First Hawaii Vacation for 20-something year olds?
I want to go to Hawaii for my 25th birthday, as this is one destination I’ve never been to but I’m dying to visit. Tentatively, I’m planning to go with a few people who I haven’t seen in awhile (24/25 year olds), and having no idea where to stay or what to do, I would be most grateful for some guidance.
A little about us: we are young professionals, who have the disposable income to have a good time, but not to the point of where we want to go into debt. We look for quality, but not the point of requiring to stay in a 4 or 5-star hotel, but somewhere decently luxurious to retreat to. We are craving sun, lying on the beach, reading good books, and sipping on tropical drinks. At night, we hope to enjoy fine dining and the hot spots most young adults visit.
With this in mind…
- What is the best month to visit Hawaii? My birthday is in the fall, but willing to travel whenever best advised. I am thinking spring/summer, but any suggested months?
- What island/city would you recommend for a first time Hawaii visitor? What’s not to miss, or what’s to avoid?
- Any hotel/resort/condo recommendations (names would be helpful)? Looking for a place that’s accessible to relaxing beaches, nightlife/dining, and shopping. Don’t want to stay somewhere too kid-friendly, but also not too chill where we’re the youngest guests…
Any advice would be most appreciated. Thank you!!

August 30th, 2009 at 2:31 am
if i were you, i would go to Oahu. Waikiki beach in downtown Honolulu is just made for people like you. You’ll have plenty of sun, beach, night clubs, pretty girls, commercialized “Hawaiian culture”, the whole nine yards.
the area has mostly five star resorts, but im sure that if you go a block or so inwards, you’ll find a perfectly suitable hotel that doesn’t cost upwards of $5,000 a night.
also, a word of advice. we hawaiians tend to be very territorial when it comes to white (or Haole, as you will most likely be referred to) tourists coming around popular local areas. if you don’t want to cause trouble with the locals, just stick to the tourist areas, there are more of them on Oahu than there are local areas anyways, so it won’t be that hard.
September 1st, 2009 at 3:01 am
Hi! Great question.
I agree with the first poster. It seems like Oahu (Honolulu/Waikiki) is what you’re looking for. The beaches on Oahu are great and there are lots of nice hotels to choose from that aren’t necessarily too pricey. There are plenty of shopping and dining opportunities and lots of nightlife. I went to Oahu twice in my 20s and had a blast there! (I’m now 40 and live on Kauai, but I go to Oahu a few times a year to shop, eat, and have a good time!)
Summer is warmer here than any other time of year, just as it is on the mainland. It is also very humid. Most kids are off school in the summer so lots of people travel here then. That makes prices higher. Supply and demand, you know! If you can wait until the second or third week in October to visit, it’ll be less crowded and prices may be lower for airfare and hotels. Kids on the mainland will be back in school so families won’t be traveling here as much and our mid-semester break (first week in Oct.) will be over.
Here are some suggestions of things to do once you arrive:
*take a catamaran sail off Waikiki beach
*hike Diamond Head
*snorkel at Hanauma Bay
*visit the Arizona Memorial at Pearl Harbor
*visit the Dole plantation and taste some REAL fresh pineapple!
*eat some good local food like loco moco, ahi poke, tako, and chicken katsu
*lie on the beach and get some sun!
I prefer staying in a hotel to a condo, but that’s just me. A condo can be more fun for a group than a hotel and less expensive if you buy some groceries to make your own breakfasts or whatever. (Keep in mind that groceries are NOT cheap here, but it’s more economical to make your own omelet than it is to buy one at a restaurant every morning!) I only personally know one condo complex in Waikiki and I won’t recommend it because I don’t think it’s what you’re looking for. I will, however, list some good hotels that I think might work for you.
Have a great trip and aloha!
