Do you want balmy, soft sand beaches and plenty of ocean activities? Do you want mountainous interiors with jungles and waterfalls? Do you want good food and drink to go with a genuine Hawaiian spirit? Guess what? You haven’t narrowed your choice of islands. It’s going to take some more effort to figure out where to go first. I will help you make that “upscale on a budget” decision.
Let’s start by narrowing the field. Hawaii consists of eight major islands, but only four are considered single tourist destinations. They are Oahu, Kauai, Maui and Hawaii (The Big Island). Now it gets more difficult. I will discuss the options, along with their pros and cons.
Why not cruise to all four islands?
In fact, all the major cruise lines serve up an itinerary of four islands in a week.
Pros:
- If your goal is to get a little flavor of each island to determine for yourself which ones to come back to, then this could be your answer. I’m adopting this strategy for a Scandinavian cruise to 5 countries, for example.
Cons:
- The cruise ports are in the worst parts of the islands; Kahului, Maui, for instance, is a good 1-hour+ drive from anything worth seeing, and you only have so many hours in port.
- It’s difficult to watch sunrise at Haleakala or sunset from Kona when you’ve got to be back on the boat.
Conclusion:
- I think the upscale traveler on a budget will be happier selecting one island and spending a week there, really kicking back and settling in to the Hawaiian lifestyle. There are better cruise options elsewhere in the world.
Hawaii (The Big Island)
The island of Hawaii is normally called the Big Island as to not confuse it with the State of Hawaii, which is made up of all the islands. Got it? And it is big, as large as all the other islands put together.
Pros:
- There is a lot of diversity, from the Kona coffee plantations on the west coast to wetter Hilo and nearby Akaka Falls on the east coast to Volcano National Park in the south.
- This is one of the few places in the world where you can walk on lava flows and actually experience new land being created; or take a helicopter ride over the volcano – these are bucket list items.
Cons:
- Big means a lot of time traveling. It can take several hours by rental car to travel between these natural attractions. Most people wind up staying on the drier west coast.
- The volcano can be spectacular or not, depending on its whim; it is possible to have expectations exceeded or to be underwhelmed.
Conclusion:
- Volcano National Park is a must see, but leave it for a future Hawaiian visit. You will be back.
Kauai
In many ways Kauai is like Hawaii before all the development changed the landscape. It lives up to its nickname, The Garden Isle.
Pros:
- This island is so beautiful it almost begs the upscale traveler to view it all from a helicopter ride and is a spectacular way to see the Napali coast (which can also be rafted).
- Be mesmerized by Wailua Falls, and then go tubing in an old sugar cane irrigation ditch.
Cons:
- Part of Kauai’s beauty comes at the expense of activities. There aren’t as many things to do here as on Maui or Oahu, for example.
- Kauai’s populated areas also tend to get more rain than their counterparts on other islands. It takes rain to create a garden isle, after all.
Conclusion:
- If your idea of Hawaii is a laid-back paradise where you can spend most of your time on pristine beaches, this might be the place for you, but I think the first-time visitor needs to experience more. Make Kauai your second or third visit..
Oahu
There is a popular tourist magazine called Oahu – 101 Things To Do. The title alone describes the appeal of this island to nearly 5 million annual visitors – it offers a little of everything.
Pros:
- If a cruise ship can offer you a taste of the Hawaiian Islands in a week, Oahu can do that without leaving the island. History, such as Pearl Harbor and Bishop Museum, check. Famous beaches, such as Waikiki, check. Shopping and nightlife in Honolulu, check. Amazing shoreline and surf, such as the North Shore, check. Well, you get the idea.
- This is the one island where you can experience a lot without needing a car. Stay in Waikiki and much is available to you, including reasonably priced accommodations and tours to other areas. Hike to the top of Diamond Head crater for sunrise, stroll the beach, shop, eat in a fine restaurant, take a sunset cruise – all without stepping into a vehicle.
- There are more international flights direct to Honolulu and generally lower prices than to the other islands.
Cons:
- Did I mention Oahu was the most popular island? Some people get to Honolulu and are dismayed to find a large city with serious traffic jams, crowded beaches, and long lines of people just to get into a touristy restaurant. This is not their tropical island paradise.
