Pickleball vacations have become a legitimate travel category, with dedicated resorts, cruise partnerships, and over 68,000 courts across the United States making it possible to play anywhere your trip takes you. According to the Sports & Fitness Industry Association, 19.8 million Americans played pickleball in 2024 - a 311% increase over three years - and that growth has created serious options for traveling players. Whether you're booking a resort with on-site courts, renting an Airbnb with a private setup, or downloading apps to find local players in a city you've never visited, planning a trip around the sport has never been easier or more rewarding.
What Do You Call Your "Guys Trips"?
- Resorts, cruise lines, and vacation rentals now compete for pickleball players with dedicated courts and programming
- Apps like Pickleheads and PicklePlay connect travelers with local games, open play sessions, and courts in any destination
- National gym memberships at Life Time and YMCA locations provide court access across the country
- Holland America Line's exclusive PPA partnership puts professional-grade courts on every ship in their fleet
- Entertainment venues like Chicken N Pickle combine food, drinks, and court time - perfect for bachelor parties and guys weekends
- Finding Accommodations with Pickleball Courts
- Holland America Line - Pickleball at Sea
- Apps That Connect You with Local Players
- National Gym Memberships That Travel with You
- Entertainment Venues Built Around the Sport
- Bringing Your Own Gear vs. Relying on Rentals
- Planning a Pickleball-Focused Trip Step by Step
- Why Pickleball Trips Work Better Than You'd Expect
The scenario plays out more often than you'd expect: four guys land in Phoenix for a long weekend, check into the hotel, and immediately ask each other the same question. "Anyone know where we can play?" Ten years ago, that conversation ended with Google searches and phone calls to recreation centers. Today, it takes about ninety seconds to find a game, reserve a court, or locate a facility that combines pickleball with craft beer and wood-fired chicken. The options have caught up to the demand, and that changes how you plan trips when the group includes players who want court time worked into the itinerary.
Finding Accommodations with Pickleball Courts
Hotels and resorts have recognized that pickleball amenities attract a specific - and growing - segment of travelers willing to pay premium rates for court access. The options range from luxury resorts with professional instruction to budget-friendly properties that converted a tennis court and called it done. Knowing what to look for separates a frustrating experience from one where you play every morning before the group even thinks about breakfast.
Luxury Resorts with Dedicated Courts
High-end properties have invested heavily in pickleball programming, often hiring certified instructors and hosting mixers that match guests by skill level. Four Seasons Punta Mita in Mexico expanded to eight dedicated courts with mixers on Tuesdays, Thursdays, and Saturdays. Mauna Kea Resort in Hawaii offers eight courts along with clinics and private lessons. The Coronado Island Marriott Resort & Spa near San Diego, California features 12 resurfaced courts with both reservations and daily open play - accessible even to non-guests.
The Broadmoor in Colorado Springs, Colorado added three courts and four certified instructors to complement its existing activities - a strong option for Colorado guys trips combining mountain scenery with court time. Rancho La Puerta in Tecate, Mexico schedules multiple "Pickleball Specialty Weeks" each year with top instructors, blending the sport with yoga, hiking, and spa treatments. These properties understand that serious players will book based on court quality and programming depth.
All-Inclusive Options in the Caribbean
Sandals Resorts became the first Official All-Inclusive Resort partner of USA Pickleball, with 64 courts across their Caribbean properties. The partnership includes USA Pickleball-approved equipment, complimentary group sessions, and coaches who can match solo players with partners. Beaches Resorts offers similar programming with 11 courts across Jamaica and Turks & Caicos locations.
According to Pickleball in Paradise, a travel company specializing in the sport, all-inclusive properties eliminate the nickel-and-diming that can plague court-focused vacations. Court time, equipment, and instruction come bundled with your room rate. For group getaways or Texas guys trips where the crew wants to play without managing a budget spreadsheet, the simplicity has real value.
Airbnb and Vacation Rentals with Private Courts
The vacation rental market now lists hundreds of properties with on-site pickleball courts, ranging from $245 per night for a four-bedroom Indiana house to $1,100 nightly for a Scottsdale, Arizona villa with two courts and a pool. The Dink Pickleball maintains a curated list of properties across the country, with standouts including a six-bedroom upstate New York home with a private court and hot tub, and a Joshua Tree villa where you play against a Mojave Desert sunset backdrop.