September 4th, 2009 at 6:37 am
Fall is perfect; the college kids and families have gone back to their routines, the crowds lessen somewhat and it is easier to get into venues and restaurants. Also, although Hawaii has almost perfect weather year-round, it is a little too hot in summer and a little too cool in winter. Now keep in mind, we are only talk a 7-degree spread; 75 in winter and 82 in summer, but it makes quite a difference with the tropical sun and humidity!
Waikiki will give you the best nightlife and a lot of young people hanging out. It is the most international island, so if you want a “Cancun” style resort area with less urban and international feel, and more rows of hotels that is Maui, in Kaanapali.
The great thing about Hawaii is they understand service and the importance of tourists. There is a high degree of hygiene and service, so even a lesser hotel although “old”, will be clean and they will usually treat you well. Given the economy don’t write off a 4-star hotel, there are great deals right now.
If you don’t mind an older-but-clean room and $$$ is a bit of any issue, the Park Shore is in a great location, right across the street from the beach (there are no buildings directly on the beach on this side of Waikiki, so you have full ocean views from the rooms), usually about $150/night or less. It is in the best area of Waikiki. Service is excellent, but again rooms are old! Near the zoo, aquarium, Kapiolani Park and a great walkway along the beach for people-watching.
If you want to be in a more sophisticated, quiet part of Waikiki, I recommend the New Otani Kaimana Beach Hotel. It is surrounded by Kapiolani Park, near Diamond Head in an area called the Gold Coast. You literally walk right onto the sand, rooms are nice but SMALL, so that is the price you pay for a room sometimes under $200/night right on the beach. Great surfing and snorkeling on this area of Waikiki. this is a low-key, non-flashy low-rise, you can literally hear the waves and rustling coconut leaves from your room.
If you want to be right in the center of things in Waikiki in a decent hotel, I think the Waikiki Marriott is the next step up and a great buy. It also is in the area across the street from the beach but again no buildings in front of the hotel in this part of Waikiki so perfect views. Usually runs about $260/night, but certainly you can get a deal with Marriotts right now. A similar hotel nearby is Sheraton’s Princess Kaiulani, but I have heard they are going to knock it down so make sure to check well in advance..also i doubt they are going to spend much $$$ to fix anything since it is (theoretically) going away.
There are two newer boutique hotels in Waikiki I always hear a lot of good things, one is called the Bamboo Hotel (managed by the Aqua chain) and the other the Hotel Renew. Prices under $200/night, but they are 2-3 blocks in from the beach but I have to tell you your experience will be so much better if you are able to walk right out to the beach, be near the action and see the beautiful views of Waikiki!
Things to do: Some simple advice: (1) absolutely rent a car so you can drive around the island and go to deserted beaches on the windward side and enjoy views of the rain forest, (2) Go to famous Hanauma Bay National Underwarter Preserve right when it opens in the morning to avoid crowds and clouded water from all the tourists (and get a parking space!), (3) Go hiking in the jungle to at least one tropical waterfall, I always recommend Manoa Falls right in the back of Honolulu.
September 4th, 2009 at 3:12 pm
To try to answer all of the questions at once it would be Waikiki on the island of Oahu. Oahu is the most populated island with the most people, biggest city, and the most things to do. The other islands are more country with less of the city life. Stay at the Hawaii Hilton Villages with the mention of the disposal income and visit another island while you are over here to see the contrast between them all. The best time to visit, with your guidance, would be the spring and summer. Sitting and relaxing on the beach is during these best times and Waikiki nightlife should be waking up from the winter months.
First thing to do is to drive your rental car around the island to see where everything is and what everything is and you can start to branch out from there.
Just another local…
September 7th, 2009 at 7:55 am
I suggest you should either stay at Ko’olina Beach Club or Ihilani Resort and Spa.. The Ihilani perferrably…!!! It is not in Waikiki but in Kapolei… It is near a waterpark and right next to Paradise Cove. At paradise cove you can experiece the polynesian culture.. There is also a waterpark near by… Paradise Cove is a good place to see at night because you’ll be able to eat hawaiian food and see a fire dance, hula, and much more…