Dates are flexible. This day-by-day plan is provisional until you choose exact travel dates.
Start at Kalahari Indoor Waterpark in Lake Delton. Give the slides and pools about four hours; the indoor setting is a good May plan when the weather is unpredictable. Wear water shoes between attractions, and keep a dry swimsuit and a small bag for wet things handy. If you’re not staying at the resort, check day-pass availability and current hours before setting out—passes and access can depend on the day. Arrive near opening to make the most of your time and avoid a longer entry queue.
Stay at the resort for Double Cut Grill, a relaxed sit-down break after the waterpark. Budget about $25–$50 per person before drinks, and allow roughly an hour or more rather than rushing back into the pools. It’s worth changing into dry clothes first; bring a light layer for the air-conditioned dining room.
Drive from Lake Delton to Downtown Wisconsin Dells—usually around 10 minutes, depending on traffic—and leave the car in a public lot or a marked downtown space before wandering. The compact main-street stretch is easy to browse at a leisurely pace; set aside about an hour for shops and a stroll. Finish at MACS (Macaroni and Cheese Shop) for a casual, filling dinner, typically about $15–$25 per person. Check that day’s hours before heading over, as restaurant and shop schedules can vary in May.
Allow about 25 minutes to reach Devil’s Lake State Park, then give the park roughly three hours. Choose a lakeside stretch of trail or, if conditions and energy allow, a moderate climb to a bluff overlook; May can be cool, muddy, or windy, so sturdy shoes, a light rain layer, and tick repellent are worthwhile. A Wisconsin state-park vehicle admission sticker is required—budget roughly $13–$16 for a day pass, depending on residency, and check current fees and trail conditions before setting out.
Head to Driftless Glen Distillery in Baraboo for lunch and river views; plan on about $20–$40 per person and allow time for the drive and a relaxed meal. Then continue downtown to Circus World for its historic wagons and exhibits. Set aside 1½–2 hours, but check its seasonal calendar and that day’s hours before you go—May schedules can vary—and confirm admission prices in advance.
Finish at the International Crane Foundation, north of downtown. The exhibits and nature trails make a lovely change of pace after the park and museum; allow about 1½ hours, plus the drive from town. It’s a seasonal stop, so verify that it’s open on your visit date and check closing time before leaving Circus World. This is a full day, especially with the two out-of-town stops, so an early start from Wisconsin Dells will give you the best chance of enjoying all four without rushing.
Head to Wilderness Resort in Lake Delton for your second waterpark day. Plan on about 4–5 hours, with a slower, resort-style mix of pools and slides rather than trying to cover everything. Day-pass access, hours, and which indoor attractions are operating can vary, so check the resort’s current schedule and buy admission ahead if required; don’t count on outdoor areas being open in May. Bring water shoes, a dry change of clothes, and your waterproof phone pouch. The drive from Baraboo is about 20–25 minutes via US-12; allow a little extra time to park and get changed before settling in.
After drying off and changing, drive to Moosejaw Pizza & Dells Brewing Co. downtown for pizza and a house-brewed beer, or a nonalcoholic drink. Budget roughly $15–$30 per person before tax and tip; an early meal helps you avoid the busier dinner rush. Then stroll the Wisconsin Dells Riverwalk for about 45 minutes, taking in the Wisconsin River views at an easy pace. It’s a relaxed, free finish to the day; bring a light jacket, since the river can feel cool in the evening.
Start downtown with Original Wisconsin Ducks, a guided land-and-river ride that gives you a good first look at the Dells’ sandstone scenery without much walking. The ride takes about 1½ hours; May departures are seasonal and weather-dependent, so check the operating calendar and reserve a suitable departure before building the day around it. Budget roughly $30–$40 per adult, with prices and schedules subject to change. Arrive early for check-in and parking—downtown lots can fill when tours are running.
Continue to the riverfront for the Upper Dells Boat Tour, a slower, water-level view of the rock formations. Allow about 2–2½ hours, including boarding, and confirm May service and departure times in advance; the boat and Duck schedules may not line up neatly, so leave a buffer rather than counting on an immediate connection. Expect roughly $30–$40 per adult. Afterward, walk to Bella Goose Coffee downtown for coffee and a light lunch; plan on $10–$20 per person and a relaxed break before the final stop.
Finish at Ripley’s Believe It or Not! Wisconsin Dells, an easy indoor visit if the May weather turns chilly or rainy. Set aside 1–1½ hours; admission is extra, and opening hours can vary by season, so check before you go. Keep a light jacket handy for the riverfront, and bring a rain layer—conditions can change quickly along the water.
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