Conclusion:
- If your traveling party wants it all or simply can’t agree on what it wants, Oahu may be your answer. There is something for everyone, although you might have to deal with the distractions to enjoy the attractions. A candidate for a first-time visit.
Maui
If there were a best of both worlds – popular, yet majestic – Maui would be the choice. More than 2 million visitors flock to this island because it offers the diversity of activities of Oahu without the urban drawbacks.
Pros:
- You can engage in every ocean-related activity you can imagine – kayaks, sailboats, catamarans, outriggers, snorkel, snuba, scuba, submarines, and more. Or just pick your color of incredible beach – white, gold, red, or black sand.
- Haleakala National Park features a dormant crater that is like walking on Mars, with a breathtaking view at either sunrise or sunset.
- Maui’s dry west side has charming little towns, like Lahaina, to go with world-class beaches, dining and golf courses. The wet east side enables the one-of-a-kind Road to Hana experience. And in the middle is everything from jungle to pineapple and sugar cane to cowboy country.
- Upscale travelers will be encouraged by a plethora of resort accommodations at all budget levels.
Cons:
- The list of cons is a very specific one. If you must have a big city, there is none. If you want paradise without any people, it will be challenging to find.
Conclusion:
- It’s easy to see why Maui County is the fastest growing county in the United States. People visit here, and they want to come back; some decide to stay forever.
Which Hawaiian island for the first-time visitor?
Not to waffle on this subject, but it is a matter of interest. If your travel group were keen on geology, it would be hard to pass up The Big Island, with Maui a close second. If you require a total laid-back atmosphere, consider Kauai. If you must have urban style to mix with the beach, the clear choice would be Oahu.
My recommendation for the greatest appeal to everyone is Maui. Personally, I have been to every island, but Maui is where we return to more than the others combined. Luxury, convenience, nature, culture, cuisine, weather, activities – Maui has it all. I can’t wait to go again soon!
Have you been to Maui before? Here is my post on 10 unusual things to do in Maui.
What’s your opinion? Do you agree or disagree? Please comment at the bottom of the page.
What’s upscale?
The Westin Ocean Resort Villas on Ka’anapali Beach on Maui are popular luxury timeshare condos that can be booked like a hotel room from the Starwood website.
My personal favorite for Honolulu is the Westin Moana Surfrider Hotel, right on Waikiki Beach.
Try numerous water activities, from snorkeling to snuba to kayaks to outrigger canoes to sailboats to catamarans; nothing is cheap, but the memories last forever.
What’s budget?
There are scores of timeshare properties in Hawaii, and the competition can drive bargains, especially outside of peak travel times. Try Airbnb, TripAdvisor and other vacation rental sites, and always read the reviews first.
Having lived on Kaua’i, I think your advice for first-timers is valid. We visited Maui first and loved it, but when we got to Kaua’i, we said this is where we must live. Visiting is different than living: visiting you want to do, living you want to be.
Betsy, I love the simplicity of your observation: “…visiting you want to do, living you want to be.” Writing this post was more difficult than I thought it would be. I have been to the Hawaiian Islands more than 20 times (although never longer than 10-day stays), but I keep wanting to return to each one for different reasons. If I decided to live there I wonder which island I would choose? Maybe just pick one and travel to the others on my 100-foot yacht. Ha ha. Dream big!
We would be interested to know if we could have Military care ( medical) .
Are there affordable rental close to beaches.
What is the best way to visit and explore.
Rozalija, If you are eligible for military medical care you need to stay near Honolulu, Oahu (with services for Pearl Harbor). There is a lot of competition for vacation rentals near Waikiki Beach. We use captaincookresorts.com which has a lot of variety, but you can try VRBO too. A rental car is not a requirement if you stay in Waikiki, as there are a lot of tours from there. Personally, we like the freedom of a car, and we use Costco.com to find the best deal. Hope this helps.
Hey Stephen,
My wife, 12-year-old son & 9-year-old daughter are taking your advice and heading to Maui next month for their spring break. But, this begs the question: where do we stay? Do we stay at a resort, a condo or house VRBO/AirBnB rental? We live in a small mountain community, so we prefer to vacation beach style. What is your recommendation?
Lewis, I am glad to hear you have chosen Maui for your family trip. Your question is a challenging one, as Maui is very popular during Spring break, and you are pretty late in booking a place. I suggest you try Airbnb and plug in the Ka’anapali/Lahaina areas. Hotels will be extremely expensive. Good luck.
