Barbados Jazz Excursion 2026
Barbados Jazz Vacation Packages + Celebrity Golf Weekend October 8–12, 2026
Reserve with 25% deposit – Starting at $436.52
Payment plan available
Secure booking via official travel partner (Island Escapes)
The Caribbean’s hottest weekend getaway is back!
October 8-12, 2026
Columbus Day/Indigenous Peoples Day Weekend
A Message From Your Host, Elan Trotman
Thank you all for considering a trip to beautiful Barbados. While Boston has become my home away from home, Barbados will always hold a special place in my heart. What began in 2015 as a small gathering of friends and family has grown into a renowned music festival that now welcomes hundreds of visitors to the island each year.
Over the years, we’ve had the privilege of hosting some of the world’s top musical talents, including Norman Brown, Peter White, Mike Phillips, Maysa, Najee, Avery Sunshine, Jeffrey Osborne, Jeff Lorber, Peabo Bryson, and Regina Belle, among many others. Our event has also attracted an impressive lineup of golf celebrities such as Joe Carter, Bronson Arroyo, Chris Spencer, Flex Alexander, Troy Mullins, Maurice Allen, Bernie Williams, Joel Anthony, and John Starks.
Beyond enjoying an unforgettable weekend in paradise, your participation helps support a cause that is deeply meaningful to me—the Never Lose Your Drive Foundation. Our nonprofit provides free music instruction and instruments to young people in Barbados, Massachusetts, and Rhode Island throughout the school year, empowering the next generation through access, opportunity, and creativity.
We know you have countless choices when it comes to vacation destinations, but Barbados truly stands among the world’s best. Our rich heritage of rum, cuisine, beaches, and culture offers an experience unlike any other.
Our dedicated team is here to assist with all your travel needs, and we can’t wait to welcome you to Barbados for a weekend filled with friends, fun, food, rum, golf, music, cigars, comedy, and sunshine.
Sincerely,
Elan Trotman
Executive Producer
Our Official Host Resort
Wyndham Grand Barbados
Sam Lord’s Castle Resort
The Resort
- Beachfront Bliss in Barbados. All-inclusive luxury resort next to the iconic Sam Lord’s Castle. Whether you’re planning a family, friends, or couple’s getaway, escape to the southeastern coast of Barbados for a stunning stay in breathtaking St. Phillip at Wyndham Grand Barbados Sam Lords Castle All-Inclusive Resort. Perched on a cliff overlooking the Caribbean Sea, this gorgeous resort is steps from a beautiful beach and next to a majestic 19th century castle with a fascinating history.
Our 422 oversized guest rooms and suites boast scenic views, expansive balconies that seamlessly blend indoor/outdoor living, 24/7 room service, and must-haves like free high-speed WiFi, stocked minibars, and flat-screen HDTVs.
Request a Staycation Package
Proof of Barbados Residency or Caricom Membership is required at time of booking.