Sunset Sports Tours

Travel far.

Play hard.

Live well.

We are

Have a passion for sports and travel? At Sunset Sports Tours, we combine the two and offer sports enthusiasts the opportunity to pursue their favorite sport in some of the best resort destinations throughout North America and the Caribbean.

Sports Adventure Travel

Get ready to experience the thrill of a lifetime with Sunset Sports Tours, where your passion for sports meets personalized adventure travel!

Whether you’re aiming to perfect your pickleball or padel serve, conquer open water swimming, or master the art of triathlon, golf, marathon running, rugby, or roller and ice hockey, our expertly crafted trips are certain to satisfy your sports cravings and deliver a perfect balance of leisure and adventure travel.

Elevate your game

With optional elite coaching components, you’ll receive unparalleled guidance from seasoned professionals who are dedicated to helping you unlock your full potential.

These bespoke travel experiences not only enhance your sports skills but also foster camaraderie and unforgettable memories with fellow sports and travel enthusiasts.

Don’t miss out on the chance to transform your athletic journey—join us and embrace the excitement of tailored sports training and adventure travel like never before!

Plan the perfect trip

Why choose Sunset Sports Tours?

Our travel specialists can build the perfect trip for you, whether you’re part of a group or traveling solo.

Customized Trips

Our elite instructors are ready to coach you to new heights while sharing their passion for sports in breathtaking destinations.

Tailored Options

Whether you're planning a team experience, a group getaway, or a solo escapade, we tailor every itinerary to fit your playbook!

Passionate Experts

Our team combines a love for sports with extensive travel experience to create unforgettable travel experiences.

Join One of Our Trips

Mingle with fellow sports enthusiasts who share your zest for adventure and love for the game.

Seamless, Hassle-Free Travel

With our team on the ground and every detail handled—from airport transfers to VIP access—you can fully enjoy your sport and the destination.

Travel Specialists in North America and the Caribbean

Explore stunning destinations paired with local music and food events.

Elevate your game

Our Sports

Trips for individual players or teams at every level, from beginner to advanced

At Sunset Sports Tours, we offer a range of the most popular sports adventure travel packages for individuals and groups. Dive into open water swimming, run in some of the world’s best marathons, enter your team in a rugby, roller, or ice hockey tournament, pack your racket or clubs and play pickleball or padel, or hit the links at some of the best vacation destinations.

We select marquee sports facilities along with the most well-regarded coaches to create memorable vacations that elevate your game. Our trips are available for individual players at every level from beginner to advanced and can be customized to meet the unique needs of your club or team.

Our inclusive sports travel packages feature accommodations, airport transfers, planned sporting activities and personalized coaching from the best instructors and coaches in your chosen sport. Many of our trips also include all-inclusive meal and drink plans and unique local sightseeing excursions.

Team Players

Meet Our Team

The Sunset Sports Tours team…

Tom Ludington

Founder, Chief Experience Officer

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With over 30 years of experience in the leisure travel industry, Tom Ludington has perfected the art of crafting sports-focused travel experiences.

His deep passion for both sports and travel led him to create Sunset Sports Tours, where he combines his expertise with extensive relationships across North America, including the Caribbean, US, and Canada.

Tom has worked closely with hoteliers, ground service providers, and excursion companies to ensure every trip is seamless and tailored to each group’s specific needs.

Before founding Sunset Sports Tours, Tom served as the US General Manager for the Cayman Islands Department of Tourism, where he gained invaluable skills in destination management and event planning.

His hands-on approach guarantees that every sports travel experience is well-organized, enjoyable, and memorable.

Choosing Sunset Sports Tours means choosing a company led by a seasoned professional who’s dedicated to delivering the ultimate in sports adventure travel experiences.

Phillip Hayman

Professional Pickleball Instructor

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Phillip Hayman, based in Boston, MA, is a professional pickleball coach, clinician, and instructor with extensive experience developing both recreational and competitive players.

