Alright folks, let me walk you through how I tackled figuring out the absolute must-sees for a trip hitting both San Diego and Milwaukee. Kinda a coast-to-lakes combo, right? Honestly, planning felt a bit all over the place at first.

First step? I gotta figure out how much time I actually have. Was it a week cramming both cities, or a bit longer? Turned out, ten days total was possible – okay, manageable but tight. Buckled down at my desk, fired up the laptop, coffee steaming. Focus was key.
San Diego – Sunshine & Seafood Vibes:
- Hit Balboa Park FIRST. Went straight there, kinda overwhelming in a good way! Spent a good chunk of the day just wandering, popping into the botanical gardens (free, awesome!), staring at the grand museum buildings. Definitely needs comfortable shoes – my legs felt it!
- Zoo Commitment. This ain’t no quick stroll. Booked tickets online ahead to dodge lines. Allocated a FULL day. You gotta see the pandas, right? And that skyfari ride? Legit views.
- La Jolla Fix. Needed ocean air the next day. Drove up to La Jolla Cove. Saw the sea lions lounging on the rocks – so smelly, but totally cool. Tried kayaking nearby (bit wobbly!), grabbed fish tacos afterwards. Perfect California moment.
- Coronado Charm. Couldn’t skip that iconic Hotel Del Coronado. Didn’t stay there ($$!), just wandered the beach, admired the old-timey architecture, had a pricey cocktail on the patio – worth it for the view.
Milwaukee – Brews, Bites & By the Lake:
- Landed and HEADED to the Lakefront. Lake Michigan is massive, almost like an ocean. Walked the Milwaukee Art Museum grounds, didn’t go inside that time but the building itself? Wow, those wings!
- Brewery Tour – Obvious Choice. You gotta, right? Booked the Miller Brewery tour well in advance. Free samples at the end? Sign me up. Kinda touristy, but surprisingly fun and the scale of the place is nuts.
- Public Market Frenzy. The Milwaukee Public Market for lunch. Busy! Ended up with an incredible Reuben and cheese curds (duh!). Buzzing with energy, good food stalls everywhere.
- Historic Third Ward Explore. Wandered around later that day. Cool old brick buildings turned into shops and art galleries. Found a great spot for local craft beer.
- Cheese Curds Mission. Made it a point to find super fresh, squeaky cheese curds. Found ’em at a smaller place near the Public Market. Holy cow, melted in your mouth fresh. Chef’s kiss.
Putting it All Together:
Looking back? San Diego was all about that sunshine, ocean, and epic attractions like the zoo/park needing time. Milwaukee vibed industrial charm, lake views, history, and CHEESE. The flight between them? Longish, required a solid travel day. Packed comfy clothes for walks and layers – Milwaukee evenings got crisp!

Final Verdict? Both cities delivered unique punches. Balboa Park, the Zoo, and La Jolla Cove in SD are non-negotiable. Over in Milwaukee, you CAN’T miss the Lakefront energy, a brewery tour (history!), the Public Market chaos, and fresh cheese curds. HIGHLY recommend combining, but be ready to hustle. Your feet will thank you later.