Advice about Going to Hawaii

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How to plan a trip to Hawaii?

Oct 2014

It's been years since our family took a real vacation together, lasting more than 2-3 days, so we're excited to go to Hawaii in the spring. However, I have no idea where to start. For those of you who travel with your family to Hawaii, do you typically book services directly (hotels, rental cars, etc.); or buy a package? If you go with a package deal, what do you recommend?,, a package through an airline? Do you have a travel agent you recommend? Thank you! A Bit Rusty

Start with a guidebook like Fodors. Once you decide on an island, for flights, I would check out Hawaiian Airlines; we just did our first trip to the islands in 10 years, and Hawaiian had the best rates. Alaskan also has some good deals, and I don't think those two are always represented on sites like Orbitz.

Many places in Hawaii are condos that are privately owned but are run like hotels. My personal favorite is the Mana Kai Maui, in S. Kihei, Maui. resort.htm. A wonderful beach with both sand and reef (for snorkeling), a shop and a restaurant downstairs, and decent rates. You can book airline and car through them too. Check out vrbo too; you can see photos and locations of the rooms. Feel free to email me; I've been to all the islands. sk8ma512

You've asked a very general question, without a lot of information about what you're looking for, so here are some general thoughts:

(1) If you want a luxury resort, using a travel agent who is affiliated with Virtuoso, and/or who is a Four Seasons Preferred Partner, can save you money, as you'll get amenities like free daily breakfast, F&B credits, upgrades, free internet, etc. for the same price you'd pay booking online. You can google 'Four Seasons Preferred Partner travel consultant' or 'Virtuoso travel consultant' to get some leads.

(2) If you're looking for a more moderate resort (Marriott, Sheraton, etc.), may do best with a package. Vendors like United Vacations can put together packages that include discounted bulk air (you save money *and* the reservations are refundable). Other vendors like Classic Vacations often have air credits or deals on rental cars when put into a package.

There are a lot of variables. A good travel agent who knows Hawaii can help you sort the possibilities and save you money. David

First decide what kind of Hawaii trip you want, so you can narrow it down to one island. Traditional vast sandy beach with high-rise hotels, big city, and touristy sites like Pearl Harbor? Oahu (Waikiki). Sparsely populated, great snorkeling, rocky beaches and volcanos? Big Island. Quiet tropical retreat in beautiful surroundings? Kauai. I haven't been to Maui but it's popular too!

Once you know your island, you know whether you'll be taking Alaska Airlines (good for Big Island) or Hawaiian Air (Oahu and Maui). Those two have direct flights out of Oakland. It's already a 5 hour flight, so connections in LA or an island you aren't going to will make the trip longer. United and Delta also go to Hawaii from the Bay Area but I find more options on the first two. Start watching fares. You can get on the mailing list for Hawaiian Air and they will send you low fare offers.

Read about your island online and start thinking about where on the island you'd like to stay, and what kinds of things you'd like to do. Do you want a car-free vacation? If so, choose Oahu. What I like about Oahu is I can get off the plane in Honolulu on to a pre-booked shuttle and go straight to the hotel and I'm on vacation!  Honolulu is also usually the cheapest fare with the most flight options. OTOH if you rent a car you can explore other parts of the island you pick, and that's fun too.

Do you want to stay in a hotel? or more like a house or condo where you can cook or at least make breakfast? Food is more expensive in Hawaii since a lot of stuff has to come in by ship so it can be economical to have some meals at home. I personally do not like to cook while on vacation so I always use Tripadvisor to research hotels, in consultation with friends who go to Hawaii a lot. Air B&B is good for finding houses. There are also resorts that rent out time-shares and offer packages. If I stay in a hotel I book directly with the hotel. I have compared Expedia to hotel websites - the prices are usually the same, but there is usually more availability on the hotel website. I also have booked airfare+hotel packages on Expedia, and come out a few hundred dollars cheaper. But I researched the price on the airline and hotel websites first, and I made sure I would get the type of room I wanted if I booked the package.

