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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.

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1. 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. Reply * Stephen Henson on April 21, 2016 at 11:09 am 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! Reply

2. Lewis Tant, RN on February 7, 2018 at 1:50 pm 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? Reply * Stephen Henson on February 8, 2018 at 11:10 am 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. Reply
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3. Karen Reilly on March 12, 2018 at 7:16 am 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.. Reply * Stephen Henson on March 12, 2018 at 8:33 pm 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: /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. Reply

4. Sharon C on May 8, 2018 at 9:26 pm 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? Reply * Stephen Henson on May 9, 2018 at 6:51 pm 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. Reply

5. VD on June 1, 2018 at 12:11 am 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. Reply * Stephen Henson on June 1, 2018 at 9:56 pm 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. Reply * VD on June 3, 2018 at 12:42 am Thanks Steve. I’ll be departing from SFO or OAK. Family of 4, 2 adults and 2 kids (9 and 3). Reply

6. Sara on June 5, 2018 at 6:25 am 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 days. Thanks! Reply * Stephen Henson on June 5, 2018 at 8:49 pm 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! Reply * Stacy on March 6, 2019 at 10:17 am 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 Reply * Stephen Henson on March 7, 2019 at 1:57 pm 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. Reply

7. renee lowrie on October 8, 2018 at 2:21 pm 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. Reply * Stephen Henson on October 15, 2018 at 10:48 am 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. Reply

8. Maria Maya on November 21, 2018 at 1:30 pm 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 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? Reply * Stephen Henson on November 23, 2018 at 11:33 am 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: /10-unusual-things-maui/ Reply

9. Mike on November 24, 2018 at 7:45 am 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??? Reply * Stephen Henson on November 24, 2018 at 10:34 am 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! Reply . Todd on December 21, 2018 at 7:17 pm 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? Reply * Stephen Henson on December 22, 2018 at 12:25 pm 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! Reply . Lorelei on December 23, 2018 at 5:11 pm 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! Reply * Stephen Henson on December 28, 2018 at 10:12 am 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! Reply . Gina on January 4, 2019 at 9:30 am 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. Reply * Stephen Henson on January 6, 2019 at 10:10 pm 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. Reply . Erika on January 7, 2019 at 12:51 pm 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. Reply * Stephen Henson on January 9, 2019 at 12:52 pm 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. Reply . Val on January 22, 2019 at 9:48 am 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? Reply * Stephen Henson on January 22, 2019 at 11:56 am 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! Reply . Nicolle on January 30, 2019 at 8:46 pm 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!!!!! Reply * Stephen Henson on January 31, 2019 at 1:02 pm 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. Reply * Nicolle on February 5, 2019 at 1:05 pm Thank you !!! It should say Kaua’i to Maui lol. Typo! Thank you again Reply . Henry on January 31, 2019 at 11:38 pm 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. Reply * Henry on January 31, 2019 at 11:41 pm 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. Reply * Stephen Henson on February 3, 2019 at 7:43 pm 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: /10-unusual-things-maui/ Reply . Jackie on February 3, 2019 at 6:33 pm 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? Reply * Stephen Henson on February 3, 2019 at 8:01 pm 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. Reply . glen on February 18, 2019 at 11:03 am 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 ? Reply * Stephen Henson on February 19, 2019 at 4:52 pm 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. Reply . Robert Miller on April 24, 2019 at 7:22 am 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? Reply * Stephen Henson on April 25, 2019 at 11:13 am 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. Reply . Laura on May 9, 2019 at 11:43 am 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! Reply * Stephen Henson on May 10, 2019 at 9:01 pm 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. Reply * Ronalee Fernandez on June 16, 2019 at 4:43 pm 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! Reply * Stephen Henson on June 17, 2019 at 12:03 pm 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: /10-unusual-things-maui/ For an exhaustive list, check out 101 things to do on Maui. Reply . andrea on June 22, 2019 at 5:42 pm 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? Reply * Stephen Henson on June 23, 2019 at 10:50 am 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! Reply . B on September 11, 2019 at 11:27 am 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 Reply * Stephen Henson on September 12, 2019 at 11:37 am 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. Reply . Tanuja Nadarajan on January 2, 2020 at 12:14 pm . Tanuja Nadarajan on January 2, 2020 at 12:18 pm 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: . I’ll be departing from SFO / Bay area. Saw a deal for $258 from SF to Maui. Would you say that’s good value? . 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? . 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 Reply * Stephen Henson on January 3, 2020 at 9:52 am Hi Tanuja. Thanks for the detailed questions. Here’s what I think: . $258 sounds like a great deal from the Bay area. . 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. . 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? Reply

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