We are going to Hawaii for the first time, altho, we are world travellers. We chose Oahu and the Big Island. I am conflicted about not going to Maui and hope the big island was a good choice…I have mixed feelings and want reassurance..
Karen, first of all, you can’t go wrong with choosing any two islands. If you have a rental car in Oahu, make sure you get out of Honolulu; drive to the North Shore for the day. On the Big Island the star attraction is the Kilauea volcano, but you are at the whim of Pele. Check the local lava flow conditions first on this site: https://www.nps.gov/havo/planyourvisit/lava2.htm. There are hundreds of things to do on both islands, from remote hiking to Pearl Harbor. I’m sure you will enjoy.
Now that we figure out which island….what part of Maui? West Maui or South shore? Do you suggest flying into Kapalua Airport If we do not want to drive an hour from Kahului airport?
I am partial to West Maui, with its beaches experiencing the best ocean breezes and magnificent sunsets. Apart from the beauty of Ka’anapali and Kapalua Beaches, the fun and historic town of Lahaina is close by too. I do not recommend Kapalua Airport, which only serves commuter flights and has limited services for necessities like rental cars. Kahului allows you to load up at Costco, then embark on a pleasant 45-minute drive (most times). Hope this helps.
Thank you Steve for this info. Very helpful.
I’m planning Maui during Summer time, like late July/early Aug; or Nov 3rd week; or Dec last week. Can you please recommend best time? Also, what is the best way to beat prices? AirBnB? Airlines? or Vacation Packages?
Thank you once again.
Well, your November timeframe sounds like Thanksgiving and late December is Christmas; these times are exceptionally busy and expensive. Summer is busy too, but the best of your three options. The weather is probably better too. Regarding airlines, you didn’t say where you are departing from, so just shop around. Airbnb is worth researching, but also search for other vacation rentals. I have used Maui Westside Properties, for example.
Thanks Steve. I’ll be departing from SFO or OAK. Family of 4, 2 adults and 2 kids (9 and 3).
Hi Stephen,
I’m trying to plan a family vacation for June of 2019 and am a little overwhelmed by all of the choices. The main things we want to do are hike, explore, and hang at the beach. Sounds like Maui is perfect for that. The other top of the list item we have is to visit Pearl Harbor, my son is obsessed with history. How difficult is it to visit there if we stay on Maui? We will be staying around 10-12 days. Thanks!
Sara, Maui does sound like the right choice for your activities. I have run a lot of small tours where we fly in and out of Honolulu (airfares to there can be cheaper) and continue on to Maui, spending a few days on Oahu on either the front or back end. That schedule accommodates Pearl Harbor very well (be sure to reserve a time). More good news for you: Southwest is planning on flying to Hawaii in 2019, including inter-island flights. More competition usually means lower prices, so keep an eye out for these developments. Enjoy!
Hi Stephen,
I just got a great deal from Southwest to Oahu, it’s been over 7 years. This time with the whole family and my 3 kids 13, 9 and 5 years old. Last time we stayed in Waikiki, this time I wanted to know which area I should stay to give the best experiences for the kids, but not too much in a busy area. Any feedback is very much appreciated.
Thank you
Stacy, considering the ages of your children, unless you hate Disney, I would consider the Aulani Disney Resort & Spa. It is 40 minutes west of Waikiki, so pretty much away from the hustle/bustle of Honolulu. Rent a car and you can still experience the Kualoa Ranch, North Shore, Pearl Harbor, and other fascinating places.
we are planning a trip to Hawaii and have know idea where to go we would love to see some sites we do not do hiking,history is good and would love to relax and kick it on a beautiful beach would love to just enjoy the beauty.
Renee, I would lean toward Oahu for you. It is probably the best island for history, including Pearl Harbor and Iolani Palace. You can choose a hotel right on Waikiki Beach. The Moana Surfrider, a Westin hotel, is also very historic. Take a tour of it even if you don’t stay there. Rent a car and do an island loop, including the North Shore and Kualoa Ranch.
