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Win a Luxurious $10,000 Value Anguilla Vacation
& Support A Worthwhile Cause!

Update: The fundraiser was a huge success and Hilroy and his team are Atlanta-bound to participate in Tough Mudder! Thank YOU for all of your support and congratulations to Michael / Ticket #67 on winning the luxurious grand prize! In case you missed the broadcast of the raffle drawing, click here to see it.

Anguilla is getting fit! Yes, there has been a huge health movement and surge in personal fitness over the past few years in Anguilla.

Hilroy Alfred with One of His Most Dedicated
Clients, Gilda Samuel, President of the AHTA
hilroy alfred and client gilda

Gym trainers and gym owners are fighting more common on-island diseases, such as diabetes, and unhealthy habits through education and enhanced gym offerings.

One of the men leading Anguilla into a healthier future is Hilroy Alfred, owner of his own personal training business, Ruff Training Sessions and member of Anguilla's leading gym, Dungeon Gym owned by Haydn Hughes.

At the young age of 23 years old, Hilroy's strong work ethic and dedication has transformed people's lives in Anguilla.

With a long list of resident and visiting clients, Hilroy is well-established in the fitness scene in Anguilla and is taking his work a step further...

His team will be the first to represent the Caribbean at the internationally recognized fitness challenge, Tough Mudder in Atlanta, Georgia this May.

To raise the funds to get his team to Atlanta, he has put together a tremendous vacation package that will be raffled off on April 29th, 2016.

What's the prize?...

The Luxurious $10,000 Value Grand Prize

With the help of friends and families who own and manage five-star properties in Anguilla, Hilroy's grand prize is luxurious and all-inclusive.

A 6 night stay at the luxurious Viceroy resort, a meal for each day of your stay, car rental, transport to and from SXM and a host of activities (sunset cruise, tubing, massages, private fitness training)... the value exceeds $10,000 USD!

If you win, all you have to do is get to Anguilla :-)

ruff training fundraiser package


6 Nights at Viceroy in a One Bedroom Suite

viceroy suite in the ruff training prize package

The Ocean View One Bedroom Suites feature 976 square feet and includes a living room with a kitchenette, spacious bathroom and a custom-designed four-poster king bed. The luxurious marble bathroom includes double sinks, a deep soaking tub and an oversized walk-in shower. Enjoy the outdoor balcony’s ocean view and private plunge pool from the chaise lounges for two.


Dinner for 2 at The Restaurant at Malliouhana

the dining room at the restaurant at malliouhana

Dinner for 2 at Dolce Vita

dolce vita anguilla

Dinner for 2 at Meze

meze lounge

Dinner for 2 at Firefly at Anacaona Boutique Hotel

firefly at anacaona

Lunch for 2 at Tasty's

tastys famous tuna salad

Lunch for 2 at Sandy Island

sandy island

6 Day Car Rental at A&D

Round Trip Boat Charter to/from SXM Aboard Calypso Charters

SeaPro Water Sports Package

  • Sunset Cruise
  • Tubing

Two 1 Hour Relaxation Massages

Two Private Beach Training Sessions

Blackout Dates: Dec. 15, 2016 - Mar. 31, 2017

Prize & Drawing Details

Raffle Ticket Price: $100 USD

Deadline to Enter: April 28th, 2016

Winner Announced: April 29th, 2016

Hilroy is selling a total of 200 tickets at $100 per ticket.

The winning ticket will be drawn on Apr. 29th on Radio Anguilla. We, Anguilla-Beaches.com, will also be attending the drawing and will be broadcasting live via YouTube. All who purchase tickets will be sent an e-vite to attend the broadcast.

Background Information & The Cause

Hilroy Alfred
hilroy alfred of ruff training sessions

Evidence of extreme determination, I was blown away by the prize Hilroy put together.

"I started body building in 2010," Hilroy explained when we chatted.

"It's not about Instagram pictures or anything like that, though," he smiled.

"For me, it's about motivating and leading, and above all, inspiring others and showing them that they can become what they believe."

"They have to want to change, of course, they have to be willing to put in that time. Every step of the way, though, I am there to help them adopt a healthier and more rewarding lifestyle," he continued.

His company, Ruff Training Sessions provides a whole host of fitness training, from helping you develop a work out routine, to creating diet menus, to building strength or working on enhancing your cardio.

A certified fitness trainer, massage therapist, winner of Dungeon's Gym Personal Trainer of the Year award and a father, too, there is no one more dedicated and passionate than Hilroy.

Words From Hilroy's Clients

Macarius Thomas
macarius thomas of ruff training

"I first started working out after I realized that I lost control of my weight. For a guy who is 5'9" there was no reason for me to be weighing over 200 lbs with no muscle, so I quickly decided to join Dungeon Gym and work with Hilroy Alfred to keep me motivated.

