Train with The King and Captain Pickleball.
Steve Kennedy and Rich Van't Hof host six nights on a private estate above Costa Rica's Pacific coast, with fourteen hours of on-court instruction they coach personally. Chef, excursions, transfers, unlimited court time. One price, all inclusive.
private courts on property
guests, nobody else
hours of on-court instruction
coach to guest ratio, maximum
Hosted and coached by Steve and Rich.
This retreat is theirs. Steve Kennedy and Rich Van't Hof built the week, and they are on court for every coached session.
Steve Kennedy
The King
- Former ATP tour tennis professional, top 200 in the world
- Former number 1 senior pro pickleball player in the world
- Senior pro gold medalist at the USA Pickleball Nationals, the US Open, and the Tournament of Champions
- IFPA certified pro instructor and master evaluator
- 38 years of coaching across tennis and pickleball
Rich Van't Hof
Captain Pickleball
- Retired US Navy captain, aviator and instructor pilot
- Retired Delta Air Lines captain and senior instructor pilot
- US Open Pickleball Championship gold medalist
- IFPA certified pro instructor and master evaluator
- More than 45 years of teaching, in the air and on the court
At least one coach is on court for every six guests in every coached session, so the instruction stays personal from your first drill to your last match.
Fourteen hours of their attention.
Not a guest appearance and not a photo opportunity. Steve and Rich run every clinic and every round robin, and they play with you between sessions. A private lesson with either of them is normally an hour at a time. This is fourteen.
Most camps put twenty people on a court and call it a clinic. Here you are grouped by level on arrival, and the pro in front of you has five other players to think about. Eighty years of teaching, four private courts, and an estate that is entirely yours.
Four acres. Four buildings. One gate.
A private, gated hilltop estate in the Macacona hills. One hour fifteen from San Jose airport, thirty minutes from Pacific beaches. Your group is the only group on the property.
Ten bedrooms across the main house, the guest house, a treehouse with its own jacuzzi, and a private standalone villa. The estate sleeps more, but we cap every trip at twenty guests to keep it intimate.
Fourteen hours on court with Steve and Rich.
Mornings are coached. Afternoons are yours: excursions, the pool, open courts, and Play with the Pros sessions through the week.
Monday, December 7
Arrive, settle in, and meet Steve, Rich and the group. Courts are open from the moment you get there.
Tuesday, December 8
8:00 to 11:30 AM. On-court instruction.
Wednesday, December 9
Open play morning, and the rain-out make-up day if we need one.
Thursday, December 10
8:00 to 11:30 AM. On-court instruction.
Friday, December 11
8:00 to 11:30 AM. On-court instruction.
Saturday, December 12
8:00 to 9:30 AM instruction, then a group round robin until 11:30. The Survivor's Party, poolside, closes the week.
Play with the Pros sessions run through the week and are included. Sunday, December 13 is departure day.
Nineteen things you will work on with Steve and Rich.
- The net game: dinking technique, footwork and strategy
- Forehand and two-handed backhand topspin dinks
- Moving to the kitchen with effective third-shot drops
- The five types of drop shot
- When to drop and when to drive
- Volleys: block, punch and swinging
- Defending against hard hitters (bangers)
- Proper groundstroke, return and drive technique
- Using the serve and return as weapons
- When and how to attack at the net
- When and how to execute a speed-up
- Optimizing put-away shot location
- Forehand and backhand roll shots
- The backhand flick
- When and how to lob
- Defending against lobbers
- Moving efficiently with your partner
- Using court positioning to your advantage
- The Disadvantage, Neutral, Advantage (DNA) philosophy
One price. Everything handled.
If it happens on the estate, it is included. This is the full list.
- Six nights on a private estate
- Four private courts, day and night
- All coaching and clinics
- Every meal, cooked by a private chef
- Daily yoga and fitness
- One massage per guest
- Excursions with transport and 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 of your week
Not included: flights. That is the whole list.
$500 deposit holds your room
Per person. Non-refundable, and applied in full to your trip price.
Balance due 60 days out
Pay the rest two months before arrival. Booking inside 60 days? Payment in full.
If we cancel, you are whole
The trip runs subject to a minimum group. If we cancel it, you choose a full refund or credit toward a future trip.
