San Francisco and Monterey – A 4 Day Itinerary

Our first trip of the New Year was a Girl’s Trip to San Francisco. My travel companion was my oldest daughter. It’s the first time we’ve ever traveled anywhere without the rest of the crew and it was so nice spending one on one time with her. She lives out-of-state with her brand new husband so this was a real treat. In total, we stayed 3 nights/4 days. One night in Monterey and two nights in San Francisco.

Day 1: Carmel-by-the-Sea and Monterey

The adorable Tuck Box cottage in Carmel. There are over 10 of these fairytale cottages in Carmel built by Hugh Comstock. We only found several. I’m told that you can stop by the Visitor’s Center in town and pick up a list of their locations (why didn’t we think of that?)

I mistakenly chose the earliest flight of the day (getting up at 3:30am is no fun!) – but it turned out to be a good thing since we landed in San Francisco at 9am which gave us an entire day there. We chose to spend our first day in Carmel and Monterey – so we picked up our car rental at the airport and hit the road. The drive to Carmel was under 2 hours and we spent the afternoon exploring the shops and walking the town. Parking is free along the main road if you can find it. We were able to find parking in a garage just a block away from the main street. Please note: the walk to the beach is down a very steep hill – which is no big deal until you try to walk back up it. Keep this in mind if you’re pushing a stroller or have mobility problems (or if you’re just out of shape like I am), you’ll want to drive and park at the beach (for free).

17 Mile Drive – Pebble Beach 

We really decided to do the 17 Mile Drive at the last-minute and I’m so glad we did. We entered through the Carmel gate entrance – no lines at all. The drive along the Monterey Peninsula was breathtaking with pull outs at various stops so you can take in the view. Don’t be put off by the $10.25 per car entry fee – it was totally worth it! Tip: Download the free Pebble Beach app to listen to the guided audio tour during your drive.


Monterey, while gorgeous – was just ok for us. We walked the too touristy Fisherman’s Wharf and were turned off by all the restaurant staff yelling at you to eat at their restaurant. We did however, enjoy exploring the town of Monterey and seeing all the old cannerys and wildlife on the beach.

While the Monterey Aquarium gets top billing, without the little one, we decided not to visit here. The admission price is steep so shop around for discounted tickets before you arrive!

Where did we stay?

Holiday Inn Express Monterey – Cannery Row

Because we spent most of our day driving and sight-seeing, we really didn’t spend a lot of time here. Room was spacious, but facing a busy street so there was some road noise. We were on the 3 floor that required taking quite a few steps so if you are staying here make sure you ask for a ground room or ADA room if you’ll have a stroller. Breakfast was one of the worst we’ve ever had. We tried it – then headed out for real food.

Room Rate: $170 inc tax or 50K IHG points. I made the decision to pay cash as I wasn’t willing to part with so many IHG points for this room.

You can earn IHG points by signing up for the Chase IHG credit card here. Only apply if offer is for 80k or more points.

Day 2 – Muir Woods & Fisherman’s Wharf in San Francisco

We woke up early to start the drive back up to San Francisco. We were a little worried about traffic in the city, but other than a little congestion through Golden Gate Park, we drove straight through without any issues. Hooray! By the time we crossed the Golden Gate Bridge it was very foggy and raining heavily. We decided to stop for lunch in Mill Valley and by the time we were done eating, the sun was shining again.

This park is very accessible! There is boardwalk along the entire loop which is great for strollers and wheelchairs.  Entry is free with your National Parks Pass or $10. There’s a great shop a few paces into the park as well as a cozy café. It sprinkled on and off during our hike, we were prepared and packed our rain jackets. Pro Tip: The park has now switched to reservation only parking so make sure to reserve your spot before driving out.

Muir Woods is wonderful. Walking around felt like we were in a fairytale land. I’d say this was one of our favorite parts of the trip. Worth a one day car rental if that’s the only way you can get there. After Muir Woods it was time to head to San Francisco. We were lucky that the sun was out and the fog was clearing as we passed back over the Golden Gate Bridge.