Private courts solve the coordination problem that plagues group trips. You don't need to book times, wait for availability, or share space with strangers. The group plays when it wants, for as long as it wants. A five-bedroom California property with a private court, basketball setup, pool, and spa can host what amounts to a mini athletic retreat for ten guys - and the per-person cost often undercuts comparable resort rooms.
Holland America Line - Pickleball at Sea
Holland America Line holds the exclusive cruise line partnership with the Professional Pickleball Association, and they've built an experience around it. Every ship in their fleet features top-deck courts with ocean views, complimentary beginner lessons from trained instructors, and tournaments that let competitive players scratch the itch while sailing to Alaska or the Caribbean.
The connection runs deeper than marketing. Pickleball was invented in 1965 on Bainbridge Island, Washington - a short ferry ride from Seattle where Holland America is headquartered. "To play pickleball is to make new friends, from around the neighborhood or around the world," said Theresa Haynie, a founding board member of Seattle Metro Pickleball Association. "This ageless sport welcomes players young and old, fast or slow."
The cruise line recently added four courts to Relax Away at Half Moon Cay, their private island in the Bahamas. Guests on Rotterdam and Eurodam christened the courts with a friendly tournament in December 2024. For players who want to combine Caribbean guys trips with daily court time, the setup delivers without requiring separate excursion bookings or equipment rentals.
Beyond the courts themselves, Holland America offers in-stateroom "How to Play Pickleball" tutorial videos and sells branded starter kits in shipboard retail shops. The approach targets both existing players and curious beginners who might pick up a paddle for the first time between port calls. According to Kacy Cole, vice president of marketing for Holland America Line, "Pickleball is the most popular sport on our ships. It's wonderful to see guests bond over their shared love of the game."
Apps That Connect You with Local Players
The real challenge for traveling pickleball players isn't finding courts - it's finding games. Open play schedules vary by location, skill levels don't always match, and showing up at a public court without knowing the local culture can mean standing around while regulars run games. A handful of apps have solved this problem by mapping courts, posting open play times, and letting players coordinate games with strangers.
Pickleheads
Pickleheads operates the most extensive court database, with over 23,000 locations indexed globally and detailed information about open play schedules, skill-level games, and local groups. The app shows active pins for games happening today, lets users browse future dates, and handles sign-ups and payments for organized sessions. For work colleagues traveling to a conference who want to find a morning game, the search function filters by skill level and time - no awkward conversations about whether you can keep up.
PicklePlay
PicklePlay positions itself as the "#1 pickleball community app," with court finding, event organization, and in-app messaging to coordinate games. The platform works well for club management and league play, but travelers benefit from its event discovery features. Filter by skill level, find courts near your hotel, and join games without needing to know anyone in town. The app is free with optional premium features.
PlayTime Scheduler
PlayTime Scheduler focuses specifically on session scheduling rather than court discovery. Local players and groups post real sessions - not outdated listings - with skill levels attached. The app sends alerts for new games, session changes, and player messages. For hanging with buddies who want to find intermediate-level games without wading through beginner sessions, the filtering tools save time and awkward conversations.
National Gym Memberships That Travel with You
If you're already a member of a national fitness chain, you may have pickleball access in cities across the country without booking separate court time or paying drop-in fees. Several networks offer courts for traveling players:
- Life Time Fitness: Nearly 700 courts nationwide, complimentary reservations with Signature Membership, open play and mixers at most locations, 70 instructional videos from Ben Johns
- YMCA: Court availability varies by branch, but reciprocal access means your home membership works at locations nationwide - YMCA of Greater Brandywine (PA) alone operates 50+ courts
- LA Fitness: Select locations feature dedicated pickleball courts, including a six-court setup in San Antonio - call ahead to confirm availability
- EoS Fitness: Growing pickleball presence at locations in Arizona, Texas, and other markets with courts included in membership
- In-Shape Fitness: California's largest pickleball-focused gym chain with indoor and outdoor courts, tournaments, and clinics across Northern California
For Nevada guys trips or cross-country travel, check whether your existing membership includes court access before booking elsewhere. The convenience of walking into a familiar gym chain and finding a game beats searching for public courts in an unfamiliar city.
Entertainment Venues Built Around the Sport
A new category of entertainment complex combines pickleball courts with restaurants, bars, and social activities - perfect for bachelor parties or guys weekend gatherings where the group wants competition, food, and drinks in one location. These venues welcome drop-in players alongside league regulars.
