What makes sense?

Question

Was married in Laguna 20years ago..haven't been back since. Planning a trip in September. My husband never spend anytime in Cali other than our wedding in Laguna. I want to take him to see San Diego, NPB, Catalina, etc. Just got tickets unexpectedly to Ohana festival (one day) it's September 26th. Wanted 2 start trip San Diego area finish up in Laguna. Now with concert, not sure it makes sense. Out actual anniversary is on 17th, we got married in gazebo infront of Las Brisas, so wanted to stay in Laguna couple nights, eat at Las Brisas on actual day. Should I start in Laguna, drive 2 San Diego for 5 days, then back to Doheney 4 concert and Newport portion? Or, just start in SD and finish in Newport/Laguna and not be in Laguna on exact date of anniversary? Since nothing g is that far, does that make sense?

Answer

Planning a California trip around your anniversary, festival tickets, and a mix of coastal destinations can definitely be done smoothly. Since none of your destinations are far from each other, it’s more about balancing meaningful experiences, logistics, and avoiding backtracking.

Here are some considerations for your itinerary:

If celebrating your anniversary at Laguna and having a special meal at Las Brisas is a priority, it makes sense to schedule your Laguna stay around September 17th.
San Diego can be a separate block of 4–5 days either before or after your Laguna time, depending on flight timing and lodging preferences.
The Ohana Festival in Doheny State Beach (Dana Point/Newport area) on September 26th will require proximity, so you’ll need to plan your Orange County portion of the trip around that date.

Option 1: Anniversary First, then San Diego, then Festival

Arrive in Laguna around September 16th, spend 2 nights to celebrate your anniversary on the 17th at Las Brisas.
Drive south to San Diego for 4–5 nights (19th–23rd/24th), exploring La Jolla, Coronado, Balboa Park, and other highlights.
Return north to Dana Point/Newport Beach area by September 25th to be ready for Ohana Festival on the 26th.

Option 2: San Diego First, then Laguna, then Festival

Fly into San Diego and spend 4–5 nights exploring the area.
Drive north to Laguna Beach around September 17th for your anniversary celebration, 2 nights at Laguna.
Stay in the Newport/Dana Point area for the festival on September 26th.

Additional Tips:

Since all destinations are within 1–2 hours of each other, neither option is logistically difficult.
Option 1 gives you the stress-free anniversary first and allows San Diego exploration without worrying about timing for your festival.
Option 2 allows you to “build up” to the festival while keeping the anniversary in a quieter, memorable spot.
Book hotels early, especially around your anniversary and festival dates, as both Laguna and Orange County are popular in September.
Consider traffic on PCH; allow extra time on festival day and for scenic drives between destinations.

Either plan works, but if the anniversary celebration is most important, starting in Laguna first is recommended. You can then move to San Diego for the longer exploration and finish near Doheny/Newport for the festival without feeling rushed.