Chicago to Santa Monica · Sixteen departures in 2027
Ten days between the BEGIN sign in Chicago and the Pacific, and ten pickleball sessions on courts booked for us alone. Beginner or 4.0, trophy hunter or don't-keep-score — there's something for you in every one.
Join the 2027 waitlist
Most pickleball trips are a resort with courts attached. This one moves. Thirty-two players board; friends emerge 2,400 miles later.
Mornings are courts. Afternoons are the road. Partners don't have to play — eight companion seats ride with every departure.
It's the same tour either way — same resorts, same landmarks, ten sessions each. Half the departures start in Chicago, half at the Santa Monica Pier. Pick the date that fits.
a sidewalk photo on Adams Street, then the welcome reception
Arrival dayindoor courts on the way out of Chicago, the big river by evening
Morning sessiona Missouri morning on the way down, then two nights at the lake
Three sessionsspray paint at golden hour, steak afterwards
The road all daya 1939 Conrad Hilton original downtown, and dinner off the old road
Morning sessionseven thousand feet, pines and painted desert on the horizon
Morning sessiona Flagstaff morning, then the old road down to two nights in the desert
Three sessions · finalsthe pier, the Pacific, the group photo — paddles up
Farewell session← Drag or scroll the map →
the sign on the pier in the last of the light, then the welcome reception
Arrival daya morning in Los Angeles, then east into the desert for two nights
Three sessionsKingman's museum and Angel Delgadillo's barbershop in Seligman, then the climb
The road all daya high-country morning, the Wigwam Motel at Holbrook, a 1939 Hilton downtown
Morning sessionthe Blue Swallow at Tucumcari, then spray paint at golden hour
Morning sessionan Amarillo morning, the Blue Whale on the way in, two nights at the lake
Three sessions · finalsone last morning on the resort courts, then the Ozarks and the big river
Morning sessiona last St. Louis morning, then the sidewalk where the whole road starts
Morning session← Drag or scroll the map →
From the rolling plains of the Midwest to the crystal-blue Pacific, across the mountains and deserts that separate them — an American boulevard of hopes and dreams for a hundred years.
Mornings are pickleball. Afternoons are all of this, at ground level.
Local pros at every club session prepare you to claw your way through the doubles, blind doubles, and singles brackets with one-on-one instruction. Seeds come from watching you actually play, not from your self-reported rating. It ends on one court at golden hour, under the lights, with the whole tour on the sideline — and the awards dinner after.
Come as a pair, compete as a pair — bring your partner and the (non-blind) doubles bracket is yours together, start to finish. Come alone and the draw deals you in.
Lose on Tuesday, you're back on court Wednesday — clinics with local pros, rec play, and games that matter to nobody but the four people laughing through them. No rating gate, no minimum, no partner required. By the pier you'll have played with (and against) all 31 of your new friends.
Every night in a hotel with a story — a lakeside resort under a landmark dome, a 1939 Hilton original, a desert resort with courts under the lights.
Executive recliners and legroom for days. The windows do the entertaining.
Breakfast and lunch every day, plus the celebration dinner. The other evenings you're loose in the best roadfood country in America.
March through October 2027. Westbound leaves Chicago on Sundays; eastbound leaves the Santa Monica Pier on Tuesdays. Same tour either way — pick the date that fits. Dates and pricing go to the waitlist first.
Waitlist members see the dates and the price first, and choose a departure before booking opens to the public. No deposit, no obligation.