I love planning the trip almost as much as I love the trip itself. So I don't mind spending some hours comparing options. But if you just want to pinpoint the island and then let someone else deal with the details, then you could use a travel agent or purchase a package on Expedia or Tripadvisor.

Have fun on your Hawaii trip!

Affordable vacation in Hawaii?

Sept 2011

For the first time, my children are not living with me. One is away at college; the other is with my former spouse. Both will be spending Christmas vacation with me, and I would like to do something fun with them. They want to visit Hawaii. I know it's a long shot -- but does anyone have suggestions for an affordable trip there, even during the winter? I've heard about a surfing school on one island that might be perfect, but I can't find any trace of it on line. Any suggestions would be most welcome. Thanks. Anon

If you are adventurous, you could try camping. My sister and I did a week-long camping trip to the Big Island. We packed tents, sleeping bags and cooking gear, but purchased an inexpensive cooler, propane, and most of our food supplies at Walmart in Kailua-Kona (we flew into the Kona airport). We stayed at Spencer Beach Park in the northwest corner and Namakani Paio near the volcano. Camping at the beach was lovely--we rolled out of bed and went snorkeling first thing (we rented equipment for the week). Both parks were pretty empty during the week but filled up with locals on the weekends. I've been to the Big Island two other times, once staying in a condo, once in vacation rentals. But I'm thinking of camping again the next time I go back.

Here's a website with Big Island camping info: Carrie

In Hawaii, affordable is relative.

Your best bet is to rent a condo and at least cook/prepare all your breakfasts and lunches to save money. All islands have condos.

We most recently visited Maui and took a lesson at the Goofy Foot Surf School: They do a good job with beginning surfers and are highly rated on Trip Advisor. We enjoyed our lesson, the instructor was very patient. We all caught at least two waves. --rookie surfers

Hawaii in the Winter?

Feb 2010

Does Hawaii (especially Kawaii) in December work if the goal is to be in the water a lot? Or are the seas too rough and cool to snorkel without a wetsuit? Is August overall a better month to visit? Thanks! 1st timer

I went to Hawaii once in December and had a great time. Was in the water every day - don't recall it being rough at all. In fact the week before xmas is one of the quie test weeks tourist wise there of the year.

GO! Hawaii in winter is lovely! In Kawaii, though, we found more rain than other islands when we went in the winter. I'd highly recommend Maui, the Kona side of the Big Island, or Oahu instead. The surf on the north side of Maui and Oahu can get choppy in winter, but the Kihei area of Maui (halfway down the island) is calm year-round. I recommend buying a guide book about Hawaii; Fodor's is good, and can give you specific advice about the best times to visit which areas, for best snorkeling, scuba, etc. You won't need a wetsuit. Hawaii is warm year- round. Have a great time! heidi

Hawaii (and Kauai) are pretty darn nice to visit anytime :)

- there is a lot more rain in the winter months (not necessarily *cold*, but very *wet*) - especially on the North side of Kauai
- in general, Kauai has rougher waters than other islands - again, esp. the N shore
- #2 means that snorkeling is not the best in Kauai - the Big Island - oh yeah!

I've been to Hawaii - both Kauai & the Big Island several times, and, although we had a great time - I was a little disappointed by our Christmas trip. It was colder, wetter, no dolphins, etc... We went swimming & surfing w/o wetsuits, but did buy wetsuit-type shirts, which made it fun to stay in the water quite a bit longer - I suggest trying to buy them before you get to Hawaii, b/c everything is more expensive there...

Enjoy - whenever you go - it is so beautiful! Kendra

Actually, the exact opposite is true in Hawaii. Winter is the best time to go. The sea isn't rough (certainly not by Calif standards, especially at a good sheltered swimming beach), the temperature is perfect (by the ocean 78-82 and lower humidity seems accurate for Feb. Hawaii is much closer to the equator than the Bay Area, more in line with Cabo San Lucas at the tip of Baja). The problem is Winter is the HIGH season so the prices are pricier. My family is in Hawaii and for budget reasons and school schedules often visit in summer when the afternoon sun is scorching for kids and the stickiness is annoying. Go now, if you can afford it (airline prices are way down from last year's crazy price spike). Aloha. Rebecca

Hawaii in the Summer?