This is our first trip to Hawaii though we are experienced travelers. We´re planning to go Oct. 2019, flying in from Miami. We love hiking, swimming, nature trails and scenery, great food, exploring and discovering. We have time sharing so we´re planning to stay at available Marriotts. We´d be traveling for aprox 21-29 days and would like to visit three islands, Maui, Hawaii and Oahu. Should we fly in to Oahu, stay a week and then hop to where? Do you think days are ok? Where would you stay for more days, where for less? Could you help with the itinerary please?
Marie, I will do my best to advise you, although I don’t know if you are a couple or a family with kids, younger or older, etc. I would research flying into Honolulu for the sake of convenience and economy. The good news is that you can do all your favorite activities on any of those three islands. I would allocate my time as 25% Oahu, 50% Maui, 25% Big Island. Now is a good time to check out the “Revealed” guidebooks by Wizard Publications. They are great “unofficial” guides to each island. After you experience the major attractions on Maui you can check out these: https://journeyswithstephen.com/10-unusual-things-maui/
I’m wanting to surprise my wife for our anniversary. I had planned Oahu and then read this and now second guessing. We like shopping and eating and beauty. Which is the best Isalmd for us???
Mike, since you mention shopping first, I think you are fine with your choice of Oahu. Every island will satisfy eating and beauty, but Honolulu is really the best for a broad range of shopping experience. Maui’s Lahaina and Makawao offer fun boutiques, as does every Hawaiian resort, but Honolulu has it all, from luxury brands to traditional malls and island favorites. For beauty on Oahu you need to get out of the city and take a full day’s island loop spending time on the North Shore. Also consider Kualoa Ranch, where Jurassic Park was filmed. Happy Anniversary!
The last time I came to Hawaii was in 1989 for my honeymoon and now we want to come back with our kids which are 27, 22 and 21. From what I see the best place for us would be Maui and it sounds like you agree. My sister booked through VRBO is that a good way to go? Lastly do you have a recommendation on where to stay? We are looking at early October in going so is that a good time?
Todd, wow, it looks like you have been busy raising a family. It’s time to share Maui with them! VRBO or Airbnb are good places to start. I recommend the Ka’anapali Beach area on West Maui. For splurge accommodations check out the Westin Ocean Resort Villas. I have also stayed nearby at the lovely Maui Eldorado. Either is a short hop to Lahaina and its attractions. October is a wonderful month in Maui. It is off-season, when most kids are in school, so prices and crowds can be lower (although the first week is also National Holiday in China, which can affect anywhere in the world). The weather in October is still warm and dry, and even if it rains it is usually only for a few hours followed by sunshine and rainbows!
I’m looking at booking a trip for my husband and me this January (2019) to Hawaii (this could change if too much $$). We have never been and have mostly done road trips from Canada, where we live. We like sight seeing, hiking, etc. We do not like sitting on a beach. I’m really not sure where to start to get the best deals possible, as we are on a budget. Can you recommend where to stay, airlines, best airport to land…anything? Do we need to rent a car? I have so many questions, so any information will help. Thanks!
Lorelei, I will use clues like your being on a budget and not sitting on a beach to recommend Oahu as the island for you. You should get the most reasonable airfare flying into Honolulu. And there is a good selection of vacation rental properties in Waikiki (check out Captain Cook Resorts rentals). You don’t need a car the whole time, but consider one for an island loop trip. Another fun place is Kualoa Ranch and Nature Reserve. There are lots of activities, including horseback riding. A friend of mine just did a Jurassic Park ATV experience there and loved it. Dozens of movies and TV have been filmed there, from Lost to Jumanji and Hunger Games. I hope you make the trip!
Hey Stephen, your information is GREAT and I have made notes for research purposes. I am hoping to get to Hawaii either June or October of this year. (I have mentioned it several times to hubby so it’s time I make it happen. lol)
First, I will have to check prices but I am hopeful we can take our son, his wife and our FIRST grandbaby :)and our daughter.) I am all about family and would love for them to come along. Not real sure if we can make that happen this year (money) but gonna try hard. With that said, we will have a 2 year old who LOVES being outside. However we are from a small town Alabama and we do not care much for crowds. We all enjoy nature, being outside and love the beaches.
Me and my husband, after 30 years, still very much enjoy each other. I would not mind a couples only place per say, secluded in order to just be free if desired yet availability to the beauty of the beaches.
I tell you all this to ask if Maui would be the best regardless if family goes or it’s just me and my husband or would there be a more exotic place that you would recommend if it was just me and my husband.
