Several years ago I entered the Escape From Alcatraz triathlon as I wanted to swim from Alcatraz to San Francisco.

Source: http://www.dolphinclub.org/swimming/escape/

I was scheduled to go on a work trip at the time and this worked out perfectly. Unfortunately the trip was cancelled and I never got to do it. I subsequently entered a couple of times later but never made it through the random entry cut; apparently it's heavily over-subscribed every year.

Obviously the major "big-swim" is a channel swim.

But really that just looks like torture and costs the price of a large brand-new car and you have to book it 5 years in advance.

Question: Has anyone got experience (whether directly or via friends/colleagues) of some reasonable but not wallet-emptying swimming event that you you would want to tell your grand-children about, like swimming from one country to another or something? I don't want to train for a year (been there, done that) for some event and end up doing something that I'm just going to feel miserable doing. I'm not looking for a race, but something with other entrants would be good. I'd prefer it not to be a marathon-solo event, but just something that contains a memorable long swim as evoked in the Alcatraz photo above.

Several years ago I entered the Escape From Alcatraz triathlon as I wanted to swim from Alcatraz to San Francisco.

Source: http://www.dolphinclub.org/swimming/escape/

I was scheduled to go on a work trip at the time and this worked out perfectly. Unfortunately the trip was cancelled and I never got to do it. I subsequently entered a couple of times later but never made it through the random entry cut; apparently it's heavily over-subscribed every year.

Obviously the major "big-swim" is a channel swim.

But really that just looks like torture and costs the price of a large brand-new car and you have to book it 5 years in advance.

Question: Has anyone got experience (whether directly or via friends/colleagues) of some reasonable but not wallet-emptying swimming event that you you would want to tell your grand-children about, like swimming from one country to another or something? I don't want to train for a year (been there, done that) for some event and end up doing something that I'm just going to feel miserable doing. I'm not looking for a race, but something with other entrants would be good. I'd prefer it not to be a marathon-solo event, but just something that contains a memorable long swim as evoked in the Alcatraz photo above.

Update: I don't like leaving a question with an unawarded answer so I reviewed the answers with a view to which event I would actually take part in.

The Hellespont / Bosphorus / Dardanelles swim(s) have a definite appeal. Swimming from one continent to another across shipping lanes closed just for the event sounds epic.

The Freedom swim sounds good too, but it's too cold for me. I can swim in cold water if I have to. But I don't have to. So I won't.

There were a few lake swims including the Sun Moon Lake swim which sound like they'd be enjoyable, but they don't really tick the "to die for" check-item. "Only 20000 other people besides me managed to finish..."

Some people took "to die for" too literally, and seemed to want to suggest something that would be the last thing I ever did...

The Rottnest swim looks amazing. A 20k swim would be a major part of my day though! Also, I'd need to organise a support boat and a qualifying swim.

Aleks G provided a pointer to the World's top 100 open water swims and I had a look through those. One of which was the Bermuda round the sound swim at (up to) 10km. The HQ for this swim is a hotel I've actually stayed at and the water temperature is 25C. Perfect.

However, I'm going to select AE's answer as accepted.

Many thanks for the great answers!

Several years ago I entered the Escape From Alcatraz triathlon as I wanted to swim from Alcatraz to San Francisco.

Source: http://www.dolphinclub.org/swimming/escape/

I was scheduled to go on a work trip at the time and this worked out perfectly. Unfortunately the trip was cancelled and I never got to do it. I subsequently entered a couple of times later but never made it through the random entry cut; apparently it's heavily over-subscribed every year.

Obviously the major "big-swim" is a channel swim:

Townsend swimming the Channel in 2014 Photo: Courtesy of Andreya Townsend

But really that just looks like torture and costs the price of a large brand-new car and you have to book it 5 years in advance.

Question: Has anyone got experience (whether directly or via friends/colleagues) of some reasonable but not wallet-emptying swimming event that you you would want to tell your grand-children about, like swimming from one country to another or something? I don't want to train for a year (been there, done that) for some event and end up doing something that I'm just going to feel miserable doing. I'm not looking for a race, but something with other entrants would be good. I'd prefer it not to be a marathon-solo event, but just something that contains a memorable long swim as evoked in the Alcatraz photo above.

Several years ago I entered the Escape From Alcatraz triathlon as I wanted to swim from Alcatraz to San Francisco.

Source: http://www.dolphinclub.org/swimming/escape/

I was scheduled to go on a work trip at the time and this worked out perfectly. Unfortunately the trip was cancelled and I never got to do it. I subsequently entered a couple of times later but never made it through the random entry cut; apparently it's heavily over-subscribed every year.

Obviously the major "big-swim" is a channel swim.

But really that just looks like torture and costs the price of a large brand-new car and you have to book it 5 years in advance.

Question: Has anyone got experience (whether directly or via friends/colleagues) of some reasonable but not wallet-emptying swimming event that you you would want to tell your grand-children about, like swimming from one country to another or something? I don't want to train for a year (been there, done that) for some event and end up doing something that I'm just going to feel miserable doing. I'm not looking for a race, but something with other entrants would be good. I'd prefer it not to be a marathon-solo event, but just something that contains a memorable long swim as evoked in the Alcatraz photo above.