Working out keeps me goal orientated and keeps me focused, all of which helps me with other things in life. When you see yourself achieving goals after hard work it makes you feel good!"
- Macarius Thomas

Gilda Samuel
gilda of ruff training

"Struggling with weight loss has been an unsolved mystery in my life for many years. My weight has not only been a physical problem but was also becoming a health issue. My journey was definitely not, and continues to not be a walk in the park.

From my first session with Hilroy Alfred, to this day I am still in disbelief that I have accomplished so much. From struggling with following his meal plan to days of going to his classes and swearing I wasn't going back - it was all worth it.

After being so heavily motivated and supported by Hilroy it became easier and easier. Although I still have a long way to go I am proud to say I have gone from a size 18 to a size 14, from an XL to a L/M, from not being able to do 2 sets to doing a full circuit work out all in the matter of two and a half months. By changing my eating habits, dedicating myself to work out sessions and having the support of my trainer and family, my weight loss campaign has had a very success beginning.

Thank you Hilroy Alfred for the marvelous jump start."
-Tynasia Rogers

client photo

"I trained with Hilroy for 10 months and I have never felt healthier, stronger or happier with my life. I have seen amazing results during that time period.

Hilroy is definitely a dedicated fitness trainer that is passionate about what he does. He brings a lot of energy to every workout session. Training with him has challenged me and motivated me to push way beyond the limits that I thought I had.

I can now say that I have way more energy than before, and great improvement in my balance and flexibility.  Though my aim was generally to improve my overall health, the weight that I lost while working out with Hilroy was definitely a great incentive to keep going."
-Caliyn Harrigan

client photo

"On July 10th 2015 I did a site inspection with two folks. As part of the site inspection I had to show them a room, which happened to be on third floor. As we passed the first set of stairs I started to feel out of breath, and by the time we got to the third floor I was completely out of breath. Luckily they started to take pictures, which gave me a couple of minutes to catch my breath. At that moment I realized I needed to do something.

One afternoon in September while browsing through Facebook I came across a video of a lady in her sixties pushing weights. At first I felt ashamed of myself, as I knew that in my current shape I would never be able to do something like that, but definitely wanted to try.

I discussed getting a trainer with my friends, but shortly after I started making excuses for myself, something I had already become good at. I decided to private message Hilroy Alfred for further information. It was one of the best messages I've ever sent.

After a few workouts I knew I was ready to commit. Workouts with my trainer are never boring, and there are always new and exciting exercises. It’s been a couple of months and I am in better shape than I have ever been. I have lost weight, gained muscle (although my friends can’t see them yet, I know they are there), and increased my endurance.

There are days which are tougher than others, and at times I want to quit, however I can always rely on Hilroy to keep me motivated. Although he calls me Lazy at least 20 times per session, it has definitely become one of my favorite words because it motivates me."

client photo

Tough Mudder

And now, it all comes down to this... competing in Tough Mudder.

Tough Mudder in Atlanta
tough mudder

What is Tough Mudder?

Tough Mudder is a series of hardcore 10-12 mile obstacle race / mud run events designed by British Special Forces to challenge the toughest of the tough. It is designed to test physical strength and mental grit. Tough Mudder puts camaraderie over finisher rankings. It is not a race but a team challenge. This is for anyone who has ever followed their gut, tried to defy gravity, chosen “dare” over “truth,” taken risks, sought thrills, or is generally awesome at life.

Tough Mudder's events have been featured in the likes of USA Today, Huffington Post and Sports Illustrated. It is revered for its team building capacity amidst challenging conditions and is a favorite for large, corporate groups.

Hilroy Alfred and the Ruff Training Sessions crew (total of 15 team members) will be the first team ever to represent the Caribbean!

Ruff Training Sessions Crew
ruff training team

Hilroy says...

"This team is both physically and mentally prepared to take on any task at hand. They aren't your "Instagram Icons" and you won't see them when you're flipping through body building magazines. These are 15 normal people who embarked on a fitness journey and are now ready to take on Tough Mudder! Our goal is to inspire the community - to let them know that you can turn your dreams into a reality!" 

All proceeds raised go to travel expenses to participate at Tough Mudder, which is taking place on May 8th. Stay tuned to this webpage for updates from Ruff Training as they make their way through Tough Mudder :-)

Until then...

Enter to Win!

The period to purchase tickets has closed.

To win the luxurious $10,000 value prize and support this worthwhile community fundraiser, purchase a ticket below by clicking the PayPal ("Pay Now") button below.

Good luck :-)

*NOTE: The merchant name that will appear on your account is: *ANGUILLA. Once we receive your donation, you will receive a confirming email from Anguilla-Beaches.com within 12 hours. Hilroy will also send you an email shortly after, documenting your ticket purchase. We will send you an e-vite to the big draw on the week of Apr. 29!

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