We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Recently Retired would like to spend March 2014 in Hawaii

Saint Paul...
1 post
Save Topic
Recently Retired would like to spend March 2014 in Hawaii

My husband and I (both 55) recently retired. We are in the beginning stages of planning a month long trip to Hawaii scheduled for March 2014.

We just returned from an organized Eco Adventure tour of Costa Rica. We had an amazing time, super active, but we did no planning ourselves, we just went along with the tour.

I have checked into Island Hopping Vacations, the itineraries look full and inviting, but I think with some time and effort and a little guidance I could plan an awesome vacation myself.

Location: In a months time how many islands would you plan to visit? I assume flying between islands the best option. Is there another mode that I am not aware of?

Lodging: I have looked at VRBO, does this seem the way to go? I would prefer to have a home base that we could prepare our meals ourselves. Is there another rental site that people have used and are comfortable with?

Itinerary: If you had a month, what would be your ideal vacation? We tend to be very active on vacation, we have always had to hurry to fit everything in. Now that we have the extra time, who knows we may enjoy a day on the beach.

Money Savers: Now that we are retired, we are looking for ways to save a buck. Any tips would be helpful.

Thanks for any tips and guidance you are willing to share!

Northern California...
Level Contributor
1,815 posts
20 reviews
Save Reply
1. Re: Recently Retired would like to spend March 2014 in Hawaii

4 weeks = 4 islands. You could easily do Oahu, Kauai, Maui and the Big Island.

Healy, Alaska
Destination Expert
for Denali National Park and Preserve, Alaska
Level Contributor
40,254 posts
44 reviews
Save Reply
2. Re: Recently Retired would like to spend March 2014 in Hawaii

I agree, though you would want to allot more time for the Big Island - at least 10 days there. :)

Level Contributor
333 posts
34 reviews
Save Reply
3. Re: Recently Retired would like to spend March 2014 in Hawaii

Congrats on your retirements - Freedom 55!

My wife & I also retired a couple years ago, I was 57, she was 55.

Since our retirement, we have done 3 Hawaii trips, in 3 different ways. All were great!

In 2011, we did 15 days, all on Oahu. We split our time between a condo in Waikiki (a VRBO unit at The Shores) and the Kahala Resort, outside of Waikiki. In addition, we rented a car on 2 separate days, spent one day at the North Shore, and one day at Kailua/Lanikai beaches.

In 2012, we spent a full month in a condo at the Palm Villas, Mauna Lani, Big Island. (also through VRBO). We rented a car for the entire month, did a lot of our own cooking, and toured around whenever we felt like a drive.

In 2013, we did a 5 week trip on 3 islands. First we spent a week in Waikiki (VRBO condo at Outrigger Regency), followed by 8 days in a private villa at Keauhou Estates on the Big Island (homeaway.com), and then 3 weeks on Maui, broken up into 1 week in a condo at Wailea (Grand Champions, VRBO unit) and then 2 weeks in one of the Golf Villas at Kapalua. (VRBO).

All 3 of these trips were outstanding, but very different. The month at Mauna Lani in 2012 was very peaceful, no moving around, and also the most economical as there were no inter-island flights and by renting for a full month we got a discounted rate on the condo and also on the car.

The 5 week trip on 3 islands was definitely the most interesting, varied, stimulating, but also the most expensive!

A couple tips:

- everyone needs to experience Waikiki, at least once!

- a week is too short on the Big Island, it is REALLY big.

I would be pleased to answer any questions if you want more info.

We prefer to rent condos or villas through VRBO or Homeaway as we like to cook, we get tired of restaurants, we love being independent, and for a long stay we save $$$ by self-catering.

Level Contributor
2,272 posts
3 reviews
Save Reply
4. Re: Recently Retired would like to spend March 2014 in Hawaii

You most certainly CAN plan your own Hawaiian vacation. Many, many people in here do and are happy to help with specifics.

I, too, would do four islands in four weeks, though I'd probably spend six nights on Maui and eight on the Big Island (it's big). : )

Yes, a condo is the way to go if you want to save money preparing your own meals. Also, this can save you on parking costs you'd pay at hotels. And vrbo.com seems to be the most-recommended site in here.

Planes are the only way to get between the four major Hawaiian islands. Hawaiian Airlines is the most recommended in here for interisland flights.

My ideal vacation would probably be a lot lazier than yours -- lots of lying around, swimming in the ocean, and eating good food. But I'd throw in some history (Pearl Harbor, Iolani Palace), snorkeling (Big Island reportedly has the best), a luau, waterfall hikes, a catamaran sail along Kauai's Napali Coast (absolutely gorgeous), a trip to the Big Island's Volcanoes National Park, and a whale-watching tour, probably on Maui.

When you're on Oahu, stay in Waikiki. The other parts of Oahu are amazing, but they have a lot of similarities with the other three islands you'll be visiting. Waikiki will give you the most distinctive experience. As to where to stay on the other islands, I'm not the best one to answer that. Though I will say that, on Maui, I greatly prefer the Kaanpali area to the Wailea area.

Level Contributor
9,211 posts
42 reviews
Save Reply
5. Re: Recently Retired would like to spend March 2014 in Hawaii

Congrats on the dual retirements!

You don't mention whether or not you have previously visited Hawaii...perhaps not, as I'm thinking you would have included the info.

We have been to all of the Islands many many times...all extended stays.....usually 3-4 weeks each visit. We are in the Islands 2-3 times a year.

I would suggest a 2 week/2 week split between 2 Islands. Economically this is advantageous in that you can fly into one and out from the other... requiring only 1 Inter-Island flight. They tend to add up.A 2 week stay will usually yield a pretty good discount with owners....less cleaning fees to deal with etc...

Vrbo is the main venue for condo rentals. Some owners utilize numerous sites...but vrbo gives a good representation.

Sure, you can logistically do a 4 week /4 Island trip....but it doesn't have to be so. Two weeks gives you a good amount of time to explore , relax and settle in a bit.

Is there a nightly accommodation budget?

Our 2 favorites are Kauai and Big Island. The whales will be putting on a show during the time of your visit. If it's anything like this year, you are in for a treat!.

Safe Travels

Kapaa, Hawaii
Destination Expert
for Maui, Hana, Oahu
Level Contributor
46,443 posts
3 reviews
Save Reply
6. Re: Recently Retired would like to spend March 2014 in Hawaii

With that much time you can do practically anything you want. I would devote 10 days to the island of Hawaii and then spend 6 each on Oahu, Maui and Kauai. Of course this all depends on what kind of budget you are on. It will cost approx. 80.00 per person one way for travel between the islands.

VRBO and Homeaway are the most cited sights for vacation rental that I know of. You can also look at TA's list of vacation rentals.

The places that drbergen went to are nice but are towards the "higher end" of the scale when it comes to costs for accommodations.

The first task you must accomplish is which islands and for how long. You can find tons of info on each island by looking at the huge amount of information right here at your fingertips. Go to each island forum, check out the Top Questions, travel articles, things to do etc. There are also links in this area on how to save money!!

After deciding on which islands, ask questions about accommodations etc. on each island's forums. There are plenty of people more than willing to help you. Knowing your nightly budget for accommodations and what YOU really like to do will be very helpful in order for us to help you!!

7. Re: Recently Retired would like to spend March 2014 in Hawaii

-:- Message from TripAdvisor staff -:-

This topic has been closed to new posts due to inactivity. We hope you'll join the conversation by posting to an open topic or starting a new one.

To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html

We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.

Removed on: 19 April 2014, 06:18