From Trailer

Take off Tie Down strap and put in towing car boat.

Put Bungs in, check oars are in or out (2 on boat under thwarts when sailing) sailing tiller (long one)

and rudder aboard. Large and small bailer with sponge on board and tied in. All surplus gear removed and placed together somewhere safe out of way.

Untie boom and mast. Leave stays and halyards fastened to foot.

2 people in boat, place/wedge foot of mast against anchor bag/bucket to steady it while lifting. Second person to lift head and walk forward until vertical. Then carry back until in mast step with mainsail groove facing aft.

Mast will remain in place resting against cut out in forward thwart/cross seat. Someone still needs to hols it in place there until the side and fore stays are fastened.

Untie forestay and side stays (and running back stays) with some one holding each of the forestay and side stays.

Look aloft (up) to make sure your stay is not twisted around anything. Then shackle side stays to chain plates. Then tie down forestay to forward shackle on the bow/stem head with lanyard, bowsting tight.

Wrap spare lanyard around itself while keeping tension on. Then 2 half hitches in the end though the tied down lanyard.

Rig the running backstays first looking aloft to make sure not tangled. Then threading the sheet (rope) through the pulley/block on the gunwale from aft/rear forward, back up to the block threading forward to aft.

Take sails from bags. Shackle tack/front corner of foresail/Jib to inside shackle on bow/stem head.

Fasten Luff/Front edge of Jib to forestay with the plastic twist clips, making sure they are rightway up.

Untie fore halyard/hoist from mast, look aloft to make sure no tangles in both the ends up to the top and tie front length to head of Jib. Never let go of either end of a halyard as they can blow out of reach or come unthreaded from the block up the mast. Thread Jib sheets from clew/rear bottom corner throughblock or eye on side of boat by mast and then through block on centre thwart.

Attach tack of main to goosekneck fitting connecting mast and boom. Thread top of bolt rope (ropeedge on luff/front of sail) into groove on mast making sure sail is not twisted. Untie main halyard, make sure no twists all the way up both ends. Tie aft end to head of main. Thread the “slug” attached to the clew along the boom groove, starting from mast end.

Thread main sheet through bottom block on floor of boat aft to forward, up to block on boomabove forward to aft, back along boom through the steel loop to the rear block, down from that to the block on the horse (stern steel rail) threading aft to forward and back up to mast block tying off with a bowline.

Boat is ready for launching.

Depending on direction and strength of wind it maybe possible to hoist sails onshore and launch with them up. However side on wind of any strength to the launching ramp makes that dangerous and sails should be hoisted once in the water and boat can lie (sit/face) head/bow to wind.

De-rigging.

Reverse the above process.

Sails lowered while on water and safely stowed in boat.

Un-thread main and jib sheets.

Take sails off and roll to go in bags. Keep dry and clean when doing this.

Undo running backstays and fasten to bottom of mast so they are taunt and will not fall off or twist/tangle.

Undo forestay lashing and tie down forestay keeping the length free to do the same to the side stays as you now unshackle those and tie down. Again some one in the boat holding in place while doing this.

Lift vertically and forward until foot of mast is wedged against the anchor bag/bucket, then lower the top of the mast by walking passing back.

Tie down mast, suspend boom below mast so it is not resting on anything, rig tie down strap.

Diagram of Standard Cutter Rigging 

Note our variations, we have no back stay. 

Source: Scouts NZ Boat Book

Learn more about the parts of a cutter