Jan 2007

Hello, Anyone could share some information on Hawaii? We are planning a family vacation with two young boys (2 and 5) and grandparents, and have some questions: 1. Is July or August a good time to visit, or are winter months better? 2. Which island would be a good choice for young children and grandparents? 3. Is there a rental or a hotel you would recommend? Any advice is greatly appreciate. Novice mom on Hawaii

Hi, I think anytime is a good time to visit Hawaii; yes, the summer months might be a bit warmer (maybe 10 degrees), but you'll also miss the rain, which falls mostly in winter (Nov-Jan). According to CNN, this will be the hottest year the earth has ever experienced, too, thanks to El Nino. But go, it will be warm and wonderful, and the water will be blue and welcoming and refreshing.

We like Maui, the southern, western shore, especially since we've had kids. The waves are gentle, and the weather is sunny. Our favorite place to stay is the Mana Kai Maui, in S. Kihei, a condo development right on one of the best beaches in Hawaii,-- a perfect sandy beach for kids, and a reef for snorkeling. The condo is run like a hotel, with daily maid service, a little store, and a great restaurant downstairs. Aloha! heidi

Summer is actually a great time to visit Hawaii. The water is warmer, and the trade winds help keep temperatures comfortable. I think Maui is a good choice for a first visit, but there's no one ''right'' answer. You have a choice of staying in a hotel or renting a condo. Condos can be more economical and offer the possibility of cooking some of your meals. There are also some fabulous ''destination resorts'' as well as very nice 3 and 4 star hotels. It depends on what kind of family vacation experience you are hoping to have!

I have been to Hawaii many times in the summer with young children, and it's a GREAT time to be there. Although it's expensive in Hawaii whenever you go, rates are cheaper and it's a bit less crowded in the summer. The weather is beautiful.

What might change in the summer is which side of an island has the calmest waters in summer versus winter.

I have been to Maui, Kauai, and the Big Island, and love them all. The north shore of Kauai is a good bet if you want to have a fairly quiet experience. The island is small and really, you can stay right near the beaches on the north shore and have a blast. If you are a family who likes to move around a lot, hiking and exploring, then the Big Island might be more ideal. I don't have specific recommendations of places to stay (can't remember), but we always stay in condos - good deal for your money. Good luck and have a great time! Nanu

Packaged Trips to Hawaii

June 2005

Looking for recommendations for packaged trips to Hawaii. I'd also like to hear about any tour providers (including airlines) to avoid.

We've travelled to Hawaii both with Sun Trips and Pleasant Holidays and we were very pleased with both. I prefer Sun Trips because they fly out of Oakland, but they both provided a wide range of accomodations from basic to luxury hotels & condos in a can't-beat-the-price package with a car and airfare. The only time we saw others from our chartered flight was the ''orientation breakfast'' (which you can definitely skip because they just try to sell bus, submarine, boat tours) and the plane flights, which was fine with us! I've found these packages a great, easy way to travel. Constance

Flying Hawaiian Air

August 2002

I'm interested in hearing comments (good and bad) from people who have flown Hawaiian Air from the Bay Area to Honolulu. I've only flown with them on short inter-island flights in Hawaii. Our family is planning a trip to Hawaii. The fact that they fly out of Oakland or Sacramento instead of SFO intrigues me (I really dislike SFO). Clarisse

I haven't flown Hawaiian Air out of Oakland, but I have flown Aloha Air from Oakland to Maui. Aloha Air also flies from Oakland to Honolulu. The attendants are pretty much the most pleasant I have encountered on any airline. You can use United Mileage Plus miles to fly on Aloha Air (or earn United Mileage Plus miles), as they are partners. This definitely beats making the trek to SFO and dealing with the craziness there!! Yearly traveler to Maui

