We normally visit Southern California, so when we had to decide on a trip to use our Southwest flight vouchers with we decided to explore San Francisco to Big Sur spending 5-days exploring and enjoying everything both destinations.
This itinerary is an exact replica of our 5-day, 5-night trip to San Francisco and Monterey, California. I included rough timestamps of our days to give you an idea of how long each visit took and in the end, I summarize how much this trip cost us. I wanted to create an actual, comprehensive itinerary to help others plan similar trips and understand how much you can do in a day and roughly how much it would cost. I won’t be sharing suggestions to other restaurants, hotels, or attractions in the area unless it’s relevant to the timeline story.
This is my first itinerary on this blog and I’ve gone back and forth between ideas on how I wanted to share this information. I hope you find it helpful in your planning process! If you have questions about the trip please drop them in the comment section or send me an email. I’d love to hear if this information was helpful for you. Happy travel planning!
Day One: Flight, Santa Cruz and Monterey
Obligatory just landed in Cali In-N-Out meal
We flew into Oakland’s airport instead of San Francisco and picked up our rental car.
Found the nearest In-N-Out restaurant for our obligatory just-landed-in-California meal. It’s become a tradition of ours.
Checking out Santa Cruz
We hopped back in the rental and continued to drive down to Santa Cruz.
We continued to drive down to Santa Cruz to visit the Boardwalk area before continuing down to Monterey. The amusement park was closed but we walked out on the pier which had great views. My favorite part was the openings at the end of the pier where you could watch the sea lions honk at each other and splash around.
Check into the Monterey Plaza Hotel & Spa
Continued our drive down the coast to Monterey and checked into our hotel. We stayed at The Monterey Plaza Hotel & Spa located in the Cannery Row district. The hotel was huge and situated directly on the shore of Monterey Bay with the most incredible views.
We fell asleep after a busy day of travel and woke up too late to go out for dinner so we ordered room service and got to bed early for our drive down Big Sur the next day.
Day 2: Big Sur Coast and Carmel-by-the-Sea
Breakfast at Wave Street Cafe
Began our morning by taking in the breathtaking views of Monterey Bay from our hotels’ deck. Parts of the hotel are literally situated over the Bay on stilts. We couldn’t believe our luck finding this place as we struggled to find a hotel in the area we liked. After taking in the sights we walked to Wave Street Cafe for breakfast before starting our trip to Big Sur.
Tip: When eating at Wave Street Cafe, ask for outdoor seating. It’s a serenely decorated outdoor area with prime views of the Bay. You won’t regret it. Keep in mind that depending on the season, early mornings could be a little chilly.
visiting Point Lobos State Natural Reserve
Starting the Big Sur coast drive
Continued driving down the coast and stopped at various Big Sur destinations from Garrapata Beach, Hurricane Point View, and Point Sur Lighthouse.
Lunch at Nepenth Big Sur
Tip: At Nepenthe, be sure to request seating with an ocean view if that’s what you want. I assumed they’d offer it if it was available but learned you need to request it.
Continue driving Big Sur Coast
Drive the 17-Mile Drive
After the drive back from Big Sur, we took a stroll through Carmel-by-the-Sea. I wish we spent more time here as it was the cutest area and felt like a little village in another country. We could have fit in more time but we just didn’t think about it until the end of the day and had so much we wanted to fit in.
Dinner + Desert at Alvarado Street Brewery + Revival
Decided on dinner at Alvarado Street Brewery on, you guessed it, Alvarado Street which turned out to be the cutest little street. We happened to be there during an outdoor farmer’s market that took up the whole street, looked so fun! We strolled through it as we made our way to Revival for ice cream.
Made it back to our hotel with just enough time to soak in the hot tubs and listen to the ocean and look up at the stars on a clear, ocean night while listening to the waves crash. A perfect ending to an adventure-filled day.
Day 3: Monterey to San Francisco
Breakfast at Loulou's Griddle in the Middle
We woke up and took in the views of our hotel one last time before exploring Monterey Bay a little more and heading to breakfast. We ate at Loulou’s Griddle in the Middle and it was awesome! There was a cute black lab that hung out in the side doorway politely waiting for scraps and pancakes the size of hubcaps… which, by the way, might be some of the best pancakes I ever had. Somehow even the middle was cooked perfectly for being so large. I wish I could have eaten it all but at some point, it was just too much. Definitely share it!
Drive back to San Francisco from Monterey
We then started our drive back up to San Francisco and stopped off at a beach that looked incredible in the coastal fog that was happening. Big Basin Redwoods State Park Waddell Beach. I took a moment then decided to climb down the small hill from the parking lot and walk up to the shore. One of my favorite things is standing right next to the ocean and listening to it so I had to get closer. Lots of surfers out and huge waves at the time.
