Pickleball Trips Reveals 2026 Schedule and Mexico, Caribbean Destinations

Pickleball Trips has rolled out a slate of 2026 departures that foreground Japan and Europe while maintaining a steady lineup of Mexico and Caribbean group getaways. The family-run operator, which includes pickleball Hall-of-Famer Scott Moore and his sons Jon, Daniel and Stephen, is pitching multi-day, multi-country itineraries that pair coaching, guided cultural excursions and group play.

Highlighted 2026 departures include Western Japan, April 7-16, 2026, and Interior Japan, April 16-25, 2026. A European excursion titled Alps to Adriatic is scheduled May 31-June 7, 2026. Other site-listed options for 2026 name Captivating Croatia in May, Dinking Dutch in April, and a Hokkaido Horizons program marked for September 2026 that is labeled "Private Only." Interior Japan also appears on the calendar for both April and September 2026.

The operator’s Japan programming is described as a mix of local play and cultural access: players will encounter cities including Osaka and Hiroshima, the ancient capital of Kyoto, the island of Miyajima and rural Okayama prefecture while honing skills with professional instructors. The Alps to Adriatic itinerary is promoted as combining professional coaching and friendly matches with local players alongside regional cuisine, wine and cultural visits in Slovenia and Italy’s Venice and Treviso.

Pickleball Trips continues active Mexico and Caribbean activity, listing several recent and upcoming group departures with named sponsors and resorts. Cancun departures include October 16-21, 2025 with Paddle Up Pickleball Club and October 23-28, 2025 with John Kleinschmidt and the JDK Team, both at Planet Hollywood Adult Scene. Earlier listings include a September 20-24, 2024 Cancun trip at SECRETS Playa Blanca Costa and a Riviera Maya October 15-20, 2024 departure at Grand Palladium Colonial sponsored by Stillwater Indoor Pickleball Club. Caribbean entries include Willikies, Antigua, January 23-28, 2025 with Paddle Up Pickleball Club at Pineapple Beach Club, and Grace Bay, Turks & Caicos, April 23-30, 2025 with Dink Away Travels at Club Med - Turkoise.

The Pickleball Trips website emphasizes the social payoff of its travel model, saying, "These are truly one-of-a-kind trips that leave lasting memories and create deep friendships." Its tagline reads, "Specializing in Pickleball Group Vacations to Mexico and the Caribbean." Contact information on the site lists a St. Louis office and phone number: St. Louis, MO, 314.441.6689. The site also displays copyright notices that include "©2016-2023 Pickleball Trips LLC" and "© 2023 by RPAS Travel, LLC."

For club organizers, group leaders and experienced players, the schedule provides concrete options to book coaching-forward play with built-in social programming and local matches. Verify trip capacities, coach rosters and pricing directly with Pickleball Trips before committing, and note that some departures are marked private only. As the season approaches, expect more detailed itineraries and booking windows to appear for the Japan and Europe departures while Mexico and Caribbean group weeks remain a consistent option for winter and shoulder-season travel.