San Diego, Completely Handled.
For executives, families, and discerning travelers who want an extraordinary San Diego experience — without spending a single hour planning it.
You know exactly what kind of trip you want. Upscale. Seamless. Worth every dollar. What you don’t have is the time — or the local knowledge — to make it happen the way you’re imagining it.
San Diego looks simple from the outside. Beautiful weather, great food, things to do. But the difference between a good trip and an exceptional one? That comes down to knowing which restaurant is actually worth the reservation, which experiences aren’t on any website, and who to call to make it all happen without friction.
That’s where I come in.
This Is For You If…
You’re visiting San Diego for business and want the days before or after your conference to feel like a genuine escape — not an afterthought.
You’re bringing your partner or family and want every detail handled, from transfers to dinner reservations to experiences they’ll still be talking about a year from now.
You’re an Executive Assistant who’s been asked to “sort out San Diego” — and you need someone you can trust to make it seamless and make you look good.
You’re a high-net-worth traveler who expects a certain standard, and you’d rather pay for expertise than spend your own time researching.
How It Works
1. We Talk
We start with a relaxed conversation about what you’re looking for — your dates, your style, who’s traveling, and what matters most to you. No forms, no pressure. Just a conversation.
2. I Design Your Experience
I take care of everything. Dining reservations at the right restaurants. Private experiences and insider access. Transfers, timing, logistics. Everything is arranged and confirmed before you arrive.
3. You Simply Arrive and Enjoy
Your itinerary is in your hands before you land. From the moment you arrive in San Diego to the moment you leave, everything runs smoothly — because I’ve made sure of it.
What Can I Take Care Of?
Every San Diego concierge experience is tailored to you. Here’s a taste of what I arrange for clients:
Upscale dining reservations at San Diego’s best restaurants.
Private and small-group experiences that go beyond the standard tourist trail — from behind-the-scenes access to unique local encounters.
Airport and ground transfers, so arrivals and departures are seamless from the first moment.
Day trips and excursions — wine country in Temecula or Ramona Valley, a day in Baja’s Valle de Guadalupe, La Jolla, and more.
Family experiences — activities, timing, and logistics that work for everyone from grandparents to grandchildren.
A detailed, day-by-day itinerary delivered before you arrive, so you always know what’s next — without having to think about it.
Your San Diego Insider
I’m Karen Cherrett, and I’ve called Little Italy, San Diego home for six years.
I’m not a visitor who researched this city from a desk. I live here, eat here, walk these neighbourhoods, and know the people who make San Diego worth experiencing. When I recommend a restaurant, a guide, or an experience, it’s because I know it’s exceptional — not because it showed up in a search result.
As a professional travel advisor, I bring the same attention to detail and care for my clients whether I’m planning a trip across the world or right here in my own backyard. Your San Diego experience will be personal, thoughtful, and entirely handled.
Ready to Experience San Diego the Right Way?
Whether you’re arriving in two weeks or six months, the earlier we talk, the better your experience will be. Let’s start with a complimentary conversation — no obligation, just clarity on what’s possible.