Midwest Family Vacation to Hawaii

[2prettygirl]

We are looking to take a family vacation, family of 4, first visit to Hawaii. We would like to fly into Maui or Big Island, spend 3-4 days and then fly to Oahu, staying in Waikiki for 3-4 days to see the North Shore area and then ending our vacation at Aulani with rest and relaxation. I am a planner and I typically plan every single trip that we take but this trip seems to be a bit overwhelming. So I am curious, when you travel to Hawaii, do you use a travel agent or do you usually book everything yourself?

I am looking for suggestions from anyone that would be willing to share, we would love to hear ideas from others who have traveled. We are looking for lodging ideas, airfare options from the Midwest (we prefer Southwest but realize this may not be an option), etc:
-Lodging in Maui for a family of 4, considering a condo but open to suggestions
-Lodging on Big Island, condo or resort?
-Lodging in Waikiki, resort or beach front resort or condo, open to suggestions as we plan to do a lot of sightseeing while here, maybe 1-2 days on the beach and 1-2 days spending time in the North Shore area touring the Dole Plantation, Pearl Harbor, etc.
-Excursion ideas in Maui
-Excursion ideas on Big Island
Has anyone flown to Hawaii using Southwest?

 

[dachsie]

I went to the BI and just did a trip report that has a lot of info for you. We stayed at Hilton Waikoloa Village which has lot for the family to do. Not sure of the ages of your kids bu the excursions we did were a Chocolate farm tour, coffee farm tour and Seahorse farm tour. There is also a vanilla farm I found out about later. Definitely go find all the waterfalls on the Hilo side. And I am sure you will want to do the volcano park.

One way I found out about things to do there was to zoom in on Google maps and see something interesting and click on it to get to the website for it. It worked for both islands. Also some of the hotel websites had ideas on them.

Happy planning!

 

[braysmommy]

For our upcoming Hawaii trip I researched and booked everything but our cruise on my own. We will fly from the east coast to Maui for 5 nights and 3 nights at Aulani prior to our Disney cruise. I booked flights and hotel on my own along with excursions using DIS board and Trip advisor for most of my research.

 

[jodybird511]

We are looking to take a family vacation, family of 4, first visit to Hawaii. We would like to fly into Maui or Big Island, spend 3-4 days and then fly to Oahu, staying in Waikiki for 3-4 days to see the North Shore area and then ending our vacation at Aulani with rest and relaxation. I am a planner and I typically plan every single trip that we take but this trip seems to be a bit overwhelming. So I am curious, when you travel to Hawaii, do you use a travel agent or do you usually book everything yourself?

I am looking for suggestions from anyone that would be willing to share, we would love to hear ideas from others who have traveled. We are looking for lodging ideas, airfare options from the Midwest (we prefer Southwest but realize this may not be an option), etc:
-Lodging in Maui for a family of 4, considering a condo but open to suggestions
-Lodging on Big Island, condo or resort?
-Lodging in Waikiki, resort or beach front resort or condo, open to suggestions as we plan to do a lot of sightseeing while here, maybe 1-2 days on the beach and 1-2 days spending time in the North Shore area touring the Dole Plantation, Pearl Harbor, etc.
-Excursion ideas in Maui
-Excursion ideas on Big Island
Has anyone flown to Hawaii using Southwest?

We also live in the Midwest (St. Louis), and fly Southwest almost exclusively. In the past (before SW was flying to HI), we flew American. For our upcoming trip, we found airfare on United/American to be cheaper than SW. Additionally, I really don't think I would want to fly SW to HI, b/c for the long flight, I want to be sure I can have reserved seats--I don't want to be stuck separated from my family on a 5-7 hour flight. We stayed in a condo in Kona for our Big Island portion of our last trip, and we rented through Kona Coast Vacations--we like them.

 

[2prettygirl]

We also live in the Midwest (St. Louis), and fly Southwest almost exclusively. In the past (before SW was flying to HI), we flew American. For our upcoming trip, we found airfare on United/American to be cheaper than SW. Additionally, I really don't think I would want to fly SW to HI, b/c for the long flight, I want to be sure I can have reserved seats--I don't want to be stuck separated from my family on a 5-7 hour flight. We stayed in a condo in Kona for our Big Island portion of our last trip, and we rented through Kona Coast Vacations--we like them.

