Costa Rica · December 7–13, 2026
Costa Rica Pickleball Camp with Steve Kennedy
Six nights on a private estate in the Macacona hills. Four private courts, day and night. Train with a National Champion, eat everything a private chef puts in front of you, and go home with a game that holds up.
This camp is for: couples, friends and solo travelers, from people who have never held a paddle to 4.5+ players who want a real training block. Non-playing partners book the same way and spend the week on an estate with a chef.
Booked and run by Rally Retreats
Steve coaches this one alongside Rich Van't Hof. Rally Retreats owns the estate side of it, handles the applications and takes the payments, so that is where you reserve. Everything on this page comes from their trip page, and if the two ever disagree, theirs is right.
View the official trip page & apply →The Experience
Two coaches, twenty guests, four courts you never have to wait for.
Steve has run more than one hundred camps across Florida and the Caribbean, and this is the version he'd design if nobody put limits on it. The estate is private, so the courts are yours day and night. The group is capped at twenty, so nobody is standing in a line of eight waiting for a turn. And there are two coaches on site all week instead of one.
Real instruction, every day
Coaching and clinics are included from the first day to the last: skill blocks, drilling, and live-ball situations. Most points at every level are won and lost in the dink game, so that is where the week starts.
Grouped by level, honestly
Brand new through 4.5+, sorted into groups that actually match. Two coaches across twenty guests means the ratio holds up even when the levels spread wide.
The rest of it is a real trip
Every meal is cooked by a private chef. Daily yoga and fitness, a massage for each guest, guided excursions off the property, and a custom paddle to take home.
Day by Day
The rhythm of the week
Tap any day to open it. Steve and Rich set the exact times on site once they've seen the group and the weather, but the shape of the week is consistent, and hard training always lands while it's cool.
Monday Arrive and settle in
Fly into San Jose. A private car collects you and runs you the hour and fifteen minutes out to the estate. Nothing strenuous today: you get your room, you meet the group, you eat the first of many meals you did not have to cook. Level placement happens on court before the real training starts.
Tue–Sat Train, recover, explore
Court time. Coaching and clinics with Steve and Rich, in groups matched to your level. Skill blocks, drilling, and live-ball situations, with the hardest work scheduled for the cool part of the day. The courts are private and lit, so the optional evening play is genuinely optional and genuinely available.
Recovery. Daily yoga and fitness are on the schedule, not an upsell, and every guest gets a massage during the week. Six days of pickleball asks a lot of a body that normally plays twice a week.
Off the property. Excursions with transport and a guide are included. Costa Rica is not a backdrop you look at from a lounge chair, and there is time built in to actually go see it.
Every night. Dinner cooked by the private chef, eaten with twenty people who spent the day doing the same thing you did. This is the part people are still talking about a year later.
Sunday Last session and departure
A final session for anyone with a later flight, then private transfers back to San Jose. You leave with a clear idea of what to practice next, a custom paddle, professional photos and a highlight reel, and usually a few new regular partners.
Where You Stay
A private estate, not a resort
The retreat takes over a private estate in the Macacona hills, about an hour and fifteen minutes from San Jose airport. Four courts, a main house, a guest house, and a couple of rooms with better stories than the rest. There is concierge, housekeeping and 24-hour security, and there are no other guests, because for six nights the place is only yours.
Your rate depends on which room you take. Everything else about the week is identical no matter where you sleep.
| Room | Per person |
|---|---|
| Shared roomBunk beds. The best value in the house, and the fastest way to make friends. | $3,400 |
| Main House Queen or Guest HouseYour own room, in the middle of everything. | $4,500 |
| Main House KingMore space, king bed. | $4,900 |
| Treehouse or Tiny HouseSeparate structures on the property. These go first. | $5,300 |
A $500 per person deposit holds your spot. It is non-refundable and applied to the cost of the trip; the balance is due 60 days before arrival.
The Fine Print, Up Front
What's included
Included
- Six nights on the private estate
- Four private courts, day and night
- All coaching and clinics with Steve and Rich
- Every meal, cooked by a private chef
- Daily yoga and fitness
- One massage per guest
- Excursions with transport and a guide
- Airport transfers and private car transport
- Concierge, housekeeping and 24-hour security
- A custom paddle to take home
- Pro photos and a highlight reel
Not included
- Flights to and from San Jose (SJO)
- Travel insurance (buy it)
- Anything you break in a moment of dink-related frustration
Straight Talk
Things you should know before you book
It's a private estate up in the hills. That is the whole point, and it is also the trade-off: no lobby, no swim-up bar, no other guests. What you get instead is four courts nobody else can book and a chef who cooks for twenty people.
Between the flight and the hour-and-fifteen transfer from San Jose, plan on most of Monday in transit. Nothing is scheduled that day except getting there and eating.
Real coaching across six days is a workout, which is why yoga, fitness and a massage are built into the price rather than sold to you. You do not need to be advanced. You need to be ready to move.
December is early dry season, but showers happen. The hard training gets scheduled for the cool part of the day, and sessions shift within the day rather than getting cancelled.
The cap is twenty guests and the rooms are not interchangeable, so the treehouse and the shared bunks go at opposite ends of the list but they both go early. If these dates don't work, Rally Retreats runs a second retreat December 15–20 and is holding a January waitlist.
Your Coaches
Steve Kennedy and Rich Van't Hof
Steve played professional tennis, reaching the top 208 in the world and qualifying for the main draw of the 1987 US Open. After 26 years teaching at Fort Lauderdale's famed Jimmy Evert Tennis Center, he found pickleball, then won the 2017 USA Pickleball Nationals Senior Pro Championship, plus titles at the Tournament of Champions and the Texas Open.
He has led more than 100 camps across Florida and the Caribbean. His coaching philosophy: "Drill, drill, drill, and don't let your game become predictable."
He's joined all week by Rich Van't Hof, who runs these retreats as Captain Pickleball. Two coaches across twenty guests is the ratio that makes the level spread work: while one group is drilling, the other is not standing around waiting to be seen.
- 1987 US Open Main Draw
- 2017 National Senior Pro Champion
- 6× US Open Medalist
- USPTA Elite Professional
- 100+ Camps Led
Reserve Your Spot
How booking works
- Talk to Steve first if you want to. Text, email or call and he'll tell you straight whether this trip is right for your game. He answers all three himself.
- Fill out the application on the Rally Retreats trip page. It asks your level and which room you want, and someone calls you back within one business day.
- A $500 per person deposit holds your spot. It's non-refundable and comes off the trip cost. The balance is due 60 days before you arrive.
Twenty guests, four courts, two coaches. When the rooms are gone, the trip is full.
- Per person, all six nights, December 7–13, 2026
- Estate, every meal, all coaching, transfers and excursions in one price
- Flights are the only thing not included
- $500 deposit holds it · balance due 60 days out
Questions first? Text Steve at (954) 461-9946 · or call him
Questions first? Email Steve · call · or text (954) 461-9946
Questions