- Chicken N Pickle: The pioneer of the format with locations in Kansas City, Wichita, San Antonio, Glendale (AZ), Allen (TX), Grand Prairie (TX), and Denver - indoor/outdoor courts, rotisserie chicken, craft beer, yard games, and tournament hosting
- Toledo Pickle Company: Opened January 2025 on Toledo, Ohio's riverfront in the Vistula Historic District - 10 indoor and 2 outdoor courts, Stay Out of the Kitchen Grill restaurant, rock climbing wall, shuffleboard, cornhole, and arcade
- Pickleball Kingdom: Franchise concept with 15 indoor courts per location, dink courts, pro shops, and Pickleball 101 courses - expanding across Texas and other markets
- The Picklr: Indoor franchise backed by Drew Brees with 30 Midwest locations planned, focused on year-round play regardless of weather
The format aligns with guys getaway ideas that go beyond a golf trip - activity-focused without requiring a full day's commitment, and the game ends twenty feet from a cold beer.
Bringing Your Own Gear vs. Relying on Rentals
Resort paddle bins exist, but the experience rarely matches what you'd get with your own equipment. Grips wear down, edges show damage, and the mystery paddle you grab might weigh differently than anything you've played with before. Consistency matters when you're competing, even casually.
Honolulu Pickleball paddles fit naturally into a travel kit - they pack easily, perform consistently, and won't require adjustment time when you step onto unfamiliar courts. Todd Skezas, CEO of Pickleball Nation, frames it simply: "Pickleball works because it meets players where they are. You don't have to train for months to enjoy it, and you don't outgrow it once you get better."
For gear standards and verification that what you're buying meets competition requirements, USA Pickleball's equipment standards provide a clear baseline. You don't need to memorize the specifications - just check that any paddle you purchase carries approval. It matters less for casual vacation play than for tournaments, but knowing your equipment meets official standards removes one variable from the equation.
Planning a Pickleball-Focused Trip Step by Step
The approach depends on whether pickleball serves as the trip's centerpiece or one activity among several. For dedicated pickleball vacations, accommodation choice drives everything else. For trips where the sport complements other plans, apps and local research fill in the gaps.
Pickleball as the Main Event
Start with accommodations that guarantee court access and quality. Resorts with dedicated programming, vacation rentals with private courts, or cruise lines with onboard facilities eliminate the uncertainty that comes with relying on public options. Book during shoulder season when courts are less crowded but the weather remains playable. Research any clinics or mixers that require advance registration - popular sessions fill quickly.
For Florida guys trips or similar warm-weather destinations, consider combining a pickleball-focused resort stay with a day at Chicken N Pickle or similar venue for variety. The programming at dedicated facilities improves your game; entertainment venues provide atmosphere and social energy that pure competition lacks.
Pickleball as One Activity Among Many
Download Pickleheads or PicklePlay before departure and search courts near your hotel or planned activities. Look for open play sessions that match your skill level and fit your schedule - morning games before the group's agenda begins work well. If you're a Life Time or YMCA member, check whether branches near your destination offer courts.
Pack your paddle in a TSA-friendly bag (paddles travel fine in carry-on luggage) and bring balls if you're heading somewhere with limited equipment availability. Outdoor balls work better in warm, calm conditions; indoor balls handle wind and cold better if your destination includes variable weather.
Why Pickleball Trips Work Better Than You'd Expect
Pickleball vacations succeed because the sport scales to the moment. A few morning games set the tone without consuming the day. Competition stays sharp enough to feel satisfying while leaving energy for whatever comes next. The network now exists to play almost anywhere - on ship decks with glacier views, at desert resorts where the courts look out over cactus landscapes, in entertainment complexes where the game ends and the beer begins within twenty feet of the baseline.
For anyone planning their next trip, consider that pickleball travel has one advantage few other sports offer: strangers become teammates within minutes. Show up at an open play session in a city you've never visited, and by the third game you'll have local restaurant recommendations, a group text chain for tomorrow's games, and maybe an invite to someone's backyard court. That kind of connection happens faster in pickleball than almost any other sport - and it gives every trip a social dimension that hotel gyms and solo runs can't match. The average player age has dropped to 34.8 years old, according to SFIA data, which means the courts are filling with guys in your demographic who travel, play, and want to meet new competition wherever they land.
