Help me plan a trip to Hawaii

I’ve never been there; my girlfriend’s never been there. We both want to go, but I’m not sure where we should go, and I’m looking for opinions and recommendations.

The trip will be for about a week in mid-April. I’m looking at a max budget of about $3000 - $1000 airfare, $1000 hotel, $1000 everything else, but I certainly don’t feel a need to spend all of that if I can find some less expensive options.

Stuff we both like: sun-and-sand, some water sports, live music and dancing. I want to try snorkeling, and she probably will, too (this is going to be a surprise trip, so I’m limited in how much I can ask her about what she might want to do in advance). I’d like to go hiking up around a volcano if possible, but that will probably be a solo trip unless there’s a very easy hike available. She will like to go shopping

So, what say you? Which island(s) should we go to? Will we need to rent a car, or can we get around by public transit/walking? What’s worth spending extra money on, and what should we scrimp on? Will the weather be nice in April?

I spent a week on Oahu in January, so that’s the only island can speak to. We (myself + two friends, all sharing 1 hotel room) were staying in Waikiki, right by the beach. We stayed at the Castle Ocean Resort Hotel Waikiki, which wasn’t really great, but it was clean, cheap, and in a decent location. Oh, and it’s close to a beach park where parking, a premium in waikiki, was free. We went carless for four days, and then rented a car for the last three. If I were to do it again, I would have rented a car for a bit longer. Even though Oahu has a great bus system it’s not really how you want to be getting to and from beaches. The only thing I really regret was not making it to the Polynesian cultural center, which I think requires a car to get to.

If you decide to go to Oahu, PM me and I’ll give you some more specifics on beaches, restaurants, etc. that we liked.

My wife and I honeymooned in Hawaii 9 years ago. Here’s what I condsider must dos.

  1. Mt. Haleakala on Maui. Watch the sunrise at 10,000 feet, than bike down to the Pacific.
  2. Volcanos National Park on the big island. You can’t go to Hawaii and not see a volcano.
  3. Pearl Harbor - obvious.
  4. Helicoptor tour.

My wife and I have been there a couple of times - Oahu and Maui both. I think a rental car is a necessity.
We rented a condo which was much cheaper than a hotel and we ate a lot of meals in - especially breakfast and lunch. Restaurants were quite expensive there I thought. Those things saved us a fair amount of cash.

previous similar thread here:

This is what I posted back then:

3 years later, and we both still wistfully remember that trip. We spent about $3K not including airfare to/from HI (but including 1 intra-island airfare).

We’d never snorkeled before but both LOVED snorkling in Hanauma Bay.

As far as I know, the only island with active volcanoes is the Big Island. (Volcano National Park). Diamondhead on Oahu is a dormant crater, and beautiful, but can’t compare with the “live” ones. Hiking up Diamondhead is a workout, but I wasn’t in very good shape then, and still made it at a hustle because they were closing soon. The “hiking” at Volcano national park is very easy, for the most part. More like strolling. There is a bit of a hike across the lava flow that overtook highway 130(?) but if you have some good boots and garden gloves, it’s just a matter of walking over flat, rough ground. (go at dusk and bring a flashlight for on the way back.)

Rental car depends on which island and how far you’re going. We rented one on each island (if you do, spring for a convertible, it’s a blast in that weather.) you could probably do a fair bit of Oahu without one, but on the Big Island, it seemed to be a must.

Andrew Doughty has written some very good guides that most everyone liked in a recent Hawaii thread. Also, Zagat has just put out a food/hotel/attraction guide.

For one week, I probably wouldn’t try to hit more than 2 islands. Inter-island flights are fairly inexpensive and fast, but be sure to book at least a little in advance.

Snorkeling and hiking can be as strenuous or easy as you want. Lots of ‘jump off the boat and swim around’ operations. The National and State parks have trails for all tastes and plenty of ‘drive up, walk ten steps and marvel at it’ overlooks. There are tons of places for both, and I’m sure people will be around shortly to point them out. You will be there during whale watching season, which is more fun than it sounds. You can see them anywhere, but west of Maui and west of the Big Island are supposedly the best.

Oahu is the most built up island, by far, for both good and ill. It is easier to find both very high end and cheap (for Hawaii) accomodations, shopping, and services, but it’s more crowded and urbanized. Pearl Harbor is there. Of course, there’s still tons of nice scenery.

