Hallbrook's Regatta

Orchestrated by it's namesake, Lord Edwin Hallbrook, Halbrook's regatta is an annual race around a small portion of Cenintal lake. The race always starts from Brook's Wharf with the finish line located at Fisher's Islet. The race takes all day, ends with the winners collecting their prizes at the finish line, and a banquet for all the competitors that finish the race. The winners are announced to the public the next morning at the starting line.

Starting Line

A festive atmosphere permeates the dockside with brightly colored streamers, delicious smells wafting from various food carts ,and stands pedaling everything from booze and candies to, toy boats and extravagant kites. Moored at various berths along the docks are the small racing boats no two of which are the same, ranging from converted fishing boats to custom built catamarans. The mooring area is closed to the general public to allow the crews to make last minute preparation although most have opted to mingle with each other, or partake in the festivities. Lord Edwin Hallbrook, a short, paunchy, jolly man in his mid to late sixties with heavy jowls and a balding head ,that seems hellbent on clinging to the last few wisps of black hair remaining, roams the docks being sure to personally meet and talk with the dozen or so teams present and will inevitably do the same with the PCs. Upon reaching the PC Lord Hallbrook will first stand upon decorum introducing himself and request the name of the team and it's crew members checking them against his ledger and verifying that everything matches up correctly, and that their entry fees are paid. After official duties are taken care of, or sooner if one of the PCs says something remotely funny or interesting, the sponsor of the race warmly and eagerly begins to ask the PCs questions about themselves and their vessel. He is able and willing to answer most questions about the race but refuses to provide the location of the 2nd waypoint and any information about the special prize being awarded in addition to the normal winnings, to commemorate the 25^th anniversary of the regatta. However, with a successful Persuasion or Bluff check he can be tricked into giving away information on one of these topics before realizing his misstep and laughing of any further questions. Upon finishing talks with the PCs, he lets them know the race will commence in roughly 30 minutes and encourages them to go mingle with the other crews and enjoy the festivities.

If the PCs decide to go to the festival they can learn information or rumors about this years race and some of their competitors. Provide any of the following information as you see fit. The truth is noted in bold.
1 Local favorite, 'The Brass Tacks' have returned to the race this year to try and win the cup one more time before retiring just like they have been for the last five years. (TRUE) 2 A new team The Grey Sails didn't show up and have forfeited their entry fee. You can tell because none of the boats have grey sails. (FALSE) 3 A last minuet entry, 'The Sticklebacks" were hand selected by an old flame of Hallbrook's to try and get back at him for something that happened in his younger days (TRUE) 4 The prize this year is some sort of magic item (TRUE) 5 The Grey Sails had to get a new sail because their original sail was stolen by a rival crew (FALSE) 6 Lord Hallbrook has hired additional security this year because of increased pirate activity (PARTIALY TRUE)           Hallbrook has hired additional security this year but it's mostly for show to make the 25^th year anniversary prize seem even more mysterious and valuable.
If any of the PCs mingle with the other teams they can learn these rumors as you see fit.
1 The Brass Tacks are by far the most experienced team in this race. (TRUE) 3 The 2nd check point is at Cardinal Bay (TRUE) 4 The Sticklebacks boat has a reinforced prow that could be effectively used for ramming (TRUE) 5 The Grey Sails are showboats and daredevils willing to take risks that other teams wouldn't (TRUE)
Teams of note
Grey Sails The Grey Sails are a team of lizard folk who are crewing a nimble looking catamaran with canary yellow sails, bright blue paint, and flying many multicolored streamers. Their team name is a typo that has yet to be corrected and that they have decided to go with for now out of politeness, and to avoid any additional paperwork. Their team name was originally The Grey Scales and referred to the color of the crews skin. The crew consists of Bsasha, Sissavis, Kivek Snag Tooth and skipper Cruzash Blue Snout. Cruzash Blue Snout is of average size for a lizardfolk and is generally unremarkable except for the small splash of bright blue scales around her nose and is generally gregarious and out-going. The Grey Sails are both daredevils and showboats who are more interested in making a spectacle than they are of actually winning the race ,however, if their willingness to take risks and push their boat to or past it's limits causes them to win more the better.
Brass Tacks Having participated in the race since its very beginning 25 years ago The Brass Tacks are by far the most experienced and oldest of the competing teams. Their length of participation and having won the regatta several times, including the inaugural race has made them one of the local favorites. Though they have been claiming they were retiring for the last 5 years they keep coming back for " One more chance at the cup". Their boat is a "by the book" racing boat and the same one they initially raced in 25 years ago. It has been painstakingly maintained and repaired throughout the years and its age is hard to notice. The crew consists of humans Max Morgens, Simon Gimble, Aubrey Stubbs, and skipper Ogden "Tiller" Barrstok a positively ancient dwarf with a neatly trimmed snowy white beard. The Brass Tacks are the most well rounded and knowledgeable team with the most experience.
Sticklebacks The Sticklebacks similar to their namesake are prickle and standoffish. They are a last minuet addition put together by Marian Dohlen, an old lover of Hallbrook that still resents him for rejecting her many years ago. She has assembled the Sticklebacks with the intention of spiting her old lover. They are under instructions to win the race by any means that won't get them immediately disqualified. Their boat is heavier than many of the others and is built more for durability than speed. The crew is composed of humans Robbin Scorzy and Vince Green, bugbear Illio , and heterochromic human skipper Paint Mancerno. The Sticklebacks are willing to use rough and dirty tactics while still technically remaining with in the rules such as "accidently" colliding with other racers or forcing them into more difficult or treacherous waters. However, since they were individually selected and a last minute entry, they are not a particularly cohesive team.
After allowing your players to interact with the other teams and the festival. Read the following.
Lord Hallbrook's voice rings out "All crews please gather at your vessels and make ready for launch. While you are preparing let's go over somethings. This race is likely to take all day and has two way points before the finish line. The first of which as you know is located out their at Clod's Teeth." As He says this he gestures to a small collection of large rocks at the edge of the bay before continuing "There you will find one of my assistants waiting to hand you the location of the next way point and a token to give to the person waiting for you at waypoint two proving that you completed the first leg of the race. The person at way point two will then give you the second token. After you have reached both way points and received both tokens you will then make your way to the finish line at Fisher's islet. Prizes are awarded to the 1^st, 2^nd, and 3^rd place teams, and will be awarded at my villa on the islet. All contestants who finish the race will be provided with a proper feast before we return to this spot and announce the winners to these lovely people tomorrow morning. Now should you get into trouble during the race you have all been provided with a red signal flare, please do not use it between here and Clod's Teeth I assure you we will be able to see you during leg one of the race. It should go without saying that un-sportsman like conduct will have you disqualified and particularly serious offences will get you blacklisted from all future races as well. A brief list of infractions include intentionally harming other crews or vessels, tampering with the waypoints or their staff, intentionally damaging vessels not participating in the race, hiring outside elements to interfere with the other teams, ect. That said, accidents and collisions with other teams are expected just don't make it a habit. Now teams please move to the starting line at the flagged buoy and upon my signal begin the race."