Thanking you in advance for your response.
Gina, I don’t think you can go wrong with Maui, but I’m a little concerned that you said you are from a small town and don’t like crowds. Nearly 3 million people visited Maui last year, many of those in the summer. You will encounter traffic and crowds. You should also research Kauai, which receives only half as many tourists. The weather is generally good in June and October, there are lots of things to do, but it is largely considered the most authentic (and most romantic) of the Hawaiian Islands.
Wow-I’m almost overwhelmed! My husband and I are planning for our 25th in 2020-we do have a timeshare, but they are limited there and we’re still doing the “should we just spend the $ to stay on the beach?” So stuck with which island to see for our first trip and right now it’s between Maui and Oahu-with us leaning toward Oahu. When is the best time to go? We don’t want high season, we don’t want spring break-but I also work at a country club in the North East and our busiest time is summer here, so I’m trying to plan around that. I’m seeing March seems to be less expensive? Budget conscious, but not worrying about spending a little extra.
Erica, if you want to avoid spring break, then choose April. Almost every college in the U.S. has its spring break sometime during March. You can check out studentcity.com for a complete list of dates. However, unlike Ft. Lauderdale or Cancun, Hawaii is big enough to absorb an influx of students and families. As to Maui versus Oahu, I suggest you reread my post; there are reasons for each. Don’t stress about it. They are both good.
This article is great! I can’t decide which island to pick either. Which is best for me, my husband and 2 daughters 21 and 19. We like to shop, dine out, walk beaches, zoo, would also like to whale watch from observatory, see hawaiian/polynesian dancer/shows and beautiful views. Also interested in Pearl Harbor and any sights unique to Hawaii. Which island do you suggest?
Val, since you mention shopping, dining, shows, and Pearl Harbor, I think you need only choose Oahu. Stay in Honolulu, but consider a day trip to the Polynesian Cultural Center. As far as whale watching, you can sometimes spot distant whales from shore, but nothing compares to an excursion by boat. Have fun!
Hello. Thanks for all the advice! I’m a travel agent and it’s my dream trip / first time. We are booked from April 6-19 staying 7 nights in Maui and then I’m stumped for the next 6 nights. I want to see Waikiki beach, pearl harbour and rent an air bnb in the north shore and check out all the beaches, drive the island etc…. everyone is telling me with 13 nights we should check out Kaua’i too which I’d love too but do we have time? Is flying to Kaua’i from Miami a waste ( time wise) I think I’m trting to do too much in 6 nights / 7 days ?
Or does it make sense to just stay 6 nights in Oahu ( 2 in Waikiki and 4 in the north shire)? Thanks!!!!!
Nicolle, it sort of depends on whether you want to settle in or see as much as possible. I did three islands in 2017, but took 20 days and flew in from LAX. Coming all the way from Miami, and allowing for some jet lag, I would lean toward just Maui and Oahu for you. If you love it, come back for Kauai and the Big Island.
Thank you !!! It should say Kaua’i to Maui lol. Typo! Thank you again
Hi Stephen, My girl friend and I are planning to fly to Hawaii this year in October it will be our first time and staying for a week. We love eating at great authentic places and curious about seeing a great luau and sharing awesome romantic moments. I am also a huge aquarium Hobbiest and have a full reef at home I’d love to see a natural reef and schools of fish and we both love sea turtles do you have any recommendations on how we can accomplish this during our visit? Also we are wondering about where to stay that is affordable and will give us a great first time experience.
We are mostly leaning towards Oahu because we also love history and culture. We’re not sure if we are going to rent a car.
Henry, as I read your comment I kept thinking “Maui.” A great luau? The most authentic in Hawaii is Maui’s Old Lahaina luau. Huge aquarium hobbiest? You must visit the excellent Maui Ocean Center. Sea turtles? Try Maui’s Honokeana Bay or a Molokini snorkel trip. Romantic moments? Maui’s Haleakala at sunset is out of this world. I would choose a vacation rental or hotel near Ka’anapali Beach. You can read more here: https://journeyswithstephen.com/10-unusual-things-maui/
Hi Stephen,
M husband and I went to Maui in 2013 and stayed at the Four Seasons in Wailea. My daughter is graduating from high school in May so we are taking her and her 2 best friends to Hawaii. My question is, would it be more fun for my daughter and her friends to stay in the Wailea area or the Lahaina area. We really enjoyed staying in Wailea, but I remember thinking, that there wouldn’t be a lot for young people to do there. What do you suggest?
