A fun start to a game. Definitely better not to get into a ight with a dragon in your first fight. Even if they could overcome a lvl 3 solo at lvl 1, they could also die. It's touch and go. It will make the adventure more meaningful if thy reencounter the dragon later, even if they are still lvl 1, they probably will have found some resources amongst the treasure that will give them a slightly sharper edge to cut with.
So people have offered you links so that you can write your own challenge, which is nice, but, if I understand you correctly you were being cheeky and asking to have one written for you ...
I see you want two simultaneous skill challenges, the Storm and the Dragon Attack, right.
And you want them to crash, pretty much ...
But I propose you make their success or failure more meaningful than just how badly damaged the ship is at what is an inevitable crash they are unable to avoid.
I would set a goal: Reach Island 3 for example. A good place to bring the ship into shore without damaging it further, a safe place to rest for the night nearby like a dry cave, good resources to repair the boat, closer to the point you want them to head towards from here, and what about a friendly NPC to help them out? The dangers here will be fewer and less lethal.
Island 2: This is where YOU want them to crash. The boat will have a rougher arrival, shelter difficult to find, hostile inhabitants, and resources to repair the boat only reached after overcoming some serious challenges.
Island 1: O dear ... things went really badly for the PCs. They have crashed on cannibal island! Thay need to get out of here as fast as possible. Make it fun, fantastic and lethal. I'm imagining Peter Jackson's King Kong type Island ... the part behind the Wall! Or maybe 1 and 2 are the same Island seperated by a wall ... and they have to get to the other side.
Anyway, no we know what success and failure mean, and they are meaningful, we can design the challenge:
The Storm: Lvl 1 challenge 6 successes before 3 Fails (400xp)
Special; Characters with any marine type background receive a +2 on all checks
The Heaving Waves and the Slippery Ship:
At the beginning of each PCs turn they must make an
Acrobatics check DC Med (12) to deal with the conditions.
Fail: -2 to checks this round
Fail by More than 5: Also Fall Prone;
If PCs roll 19 or higher they gain a +2 on checks this round for Being in the Zone; 3 successes in a row means they no longer need to make these checks and have a permanent +2 bonus towardds all checks made towards this challenge.
Task Completion required for at least Partial Success: Tie down 1 Sail before destroyed, Steer Ship, Batten Down the Hatches
For full Success: Requires 6 Overall Successes before 3 Overall Fails
Round 1:
The Sails pushed severely by the torrential wind begin to tear, they need to be furled before they are torn to shreds.
Task: Furl both of the Main sails as fast as possible
Climbing the Masts in the pouring rain and howling wind:
Athletics/Acrobatics DC Medium+2 (14); Requires 2 Move Actions.
Fast Climb: DC becomes Hard +2 (21); Requires 1 Move Action
Safe Climb: DC becomes Easy+2 (10); Requires 3 Move Actions
Attempts to counteract the weather factor: Nature DC Medium (12) (Minor): Benefit: remove the +2 modifier on checks caused by the terrible weather.
Using rope or gear to make climbing safer: Dungeoneering/Thievery DC 14: +2 bonus to checks and SThrows if PC falls.
(Getting this gear ready will cost the appropriate actions. Simply using a rope to lash self down: (Minor). If PCs are very thorough this benfit becomes +3 but more actions will need to be spent.)
Falling: If a PC fails the attempt to climb by more than 5 they slip and fall: Make a STwith a -2 weather penalty;
Success: Hanging on for dear life: Requires Move Action to cling back to Mast and be able to continue climbing
Fail: Fall 20ft or 30ft down below; 2d10 or 3d10 falling damage (first sail 20ft high, 2nd 30 ft
Furl the sails: (Minichallenge: 3 success before 3 fails)
Pull the heavy wet sails up: (Minor Action) Endurance DC Med +2 (14);
A STR or DEX DC med (12) to pull faster gives a +2 bonus to checks; a failed check receives a -1 penalty;
*If more than 1 PC has climbed up to do this, reduce the DC by 2 for each PC involved as they automatically Aid each other
If PCs gain 3 fails here, the sail slips out of the hands and must be regathered from the start and a HSurge is lost due to exhaustion. Only penalty is time lost and time spent vulnerable high up on the Mast
Balancing Up High:
Each round the gusting wind threatens to shake the PCs loose:
+4 vs FORT; Hit: Push 2
If a PC is pushed they can make a Sthrow at -2 to grab hold of the riggings; requires a move action to right themselves to continue furling the sail etc.