As a PTR and USPTA tennis professional, Phillip brings a wealth of knowledge from various court sports, understanding how athletic disciplines crossover to benefit pickleball.

Whether you’re a casual player seeking socially engaging play or an ambitious competitor aiming to ignite your competitive spirit, Phillip’s expert teaching acumen ensures you reach your full potential.

Certified by PPR, IPTPA, and IFP, Phillip is also a PPR Coach Developer who has spoken at international conferences in Hilton Head, SC, and Rancho Mirage, CA.

He has traveled extensively, certifying future pickleball instructors. Currently, Phillip runs the Hayman Pickleball Performance Academy (HPPA) at Thayer Sports Center, an ESG facility in Braintree, MA.

Join Phillip for a unique opportunity to elevate your pickleball game while enjoying luxurious travel to top Caribbean destinations.

John Schiavo

Professional Hockey Player & Coach

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John Schiavo, from Long Island, NY, began skating at age 3 and has since built a remarkable career in both roller and ice hockey.

Turning professional at 15, he later earned invitations to the New York Islanders Rookie Camps in 2015 and 2016, marking the start of his pro ice hockey journey.

John has also represented Team USA, winning gold at the 2017 IIHF Roller Hockey World Championships and the 2019 World Roller Games in Barcelona.

Now entering his 8th pro ice hockey season, with 13 seasons of professional roller hockey behind him, John is one of the few athletes to excel in both sports.

As a coach with Sunset Sports Tours, he will lead camps and tournaments for adults and youth across destinations such as Grand Cayman, Turks & Caicos, the US, and Canada.

Starting in 2025, John will bring his camps worldwide, inspiring the next generation of players through his passion and expertise.

Rob Cassidy

Professional Pickleball Player, Commentator and Instructor

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As a leading pickleball professional, Rob Cassidy specializes in focusing on developing one’s personal game while maintaining a strong emphasis on the fundamentals.

With 4 years of teaching experience, Rob is known to transform a player’s game at any level. He has coached in over 30 states and 3 countries with LevelUp Camps, Engage Pickleball Camps, Boost Camps and Pickleball Getaways.

Rob has been competing professionally since 2013. He has won several titles and has medaled at the following pro level events: International Indoor Championships, New York State Championships, Hawaiian Open, The Toronto Cup Championships and US Open.

Rob also holds a bachelor’s degree in psychology and comes from a diverse sports background which includes ultimate frisbee, volleyball and ping pong.

With over seven years of Pickleball experience, Rob Cassidy brings a positive and insightful perspective to all players.

“I enjoy giving back to the game and teaching is a great way for me to do that.”

Aidan Ludington

Marketing & Event Coordinator

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Aidan Ludington is an Event Manager known for his commitment to creating memorable experiences for clients. A graduate of SUNY Oswego, he played on the D1 Club Ice Hockey team, which fueled his passion for sports. An avid golfer and roller hockey player, Aidan brings his enthusiasm for athletics into his work.

With a strong background in destination marketing, customer service and property management, he assists with digital marketing and collaborates closely with coaches, the entertainment team, local transportation providers, sports venues, event managers, and resorts both before trips and on-site. This comprehensive approach ensures that every detail is handled, allowing for seamless and unforgettable trips for all participants.

James Geary

Director of Entertainment

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James Geary, based in Grand Cayman, is the Director of Entertainment at Sunset Sports Tours and a prominent figure in the Cayman Islands entertainment industry.

Known for his warm and friendly personality, James brings a personal touch to every event, ensuring each group feels welcomed and engaged.

His dynamic approach to curating entertainment experiences, whether performing himself or sourcing the perfect talent, guarantees that the unique needs of every group are met with care and precision.

With an extensive network of entertainers across the US, UK, and Caribbean, James is able to deliver unforgettable musical experiences that resonate with diverse audiences.

His expertise in creating memorable events, combined with his deep industry connections, makes him a key asset to Sunset Sports Tours, bringing excitement and energy to every destination.

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