If you want a great spot to take in the Golden Gate Bridge – take the last exit BEFORE heading back over the bridge and look for signs for the Marin Headlands. You’ll find two parking lot/pull out areas at the top of the hill. Both of the lots were full when we pulled up, but we only had to wait a few minutes for someone to leave, so wait it out – the view is worth it!


After taking in the Bay and Golden Gate Bridge we headed back across the bridge and to Fisherman’s Wharf. Just a quick note about driving over the bridge. You will be assessed a toll when you drive south over the bridge (but not when driving north). There is no toll plaza and no way to pay in cash. Our rental car company provided us with a phone number to call to pay the toll within 48 hours. So if you are renting a car find out how they handle this toll before you leave their facility.

If you are driving, there are several options for parking around Fisherman’s Wharf. We made the mistake of pulling into a parking garage right across the street from Pier 39 which was around $10. When driving out we noticed there were parking meters up and down the wharf that would have been a way cheaper option than the garage for us. Make this decision based on how long you plan to visit the wharf.

Fisherman’s Wharf is very touristy. It is lined with not so great restaurants and souvenir shops. But, if this is a first trip to San Francisco for you – you have to see it. Follow the sounds of barking to the end of the pier to watch the famous California sea lions resting and playing on the docks. Take in the views of Alcatraz and the Bay and don’t forget to turn around and take in the views of the city! While we didn’t visit Alcatraz this trip it really is a must do. If you splurge on anything during your trip – make it Alcatraz!

Returning our rental car was easy. There is a large rental car garage facility in Union Square – it was right across the street from our hotel. While we really enjoyed having a rental car, there was no way we were going to pay the $60/night parking fee at our hotel. I would say that if you want to venture outside of the city to Sonoma, Napa or Monterey, that renting a car was easy and a much cheaper option than any tour (around $30/day for our SUV).

Day 3: Chinatown, Lombard Street, Painted Ladies and Outer Sunset

From our hotel we walked to Chinatown. We spoke with our concierge who gave us some tips on what to see there. We really enjoyed the Fortune Cookie factory! We made the choice to Uber from Chinatown to our other locations.  It was cheap ($5-$7 each trip) – less than $40 for both of us to see all the sights – much cheaper than a hop-on hop-off bus tour.

Have your Uber drop you off at the top of Lombard street and walk down.


Our next stop was Alamo Square for a glimpse at the famous Painted Ladies
Make sure to walk around the park and even down the side streets – there are gorgeous Victorian homes in the neighborhood.

Day 4: Ferry Plaza, Ghirardelli Square, Hyde Street Pier & Baker Beach

Our flight was at 1pm this day so we only had a few hours to cross of what was left on the list. I made the last-minute decision to rent another car. With the rental car facility right across the street, I knew it would be the easiest way for us to see it all and count as our ride back to the airport.

Head down to the Ferry Plaza on a Saturday for the famous Farmer’s Market. Lot’s of great dining and shops inside too!
We headed over to Ghirardelli Square to explore and visited National Historical Park Hyde Pier. If you have time, take a ride on the Powell Hyde Cable Car
The weather wasn’t good enough to see this on Day 2. So before heading to the airport we drove over to Baker Beach for a last look at the Golden Gate Bridge.

Where did we stay?

Hilton San Francisco Union Square

I booked a double standard room and we were upgraded to a two room corner suite with city and bay views. The hotel is in a highrise in Union Square and walking distance to just about everything. This is the first time in a long time that we’ve stayed at a Hilton and I have to say we were very pleased! Service was outstanding.

Room Rate: $299 or 60K Honors points/night. We earned Hilton Honors points from the American Express Hilton card. You can apply here and earn 75Kpoints.

Final note: There are a lot of cool little pockets in and around San Francisco. We took advantage of having a rental car and Uber to visit some great local shops in the Mission District, Outer Sunset and Haight-Ashbury. So glad we got a little glimpse of the city outside of the main touristy areas.

We enjoyed cute shops like the General Store in Outer Sunset
Grab lunch and coffee at the Tartine Bakery in the Mission District

Have you visited the City by the Bay? What are your must do’s while in San Francisco? Please share in the comments!





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