My husband and I had a bad experience traveling on Hawaiian Air about 18 months ago. There were mechanical problems and the company seemed to be really unorganized in terms of getting all the passengers on other flights and in terms of keeping passengers posted as to the status of the mechanics working on the plane. They also failed to announce that there were free vouchers available for food at the airport during the long wait. Once we made it on the flight, I found out from a seatmate that if you ASKED for vouchers they were given out and my husband and I had just spent about $35 of our own money on meals. It seemed rather unfair. We sat in the airport for about 20 hours. It was horrible and I don't think we would fly them again. The one thing they did handle well was that they gave everyone free round trip tickets (on Hawaiian Air) to fly to Hawaii again in the next 12 months. Good luck. Julie

We flew Hawaiian from SFO - HNL several times and will not use them in the future. We had one flight where all the attendents were fighting with each other. On another flight, where we used our free mileage, they totally messed up our reservation. On the other hand, we most recently used Aloha from OAK - HNL and we were very pleased with the customer service and professionalism. I think they do fly a smaller plane than other airlines, and my partner felt quite cramped. Nonetheless, we plan to use Aloha again. Regards, Michele

How to find a timeshare in Hawaii

Dec 2004

I'm inquiring about any timesharing in Hawaii, in general, what may be available in November 2004. With such short notice - anything out there for around 7-10 days? (For one person initially - young child and another adult to follow). El Bee

A great place to look for timeshares (even last minute ones) is Ebay. Good luck. Anon

try It's a great place to look for something last minute because you may be able to get it dirt cheap since I think they figure some amount of money is better than none. erin

Family Reunions & Trips with Grandparents

March 2010

We are looking to meet in Hawaii (Oahu, to be exact) for a family reunion. There's the matriarch and 5 of us sibs and our kids, ranging in age from 8-17. There will be a total of 23 of us if everyone can come. Anyone have recommendations for accommodations for this number of people? We want to be able to get around easily to beaches, sights, outings for the grown ups, some independence for the teens. Am I dreaming, or can this be done? Thanks for any suggestions! Aloha Amy

With that many people, I would try to rent a couple of houses in the Lanikai/Kailua area through Vacation Rental by Owner. You will be near beautiful beaches and out of the craziness of Waikiki (but maybe you want that!). Good luck...sounds fun! anon

Hi Amy - My extended family (my mom, me and my 3 siblings, our 7 kids ages 1 - 12 years) are going to Maui in July. We're staying at Aston Kaanapali Shores in Honokawai, on Maui. They have a camp for the kids ($25 day, including meals) and special deals for families. The Expedia reviews are great.

The packaging company our travel agent used is Classic Vacations. We rented three mid-size cars and a minivan (7 passengers). I undersatnd that you want to go to Maui but I thought I'd share this info for comparison. Have fun! Katy

I cannot make any specific property recommendations for Hawaii, but you could probably find a property (or properties) on that would meet your family's needs. I have friends who have held family reunions and rented houses off of VRBO. We are vacation home owners who also advertise on VRBO, and I believe it is a safe website to research properties (vs. Craigslist). anon

April 2002

Any recommendations for good spots in Hawaii to take a senior citizen who's always wanted to see Hawaii, but isn't very active (can't do a lot of walking)? Accomodations can't be rustic, but we're also not looking for ultra-luxury (finances are an issue). Some historical spots, some shopping would be good, but don't need a lot of either. Probably most important is that it be a beautiful setting (since she's probably got some classic Hawaiian image--crystal blue water, palm trees, sunsets, etc.--in her mind). Nice beaches are important, too, to keep the grandkids happy. Plan is to go around Thanksgiving. Thanks in advance for any recommendations. (Yes, I've looked at the Hawaii recommendations already, but nothing struck me as the perfect place to meet these needs. Hoping my request will spark a response from folks in a similar position, or who see their favorite Hawaiian spot as perfect for taking both a senior and kids...) Judy

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