We are from the Columbia area but most generally fly out of KC or STL. I will definitely price American over Southwest before booking, thank you for that tip.

 

[Hannah nz]

We used VRBO for condos in the Big Island - We stayed at Waikoloa beach and it was great. The beaches in the area are good but you do have to drive to get to a sandy area - there is a lot of lava rock beaches. I will say its a huge island so in 3 or 4 days you won't be able to do it all. I would pick either which side of the island you wanna stay and go from there. (We chose Kona side but didn't stay in Kona town as its way nicer farther up)
We used groupon for some excursions (zipline, Segway garden tour, manta ray night swim) but splurged on a heli flight.

For Waikiki we used Koko resorts for a condo rental. It was a block back from beach but ours had ocean view and pool plus free parking which was a huge benefit. It was one bedroom but slept 4 or 5 with a twin plus queen bed in the room and a murphy bed in the lounge. it is closer to the zoo and aquarium end if you are keen on those. The condo was also closer to the better part of the beach where there is more sand to sunbath on and more room
For car rental we used Discount Hawaii Car Rental - it was very easy to get at airport.

I booked everything myself and its super easy.
We did a dolphin viewing/snorkel boat trip which was amazing.
Otherwise we just self drove to things we wanted to do including a North Shore day and day at Pearl Harbour including the Missouri tour - have to be there early to get a park.

 

[jodybird511]

We are from the Columbia area but most generally fly out of KC or STL. I will definitely price American over Southwest before booking, thank you for that tip.

Small world! Having just priced out flights for June, FYI, I saw plenty of round trip prices on American around the $750-$800 range. This time around, though, we're adding a little craziness and hitting Disneyland for a couple days, followed by the Big Island for 3 days, and THEN to Aulani, so we did some creative flights--SW from STL to LAX, United from LAX to Hilo, SW from Hilo to HNL, then American home from HNL to STL. Phewsh--that took a lot of research and coordinating. Given that you have over a year to plan, I think there are plenty of resources out there to do it yourself. It really depends on whether you want to or not. For me, the planning and research is almost as much fun as the trip itself!

 

[Sunnywho]

We recently flew Southwest to Hawaii from Minnesota. We were able to get seats together for five despite having early C group boarding. On the way back, we had to overnight in Oakland because our flight got in at midnight. Holiday inn Express Oakland airport had a shuttle operating at those hours. I think I preferred overnighting in Oakland to the red eye flights leaving Hawaii on the major carriers I've used in the past but it's something of a toss-up. Early bird check in is $25 not $15 on the Hawaii flight. We used that on the way back after the unnecessary stress over being C group on the way out.

 

[Sunnywho]

Just to add, I used autoslash to book a minivan through national car rental. Very quick pick up and return of the rental. One of our best days was the Kuoloa ranch movie tour followed by an afternoon at Kailua beach. Gorgeous beach, very different from Waikiki beach or the aulani lagoon.

 

[nkereina]

We did 16 days with similar thoughts as you - my trip report is in my signature.

We flew from the east coast and found that if we wanted to fly directly to Maui or Kauai (we did Kauai instead of Big Island), we would have had two layovers instead of just one. It was also more expensive. To avoid that, we decided to bookend our trip by flying roundtrip to Honolulu. When we arrived, we stayed our first 3 nights in Waikiki which was great for adjusting to the time change because many things open quite early, since so many people are in the same boat adjusting to the time as well. We opted not to rent a car here to save on parking costs and hassles, and instead booked bus tours to Diamond Head and Pearl Harbor. This worked out great because those two tours are best done early in the morning, and we had no issue with that since we were up early our first couple days still adjusting to the time. After our 3 nights in Waikiki, we flew to Maui for 3 nights, then Kauai for 3 nights, and then back to Oahu to end our trip at Aulani for 6 nights. Flew home from Honolulu.

do you use a travel agent or do you usually book everything yourself?