We tried to find Half Moon Bay but ended up at Maverick’s Beach… and couldn’t find how to get to the actual beach part where Nathan tells me is a huge surfing spot so we continued. We stopped at JV Fitzgerald Marine Reserve, a little spot with tide pools and crashing waves but it was high tide so there wasn’t much to do. Onward to San Francisco!
Tip: We didn’t plan this part of our trip very well. If you want to make the most of it, check out stops on Google Maps before so you’re not just randomly stopping… unless you are into that. Nothing wrong with it!
Sutro Bath Ruins, First Stop in San Francisco
We made it! We’re in San Francisco proper and we decide our first stop will be the Sutro Bath ruins. What an interesting stop – I had seen information and photos on what this place used to be and it’s wild to see ruins today. One thing I am noticing about San Francisco is there is graffiti everywhere! I really wanted to take the Lands End trail to the Lands End Labyrinth, however, it was far too daunting for our energy level at the time. If we ever come back, though, we’ll definitely do the hike.
Golden Gate Bridge Views at Baker Beach
We find our next destination at Baker Beach. I read about a lot of beaches to visit with optimal views of the Golden Gate Bridge, but this one was a perfect choice. Wide sandy beach with an incredible bridge view.
Lunch at Boudin in Fisherman's Wharf
We decided to have a late lunch at Boudin at Fishermans Wharf. I really wanted some soup in a bread bowl but they didn’t have the soup I wanted so we opted for grilled cheese sandwiches. They were pretty good. They had so many cute animal and character shaped bread and I wanted to take all of them home with me! We then decided to take a walk down to Ghirardelli Square and had some ice cream as a snack.
Drive down the Crooked Lombard Street
Next, we decided to go check out Lombard Street… you know it. It’s the famous crooked street that has tight zig-zags that goes down a huge hill. Tried to get photographs looking up but it’s not the most optimal spot to shoot – there are a big sign and some wires in the way. Plus – a real Instagram vs. real-life situation as there is probably going to be dozens of people doing the same thing. We decided to drive down the hill instead – and it’s fun and you should do it because obligatory tourist thing to do but you’ll need to ride the brake the entire ride down.
Coit Tower and The Painted Ladies
Drove up to Coit Tower to check out the views… and boy were their views! You can see a huge panoramic of San Francisco from a hint of Lombard Street to Alcatraz and the Golden Gate Bridge in the distance. A nice little break and worth it for the views.
Time for our Full House moment. We went to see the Painted Ladies next to Alamo Square. It was pretty cool, they were neat looking… but I was actually more enamored with the houses around the block. There was some live music playing on the hill and great views of San Francisco.
Dinner at The Italian Homemade Company
We decided to eat dinner at this cute little Italian spot called The Italian Homemade Company and it was quite good. They even had my favorite dish, pappardelle bolognese.
Headed back to our hotel and hung out at the pool for a while before calling it a night. We stayed at the Four Points Sheraton in San Rafael.
Day 4: San Francisco
Breakfast at The Black Bear Diner
Breakfast at Black Bear Diner, we really dig this place. It had cute, outdoorsy decor and a lot of food for a good price.
Marin Headlands and Battery Spencer
Drove through the Marin Headlands and took in the views of the Golden Gate Bridge at Battery Spencer, an old reinforced concrete 12″ gun battery deactivated in 1942. Now it’s a lot of ruins and an amazing view.
The Presidio + Lyon Street Stairs
Visited Andy Goldsworthy’s “Wood Line” installation in the Presidio of San Francisco. Wood logs line a path as far as the eye can see. Pretty cool. Afterward, we drove over to the Lyon Street Stairs to take in the views.
Late lunch treats at Tartine + Bi-Rite Creamery
We made our way to the Mission District and walked around. Saw some fun street art and had some goodies at Tartine and Bi-Rite Creamery. I got a brownie at Tartine that took me two days to eat it was so rich.
Visited Haight-Ashbury neighborhood and walked around visiting some of the shops. It was during the day so there weren’t a lot of people around. Enjoyed seeing the interesting shops and strolling through this historic place. The storefronts were fun and eclectic as expected and there was plenty of street art to look at.
Drive up to Twin Peaks
After leaving Haight-Ashbury, we drove to the top of Twin Peaks and were rewarded with a view of all of San Francisco. The picture above is only a fraction of what you can see. It’s probably a little over 180 degrees of amazing city views. There are parking lots but it gets pretty busy. You should be able to squeeze in a good view if you get a parking spot.