We call a month before
Reserve your room and you are on the list for it. About a month out we reach every guest to set dietary needs and allergies, how you want the room set up, which sessions you are joining, and anything else we should know.
Executive Chef Eugene H. Yarbrough III
Founder, SVVOIR Hospitality Group
Eugene is an executive chef, hospitality entrepreneur, and creative culinary director. He cooks for private clients, brands, and high-level events, and his food brings together exceptional ingredients, presentation, and hospitality.
For the Training Retreat he is head chef for the week, building the menu around the group, the training, and the estate. Every meal is included.
A few plates from Eugene's private events. About a month before you fly, we ask every guest about allergies and dietary needs.
Nine rooms. Twenty guests. Pick yours.
Prices are per person, all inclusive except flights. Nine rooms across the main house, the guest house, a treehouse and a standalone villa. You pay for the bed you get — a bunk costs less than a queen, and a queen in a shared room costs less than one you have to yourself. Travelling alone? Take any private room to yourself for 78% more. A $500 deposit reserves your bed.
The Treehouse
King bed, private treehouse with its own jacuzzi
Sleeps 2
The Treehouse
King bed, private treehouse with its own jacuzzi · Sleeps 2
A standalone treehouse for two. King bed, a living room of its own, and a private jacuzzi on the deck under the tree.
A king in the bedroom and a sofa bed in the treehouse’s own living room, so the two of you can sleep separately if you would rather. Tell us and we will set it up that way.
Availability:
Balance of $9,600 per booking due 60 days before arrival.
Balance of $8,434 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
The Tiny House
Queen bed, private standalone villa
Sleeps 2
The Tiny House
Queen bed, private standalone villa · Sleeps 2
A standalone one-room villa for two. Queen bed and a jetted tub. The honeymoon suite.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $9,600 per booking due 60 days before arrival.
Balance of $8,434 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Main House Bedroom 1
King bed, main house, downstairs
Sleeps 2
Main House Bedroom 1
King bed, main house, downstairs · Sleeps 2
Your own room on the main floor of the main house.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $8,800 per booking due 60 days before arrival.
Balance of $7,722 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Main House Bedroom 2
King bed, main house, downstairs
Sleeps 2
Main House Bedroom 2
King bed, main house, downstairs · Sleeps 2
Your own room on the main floor of the main house.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $8,800 per booking due 60 days before arrival.
Balance of $7,722 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Main House Bedroom 4
Queen bed, main house, upstairs
Sleeps 2
Main House Bedroom 4
Queen bed, main house, upstairs · Sleeps 2
Your own room upstairs in the main house.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $8,000 per booking due 60 days before arrival.
Balance of $7,010 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Guest House Bedroom 1
Queen bed, guest house
Sleeps 2
Guest House Bedroom 1
Queen bed, guest house · Sleeps 2
Your own room in the guest house.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $8,000 per booking due 60 days before arrival.
Balance of $7,010 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Guest House Bedroom 2
Queen bed, guest house
Sleeps 2
Guest House Bedroom 2
Queen bed, guest house · Sleeps 2
Your own room in the guest house.
One bed in this room. If the two of you would rather not share a bed, we can add a second one — tell us and we will set the room up that way.
Availability:
Balance of $8,000 per booking due 60 days before arrival.
Balance of $7,010 per booking due 60 days before arrival.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Main House Bedroom 3
Queen bed plus a bunk, main house, downstairs
Sleeps up to 4 · queen $3,900, bunk $3,400
Main House Bedroom 3
Queen bed plus a bunk, main house, downstairs · Sleeps up to 4
A shared room downstairs in the main house with a queen bed and a bunk. You pay for the bed you take.
Availability:
Balance of $6,800 per booking due 60 days before arrival.
Balance of $2,900 per booking due 60 days before arrival.
Balance of $12,600 per booking due 60 days before arrival.
Book it with your own group, or tell us you would like to be matched — we will introduce you before anything is confirmed.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
Guest House Bedroom 3
Two bunk beds, guest house
Sleeps up to 4
Guest House Bedroom 3
Two bunk beds, guest house · Sleeps up to 4
A shared room in the guest house with two bunk beds, four spots in all. The room friends book together.
