Listed below are just some of the exclusive games, and entertainment events for High Seas Rally participants. 

Our "HIRED GUN" Comedian; Roy Riley

For over 30 years, Roy has been entertaining crowds from coast to coast as a stand-up comic, hosting events with audiences from a few into the thousands and has been a huge hit on every High Seas Rally from the start. Since the first High Seas Rally in 2003, Roy has been behind the microphone keeping the laughs and fun rolling at our shows, events and gatherings. When not cruising with HSR, you will find Roy working the crowd emceeing numerous events ranging from auctions to weddings and all things in between.

Roy is a transplanted northerner, having spent his wonder years growing up in upstate New York, and moving to Snowshoe Mountain Ski Resort in West Virginia in the early 1980’s. For the next 25 years, Roy enjoyed the road less traveled on his stage at The Comedy Cellar with a million laughs and countless memories. After all those years high atop Snowshoe Mountain, hours from the mall and grocery store, Roy and the family heard the call of the real world. With his wife, Melissa, and their twin boys, they relocated from the mountains in West Virginia to bluegrass pastures of Kentucky to begin the next big adventure…

Check out Roy’s website: www.royriley.com

If you think you’ve seen all of Roy’s antics, you ain’t seen nothin’ yet!!!

Belly Smacker Contest

Always a crowd pleaser. We have turned this event into an even more painful sport. In case you are not familiar with the ancient art of the "belly smacker" here's what it is: Jumping into a pool from a 3 foot tall platform, arms spread, belly first, hitting the water flat and real painful like. This ain't no sissy "belly flop".
Extra points awarded for redness of body parts and the oooohing of the crowd. Roy Riley (our M/C Comedian) has brought this to a new level. You could see anything from nuns to judges to Superman capes and after their bodies are good and numb the real fun begins. Oh Yeh! you do it more than once. Don't worry, we have a perfect survival record!
Custom High Seas Rally Gold Medal for the winner. P.S. the biggest guy rarely wins...it's all about the sound of the splash. Everyone knows the sound of pain. Judging by specator applause/noise. Over 2,000 spectators every year.
Must enter ballot box. The sacrificial contestants...  I mean, lucky contestants, will be drawn at the beginning of the contest. 10 entries drawn.  Last years defending champ gets a free entry if they want to relive the pain again.

2015 Belly Smaker Winner, 7 time HSR cruiser 
Iris Hash from Raeford, North Carolina.
Yes, girls win this event too! Hey! we don't descriminate against pain but she's not likely to be in the Treasured Chest contest later that week with the upcoming bruises.

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World's Largest T-Shirt Swap

Bring a NEW extra biker T-shirt and join the fun. Have yet to determine a location since we have no private Island this cruise but we'll find a spot and we have the entire ship! Usually,over 900 participants bring a NEW biker T-shirt that you are prepared to randomly exchange for another shirt each year. We'll explain the new rules on the ship. First. show us your NEW T-shirt, then get in line directly across from each other. Display your shirt in front of you. It's a mystery swap. No running needed and takes half the time. You never know what you will end up with till it's over. We'll give you the directions once we start. Space  is becoming a real issue with this game having nearly 1,000 participants. We hope we have solved this problem and with no running now, everyone can participate.

Best Beard Contest

NEW RULES FOR 2017: FACIAL HAIR MUST BE AT LEAST 3 INCHES LONG TO ENTER. This event also includes mustaches, goatees, etc. Remember, must be over 3 inches long. Not a back or ear hair contest. Anyone that qualifies can enter. Top 10 contestants are narrowed down by crowd applause (style) to participate in this contest. Then the the women get to decide the winners with the "touchie-feelie" and smell method.  Lots of fun. A lot of unscrupulous characters enter every year. Just a heads up, you need to get a little creative to stand out in this crowd! Special shampoos, fragrances, softeners, styles, even colors can help.

Custom High Seas Rally Gold Medal for the winner and an additional prize for the Longest Beard. No ballot box entry needed. Just be qualified.

2015 Best Beard Winner
Frank Brzychcy of New Jersey. 


The "Treasured Chest" Contest

The "Treasured Chest" contest goes with our slogan "there's a little pirate in every biker". In this case some of the pirate is a little more exposed with more emphasis placed on a woman’s frontal area, Which is a favorite watched area by us male pirate types... although other areas may also play a part. The wench that collects the most money from our audience in approximately 15 minutes (5 songs) is the "Treasured Chest Contest " winner. Bring your paper money and get your eyebrows raised.
100% of all the money collected goes to Debbie's Dialysis Fund.

In 2015, the contestants raised $2,868.00 in 15 minutes. The Gal that collects the most money wins a Custom High Seas Rally Gold Medal.
To participate you must place your entry ballot in the ballott box the day prior, be qualified...if you know what I mean... and dress for the part.
Treasured Chest  Winner 2015:
Kayla Slenbaker: 1st time HSR cruiser  from Essex, Maryland.


Pirate Biker Bingo

Because it's a Biker Pirate cruise! Big Money giveaways!! At our Pirate Biker Bingo $10,000.00 in CASH giveaways is not uncommon, it’s the norm. This isn't your normal bingo and it’s probably the only time and place you will ever see hundreds of partying bikers so quiet you can hear a pin drop. 50% of bingo cards sales go to Debbie's Dialysis Fund. The other 50% goes to the winners.