Jackie, I took my daughter and 3 of her friends to Maui when they were that same age. I would recommend the Lahaina area.. As you mention, there is simply more for young people to do there. Check out 2-bedroom vacation rentals on or near Ka’anapali Beach, such as the Westin Ka’anapali Ocean Resort Villas or the Eldorado, if you want to all stay together. We rented a minivan and still drove all over the island. I’m sure you will have a memorable trip.
Hi there we are a family with two kids ( 10 ,12 year old) from Canada.
We love to travel and explore new things. We only have 8 days in Hawai, which Island would be your recommendation. West Maui seems ideal
Is end of May good time ?
Hi Glen. You can’t go wrong with your choice of West Maui. May is an excellent month, as both prices and crowds go up in June when kids in the U.S. are out of school and families take their summer vacations. The weather should be great too.
My wife and I are traveling to Oahu and staying at the Sheraton Waikiki. It’s our first time and being teachers, probably our last. What is the best piece of advice you could give to first time visitors and probably last time visitors?
Robert, I could write pages of advice based on your interests — adventure, history, beaches, culture, shopping, etc. Here’s a quick list. You are staying in a nice place right on Waikiki Beach; there is a lot to do within a short distance. I love to hike to the top of Diamond Head for sunrise and look out over the beautiful shore and city alike. If you want history, of course there is Pearl Harbor; but don’t ignore a tour of Iolani Palace for an understanding of Hawaiian culture. By all means, take a full day to drive the island loop. This would include stops at Byodo-In Temple, Kualoa Ranch, lunch at a shrimp truck and a visit to watch surfers on the North Shore, even a quick stop at Dole Plantation. That’s my short answer.
My husband and I will be celebrating our 25th wedding anniversary in August and are planning on going to Hawaii for 2 weeks. This will be our first time visiting there and are hoping you can give us some advice on where to go. I’m 52 and my husband is 65. We love sightseeing, beautiful scenery and exploring different places and don’t enjoy just sitting at the hotel or on the beach. We’ll be there the last week of August and first week of Sept. Is this a good time to go? Should we go to just one place or two since we’ll be there longer? Any suggestions you have would be much appreciated!
Laura, first, congratulations! Hawaii is a memorable place to spend an anniversary. Your timeframe should present you with good weather and crowds that are beginning to thin as kids go back to school. I think two weeks is enough time to visit two islands for some variety. I would select Maui as one of them because of the diversity of sights and activities. The other could be Oahu if you want more history, nightlife, etc. Or choose The Big Island if the volcano is cooperating. Really, you can’t go wrong.
Hi Stephen,
My husband and I are traveling to HI in September for 5 days. We would like to stay in West Maui. Any suggestions for accommodations and not to miss destinations? Thank you for assistance!
Ronalee, for accommodations you can check Airbnb, but 5 days may be a little short for them. If you opt for a hotel, I like the ones on Kaanapali Beach, such as the Westin or Sheraton. First-time must-see destinations include the road to Hana, a trip to Haleakala (I prefer sunset), and the Old Lahaina luau. For a more eclectic list, see my post: https://journeyswithstephen.com/10-unusual-things-maui/ For an exhaustive list, check out 101 things to do on Maui.
We are planning a 20th anniversary trip in December 2019 (the 13th-20th); torn between Maui, the Big Island and Kauai. Love all the activities that Maui offers (volcano, snorkeling, hiking, whale watching, etc), but have friends who LOVE Kauai. Is it worth it at all to island hop on such a short trip, even for a night or 2?
Andrea, I would say, if you only have a week, that’s a little short for island hopping. By the time you check out, drive all the way to Kahului, fly to Kauai, drive to a new place and check in, you have spent most of one day just doing that. How much more could you have enjoyed Maui instead of airports and other logistics? Kauai is beautiful and pretty spread out. I think it deserves its own trip sometime after Maui. Happy Anniversary!
Which island would you recommend for March timeframe? Interested in sunsets, good food, beach, and activities. More on the beach, relaxation side. Planning a 50th birthday celebration. Never been to Hawaii. Prefer a rental versus hotel
I would recommend Maui to best satisfy your list. For rental properties, search the North Ka’anapali Beach area. I particularly like the Eldorado condos or the most expensive Westin units.