Availability:
Balance of $2,900 per booking due 60 days before arrival.
Balance of $5,800 per booking due 60 days before arrival.
Balance of $11,600 per booking due 60 days before arrival.
Book it with your own group, or tell us you would like to be matched — we will introduce you before anything is confirmed.
Every booking is confirmed on a quick call within one business day. If we cannot confirm yours, your deposit is refunded in full.
There is one treehouse and one standalone villa. When a room is taken, this page will say so. Rooms are confirmed on a call, in the order deposits arrive.
Everything people ask before they book.
How is this different from The December Retreat?
This week is Steve and Rich's. They built it, they host it, and they coach it themselves across six nights, December 7 to 13. The December Retreat the following week is Rally's own five night trip with our three pro coaches. Same estate, same twenty guest cap, same all inclusive format. This one is a night longer and $500 a bed more. Choose it if you are here for the instruction.
What skill level do I need?
Any level. We ask for your rating before you arrive and you are grouped by level on arrival, so clinics and match play put you with players close to your game. Strong players get real games. Newer players get real coaching.
Who is actually coaching?
Steve Kennedy and Rich Van't Hof run the week themselves and are on court for every coached session, supported by their coaching team. At least one coach is on court for every six guests in every coached session.
I do not play pickleball. Can I still come?
Yes. The estate, the chef, the pool, the spa, yoga, and the excursions are all yours too. Plenty of guests come for the trip and never pick up a paddle.
How do I get there?
Fly into San Jose, Costa Rica (SJO). We pick you up at the airport and drive you to the estate, about one hour and fifteen minutes. Transfers are included.
What is the food like?
A private chef cooks every meal on the estate, from fresh Costa Rican breakfasts to family style dinners. Tell us about dietary needs when you book and the kitchen will handle it.
What does my deposit actually do?
A $500 per person deposit holds your specific room and is applied in full to your trip price. In a shared room, your deposit holds your bed, not the whole room. The balance is due 60 days before arrival. If we cancel the retreat, for example if it does not reach its minimum group size, you choose between a full refund and a credit toward a future trip.
What if I need to cancel?
The deposit is non-refundable. Beyond it: cancel more than 90 days out for a full refund of the rest, 60 to 89 days out for half, and inside 60 days there is no refund. You can also transfer your place to another guest up to 30 days out for a $150 administrative fee. Full details are in our Booking Terms, and comprehensive travel insurance is required for every guest.
Do I need travel insurance?
Yes. Comprehensive travel insurance is required for every guest. Any provider works, and we will ask you to confirm coverage before the trip.
Is it safe?
The estate is private, gated, and staffed with 24 hour security. All transport, including airport transfers and excursions, is private and arranged by us.
Is there wifi at the estate?
Yes. The estate has wifi. Stay reachable, share the week as it happens, or fit in a work call between morning play and the afternoon excursion.
When is it, exactly?
Monday, December 7 to Sunday, December 13, 2026. Six nights, arriving Monday and departing Sunday. Rally's own five night retreat follows the week after, December 15 to 20.
What should I bring?
Court shoes, sunscreen, and swimwear. Bring your paddle if you love it. A custom paddle to take home is included either way.
Will I have to share a room?
Only if you choose to. Seven of the nine rooms are private, yours alone or shared with whoever you book with. Two rooms sleep three or four and cost less; they are usually taken by friends travelling together. If you are on your own and would like a shared room at the lower rate, say so and we will introduce you to whoever you would be sharing with before anything is confirmed.
I am travelling alone. What does it cost?
Any private room or villa can be yours alone for 78% more. Or take a bunk in a shared room at $3,400 if you would like to be matched. Plenty of guests come on their own, and the week is built around a group of twenty who eat together every night.
How many people are on the retreat?
Twenty guests, plus Steve, Rich and their coaching team, and someone shooting photo and video all week. Nine of the ten bedrooms are guest rooms; the tenth is where the coaching team sleeps.
Want to talk to someone first?
Rooms are reserved on this page — choose yours above, and a $500 deposit secures the bed. If you would rather talk it through first, leave your details and a team member will call you within one business day. This form is also the waitlist for any room that sells out.
Rally Retreats · Fla. Seller of Travel Reg. No. pending