I was lucky enough to get to make one. Bumped into an friend who was leaving Seward bound for Mexico, he needed crew crossing the Gulf of Alaska.
The boat is a 65 year old wood hull/steel house 36' cutter. The owner/skipper is a retired Alaska State Ferry Captain who has sailed these waters for many years.
The usual route from Seward is across the northern gulf to Cross Sound, then inside to points south. For us weather wasn't conducive to that passage with easterly winds to 35 knots along the northern gulf. Instead we went south 150 miles to Kodiak where we sat for two days before heading east to Sitka.
The first two days out of Seward were lumpy with the remnants of the most recent low passage. Winds S or SE 10-15 with seas 6 - 10'. As we rounded Cape Aialik at the end of Resurrection Bay we were motor-sailing with reefed main and staysail. The skipper had rigged an additional headstay (at base of bowsprit) before departure give us three forward stays, end of sprit, base of sprit and the staysail stay just aft of the bow. A check of the mast (wood) showed a distinct forward bend at the top so we put into Aialik Bay to spend the night and adjust the mast rigging. We were able to ease the headstay tension and get a better shape to the mast. The next day we continued south in lumpy seas than gradually lessened as we got closer to Kodiak.
Our watch system was 4 on, 8 off. The skipper had the 4 to 8 watches and did the cooking, I was 12-4 and our third crew had the 8 to 12. This spread the experience out allowing the skipper or I to help Galen with some overlap in watch if needed. I found the 4/8 to work well.
Out of Kodiak east bound to Sitka we had great weather. Sunny, clear skies with warm temps. The nights were spectacular with a sky full of stars and the northern lights putting on a show across the northern sky. The first two days we had significant swell from the south but it is a heavy boat and we were motorsailing with main and headsails which helped to dampen the roll. This being only my second time offshore the 12-15 foot swells were impressive but without drama.
On our last full day the winds swung to the NW and came up to 10-15 knots as predicted. By that afternoon we were broad reaching at 5-7 knots under sail alone. The ride was a bit sporty with beam seas of 4-6 feet but we were making progress and using the Monitor to steer.
About an hour before my night watch was to start the boat motion became rather violent, sharp rolls, things moving around in the boat and the mast making some ugly noises (wedges working a bit in the partners). After a particularly nasty roll the skipper and I went on deck and found the Monitor rudder had kicked up so the boat was just wandering along. Galen had little sailing experience and didn't realize what was happening. We ended up going back on the tiller pilot and motor sailing the remainder of the night. Was a wild ride until we were in the lee of Cape Edgecumbe where the wind and seas eased and we motored in under clear skies and glassy water.
For this trip I got an Rx for Scopolamine patches which I found to be ineffective. Marked queasiness if below for extended period. I also had Rx Zofran which I believe to be the nectar of the gods. After about 10 minutes all uneasiness went away, I was able to sit below eating greasy pork chops while rocking and rolling without issue.
To keep the Admiral informed of our progress I purchased an InReach tracker to use on the crossing. It is similar to a Spot, you can send/receive messages and it has an SOS button if needed. Here is a link to the tracking map if you want to see what it looks like. Clicking on a position or message give lat/long, course, speed and time.
The skipper teaches celestial nag so we were able to play around with a sextant, determined latitude at local apparent noon ---- finally had the mystery removed from sextant use.
Here's a link to some pics and video of the trip.
It was a good learning experience. What doesn't kill you makes you stronger.