Counteract: A PC can make an Acrobatics roll; if it is higher than the gust of winds attack roll, they are unaffected even if they were hit.
If PCs fall: 2d10 falling damage (1st Sail) 3d10 (2nd sail)
Tying the Sail Down: (Standard Action) DC Medium: INT or DEX (12); Allow thievery instead of DEX; allow appropriate Knowledge check if player is creative with why he is knowledgeable about knots and sails (either Dungeoneering, Nature or History perhaps)
Tie Down Fast: DC becomes Hard (19) but action is reduced to Move
At the end of every 2 rounds the condition of the Sails worsen: --> Lightly damaged (10 HP)--> Badly Damaged (+20 HP) --> Very Badly Damaged (+20 HP) --> Destroyed beyond repair (50 HP).
Each sail furled before becoming Very Badly damaged gains 1 Overall Success for the challenge
Each sail that is Destroyed beyond repair gains 1 Overall Fail for the challenge
Round 3:
Massive Wave Hits: Targets: (PCs on deck and at height of first sail);
+4 vs FORT; Hit: Lose a HSurge; Push 4
(PCs that are Pushed Overboard can make a ST to fall prone and cling to edge
Players at height of first sail can counteract with an Endurance or Acrobatics check to cling on to the riggings; must roll higher than attack roll that hit. They also receive a ST to cling on but require a move action to right themselves before continuing any climbing or furling.)
Situation:*The captain/helmsman is pushed overboard and the wheel of the ship spins wildly out of control!!!!*
Man Overboard!!
PC in the Water: A PC overboard must make an Endurance check at beginning of their turn:
DC Easy (8) and Athletics Check DC (Med) each round they are in the water.
If Endurance check fails: Athletics check receives a cumulative -2 penalty
If Athletics check fails: Gone under and taken a mouthful of sea water; attempts to rescue them receive a -2 penalty and they lose a HSurge.
After 3 failed Athletics checks PC begins drowning (see drowning rules);
Make drowning a 3/3 skill challenge: If the succeed they become
Lost at Sea
Fail: err ... Drowned?
PCs have 3 rounds to act to save man overboard before the boat is too far away; if they don't make it they become:
Lost at Sea: They are washed up on the same island as the other PCs, unconscious with 1 HSurge remaining and a -2 penalty on all rolls til they take an extended rest.
Losing a Man at Sea gains 1 Fail for the challenge
Rescuing a Man Overboard:(Minichallenge): 3 successes before 3 fails
Getting an object (rope or life ring) to the person: (1 success) Standard action: DEX or STR vs DC Med+2 (14)
(A player can used a ranged attack ability to substitute this throw if they are creative with how it works. The AC or Defense (REF or FORT not WILL) is 14)
Pulling them In: Requires 2 successes;
(move action) Athletics DC Difficult (19)
Tireless Effort: Endurance DC Med (12) gives a +2 bonus to Athletics check
MB: Any amount of PCs can
AID to give a +2 cumulative bonus (DC 10); failed AID attempt -1 penalty
Saving the Captian gains 1 Success for the challenge
Round 4: The boat is out of Control!! Look out for those Rocks!!!! Crates begin to slide around the Deck!! Oh dear!
