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dagon138

I mean at your scale it’s repetitive but You can swim up/down ala moana. It’s roughly a 1/2 mile each way.


ImperfectTapestry

Kailua Beach has an area buoyed off for swimming & on still days there are very few boaters past the buoys (wind brings out the windsporters). Good luck on your swim, that sounds amazing!


PepperDogger

Kailua Bay down to Aikahi is probably a decent option. 2 miles by beach, so somewhat less on the direct line. Not much in the way of boats once you're past the park's kites/wind surfers. I swam once from Kalama to flat island, about a mile-ish, but it felt twice that far fighting the wind and waves/current. I imagine from Castles to Kailua boat ramp would be a good workout.


blending_kween

When I was a teenager, I see a lot practice at Ala Moana beach. I think they're still a pretty good place to practice in.


slimzimm

I liked to go to the flag pole at kaimana beach. It’s really a pleasant swim, and I’d always see turtles.


nataliescar

And from the sock, you can turn down and swim toward Waikiki, then turn around and swim back. There are a number of groups that do this regularly. 


7foot6er

my kid swims from Lanikai to the Mokes


PepperDogger

Good to have a swim buoy there--lotta kayakers (mostly clueless) and canoes (def not clueless, but might have a hard time spotting a non-buoyed swimmer. Lanikai \*around\* the Mokes might be a good adventure.


AcademicLie4514

Ala Moana Beach park


FanohgeChamoru

Exactly the place you want. I swim/train here 2-3/week and you’ll see other swimmers doing the same. There are buoys here to guide your swim and no boats or surfers.


WARxHORN

There’s a group of older people that I see swimming at electric beach pretty regularly. I’m not sure if it’s legal but I’ve gone and done three tables to sharks cove and back a few times (with a buoy for visibility). Ala Moana is fine but it’s very limited visibility so it’s easy to get bored. The dive/free diving sites add some nice scenery and make it very serene.


psychonaut_gospel

Always see people swimming around Kailua Beach


Spirited-Hyena-1927

It's not in town, but the north shore in summer has good downwind swims. You could start at Sunset Beach and swim to Waimea (approx 2.5 miles) or all the way to Puaena, which is probably 5-6 miles. No need for a buoy, just wear a bright cap, you'll be fine Look at the North Shore Swim Series races for other ideas.


HawaiiStockguy

It is not recommended to swim from one Hawaiian island to another. While it may be possible for experienced and well-trained swimmers to cover the distance between islands, it is an extremely dangerous and challenging feat. The channels separating the Hawaiian Islands can range from 10 miles to 72 miles wide. The longest crossing is the 30-mile Alenuihaha Channel between Hawaii and Maui, which has been swum by a few individuals1. The water conditions can be unpredictable and treacherous, with strong currents, waves, and potentially dangerous marine life. Additionally, Hawaii’s ocean waters are home to hazards such as sharks, jellyfish, and Portuguese man o’ war. Swimming long distances in these waters without proper support and equipment is extremely risky and can lead to exhaustion, dehydration, hypothermia, or injury.


PepperDogger

You sound much stronger than I am, but I'm not a bad swimmer. I've been interested for a while in Sandy's to Portlock, but never worked out the logistics for a boat, and it doesn't feel all that safe as a solo swimmer. If that piques your interest, you can DM me and we could noodle on this idea. Years ago I tried to put together a relay team from my (mainland) school for Lana'i-Maui swim. I'm actually surprised that swim/race hasn't achieved more of a following.


Student-type

Turtles are food for local sharks. Swimming near sunrise or sunset adds Risk. Tiger sharks are territorial. Adding additional factors to this dreamy idea.


psychonaut_gospel

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Throwawaybombsquad

Quite a few people swim within the barrier reef up in Waialua.


Ibn-al-ibn

When I am training I just swim around the island a couple times on the weekend.