Start slow at El Retiro Park, which is exactly the kind of first stop that works with a stroller: broad paved paths, plenty of shade, and enough open space that you never feel boxed in. Enter from the Puerta de Alcalá side or the Paseo de Colombia entrance if you’re coming by taxi, and just let the park set the pace for about 1.5 hours. If your baby needs to nap, this is one of the easiest places in central Madrid to wander without a fixed plan. The park is free, open daily from early morning until around midnight in spring, and there are benches everywhere for snack breaks or a quiet feed.
From the park, walk a few minutes to Puerta de Alcalá for the classic Madrid photo stop. It’s not a long visit — 15 minutes is plenty — but it gives you that “we were really here” city moment without overdoing it. The crossing around Plaza de la Independencia can be busy, so if you’ve got the stroller, use the wider sidewalks and keep the stop short. Taxis are easy to grab here, but the next leg is also a comfortable walk downhill toward the museum area if the baby is happy.
Head along Paseo del Prado to Museo Nacional Thyssen-Bornemisza, which is the most family-friendly of Madrid’s big art museums for a quick visit. It’s compact compared with the Prado, so you can see a good selection in about an hour without museum fatigue. Tickets are usually around €13, and the museum is typically open Tuesday to Sunday, with extended hours on Saturday; check the day’s schedule before you go. There’s a cloakroom, elevators, and enough breathing room to make a stroller manageable, though it’s often easier to leave the stroller folded if your baby is in a carrier. If you need a reset afterward, the cafés around Paseo del Prado are good for a coffee or water break before dinner.
For an easy early dinner or snack, head to the Plaza de Santa Ana / Huertas area and stop around La Casita del Príncipe (Café area nearby on Plaza de Santa Ana), where you’ll find plenty of casual tables and pedestrian streets that feel lively but not overwhelming. This is a good zone for an early meal between about 7:00 and 8:30 p.m.; expect roughly €15–25 per person depending on whether you do tapas, sandwiches, or a more proper dinner. After that, wander the short walk to Plaza Mayor for a final, low-effort stroll — it’s especially lovely in the evening when the arcades glow and the square has that classic Madrid buzz. Keep it unstructured here: just let the baby stretch out, take a few photos, and enjoy a relaxed finish before heading back.