As much as I love to travel, planning trips in today’s day and age can feel too overwhelming- there is an over-saturation of experiences from others, dozens of articles titled “the best of…”, and scouring every corner of the internet is nothing short of daunting.

So, I thought, "Why not jump on the bandwagon and see if it can tackle the task of planning our family trip?"

I provided Chat GPT with some important details about our little crew—me, a luxury lodging enthusiast with a penchant for photographic accommodations, my husband, a wine aficionado, and my two youngest adventurers, aged 10 and 14. With one simple click, we set off on a digital quest to map out our spring break journey from San Francisco to Pasadena. This part of my blog post will tackle the San Francisco portion of our journey.

The Lodging

Our lodging choices were, naturally, dictated by aesthetics and my unapologetic hotel snobbery—a trait finely honed during my consulting days with Accenture. I did not use AI for this….just good ol’ Google and the Amex Fine Hotels and Resorts. I love using our trusty Amex card, tapping into the Fine Hotels and Resorts program which comes with some pretty sweet perks: early check-in, late check-out, upgrades when available, a $100 resort credit, and complimentary breakfast for two.

The Fairmont in San Francisco was number one for me, and not just for its stunning visuals. I mean, Le Labo products? Yes, please. They'll have to peel me away from my Rose 31 scented sanctuary to kickstart our daily adventures.

This trip promises a bit of everything. AI, our digital concierge, not only mapped out our trip but sprinkled in some local wisdom by highlighting which attractions came with cable car adventures—a quintessential San Francisco treat. It didn't stop there, though. Knowing our craving for settings that boast "great ambiance," it pinpointed dining spots that promise to be more than just a meal, all conveniently located near our planned stops. And with a gentle nudge it reminded me which adventures required a reservation in advance.

So here we are, on the cusp of our spring break, guided by AI, through the scenic vistas of San Francisco to the charming streets of Paso Robles ending in Pasadena. With the itinerary below, we're ready to dive into a mix of city exploration, lots of food, and, of course, those inevitable moments of relaxation bathed in the scent of Le Labo Rose 31.

If anyone has been to San Francisco and has any suggestions to add or remove - I am all ears!

Let the Adventures Begin

DAY 1: ARRIVAL

Arrive 3:15 PM SFO - we plan to just Uber it to the Fairmont Hotel.

(Note about the rental car to drive down the coast…..we don’t seem to need a rental car to travel around San Fran and I also did not want to pay exorbitant parking fees to keep the car overnight so we will pick up a rental car at our hotel later in our stay. )

Stay: Fairmont Hotel, San Francisco

I told Chat GPT that we were staying at the Fairmont and would probably be tired after our our flight so we wanted to stick close to the hotel. I explained that this had to be nice but have foods to accommodate a picky 10 year old. I also requested beautiful ambience. This is what it came up with…

Dinner: at the Tonga Room & Hurricane Bar -which is right i our hotel! Chat GPT says we will have an unforgettable dining experience with unique tropical ambiance. Oh and since we booked through the Fine Hotels and Resorts we received a $100 experience credit from Amex can help cover the cost or at least buy Jim and I a few umbrella drinks!

DAY 2: San Francisco Exploration

Through the Fine Hotel and Resorts Program we receive 2 breakfasts free - so while we let Jim and my 14 year old sleep in - my little guy and I might sneak down for a quick hotel breakfast.

Breakfast: Café de la Presse

ChatGPT suggested that this was a great spot for a Parisian-style breakfast. Love a good Parisian Cafe.

Morning visit to the Exploratorium for hands-on science and art exhibits. I also suggested to Chat GPT that we would love to experience taking the Cable Cars and that we didn’t mind doing some walking.

Option to take a cable car from Fairmont to Exploratorium. ChatGPT suggested that one of the most scenic routes involves taking a cable car from the stop near the Fairmont Hotel down to the end of the line at Powell and Market Street. From there, you can either enjoy a leisurely walk to the Embarcadero and along to the Exploratorium (about 25 minutes)

After the Exploratorium we would be up for a late lunch. Remembering my crew and our culinary preferences it recommended that we walk from Exploratorium to the Ferry Building (10 min walk).

Lunch: Ferry Building Marketplace for a variety of local eats and artisanal shops.

Afternoon Activity: Shopping at Union Square. Having a 14 year daughter I suggested that ChatGPT throw some shopping options into the itinerary. Union Square was the suggestion offering a range of stores from high-end boutiques to popular retail chains. I also found out I can get my Le Labo perfume refilled at the Le Labo in San Francisco only 6 minutes from the Fairmont. Bonus!

Dinner: The Waterbar San Francisco - need reservation for this one…

Another ambiance suggestion by ChatGPT that looks to accomplish all of our culinary and ambiance needs!

Day 3 - More San Francisco Exploration

2 Free hotel breakfasts from Fine Resorts and Hotels but we may grab a quick bite with the ChatGPT suggestion….

Breakfast: Mama’s on Washington Square for a classic San Francisco breakfast experience.

Morning Adventure: Alcatraz Island tour Here are some tips from ChatGPT….remember to book tickets in advance. Oh and since I am a photographer it suggested that we sit/stand on the .eft side of the boat for best views - get there 30 min early so that we have that choice!

Back to hotel to rest up.

Late Afternoon: Golden Gate Fortune Cookie Factory in Chinatown - I have a ten year old that loves Chicago Chinatown and a husband that loves soup dumplings so I knew a visit to San Francisco’s Chinatown. ChatGPT recommended the Fortune Cookie Factory as well at dinner Bund Shanghai for soup dumplings. Only a 2 minute walk!

Day 4 - Friday - The Redwoods- Muir Woods

This is our last day in San Francisco. We were able to find a rental car company right in our hotel. I am happy to pay a little more for the convenience of not having to travel back to the airport to find a car. I had told ChatGPT that I had a 4th grader and wanted to take advantage of the National Parks program so it suggested a visit Muir Woods to see the Redwoods.

We plan to take advantage of the free hotel breakfasts to save time.

We will depart early for Muir Woods and njoy the redwoods and nature trails. It suggested we reserve parking in advance because we have a 4th grader print out a parks pass.

Lunch: Stop in Sausalito for lunch with a view of the San Francisco Bay.

We are going to try the The Trident which will have great views of San Francisco. Then we will stop by Cavallo Point for family pictures. I am going to bring a tripod along to see if I can figure out how to grab some self-portraits of the family. Wish me luck on this one!

And we’re out…..Drive to Paso Robles: Begin your journey to Paso Robles in the early afternoon.