Getting control of the Spinning Wheel: (minor)
Dexterity check DC Easy (8); fail: whack! Stinging fingers: (1d4 dmg); -2 to physical checks (STends)
Pulling the wheel the other way to avoid the rocks: (minichallenge: 3/3)
Minor: Athletics DC Medium (12)
Allow appropriate player actions gain a +2 modifier; If you deem a check needed to gain this bonus use Moderate DC
1 PC can Aid here (DC 10); if Aid is successful 1 success is gained for Pulling the Wheel
For each Fail acrued Pulling the Wheel scraping is heard at the hull of the boat
1 Fail: Boat takes 10 HP dmg
2 Fails: Boat takes another 20 HP dmg and all PCs must make an Acrobatics check DC Med (12) or fall prone
3 Fails; Boat takes another 30 HP dmg and all PCs fall Prone; 1 Fail is gained towards overall challenge
Righting the wheel before three fails gains 1 overall Success
Batten down the Hatches: Secure all the loose crates and stuff before they kill anyone and are lost at sea.
Until the Crates are secured: At the start of each PCs turn on Deck:
Loose Object!!! Look Out!: +4 vs Ref; 1d8+4 dmg and Push 1; Crits also Daze (STends)
Finding the right gear: Tarps and ropes
Int or Wisdom DC Moderate (12) (Minor): Allow a knowledge check if PCs are clever about how this knowledge apllies to where things are kept on boats.
Stacking the Loose crates: (minichallenge: 3/3)
Str or Athletics DC Easy +2 (10); (Standard Action)
Fast Stacking: (minor) Endurance DC Medium + 2 (14) reduces Athletics check to Move Action but DC for check becomes (14) as well.
Allow PC actions provide bonuses or reduction in time where you think appropriate; Excellent ideas or group coordination gain 1 auto success here.
For each Fail here:
Crate slides Loose across Deck; Target anyone involved Stacking, and anyone in straight line from that area; +6 vs Ref; Hit; 1d10+3 dmg and Push 3 and knocked Prone.
Boat takes 10 dmg as it impacts the side and splinters. When it impacts side: Burst 1; All creatures in burst; +4 vs REF; Hit 1d6+3 dmg: Miss: 1/2 dmg
Success: Gain 1 success for the challenge
3 Fails: The crates come tumbling down on the PCs as the ship lurches; the weight smashes them through the decking:
+6 vs REF; Burst 3; 1d6 +5 dmg + 1d10 falling dmg; prone and below deck + immobilised (STends); miss 1/2 dmg + can make a saving throw to fall prone on area next to where deck has collapsed;
Boat takes 30 HP dmg
Battening Everything Down: (minichallenge: 3/3)
3 areas of ship need battening down including the area where crates are kept.
DEX or INT/WIS vs DC Easy +2 (10) Standard Action; Allow Thievery or Knowledge check if Player justifies it convincingly
Speeding up the Process: DC becomes Med +2 (14); becomes Move action
Success: 1 Success for overall challenge
Each individual fail:
Something flies loose: target: PC battening down: +4 vs REF; dmg 1d8+4 dmg and Dazed (STends)
Total Fail: Some valuable chest/crate full of useful tools/items goes overboard that would have helped with the repairs in the future
Overall Success: PCs won't land on Island 1; No matter what happens with Dragon
Partial Success: PCs fail challenge but complete the required Tasks; PCs will land on Island 1 or 2 but not 3; This will be determined by success with challenge with Dragon and amount of HP of damage boat has received; Boat receives an additional 20 HP dmg as rudder is partially torn off.
Failure: heading towards Island 1 or 2, definitely not 3. This will be determined by success with Dragon challenge; Boat receives an additional 50 HP dmg due to the failure as rudder is torn off
So ... you can see how I do my skill challenges. Completing tasks or failing them determines success or failure, degree of success an important factor. I have things occur at certain times, new elements that need to be dealt with. I make them dangerous, potentially lethal. And i try and leave enough room so that players can think outside the box but defined enough so I have it ready how to ajudicate actions I haven't forseen.
From here you'd need to determine the amount of HP the boat can receive to make it to each Island and decide at what stage the Dragon appears. I'd probably have it show up in Round 6 for its first fly by attack and then again in Round 8; enough time for PCs to have dealt with the storm and recpover from any man over board situations hopefully; then the focus should switch to the dragon in a similar way. If i find time I can 'stat that challenge up' as well.
But you see where I'm going and hopefully it will give you a good start to take it from there
Good Luck!