I'm a big researcher so I normally book everything myself, but opted to use Liberty Travel for this since it was our honeymoon and a long, complex, and expensive vacation! I basically knew what we wanted, but had the agent take care of the logistics. She also helped us find a flight to our liking because the type of plane was important to me - with just two of us, I knew I didn't want seats that were 3 across in a row and I wanted entertainment options. Comfort on the long flight was more important than cost to us. So she helped us narrow that down. She also was able to provide us with a good travel insurance that we added on. And we were able to pay in installments over the next several months after we booked it until our final payment was due. When we got our travel documents, everything was nicely organized and I didn't have to do much legwork to keep myself sane with all the moving parts of the trip. Everything went perfectly!

-Lodging in Maui for a family of 4, considering a condo but open to suggestions

We stayed at the Westin Maui which we LOVED. There is a separate Westin property down the road that are villas which would be akin to condos. Its in the Kaanapali beach region and they offer a free shuttle between all Starwood properties to Lahaina, which is the closest town with shopping and dining.

-Lodging in Waikiki, resort or beach front resort or condo, open to suggestions as we plan to do a lot of sightseeing while here, maybe 1-2 days on the beach and 1-2 days spending time in the North Shore area touring the Dole Plantation, Pearl Harbor, etc.

Waikiki Beach was nothing to write home about, IMO. Very busy. We saved our beach time for the other parts of our trip. As I mentioned above, we did Pearl Harbor and Diamond Head from Waikiki. We also made time for exploring the strip and checking out the many dining options. And people watching! We did North Shore from Aulani because its a faster and easier commute. We stayed at the Waikiki Beach Marriott. It was not beachfront, which was fine with us, but it was very centrally located, updated, and a good price point. They have a bus tour lobby making it easy to book and locate tours.

-Excursion ideas in Maui

We spent most of our time in Maui exploring Lahaina and relaxing, but we did do the Feast at Lele. This luau and the Old Lahaina Luau, which is down the street, are two of the highest rated luaus in all of Hawaii. If you are planning to do a luau, I would choose either of these. We opted for the Feast at Lele because you sit at your own table and have servers. At Old Lahaina Luau, its more authentic and traditional sitting at communal tables and eating from a buffet. Feast at Lele was also unique because they do performances from several South Pacific cultures and serve you courses aligning to each culture. This also includes Togan which has fire dancing. Old Lahaina Luau keeps it traditional Hawaiian, and does not include fire dancing.

 

[Daisy7425]

We got back from Oahu last week and we flew from Wisconsin on Delta. We had the best flights and we were incredibly impressed with Delta's service.

The first thing I would recommend to you is to research cost of flights from the big island to Oahu. We were originally interested going to the big island, but flights were $200+ per person, so for our family of four it would have not been justifiable.

I couldn't find the ages of your children. My sons are 9 and 6. Because of their young ages and the prices of the island hopping flights, we decided to stay solely on Oahu at Aulani for 7 nights. We rented a car, which allowed us to very easily explore the whole island.

If you want to see Waikiki, the north shore, etc, it is a very easy drive from Aulani. Moving resorts is a lot of research and a big pain. If you can afford a whole stay at Aulani, I whole heartedly recommend it. We absolutely LOVED it.

I'm also a big planner, and did so so so much research for our Oahu trip and I'm happy to share my research pages with you - itinerary, prices, details, etc. Just let me know and I can email it to you or share another way.

 

[cedricandsophie]

We have been to all the islands and go to aulani every year.

you didn’t mention kuai which is our favorite island. Beautiful. The last there many years ago I rented a house on VRBO for a few days and drove around on our own, we also did a helicopter ride over the part of the island That you can’t do via car.

On Maui I don’t remember where we stayed last when we were there but you definitely want to do the Road to Hana. It’s spectular and lots of pullouts to The view. Be sure to stop for banana bread along the way at the food trucks. Mamas fish house On the ocean is a landmark and is expensive but you can just go for a drink and watch The surfers. My husband did the predawn bike ride to the top of the mountain,,,sorry don’t remember name. The tour picks you up at 3 am, you drive up the mountain and bIke down as the sun is rising.

the big island while interesting is probably my least favorite.

We have been all around Oahu so we never leave aulani any more. But Pearl Harbor is a must do. The north shore drive is great. There are lots Of condos and hotels around turtle bay. But you actualy do it in a day Unless you really want to stop for a few days. There is dole plantation and Waimai (spelling?) falls which is an easy walk and pretty. Of course diamond head is great for hiking.


personally Waikiki holds little interest for us, the traffic is a pain, the beach is crowded and often not very clean.

we fly on united every year nonstop from Chicago. Our tickets for our upcoming trip in may were about 750 each which is a decent price and i can upgrade all 4 of us to business.