After the PCs and all other teams have maneuvered to the starting line a firework is set off bursting in the sky and marking the beginning of the race.

Race Leg I

Leg 1 is where the team will have the most interactions with the other racers and will be where you have to keep track of the most things. It is recommended that you only keep track of a few key teams and use the rest as set dressing.
To retrieve the token and the next location, the PCs must navigate to the checkpoint near the center of Clod's Teeth a convoluted mess of large rocks poking above the surface at varying heights resembling jagged teeth waiting to shred unwary or careless ships. As the PCs approach the rocks those with high perception will begin to notice the currents around the rocks becoming increasingly erratic. Maneuvering through Clod's Teeth will require the PCs to make a number of skill checks of varying difficulty. Raise or lower the DC as you see fit depending on things like how fast or slow the PCs decide to attempt the maneuvers. To create a sense of urgency or danger have some of the other teams succeed or fail around them.
However you manage this section, the party must make three successful checks before two failed checks. For each failed check the party's boat takes 1d8+1 damage as the boat is smashed against the rocks, and for each three failed checks the party is passed by one of the other teams. Despite the differences in appearance most of the racing boats have 40hp. Should two boats collide with each other they each take 1d6 points of damage, unless the collision was intentional in which case only the rammed vessel takes the damage.
While outright attacking the other racers is not allowed "accidents" can happen, and as long as they aren't blatantly obvious the PC's can attempt to knock other racers off their boats, provided it is in someway hidden behind some form of deception. The Stickle Backs will attempt to use these forms of dirty tactics in the tight confines of Clod's teeth and are the only team who's boat has 50hp instead of the standard 40hp.

Race Leg II

To retrieve the token for this leg of the race the PCs must travel to Cardinal Bay. At Cardinal Bay there is a man waiting for them at the end of a rickety pier outside of the small settlement of Crent near the Rust River. The water around the pier is choked with water lilies making it difficult to reach with any amount of speed. This coupled with the shallow nature of the water is what led to this piers being replaced and abandoned. The plant life choking the water will prevent the players from sailing directly to the pier. The obvious way to overcome this obstacle is for the PCs to simply row through it instead of sailing. However, this is difficult and time consuming. Other ways the PCs could bypass this difficulty would be to have a taller party member get out of the boat and pull it behind them, or to magically manipulate the water or plant life. Allow the players to come up with creative solutions on their own, just remember ultimately they only need to get to the pier and collect the token, so simple plans might work the best. Should they come up with a particularly novel or effective way of performing this task move them ahead in the race positioning, or if they are already in first place extend their lead.

