Sounds like a fun trip. Because you are a new keel boat sailor I'll remind you of basics in case you forgot anything. In case I forget anything others will remind me. Check your boat is OK for the ocean. Seaworthy, fittings under waterline secure, life jackets, EPIRB, VHF. Estimate your boat speed and mark it on a chart so you know how far you will get in a give time period. Check the wind and weather and leave when it suits you. The wind and weather will determine boats progress. Take plenty of fuel, food and drink (and perhaps recreational drinks - we take beer and port) if you anchor overnight or get marooned. If you will be overnighting make sure your lighting works. And check in with Marine Rescue as you progress. They are very good at keeping tabs on boats. If I had time I would love to do it but stuck at work!

Very good posts from Trek and R13. Read several times.

We did Sydney (Watson's Bay) to Greenwell Point on the delivery in March 2021 and it was a formative experience. We left late (0930) and that was the first mistake. Good progress but we arrived off Greenwell Point after dark (second mistake). The skipper had not been into Greenwell Point before but we still decided to go in (10 kts wind, 1.5m seas). Third mistake. The skipper was using Navionics on a tablet and kept telling me to go to port despite that being off the lead lights (fourth mistake). I didn't understand my responsibilities as owner and didn't know enough to point out the wrong course to the skipper (fifth mistake). As we came down off a wave, the keel struck a rock, part of the breakwater on the southern side of the entrance. The next wave lifted the boat up and the rudder struck rock on the way down. Panic. I added revs, steered to starboard and we got away. The boat was on the slip at Greenwell Point for a week while we repaired the bottom bearing of the rudder. We were very lucky, it could have been much worse but I learnt a great deal about responsibility and what not to do.

Don't allow 1 person to be responsible for everything, everyone (especially the owner) should know how to get into the harbour you're entering. Don't enter a harbour you don't know well in darkness unless you really have to. Plan your trip so you get there in daylight. Always believe the lead lights not Navionics. Basic seamanship, I guess.

I would recommend doing it in 2 legs, the days are short right now. Shell Harbour has a marina, supposed to be good. Wait for a weather window and leave early. As Trek says, tell Marine Rescue what you're doing and let them know when you get there.

If you prepare well and follow the excellent advice on this forum, you are very likely to have a fantastic time.

Cheers,
Kinora

garymalmgren said..
RE: kept telling me to go to port despite that being off the lead lights (fourth mistake).
If in doubt SPEAK UP.
There is nothing worse than hearing, "I thought that would happen," after the event.

gary

Hope you weren't affected by the recent earthquake, Gary.

K.

My thoughts as follows, but you have to be comfortable with your own decisions.

You don't want the wind on the nose. Check the weather frequently until you see when there will be favourable winds. Looks like southerly at the moment but turning Nor'Easterly on the weekend. Sunday may be your best day for making good distance. But you really need 3 days of favourable winds, I suggest.

Have you used the anchor? Anchoring single handed may require a bit of getting up to the bow then back to the helm. If you haven't done it before, then it may be good to have a practice before you need to do it solo when it's critical. Might be a good idea to get out through the Spit Bridge the day before you actually head out the heads, so you can anchor or moor and get an early start on your first full day of passage making.

If it's a short first day due to waiting for Spit Bridge, Port Hacking can be fine. It's about 20 nautical miles from Sydney Heads, so perhaps 4 hours if you can average 5 knots. There's a visitors' mooring in shallowish water (2-5m) in Bundeena Bay. May be too exposed in a northerly, though. If you draw less than 2m (say 1.5 or less), it may be OK for you depth wise. Otherwise perhaps not. Also only if its not already occupied - fair chance it wont be in mid-winter. Lowest tides are between 0.26 and 0.29m on 1 , 2 and 3 of Aug between 0400 and 0500 in the morning. I'm told, but haven't done it myself that anchoring in Gunnamatta Bay is good, noting it's a narrowish marked channel up the west side to get into that bay (and there's a ferry using the channel also as I recall, though shouldn't be an issue) . If you've no other workable option, you may be allowed to tie up at the end of the marina at the Royal Motor Yacht Club at sundown provided you're off again by 0700. You can call them to ask if you need to.

As has been said, days are short at the moment. Plan to still have at least an hour of light at the end of the day to point into the wind and drop the main, pilot into anchorage or marina or onto courtesy mooring and faff around stowing what needs to be stowed, etc. You want to be all secure before the sun sets. and preferably with a hot mug of tea made.

Plan to leave any anchorage or marina pretty much at sun up - have brekky and do your prep to go during first light. This gives you the maximum amount of time for making progress in daylight hours. So as much as nine hours if you're under way by 0700 and heading in to be on anchor, mooring or dock by 1600.

If your boat happily averages 6 knots in the winds you're expecting, do your passage planning assuming 5 knots average. Always better to arrive earlier on each day than your plan suggests, than to be still out as the sun goes down eg because the winds weren't what was expected.

Keep a reasonable distance off the shore before you head in to wherever you're going to anchor or tie up. Swells get steeper as they approach the shore and can also reflect back off bluffs and cliffs in deeper water creating confused seas close in.

Do tell Marine Rescue what your plans are (and update them if your plans change), but I suggest tell them you will be arriving at your next overnight destination 30 mins to an hour after you actually expect to be there. In my experience they'll be on the phone hassling you 5 minutes after you've not yet arrived, so leave yourself a bit of a margin, in what you tell them. In my experience they're more used to power boats and fishing tinnies, and don't get that progress when sailing is a little less predictable. If you then end up reporting arriving for the day earlier than you told them, no harm done.

Have the phone numbers already in your phone contacts for each Marine Rescue and any marina/harbour master you may need, so you don't have to search them up when you do need them.

I assume your engine works and you have enough fuel to motor if the wind dies and to manouever when anchoring, getting into a marina, putting the head into the wind and so on.

The new marina at Shellharbour is big and good, and 2 years ago was half empty when I stopped there when heading north in early July. It's about 40 nautical miles from Port Hacking, so 8 hours at 5 knots average and just under 7 hours at 6 knots average. So I'd call that a good days sailing and wouldn't try for more than that in a day.

From Shellharbour Marina to Greenwell is about 25 nautical miles, including getting out of the marina and east of Bass Point before heading south. So that's a short day's sailing of 5 hours or so if you have enough of the right wind. I am not sure how challenging the bar crossing into the river there is. Assuming you want to be entering late on the incoming tide - ie on the incoming close to high tide, if depth is an issue. High tide at Crookhaven is at 1144 on Monday 3 Aug and 1229 on Tuesday 4 August. So you'd want to be out of Shellharbour marina first thing to be sure to make it to the entrance for the crossing before the tide turns to go out. You've more time, tidewise, later in the week, but by Tuesday afternoon the wind is likely to be westerly and later in the week becoming southerly, so not favourable for heading south.

All the best.