I like to think if we're limited to south of Padstow it will still be some great sailing time, but part of me also wonders if we were to rethink the trip as more of a 'bomb it up to Scotland' including multiple nights at sea (with or without the 20nm limit) and make the most of West Scotland before shooting back down again, might that be a better use of time and a greater overall experience than holiday-making on the south coast.......
There is a potential plan - hire a boat in Scotland for a month then the other boat from Portsmouth later on. Skip the delivery trips in between.
My approach would be driven in a similar manner to yours I think. To reach a realistic area. What I would suggest which I’m sure you are will may do is go with the flow. Visit some key stop towards lands end perhaps Weymouth, salcombe, Fowey and Dartmouth. Really key places for enjoyment. A strategic stop at Newlyn. Then head north With 1 or 2 night sails early in your charter and assess if you can and are comfortable doing so. Then you may reach the west coast sailing grounds which may be your target. I would assume this may be achieved weather permitting with 2 weeks. If so your have time to explore the area and have plenty of time to return and there so many other places to visit on the way back inc a stop at Scilly isles of course.
Personally I wouldn't run for Scotland. It'd be a lot of faff just to add miles and the planning with a 20nm limit would be tedious. Without Holyhead in the mix you'd also have very few places to run to as we'd usually do Dublin or Arklow.
As you will have seen from the responses, most question the wisdom of chartering a boat for such a long period going into the time of the year when most people are putting their boats away for the winter. 6 weeks from the middle of August onwards makes some sense, but October is really poor for continuous sailing. Getting from Portsmouth to Scotland to again arrive when the best is over does not make sense if the objective is leisurely cruising. Different if the objective is to cram as much challenging sailing in whatever the weather..
Once you "bomb it up" to the north end of the Irish Sea you have the options of east of the Mull of Kintyre and into the Clyde, or up the North Channel with a stop at Isla, (Port Ellen has a small marina) and the West Coast. If the longer range forecast looks grim then the Clyde may be a better bet but there is then the option of using the Crinan Canal to cut across to the west later. I have sailed on the Clyde during November in three different years and had both good weather and one full gale.
Agree, but that would mean a different charter boat coded to Cat 2 which is 60 miles from safe haven. Most charter boats are of this type (and therefore bigger and more expensive) as they offer more possibilities for charterers.
The OP is already considering different options based on suggestions by others. So fair degree of agreement (including the OP) that the original plan based on the information given was probably not feasible.
Trail or racing?
You don't want a bike. What you want is a camper van.
Just out of interest then, why have you done it? There is a bit more than a few ragged rocks to experiance.
No, not since some marketing prat came up with Route 500 around the north of Scotland - part of which is single track roads. When sailing in years gone by we used to laugh at cars with caravans crawling along narrow roads at walking speed breathing each others exhaust fumes, now its camper vans and motor homes mixed with tour buses. Though admittedly by October and November the roads were a bit quieter, but that was over ten years ago.
The OP is planning to use a charter boat which is for a very specific limited time period which inevitably closes off many of the options.