Maui is less built up than Oahu. Good sights include:
Haleakala (dormant volcano) where you can drive to the various overlooks and observation points, hike around or into the crater and see cool indigenous plants and animals, watch the sun rise/set, star gaze, or ride up then bicycle down. The last looks way too dangerous for me.
Snorkeling at Molokini is fairly cheap and has a good fish/difficulty ratio.
The drive to Hana is excellent, but there’s not a lot to do once you are there.

The Big Island is hard to explain, it’s more rural and less populated, and the regular folks (and the
businesses that serve them) are adjacent to much of the tourist stuff. Kind of like going down to your local supermarket and passing a jaw-dropping waterfall. Bear in mind that the east side of the island (including the volcano) is windward and you are likely to get rain and cooler temperatures, especially at altitude, so bring a jacket. Good sights include:
Volcanoes National Park (Kiluea), which is just awesome. Lots of stuff is a short walk from the road, if she really doesn’t want to walk. Sulfur vents, craters, lava tubes, fern forests, all kinds of rocks. Check on the eruption before you go, there might not be flowing lava anywhere easily (or legally) accessible. If you must see lava, book a helicopter tour in advance, but be warned, they are expensive. Don’t hike off trail through lava fields alone, the lava is very sharp and friable and a slip could result in a medical emergency.
Lava Trees State Park is a nice forest with, as implied, lava casts of trees in it.
There are lots of cool beaches with all manner of different sand compositions: black, green, and brown being most common.
Mauna Loa has a weather station and Mauna Kea has the Observatory. Both have snow and great views on clear days.

Can’t help with Kauai, Molokai, or Lanai.

Do you have definite dates for travel? If not, you should be able to do a lot better than $1000 for plane tickets from California. Check out the ‘flexible date’ searches on Travelocity, Kayak, and Cheapair. Most of these tickets have 21 day advance purchase, so you’ve got time.

Be prepared for things to be more expensive than you thought. The weather is just nice. It should be somewhat warmer than Southern California at sea level and possibly much cooler at altitude. Expect at least some pleasant rain.

Thanks for all the suggestions (and links) so far. I think I’m leaning toward mostly Oahu, with some time on either Maui or the Big Island.

I hadn’t thought of Pearl Harbor, but I’d like to see the memorials there.

Riding down mountain in Maui sounds awesome to me, but I don’t think my girlfriend would be interested. She doesn’t like bicycles. But it’s early enough that I could do it on my own and be back for lunch.

I can’t adjust travel dates by much. My girlfriend only has the week of April 13-17 off, so every day that I adjust my preferred dates is a day that we aren’t in Hawaii. A few days ago, the best Sat-Sun or Fri-Sun flights I could get were around $450. Now, it looks like I can find a few for closer to $400. But if we do any island hopping, it could get back to $1000 or more pretty easily.

As far as the islands go, IMO, Oahu is like a city, Kauai is like a small town, Big Island is like the country, and Maui is like the suburbs. Weather is ideal year round on Hawaii, with certain sides of each island being rainier and windier than the other side.

If you want an active night life and tons of activities/restaurants, go to Oahu. There are tons of affordable places to stay, esp on the north shore, but you’ll want to stay on Waikiki if you’re looking for action. Waikiki comes alive at night and has a constant urban buzz about it. The other islands tend to go to sleep or slip into low gear once the sun sets. (The sun rises and sets early in Hawaii.) Car rental isn’t a necessity on Oahu as you can get to plenty of places via the bus. And you can rent a car on a daily basis via rental places in hotels. (Hilton Hawaiian Village has one, for instance.)

If you’re a nature lover and love hiking, snorkeling, and just cold chilling, head to Kauai. This is the least developed of the four island I mentioned, so there’s not a ton of touristy things to do, but there’s plenty of affordable lodging and awesome scenery. It’s very laid back. You have to rent a car on Kauai.

Big Island offers one big thing that the others do not and that’s an active volcano. It also has plenty of lodging, from huge resorts such as the Hilton Waikola to a tree house that you can rent. But it’s big (hence the name) and you’ll be driving plenty if you’re intent on hitting areas of interest. I’ve never been so I can’t offer much advice. As you can imagine, you have to rent a car here.