 

[jodybird511]

The first thing I would recommend to you is to research cost of flights from the big island to Oahu. We were originally interested going to the big island, but flights were $200+, so for our family of four it would have not been justifiable.

We are flying Southwest interisland, and it was only $59 per person from the Big Island to Oahu!

 

[dachsie]

We are flying Southwest interisland, and it was only $59 per person from the Big Island to Oahu!

Our flight from BI to Oahu was $49 on Hawaiian

 

[2prettygirl]

We got back from Oahu last week and we flew from Wisconsin on Delta. We had the best flights and we were incredibly impressed with Delta's service.

The first thing I would recommend to you is to research cost of flights from the big island to Oahu. We were originally interested going to the big island, but flights were $200+ per person, so for our family of four it would have not been justifiable.

I couldn't find the ages of your children. My sons are 9 and 6. Because of their young ages and the prices of the island hopping flights, we decided to stay solely on Oahu at Aulani for 7 nights. We rented a car, which allowed us to very easily explore the whole island.

If you want to see Waikiki, the north shore, etc, it is a very easy drive from Aulani. Moving resorts is a lot of research and a big pain. If you can afford a whole stay at Aulani, I whole heartedly recommend it. We absolutely LOVED it.

I'm also a big planner, and did so so so much research for our Oahu trip and I'm happy to share my research pages with you - itinerary, prices, details, etc. Just let me know and I can email it to you or share another way.

I would greatly appreciate this, if you really don't mind sharing. You can email to me at kerri.bentley80@gmail.com
Thank you!

 

[harmon54]

We got back from Oahu last week and we flew from Wisconsin on Delta. We had the best flights and we were incredibly impressed with Delta's service.

The first thing I would recommend to you is to research cost of flights from the big island to Oahu. We were originally interested going to the big island, but flights were $200+ per person, so for our family of four it would have not been justifiable.

I couldn't find the ages of your children. My sons are 9 and 6. Because of their young ages and the prices of the island hopping flights, we decided to stay solely on Oahu at Aulani for 7 nights. We rented a car, which allowed us to very easily explore the whole island.

If you want to see Waikiki, the north shore, etc, it is a very easy drive from Aulani. Moving resorts is a lot of research and a big pain. If you can afford a whole stay at Aulani, I whole heartedly recommend it. We absolutely LOVED it.

I'm also a big planner, and did so so so much research for our Oahu trip and I'm happy to share my research pages with you - itinerary, prices, details, etc. Just let me know and I can email it to you or share another way.

I would love this also as we are headed there in March - my email is harmon54@hotmail.com if you don’t mind! Thanks

 

[lovetotravel]

.

 

[dez1978]

We are from the Columbia area but most generally fly out of KC or STL. I will definitely price American over Southwest before booking, thank you for that tip.

Hey! I’m in Jeff city!

 

[tidefan]

One thing to consider when comparing pricing and Southwest is that you usually have to stop overnight in California if you are coming from the East Coast (not sure about Missouri). This does add a couple of hotel nights (though I am fortunate enough to have points), however, we find that is usually offset by the fact that checked bags (2 per person) are included in Southwest's fare.

 

[ChanaC]

I haven't been yet, but have been planning a Big Island trip for about a year now (waiting for Covid to really calm down first).

From my research, where you want to stay on the BI is really dependent on what you want to do. The Kona (west) side appears to have the best beaches, but the Hilo (east) side has a lot of exciting, adventurous things to do. If I was you, I would think about what kind of trip you are interested in doing. If I could make a suggestion, since you are staying at Aulani to rest/relax/do the pool and beach thing, you should look at doing stuff more adventurous while on the BI. For example, there is Volcano National Park, black sand beaches, waterfalls, gardens, farms, etc. If it helps, I'm eyeing staying at the Hilo Seaside Hotel. It looks like a pretty basic hotel, but the reviews are all pretty good and it's in a great area, plus the prices are great. Personally, I don't want to spend a lot of money on a resort when I'm going to be spending a majority of the day away from the resort and thus not taking advantage of a lot of the features.