Hidden Swing at Bernal Heights
Decided we were going to find the hidden swing in Bernal Heights. It’s not really where you’d expect to find it… meaning the looks of the place it was at didn’t seem like there’d be anything really good there till you climbed the hill. There were a few people waiting and everyone took their turn. Again, incredible views of San Francisco and… a swing! So much fun… and a little scary when the swing went out over the hill.
Tip: “Secret” spots like this are really fun finds so be cool and leave it as good or better than you found it. If there are other people waiting, take a few swings, get your photos, and let others enjoy it. There are other “secret swings” throughout San Francisco but this is the only one we tried to find.
San Francisco's China Town
Drove through the Castro and found ourselves in Chinatown. We almost didn’t go but I highly recommend a visit! It was so colorful and there was so much to see. We ended up visiting the Fortune Cookie factory watching some ladies make fortune cookies.
Tip: If you want to take photos inside the Fortune Cookie museum be sure to bring some change with you as they kindly request 50 cents a photo.
Dinner at The Stinking Rose
After leaving Chinatown we made our way to catch our reservations at The Stinking Rose… a garlic restaurant. (mmm, garlic!). Very unique looking inside and tasty food.
Visiting City Lights Bookstore & Strolling around
After dinner, we walked around and checked out City Lights Bookstore and I wish we had so much more time as it was really cool! Two stories and so many books, I love me a good bookstore but they are so hard to spend too much time on vacation. There was also this amazing flying book installation at the intersection nearby, so cool. We saw our second Banksy out in the wild on a building across the street, too.
Tip: If you’re into books be sure to allow enough time to really look through this awesome book store! There are at least two stories and rows and rows of books.
Back to the hotel for some pool and hot tub time before calling it a night.
Day 5: Muir Woods National Monument and Point Reyes National Seashore
Breakfast at Black Bear Diner (again)
Breakfast at Black Bear Diner, again, it was just easy and familiar at this point… and yummy.
Seeing Redwoods at Muir Woods National Monument
Drove through the Marin Headlands and through Golden Gate National Recreation area. The road gets pretty winding here and I found myself feeling a little seasick.
We made our way to Muir Woods! Super excited to see the redwood trees.
We walked through Muir Woods and experienced the beauty of the Redwood tree. We took the main trail into the park as far as bridge 4 where we crossed and then took the Hillside trail back to bridge 2 connecting us back to the main trail leading us out to the exit. Be sure to get photos at the hollowed-out tree at the end of the Hillside trail! You can stand inside this one for a great photo op.
Tip: The park is experiencing a renewal process that will be ongoing until 2023. This may cause some areas of the park to look as if it’s under construction with fencing, pipes, cones, etc.
Point Reyes Shipwreck and Tree Tunnel
After leaving Muir Woods we made our way to Point Reyes visiting several points along the way. Our first stop is the Muir Beach Overlook. There’s an ample parking lot with a long walkway out towards the ocean where you will get some incredible views. You can see as far as the Golden Gate Bridge and parts of San Francisco in the distance. Took some time to take in the incredible ocean panoramic before heading to our next stop.
We drove through a little town and pulled into the parking lot for Stinson Beach before we decided it was too crowded and kept driving. It took a while before finding our next stop – the Point Reyes Shipwreck. We almost missed it as we entered a small town and noticed it was behind a building. We got out of the car, stretched our legs and took some fun photos before continuing our journey.
Tip: The shipwreck is hidden behind some buildings. Keep an eye out for the Inverness Store as you can access the wreck behind the store. There is some street parking and you should be able to do a quick visit by parking in the shops’ lot. If it’s during business hours consider stopping in to grab a drink or snack to support the shop for using their lot. 🙂
Driving for a while along a dirt road passing farms and lots of cows, we finally find the Cypress Tree Tunnel. We parked and walked around noticing there was an old radio station at the end of the trees. We were mostly alone with only 3-4 other people visiting this spot. It felt very secluded.
Point Reyes South Beach Overlook
We got in our car and drove further onto Point Reyes finding ourselves at the South Beach Overlook. We parked in the Point Reyes Lighthouse Public Parking and walked over to the overlook. The views felt like they weren’t in this country but like you were in Ireland on a cliff overlooking the sea or something. The lighthouse was closed to the public at the time we visited.
A few moments later we walked to the other side and walked up Sea Lion Overlook. We passed some ladies who told us there were some killer whales out in the distance. We were so excited we booked it to get to the edge. After staring for a while and almost giving up we saw them! They were very small, I used my camera to zoom in on the view. It was such a cool moment to see them out in the distance! Worth the drive.