Finish Line

The final leg of the race is getting from Cardinal Bay to the finish line at Fisher's Islet. Sailing through this last part of the race is much simpler. At this point the day is almost spent and dusk has set in. While this does provide the party with an impressive sunset back drop, recent storms in the area have caused a cluster of Aviator Bass eggs to dislodge and drift into the path of the PC's, much to the dismay of the mother bass who is very aggressive in the protection of her displaced eggs. To defend them she will attempt to drive off the players, or any other racers that come near, by flinging herself through the air at them.
Once clear of the irate fish the path to the finish line is open. If you want more drama have some of the other teams either be just a head or just behind the PC's with a few last minuet checks to see who crosses the finish line first. Hallbrook is excitedly waiting at the finish line to greet the first several teams to arrive. After the players arrive and have a chance to talk with Hallbrook, jump to later that night at the celebratory dinner for the  finishing competitors. Allow for some time for the PC's to interact with the other racers. Once you feel enough time has passed Hallbrook moves to the front of the room to give the following speech.
NOTE Anywhere you see a *** mark insert the name of the team that finished in that position. Anywhere you see a $$ mark select a denomination of currency that you feel is appropriate.
" Firstly I would like to thank you all for competing and congratulate you all on completing the regatta! While you all are deserving of recognition I would specifically like to recognize our winners! In third place we have ***! Please come to the front of the room. For our third place team the prize is $$ and again congratulations to our third place team. In second place we have ***! Second place team members please move to the front of the room. The prize for second place is $$. Congratulations, second place. And finally in first place ***! As you have all heard, do to this being the 25th year of this race we have a special prize for our first place victor, not only will they be receiving $$ and the regatta cup but this year the wining team will also be receiving a much coveted ,and might I add very expensive, victors pennant!" With that closing statement and to raucous applause Lord Halbrook presents the winning team with a small bright green pennant with a stylized 25 embroidered on it in silver thread.
With the speech finished the racers return to parting and eventually are shown to private quarters for the night.

Surprise Attack

On the return trip to Brook's Wharf, once the players are out of sight of Fisher's Islet another larger boat , roughly double the size of the parties, is in the area. Have the players make a Perception check, on a success the PCs notice that this other boat is on an intercept course with them. As the boat closes in another perception check reveals that its crew is armed. As soon as the boat is nearly upon its intentions become clear, if they weren't already, as it raises a grey flag emblazoned with a jagged toothed pikes skull. This is a small pirate vessel likely drawn in by the rumors of the particularly valuable prize this year. As the larger vessel bears down on them the wind dies down unnaturally as one of the pirates uses magic to manipulate it. This pirate must be neutralized before the party can escape with the wind if they choose to. At this point roll for initiative and begin combat.
The pirate crew consists of five members. The Captain, the mage, an archer, and two fighters. As the attacking vessel comes in range the captain yells at the party to surrender. If the order is not immediately complied with, they order the archer and the mage to open fire on the PCs. The pirate vessel will continue attempting to close with the PC's boat at a rate of 60ft each round, provided at least one pirate spends their entire turn to maneuver the vessel. Once the pirates have moved within 5 feet or made contact with the players boat, the fighters will attempt to jump onboard and engage the players in melee combat. If the pirate captain dies or the pirates lose three or more members of the crew, they will attempt to retreat from the players. This retreat is likely to be disorganized because the unexpectedly stiff resistance of the PCs has caught them off guard.
Once the pirates have been killed or driven off the way back to the starting line and the end of the adventure is clear.

Themes

Boat Race Water Adventure Pirates

Please note that the difficulty of all skill checks has been left blank to accommodate any system you wish to run this adventure using. All called out skills are based on the types of skills you may wish to use, for example Bluffing could be replaced with any similar verbal form of deception.

In this adventure the players have the opportunity to acquire a magic item called a Victors Pennant. The properties of this item are listed below.
Victors Pennant Three times per day this colorful pennant can magically repair any vehicle it is flown from. On activation the vehicle will immediately heal 20hp. Additionally, any vehicle that is flying one has its base speed increased by 10 feet. The pennant must be flown for at least one hour for a vehicle to benefit from these effects.

Provided here is a DnD stat block for the Aviator Bass Aviator Bass feel free to modify or change it to fit the needs of your party and system.

For the pirate attack use any generic bandit npc template that is convenient for you and which ever system you decide to use. Be sure to differentiate them enough that the four listed types feel different from each other.