In 2015, six of our passengers split $13,740.00CASH + $1,750.00 in Vendor prizes to lucky crewmembers that just happened to be sitting next to the winners. Thats How Us Pirates Share The LOOT!!..Largest of the 5 games was $6,250.00. Split between 2 lucky winners this year.

In addition, Debbie's Dialysis Fund raised $13,740.00. Bingo card sales begin first night (Monday)

BIG CASH WINNERS, lots of fun. Great cause. Money makes you smile.



Topless Man Contest

The ladies have fun with this every year and so do the lucky men being judged. Judges & contestants are randomly drawn from our ballot box entries earlier that week. This event involves men with no clothes from the waist up and blindfolded women judges and some baby oil. Of course it requires touching by the female judges-that’s how they judge!
WINNER gets the Custom High Seas Rally Gold Medal. Yeh..we're still asking ourselves why we give these men prizes?? As an extra bonus in 2013 it rained during this contest and became a wet t-shirt contest for the female judges.  I didn't plan that, I swear.

 Ladies that want to be judges..there's a ballot box for you too!

Topless Man Winner 2015:
1st time HSR cruiser and dialysis patient husband,
Mike Fennelly from South Portland, Maine 



Poker Walk

Still undecided if this game will continue/be modified or replaced for 2017??
First you purchase one or more Poker Walk sheets no later than Tuesday for $20.00 each. Then you draw a playing card at 5 different locations on both ship or onshore. To spice up the pot our vendors and the local businesses kick in 96 vendor prizes at selected Poker Walk stops that are instant winners of  an approx. $14,022.00 of FREE prizes (just by drawing a joker). Again, winners get 50% of the cash, Debbie's Dialysis Fund gets 50%.
          2015 CASH totals: Winners take $9,650.00
  • Best Hand 30% of pot- $5,790.00
    Aubry Sanford-donated back $1,000 to Dialysis Fund
  • Mystery Hand 10% of pot - $1,930.00
    Manny Escamilla
  • Worst Hand  $1,930.00
    Calvin Fiscus
  • PLUS 96 Instant Vendor Prize winners ($14,022.00)

  • HSR Dialysis Fund gets 50% ($9,650.00)

50/50 Drawing

Throughout the day and at every H.S.R. GIVEAWAY SHOW you can buy 50/50 tickets before the H.S.R. giveaway show starts. The matching number from your ticket stub is put into the pot. The money collected from the ticket sales is totaled and then divided in half. We draw a ticket for the winner during the first portion of every HSR Giveaway Show . The matching number drawn will receive half the money collected. The other half goes to Debbie's Dialysis Fund.
At our 2015 Western Caribbean Rally 5 winners spilt $29,952.00 in CASH and ($29,952.00) went to Debbie's Dialysis Fund. 



Debbie's Dialysis Fund Cash Raffle

BIGGEST CASH  $$$$$$$$$$$$$$$$$$$$$$$$$$$  payout and best odds of winning game on the cruise every year is the Debbie's Dialysis Fund CASH raffles.
Paying out as much as $80,000 CASH some years with a Custom bike as the Grand Prize.
This year with a FULL SHIP CHARTER for 2017 we expect the cash payout to reach $100,000.00!!! CASH and instead of an additional custom bike for the randomly drawn Grand Prize Winner of these raffles... how about $20,000.00 in their pocket. Gonna need some big pockets in this game.

Tattoo Contest


That’s right! We actually pay you if you have OUR H.S.R.or Debbie's Dialysis Fund LOGO in ink. Use any of our past or this year’s logo’s from our website Entertainment page. The judging will be done by actual voting in a ballot box. Each passenger has 1 Tattoo ballot in there welcome packet.
Each passenger that enters the Tattoo Contest must produce a 5 x 7 picture of THEIR HSR Tattoo. Bring your picture to us inside the Conference Room Vendor Area at the center of the photo dept. (Don't have a picture..get one taken here in the photo dept.)    After you fill out the tattoo form, present your HSR tattoo picture and show us your HSR tattoo, you will receive $50 for each 2017 HSR tattoo, $50 for each Debbie's Dialysis Tattoo and $20 for each past rally tattoo. 2017 Tattoo logos will be ready by late fall 2016.
Maximum $250 CASH pay out per person. Your best tattoo picture will be placed in the ships photo gallery to be voted on by our passengers. There will be no visable name on the picture in the gallery, only a number.
 Voted Best Rally Tattoo gets an additional $500.00 CASH . Winners announced Saturday at the Grand Prize Giveaway show.
In 2015 we handed out $3,150.00 in CASH for past and present HSR Tattoo's.

2015 TATTOO Winner: Manny Escamilla from Huntington Beach, California.
7 time HSR cruiser. "Top of the skull" HSR Tattoo. P.S. he has many more H.S.R. Tattoo's too.


Formal Night /Leather preferred but not required, Dress up Dinner

Don't get excited!! It's not that kind of formal.This is a trademark of our rallies. Our 2 formal nights for dining are LEATHER optional, not the usual suit and tie or formal gown. (Unless it's leather and we do have a few pretty snazzy outfits.) This is one fancy dining hall!  All our dining is of course regular biker attire, even the waiters. Most of our passengers will also wear ther pirate type dress up for dinner on our big Pirate party night too. Expect at least 1 party night on the ship and of course FREE drinks on Debbie again for the first hour.

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