
Cruising can be a wonderful pickleball-friendly vacation choice: you get changing destinations plus daily opportunities to stay active on deck. Many mainstream and luxury cruise lines now feature courts and even organized play times.
✨ Holland America Line
⚓ Celebrity Cruises
🛳 MSC Cruises
🏝 Virgin Voyages
💎 Regent Seven Seas Cruises
🌴 Margaritaville at Sea
🏖 Pickleball-Focused Group Cruises
There are specialty group cruises organized around pickleball play and clinics — ideal if structured play, clinics, and meeting other enthusiasts are your priorities. These usually include scheduled sessions on board plus social events and excursions.
💡 Pro tip for retirees/active adults: Outdoor courts are fine on calm sea days, but indoor or sheltered courts (offered by some ships and group cruises) are a great choice to avoid wind, sun, or heat issues for longer rallies.

If staying grounded suits you better, there are several all-inclusive resorts with pickleball courts, clinics, and socials — perfect for active retirees who want daily play without planning logistics.
🌴 Beaches Resorts (Turks & Caicos & Jamaica)
☀️ Sandals Resorts (Caribbean Adults-Only)
🏝 The Verandah, Antigua
🏖 Elite Island Resorts (Caribbean)
Other Resorts With Pickleball
📌 Note: Some popular resorts like Margaritaville Island Reserve Cap Cana also offer pickleball programs, and many chains are expanding court offerings rapidly.
Whether you’re dreaming of sunrise rallies under palm trees or sea breezes while you dink at deck level, the growing world of pickleball travel has something for every active player — especially those who love doing it together.
Plan your next pickleball vacation with Legacy Travel Designs. Contact us at 240-242-7291 or sandy@legacytraveldesigns.com.
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