I personally prefer Maui the best because it’s a hybrid between Oahu and Kauai. It has a small “downtown” with bars and restaurants and shopping, but it’s nightlife is pale in comparison to Oahu. It’s small enough to traverse in one day if you were so inclined, but large enough that you never run out of things to do. It has good snorkeling, good surfing for beginners, a 10,000 foot high mountain, a bohemian town, and a good sprinkling of touristy things such as ziplining (book early), ATV rides, golfing, horseback riding, and sunset cocktail sails.

Maui is also the only island where you can take affordable day trips to other smaller islands (Molokai and Lanai) via a ferry. If I had one week to stay, I’d make Maui my destination. If I had longer, I’d first spend two or three days on Oahu to check out the USS Arizona, Fishbowl Cemetery, and Mighty Mo and the nightlife of Waikiki, then I’d head off to Maui for five or more days.

I wouldn’t go to more than two islands because you’ll waste almost a whole day of your vacation getting to the other island and waiting to check in. (Check-out is usually 10 or 11am and check-in is usually around 3 or 4pm.) If you’re on a budget, weekly (5 days or more) car rentals are usually far more affordable than daily rentals. Also, note that some airlines will fly you into one island and out of another for the same price.


There are tons of ways to make Hawaii more affordable. First and foremost is your lodging. Booking mountain view will save you tons of money over ocean front. Booking one of the many specials (e.g. Hyatt’s Pay for 3 nights, get one free) wlll save you money. Call directly and ask for AAA and/or Entertainment rates even if you don’t have a card. (If the deal is great, you can get the card later.)

If you are content to stay someplace other than a hotel resort, there are literally thousands of private rentals on VRBO.com. However, these generally only rent by the week. (One place I’ve always wanted to check out on Maui is Maui Kai as those units are very affordable and right on the beach (and I mean literally right on the beach) so the view from your lanai is remarkable. The hotel pool is meh as it sits behind the building, but at $200 a night, what do you want?

You might also consider renting a timeshare. There are two very nice timeshares on Maui (Marriott Maui Ocean Resort and Westin Kaanapali Ocean Resort Villas) and plenty of owners rent out their units out on Redweek.com, Tug2.com, MyResortNetwork.com and/or VRBO.com. (Don’t worry, since you’re renting from an owner, you won’t need to attend a timeshare presentation.) Timeshares offer a great hybrid between a hotel resort and a condo community. You’ll have a kitchenette and washer/dryer, plus an on-site restaurant and great pool. The Westin also offers a free shuttle to Whalers Village and Lahaina (“downtown”) so that you don’t have to worry about drinking and driving.

Another way to save money is on food. Book a hotel that includes breakfast and you’ll save $50/day. Pack a soft sided cooler and stop at the grocery for a loaf of bread, some lunch meat, chips and soft drinks and you’re set for lunch. If you rent a condo or timeshare, you’ll have full kitchens and grills, too. We tend to eat in for breakfast and most lunches and then get dressed up and go out to dinner.

I’ve found the best car rental deals at Alamo via Costco and you tend to get a nice break at 5 days. Go to their site and click through for their codes.

Have fun on your trip! Hope this helps.

If you do island hop, it’s usually far more affordable booking mainland to Hawaii and back on one round trip itinerary and separately booking Hawaiian Air for the intraisland fare. If you put them on one ticket, the big 5 airlines will charge you an arm and a leg for that intraisland flight. (FYI, one way HA flights are usually $75 or less pp.) And, like I said above, many airlines such as Delta and American will allow you to book into one island and out of another for the same RT fare.

A typical itinerary for me is to fly into Oahu, stay 2 days, island hop to Maui, then fly home. So I’d book Cincinnati to Oahu and Maui to Cincinnati on one itinerary. And I’d book a 1pm flight out of Oahu to Maui via Hawaiian Air on another. Oahu is usually the most affordable place to fly in so it MAY make sense for you to book in and out of Hawaii, but I’ve usually found it to be cheaper and easier to do a one way and fly home from the last island.

Hanauma Bay is closed every Tuesday, and they will also close whenever jellyfish invade, as they did this past week. So if you are going to try snorkeling there, check ahead of time if that’s doable that week.