach, hiked Diamond Head and would have done a hike int he rain forest if I hadn't gotten a very bad sunburn. We also went to the Iolani Palace and the USS Arizona. We drove to the Overlook that is famous on Oahu for the tribe jumping over it to their death. We ate coconut shrimp many times and had umbrella drinks.

I've heard great things about the big Island and Kauai as well.

Enjoy!

[Marie @ My Personal Finance Journey]

One of the places that I really want to visit, especially when talking about the nicest beaches. My relatives just went there last month and I saw their pictures and how amazing the places in there.

[FMF]

Thanks, everyone! Great advice!

AJ -- Thanks for the offer. I'll email you if I decide I need the help.

FYI, I talked to a friend since this was posted and his advice was clear: stay on Maui and take a day trip (or two) to Oahu. That's what I think I'll do.

[B]

Just went to Oahu for the first time a few weeks ago. We stayed in Honolulu at a hotel on Waikiki. If you are interested in seeing Pearl Harbor (touring the Arizona memorial and the Mighty Mo) then one of your islands should be Oahu. I think the walk up Diamondhead is worth doing and the view is spectacular. Honolulu is a city with tall buildings and feels a lot like Florida to me (without that musty Florida smell). Three days is enough. The Hilton Hawaiian Village is not where we stayed, but we did eat lunch there and it looks very nice. Having done all the above, when I go back to Hawaii, I think I'll go to Maui and/or Kauai.

[Mike Hunt]

Hi FMF,

We got married on the Big Island (Waikaloa), and I have been to Hawaii about 8 times in total. Been to the islands of Oahu, Kauai, Big Island, Maui, and Lanai.

I can give you some advise if you'd like. Please feel free to email me.

Cheers.

Mike.

[Ryan]

We went to Maui for our honeymoon and stayed at the Sheraton which is where Black Rock is located.

We arrived late afternoon and just hung out and then got up extremely early the next morning to see sunrise on Haleakala and then we road mountain bikes all the way down (with the time zone difference it didn't seem early to us).

Definitely drive the road to Hana to do some hiking, swimming, see waterfalls etc. The bamboo forests there are pretty cool.

We also pampered ourselves at the Grand Wailea spa. It was pretty nice.

We took a snorkeling trip that took us to Lanai and on the way back to Lahaina we got to stop about half way between the two islands and jump in the ocean and swim around. It was very deep but the water was clear.

I think Maui offers the best of all the islands in one. Of course we only had a week so we crammed a lot of stuff in.

[Catherine]

Kauai was our favorite. Everything we wanted to do was there and it was the least crowded, but a great vacation can be had on any one island. Flying between islands is a breeze, too.

You'll be there during a good time to see albatross on Kauai. If any of you are bird lovers, this is a must see.

[Steve]

Have enjoyed reading your column for the last several years. We have been visiting Maui for the last 40 years, owned rental property there for the last 15 years or so and transitioned it to our retirement home last year. I'm not a big fan of the tourist zones (Kaanapali and Wailea), but enjoy visiting them as long as I can head to a quiet condo at the end of the day. January tends to be pretty busy here because of holidays and whales, so you should make your decision on where to stay fairly soon. Would be happy to correspond by email if you're interested. Lots of opinions ...