More days in San Diego, none of the guesswork.
Whether you’re adding time before a cruise, extending a conference, or bringing the whole family, San Diego Sightseeing Vacations builds your stay around who you are and what you want to experience — so you land and everything’s already planned.
Built around who you are, and what you want to experience.
San Diego’s a playground for every age.
Between the beaches, the zoo, and the balance of easy days and big outings, San Diego works for grandparents and grandkids alike. Tell me who’s coming and what they love, and I’ll build the days that actually fit your family — the right home base, the sights worth the drive, and pacing that doesn’t wear anyone out.
Sunset sails, quiet coves, and a city built for slowing down together.
Anniversary, babymoon, or just time away together — San Diego has the kind of golden evenings that are hard to find elsewhere. I’ll build your days around what the two of you actually want, whether that’s wine in the valleys, a boat out on the bay, or nothing on the calendar at all.
Extending your stay, without the extra planning.
In town for a conference or work trip and want to stretch it into a few days of leisure? I’ll build an itinerary around your schedule — the right hotel, the best use of your bonus days, and a plan that feels like a real trip, not something bolted onto a business schedule.
Land a day or two before you sail, and actually see San Diego first.
Flying in ahead of your cruise? I’ll build out your pre-sail days so you get more than a hotel near the terminal — a properly planned day or two in San Diego before you’re back on the water.
Karen Cherrett, Owner
San Diego Sightseeing Vacations is planned personally by Karen Cherrett — a San Diego local and working travel professional who builds every itinerary herself. No call centers, no templates: just a local’s knowledge of the city, applied to your trip.
- San Diego based & local
- Working travel professional
- Every itinerary personally built
- Planned around you, not a template
Tell us a bit about your trip.
Send over your dates and what you’re looking for, and Karen will follow up with ideas for building your San Diego days.
Email Us to Start Planning