Two days in the Hill Country is enough — just barely. Here is the itinerary we'd give a friend visiting for the first time, calibrated for a couple or small group staying at a vacation rental, with built-in slow mornings and one good sunset.
This is the weekend we recommend to guests at our Wimberley vacation rental, with substitutions noted depending on the season and which day you happen to be in town. It assumes a Friday-evening arrival and Sunday-afternoon departure — the most common weekend pattern.
Friday: Arrive slowly
4:00pm — Arrive in Wimberley
Coming from Austin, you'll exit I-35 around San Marcos and take RR-12 west — the road bends into the Hill Country and the temperature drops a couple of degrees the moment you cross into the cedar. Stop at the H-E-B in Kyle or have groceries delivered to the house. Coffee, breakfast supplies, snacks, a couple of bottles of wine. The 48 hours starts as soon as you walk in the door.
5:30pm — Settle in
Drop bags. Don't unpack everything. Pour a drink. Sit on the deck for fifteen minutes and do nothing. This is non-negotiable. The Hill Country pace requires a deliberate downshift, and the first half-hour is what makes the next 48 actually feel like a weekend instead of a checklist.
7:00pm — Dinner at Community Pizza
The locals' restaurant on the corner of Wimberley Square. Wood-fired pizza, good wine list, an outdoor patio that catches the last light. Reservations not usually needed for two on a Friday, but worth calling ahead in summer. If Community is full, The Let Go next door (same owners, more casual) is the easy backup.
9:30pm — Hot tub, stargazing
Back at the house. The drive from town is ten minutes; the temperature shift between the Square and the property is noticeable. The Hill Country sits inside one of the darkest sky pockets near Austin — on a clear, moonless night, you'll see more stars than you have in years. Bring a glass of wine. This is the actual point of the trip.
Saturday: The big day
8:00am — Coffee on the deck
The light at this hour, with the morning mist still in the valley, is the photo you'll text people. Don't rush.
9:00am — Jacob's Well Natural Area
Five minutes from the house. Hike the 0.25-mile trail to the spring overlook, then take the longer 3-mile loop through the cedar and limestone. Free, no reservation needed for hiking. Swimming has been suspended since 2022 due to low water — see our full Jacob's Well visitor guide for context.
11:00am — Breakfast at Wimberley Cafe
Pancakes, migas, breakfast tacos. Old-school small-town Texas diner energy. Cash is appreciated but not required.
12:30pm — Wimberley Square + Old Baldy
An hour wandering the Square — galleries, antiques, the Glass Works for a live blowing demonstration. Then drive five minutes to the Old Baldy trailhead, climb the 218 steps to the summit, take the view in for ten minutes, climb back down. Free, dawn-to-dusk.
Substitution: If your visit lands on the first Saturday of the month, skip everything above and go to Wimberley Market Days starting at 8am. See our Market Days guide.
2:30pm — Driftwood wineries
Drive 15 minutes to Driftwood. Hit two of: Duchman Family Winery, Driftwood Estate, Fall Creek Vineyards, Hawk's Shadow. A full tasting at one, a half flight at the other, and split a cheese board. Don't push for three — your palate is done.
Our full Driftwood wineries guide has a recommended route and what to taste at each.
5:00pm — Salt Lick BBQ
The original Driftwood location. BYOB, cash only, picnic tables under live oaks. Brisket served on butcher paper. This is the iconic Texas BBQ experience and one of the actual reasons people fly here.
Substitution: If you'd rather a fancier dinner, book Tillie's at Camp Lucy in Dripping Springs — voted Most Beautiful Restaurant in Texas. Wagyu, octopus, the works.
8:30pm — Back at the house
Hot tub. Fire pit (if it's winter and not under the Hays County burn ban). The bottle of wine you bought at Driftwood. Bed early.
Sunday: A slow morning, then home
9:00am — Slow breakfast at the house
Make breakfast. Read on the patio. Take the second-best photo of the trip.
10:30am — Blue Hole Regional Park
If you're in town during swim season (May 1–Labor Day) and reserved ahead, this is the morning. Spring-fed Cypress Creek, cypress trees overhanging the swim lawn, rope swings. See our Blue Hole reservation guide.
Substitution: Off-season, spend the morning at the Wimberley Cypress Creek Nature Preserve or the trails inside Blue Hole Regional Park itself (free, no reservation needed for hiking). Or just stay at the house. There is no wrong answer.
12:30pm — Brunch at The Leaning Pear
Farm-to-table, on a hill above Cypress Creek. The nice-meal pick of the weekend. Reservations recommended for Sunday brunch.
2:00pm — Last walk through the property, pack up, drive home
You'll be back in Austin by 3:15pm. San Antonio by 3:30pm. You'll already be planning the next trip.
Substitutions and variations
If you're traveling with kids
Swap the wineries for a Saturday-afternoon float trip on the Blanco River, and swap Salt Lick for a Wimberley Square dinner that's more family-paced. Blue Hole is more kid-friendly than Jacob's Well — the swim lawn and rope swings are made for it.
If it's an anniversary or honeymoon
Push the wineries to a full afternoon, dinner at Tillie's at Camp Lucy on Saturday, and Sunday morning at Solaro Estate or a long brunch instead of Blue Hole. See our romantic getaway guide.
If you have three nights instead of two
Use the extra day for Fredericksburg (an hour west) — different town, different feel, more wine. Or a day in Austin for live music. Or simply for doing less.
Where to stay
This itinerary assumes you're staying somewhere with a hot tub, an actual kitchen, a deck, and a quiet location outside the Square. The whole pacing depends on it — the mornings and evenings at the house do as much work as the days in town. La Paz is our 2-bedroom Hill Country vacation rental built around exactly this kind of weekend: 5 minutes from Jacob's Well, 7 from the Square, 15 from the wineries, and quiet enough that you'll hear the wind in the live oaks all night.