Tip: Consider bringing binoculars or a telephoto lens for your camera to see or photograph amazing views.
Chimney Rock Hike
We continued driving along Chimney Rock Road until we got to a parking lot. It was pretty crazy to drive as it was a one-lane road and the whole time we were hoping no one was coming up because honestly, what would you do?! We lucked out and made it to the lot. This was our last stop of the day so we decided to go for it. Thinking it was a shorter hike than it was, we made our way to Chimney Rock – which turned out to be over 2 miles there and back. What a way to end a day of hikes, hah!
The views, however, were absolutely worth it. Absolutely breathtaking cliff views overlooking the ocean waited for us at the end of the trail. On our way back we came pretty close to a coyote in which I saw first, slightly panicked as I wasn’t sure how they reacted to humans and in the few seconds I turned to look at Nathan and mentioned I saw the coyote, he turned around and trotted away from us. It was crazy!
We finally make it back to our car and start the long drive back to our hotel in San Rafael. We see so many cows and I make jokes about them being Happy California Cows like the commercial.
Dinner at La Toscana + ice cream at Silbermann's
We get back to our hotel and freshen up before heading out to dinner at Ristorante La Toscana. We found a local ice cream shop called Silbermann’s and got an ice cream treat before heading back to the hotel.
Headed back to the hotel and hung out in the pool before it closed for the night. Really wanted to soak in the hot tub but some people were hogging it for a long time and there was no room. Ah well, I swam a few laps while Nathan sat on the lounge chair. I love swimming at night in California – in most destinations we are at you can see so many stars. I just do a back float sometimes and look at the sky.
Day 6: Travel Day
Breakfast + Flight Home
We found a Boudin at a strip mall and ate breakfast before heading to the Oakland Airport.
How Much Did It Cost?
As part of showing a full, comprehensive itinerary I am going to share with you how much this trip cost us. While we do what we can to find ways to save when it comes to paying for the initial trip when we are at our destination we aren’t exactly being budget-friendly. We fall in the mid-range of spending so if you are on a tight budget you can definitely find ways to do this trip cheaper. Also, prices are always fluctuating and depending on where you travel from it could cost less or more. The idea behind sharing the amount we spent is so you have a general idea of how much a trip like this cost.
This trip was in the fall of 2019 flying from Cleveland, Ohio to Oakland, Calfornia. We rented a car for the entire trip and stayed at two hotels. These are the items we bought before arriving at our destination.
Here's what we spent
Before any savings, we spent $3198.52 total on our 6-day, 5-night trip to San Francisco and Monterey areas. Here’s the breakdown:
2 Round trip flights: $824
Food (excluding any food from airports): $647.48
2 Hotels: 1130.56
6 Day Car Rental: $205.86
Parking & Tolls: $53.03
Park Entrance Fees: $50.50
Airport (parking, food, snacks, etc): $150.15
Misc. (souvenirs , etc) : $56.33
Here's How We Saved
Airline credit: $500.00
Credit Card Miles: $521.00
Rakuten Cash Back: $39.04
Gifted Dinner: $107.35
Savings of $1167.39
Making this trip cost us a total of 2031.13
The fun part is with our credit card we also earned travel points on the total $2698.52 (the total minus the $500 flight voucher which was never officially charged to us) which we get double points 5,397.04 which gives us back around $53 for future purchases. We use the Capital One Venture Card (we also pay almost every bill with this card and pay it off monthly to build up points)
We also earned points by flying on Southwest Airlines. If you stick with an airline you can continuously build up your points.
Other ways we saved
We flew into Oakland Airport instead of San Francisco’s. There was a significant price difference.
We switched our itinerary around. Initially, we were going to start up north and go to Monterey at the end of our trip. By experimenting with dates at the hotels, rental cars and beyond.
We didn’t stay in the heart of San Francisco – hotels were insanely expensive running $200 a night for a rundown looking motel. We stayed in a suburb which gave us significant price savings.
We utilized Hotwire.com’s “Hot Rate” deals. With a Hot Rate, you won’t know what your hotel is until you book it – but you can determine what star rating it is and what general location it’s in. Pro tip: most Hot Rates will have an actual photo of the hotel room that you can see. If you do a Google Image search of the photo you should be able to find out what hotel it is. The savings are often worth the runaround.
Happy Travel Planning!
I hope this itinerary was helpful for your trip planning or just general curiosity! Travel is one of the best experiences and I truly hope you can all find ways to fit it into your life and that my itineraries help you do just that. I’d love to hear if this itinerary helped you with your planning! Let me know in the comments below.