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Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Toronto, Canada
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Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Hoping for some expert input into my planned itinerary. Here are the basics:

*Sept 6-20

*1st week: 2 friends, 1 surfer, 1 who will just relax / read

*2nd week: 6-10 friends (1 surfer, rest for relaxing, going out)

Week 1 near Kona - by Kahaluu. Perhaps look for a condo at the racquet club. We'd like accommodations with a pool. I think I can surf at Kahaluu in September as there's the south swell. Is there enough to do in the area for a week? I imagine we will need to rent a car? I know there are some bigger resorts as well but if I want to be near the beach to surf, I think as close to Kahaluu as possible, right?

Fly over to Oahu and spend Week 2 on the North Shore. Although waves aren't ideal in Sept., but the end of the month they could be ok. But, since it's a larger group, we also want to be near places to go out / have fun. Does Haleiwa make sense for this? We were thinking of renting a condo - any specific area to consider? We are hoping not to have to have a car.

Ideas and input welcome! Thank you.

Northern California...
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1. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Haleiwa last year was flat at the end of September. As in, "let your toddlers play in the waves" flat at Waimea bay. There were some 2'-3' swell coming in from the south, but that was about it. The first week in October wasn't much better so your surfer friend should have a plan "B" in case the wave's aren't around - boogie boarding down by Queen's beach or SUP over by Haleiwa harbor.

Washington DC...
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2. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

For your week 2, I think it makes more sense to stay in Waikiki. You will need a car if you stay in Haleiwa, also for going out at night, I think Waikiki would be much better.

For help with accomodations on the Big Island, I'd post directly on the Island of Hawaii forum with all the details you provided in this post of what you are looking for, as well as your nightly accomodations budget.

Toronto, Canada
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3. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Thanks! I'm the surfer friend :) For the second week, if it's flat, so be it. That's why I figure first week in the south to stand a better chance of something. If it's flat there too, I'm always happy to SUP instead.

We were wanting to avoid too much busy / city, that's why we stayed away from Waikiki. Are there chill parts that don't feel like you're in a big town?

Northern California...
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4. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

In a word "nope". Waikiki starts with high-rise hotels/condos on the west and continues that way until it hits the Kapiolani park on the east. However, it is the easiest area to get around without a car - especially with a larger group. You'll have to decide what you are willing to give up because there really isn't any place that meets all of your requirements for the end of September -

Haleiwa - flat / need a car / not a big town / not as many places to go out at night with a group

Waikiki - maybe small surf / no car needed / big town / lots of places for people to go at night

Kailua - flat-ish / need a car / small town / more places to go than Haleiwa at night

Toronto, Canada
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5. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Thanks Kauai_No_Ka_Oi - looks like I can't 'have it all'!

For the second week, any other spot in Hawaii (any island) that you recommend having a combo of beach / nature + small town with nightlife (not necessarily needing a car)? No surfing needed. Really, we can go anywhere we want. Haleiwa was just a first though. I don't think the gang will be into Waikiki.

Kapaa, Hawaii
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6. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

You need to rent a car if you go to one of the other islands. Like Maui or Kauai. Oahu is the only island that has a really decent mass transit system or any real nightlife to speak of. The surf is high on the south shore (Waikiki during the summer months) A year ago last September they were fitting 25 feet. You could go to Kaanapali on Maui but it's a planned resort complex, not a small town.

Nanaimo, Canada
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7. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

What about the north shore on Kaua'i? Hanalei is a wonderful place any time of year, but FANTASTIC in the summer months and September.

Washington DC...
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8. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

I think Maui may have more along the lines of what you are looking for as far as less busy/ less crowded than Waikiki, but still has a few bars, etc. for some nightlife. Kauai and Big Island have generally very little night life, and are generally very quiet. What is the age range of people in your group? Also what is your nightly budget for accommodations?

I'd hop over to the Maui forum and post a question there, maybe Kaanapali/ Lahaina or Kihei on Maui would work for you, although as fishdiva mentions, Kaanapali is not really a town, more of a resort area.

Hanalei on Kauai that Joan mentions is stunningly gorgeous, but it is a really really tiny town, and has very few options for "going out". Tahiti Nui restaurant/ bar might be fun for a night or two, but not too many other options. I think people tend to stay in Hanalei/ North Shore of Kauai who want to see the beautiful scenery/ beaches and who don't care very much about night life.

You definitely need a car (or two) for your group if you are staying anywhere except for Waikiki/ Honolulu.

Healy, Alaska
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9. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

small town + nightlife really don't exist unless by nightlife you mean a simple guitar playing in a quiet bar. :)

And any area with small towns does require a car, so I guess you need to decide what factors are most important. Good luck! :)

Big Island, Hawaii
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10. Re: Itinerary for Relax + Surf in Sept: Kona & Haleiwa?

Ok, Kahaluu really isn't a beach. It has some patchy, rather dirty sand but that's about it. In addition it is not anywhere where a surfer would want to be. It's a zoo. All the surf schools cram in because it's one of the few places with relatively small waves suitable for beginners but all the snorkelers and cruise shippers crowd into the bay as well making for a lot of conflicts. It has been a front page new story here more than once, including the description of a "war zone". In addition, September is the hottest month on the island and you'll want central air conditioning or direct oceanfront. Most Kailua Kona area condos do not have air con. You'll also bean hour from the beach district of South Kohala.

September is usually flat as a pancake everywhere on the Kona-Kohala Coast. Even Kailua Kona doesn't usually get any summer south swells, as it's west facing. It's not surf season. It's a great time for swimming, diving and snorkeling. In addition, surfing on the BI is very territorial and most surf spots are intermediate to experienced only. Locals don't take kindly to visitors surfing at most area breaks, even if you're good it can take a lot of time to be accepted and move into the ranks.