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Sorry – ignore the above accidental comment.
Hi Stephen, thank you so much for your post! I’m leaning toward Maui based on your post (first time visit to Hawaii) and have a few questions:
1. I’ll be departing from SFO / Bay area. Saw a deal for $258 from SF to Maui. Would you say that’s good value?
2. I can’t drive – is Maui still okay for me? What activities would I likely have to skip, and what other islands should I consider that are more car-friendly?
3. My trip would be some time in March – Still a good time for Maui? How wet / cold have you seen it get during this time of year? Other islands better at this time of year?
Thank you so much for your help!
Tanuja
Hi Tanuja. Thanks for the detailed questions. Here’s what I think:
1. $258 sounds like a great deal from the Bay area.
2. You can enjoy Maui without a car. For example, if you stay on Ka’anapali Beach, there are shuttles around the area. Then you can take a tour to Haleakala or the Road to Hana. Honolulu can easily be visited without a car. Personally, I would not recommend a visit to the Big Island or Kauai without a car.
3. March can be splendid in Maui, but also the rest of the Islands. It’s Hawaii…it’s not cold. And rains are usually brief, leaving rainbows behind. How good is that?
Hi Stephen, My husband is turning 50 in September of 2025 and has chosen to go to Hawaii as his birthday destination! It will just be him and I as of now unless things change and we invite others. I am having a hard time choosing which Island to go to but am looking at Maui and Oahu due to those islands having a little bit of everything to offer. We enjoy good food drinks, activities options of different kinds like tours, cruises, We are also coffee lovers so the coffee plantation tour definitely is an interest of mine, dinner shows (Luau) recommendations would be nice as I have read up on some of those, Shopping and rest/chill time are all of interest. we also enjoy a good pool and spa for massage options. I don’t mind a beach but my husband is not big on it but does’nt mind it’s presents as an option. Hope you can help.
Hi Dawn. From what you have described I’m going to give a slight nod to Oahu over Maui for you and your husband. Maui, still recovering from the Lahaina tragedy, has better beaches and outdoor adventures. Oahu has the nightlife, shopping, Pearl Harbor, tours, etc. I suggest you check out the Polynesian Cultural Center and this cruise I have written about: https://journeyswithstephen.com/see-waikiki-from-a-private-sailboat/ Note that coffee plantations are mostly on the Big Island and are few and far between on either Maui or Oahu. But plenty of other things to do!
We are heading to Oahu this summer. We are planning on seeing Pearl Harbor, Diamond Head, Kuala Ranch, Dole Plantation, and North Shore. Do you have any other recommendations and are each of these a day event?
Hi Craig. I assume you are staying in Honolulu and renting a car? Here are some things to keep in mind. If you drive to Pearl Harbor yourself, you can see everything and be back mid-afternoon. Be sure to make a reservation. Believe it or not, Diamond Head also requires a reservation these days. Sunrise is the best time to go, in my opinion. Then you have the rest of the day free. Kuala Ranch is a day event. You can drive to the North Shore, spend several hours, and quickly hit the Dole Plantation (pretty touristy and not much there) on the way there or back. I am now recommending the Polynesian Cultural Center (expensive, but worth it). Finally, the best way to see Waikiki is from a boat. Read my story about it here: https://journeyswithstephen.com/see-waikiki-from-a-private-sailboat/
Hi Stephen!
I’m from Chile and I’m planning a trip to Hawaii for 2 weeks in September. I haven’t decided which islands to visit, but I’d like to stay in 3 of them. My biggest doubt is Maui due to its recovery.. is it worthy to visit in these times? What would you recommend for a solo trip, 2 weeks in Hawaii.
Many thanks!!!!
Hi Teresa. I’m glad you are allowing 2 weeks, which is enough time to visit 3 islands. Maui is a tough call right now — so much tragedy, and yet they need the tourism revenue. I don’t know what you like to do — lay on a beach all day or hike wilderness trails? With that disclaimer, I am going to recommend Oahu, Kauai, and the Big Island. Stay at Volcano village on Hawaii a few days and experience Kilauea. Kauai is truly the garden island; check out my article, https://journeyswithstephen.com/8-unique-things-to-do-on-kauai/ for things to do. Oahu has a lot of diversity. I have recently written https://journeyswithstephen.com/explore-oahu-by-car/ to describe an itinerary. Let me know if this is helpful.
