How to Plan a Multi-Beach Itinerary Without Losing Your Mind

Man, jumping into a multi-beach itinerary sounds fun until you’re knee-deep in tabs and spreadsheets, right? I’m sitting here in my Denver apartment, snow flurrying outside on this January 2026 morning, heater humming loud, wishing I was back on last year’s California coast hop that I barely survived planning. I double-booked a night, lost a reservation email, and packed way too much crap. But hey, it happened, beaches were great, and now I’ve got some battle scars to share on doing a multi-beach itinerary without going fully insane.

One of the 13 ways of getting intimate with a beloved writer… moi handwritten Joyce
One of the 13 ways of getting intimate with a beloved writer… moi handwritten Joyce

Starting Out on Your Multi-Beach Itinerary the Right(ish) Way

You gotta start simple with a multi-beach itinerary—decide how many stops. I went for four last time: Big Sur down to San Diego-ish area, thinking it’d be epic drives. Mostly was, except traffic ate my soul one day. Pick spots that flow—don’t zigzag across states unless you love airports. I use Google Maps a ton but always add extra time ’cause, life.

Weather check is key too; I hit fog that hid views, kinda bummed but whatever, found cool tide pools instead.

35,464 Vintage Map Lines Stock Vectors and Vector Art
35,464 Vintage Map Lines Stock Vectors and Vector Art

Choosing Beaches for My Multi-Beach Itinerary (Overthinking Included)

Choosing the beaches? That’s my weakness in any multi-beach itinerary—I scroll reviews forever, change my mind, add one more. Ended up dropping a crowded spot for a chill cove with sea lions barking like crazy, best switch ever. But I still wonder “what if” about the one I skipped. Keep it to drivable or quick hops; flying between adds stress and cost.

Mix vibes: one party beach, one quiet, maybe one with hikes. For route ideas, this Pacific Coast Highway beach guide was helpful when I was stuck [https://www.visitcalifornia.com/road-trips/pacific-coast-highway/].

Money Stuff and Mistakes in Multi-Beach Itineraries

Budget for a multi-beach itinerary—I’m inconsistent here. Track gas, stays, food, but I always underestimate snacks or random fees. Splurged on a nice dinner one night, then cheap tacos the rest—balanced out okay. Use points if you have ’em, stay in cheaper spots mid-trip.

The Packing Nightmare of a Multi-Beach Itinerary

Packing multiple beach stops? I stuff everything, then regret the weight. Forgot towels once, bought overpriced ones. Now I roll clothes, but still overdo shoes.

What's the funniest first-time cruiser mistake?
What’s the funniest first-time cruiser mistake?

Logistics: confirm bookings twice—I didn’t once, showed up to a closed hotel. Oops. This multi-stop planning post has better checklists than mine [https://thepointsguy.com/guide/how-to-plan-multi-city-trip/].

Surviving the Trip Itself in Multi-Beach Mode

On the road, flexibility saves your multi-beach itinerary. Bad weather? Skip ahead or chill longer somewhere. I take photos, note favorites, helps process the rush.

Anyway, that’s my scattered thoughts on making a multi-beach work without total breakdown. Not perfect advice, just from my experiences—good and cringey. Snow’s still coming down here, making me itch for sand again. Go plan yours, mess it up a bit, it’s fine. Tell me your stories in comments, or just get out there.

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