Awesome! Thank you!!! I like both, lay on a beach and hike wilderness trails, I would like to do both, though I don’t want to spend much time laying on a beach. I’ll start with Oahu and then Kauai, should I just go straight to Big Island then? Or stop by Maui before Big Island?
Many thanks!!! you’ve been extremely helpful!
Teresa, I’m a pretty intense traveler (55 countries), but Hawaii is the one place I always slow down a little to experience. I think 3 islands should be fine in 2 weeks. Maui isn’t really a “stop by” kind of place anyway. And Kilauea just started erupting again; if you are lucky that will still be happening in September. It’s amazing!
Hi Stephen,
We are planning a trip to hawaii in August from the east coast. Want to go to maui but is it worth the money we will be spending to go there after the fire devastation . Please advice. This will be our first time with our 2 kids.
I have a friend who just came back from Maui and reports that other than Lahaina being off-limits, the rest of the island is fine, including nearby Kaanapali Beach. So, I am back to recommending visits to Maui. Tourism is the biggest part of their economy, so you can help the island while you are having a great time.
Hi Stephen,
My girlfriend and I booked a vacation to Kona Hawaii from August 30 to September 7th. It is our first time in Hawaii, and also our anniversary, I would like to know what you recommend that we should do and visit in Kona, and should we island hop to another one of the islands? We enjoy beaches, hiking, waterfalls, snorkeling, sunsets & sunrises, volcanoes, & having some drinks lol.
Hi Junior. Congrats! Kona should check the boxes for beaches, snorkeling, sunsets. For volcanoes, you just have to drive across to the other side of the island. It is about a 2-hour drive, but I recommend you spend a night there. There are charming vacation rentals that accept one-night stays. Check VRBO. If your trip is 9 days, that is enough time to hop to another island for a couple of days. I recommend Maui or Kauai for that. Check my site by scrolling through North America; I have written articles about both islands!
Hi Stephen,
First thank you so much for your valued opinion for this first time traveler to Hawaii. My husband and I set out to have our two daughters visit all 50 states before they graduate and we have conquered the lower 48 this summer! However, this leaves Alaska and Hawaii. We are planning on visiting in late June/early July of 2025. I am so mixed about which island to visit but I think I have made a choice and just need some validation. My family of four plus my beach loving mother-in-law will be attending. After all this travel around the US we really are in need of a relaxing vacation. We want time to unwind and connect with each other. I will say my mother-in-law would love nothing better than to sit ALL day on the beach and look at the waves. My family doesn’t love crowds. When traveling we stick a lot to national parks and out of big cities. We LOVE nature and taking hikes that aren’t too strenuous. Any help would be greatly appreciated.
Hi Jaclynn. From what you have described I am going to recommend Maui. Amazing beaches at Ka’anapali, Kapalua, Wailea, and more. And for when the family needs to get out and explore, there are so many nature things to do (and no cities). Check out my article: https://journeyswithstephen.com/10-unusual-things-maui/ Bonus answer! Think about taking a cruise when you go to Alaska. Here’s another article to get you in the mood: https://journeyswithstephen.com/luxury-and-adventure-alaska-cruise/
Wow! Lots of ideas and suggestions on visiting Hawaii. My husband and I are both retired and ready to travel. We want to feel like it was all worth it, then want to go again! Staying near the beach so we’re able to take a walk, experiencing the beauty of Hawaii’s overwhelming landscapes, sunsets/sunrises, possibly waterfalls. Would love to meet the people, eat at their restaurants and enjoys the home-owned shops. Do you suggest we rent a car rather than take shutters to places of distance from where we stay? Love to see the whales – is there a prime time to go for that? Crowded . . . not our thing.
Hi Diane. My suggestion is to visit Maui or Kauai (or both, if you have a few weeks. Kauai is more laid-back, with its beauty a little less commercialized. Maui, my favorite, needs tourists to support the local businesses that have suffered in the aftermath of the Lahaina fire. I highly recommend a rental car for both islands (I compare companies using costco.com). Maui is the answer for whale watching (they migrate from Alaska), and winter is the season.