CALIFORNIA (Central Coast + Bay Area): 10-year Anniversary Trip
- Holly Sims

- Sep 7
- 10 min read

This trip was inspired by a mix of our favorite things: my love for charming coastal towns, great wine, and relaxing spas, paired with Ryan’s dream of golfing Pebble Beach. We planned it as an early celebration of our 10-year anniversary—spending time away recharges us and I feel like it makes us better parents when we come back.
That being said, leaving the kids behind is never easy (hello mom-guilt and anxiety), so most of our kid-free trips are usually just 3–4 days. But, with so many places on our wish list this time, we knew we needed at least 6 days and it ended up being the perfect length.
The central coast was really the heart of our itinerary, but it left me dreaming of future trips—I think next time we come back we will try again for Napa/Sonoma paired with Montecito and Santa Barbara... and Tahoe will always be on my California bucket list, too 😊
DAY 1: San Francisco to Tiburon to Half Moon Bay
We had a half day in Napa planned out (Cliff Lede, Far Niente, Alpha Omega vineyards + Bouchon for dinner) butttt American Airline screwed up our flights so we had to redirect & cancel all of those plans…
We ended up having to fly into San Francisco (vs. Sonoma) and picked up a rental car (took forever - so if you do this, factor in at least 45 mins-an hour). Note: we wanted to use Turo but we are dropping the car off at a different airport at the end of our trip so you can’t do that with Turo. Instead of going to Napa, we went to Tiburon (cutest little town near Sausalito) - a friend from college recommended instead of trying to make it to Napa in rush hour traffic. We crossed over the Golden Gate Bridge and stopped at Sam’s Anchor Cafe, which was so cute—we ate on their back deck right on the water. They had the most amazing spicy marg and we had some apps (tuna poke and fries OFC) - so fun with sailboats all out there.

Then we walked down the street to Bungalow Kitchen for dinner. It was also delish—great vibes, fun music, and we got to sit outside. Ryan got filet and I had a salad & lobster corn chowder - all fab. The drinks were incredible too. They brought us complimentary champagne and a dessert for our 10-year anniversary - so sweet. The entire staff was over the top nice! We loved this charming little town!

After dinner we stopped to snap a pic of the GG bridge at sunset and then drove on to Half Moon Bay. The drive was lovely at sunset - it took us a little over an hour to get from Tiburon to HMB. We checked into the Ritz HMB (our room was lovely with a direct ocean view) and headed down to the Conservatory Bar for an after-dinner cocktail which we took out by the fire pits overlooking the ocean.

DAY 2: Half Moon Bay
We woke up in Half Moon Bay to the most incredible views from our room and ordered room service to kick off the day 💁🏼♀️ I had a spa appointment (facial+ scalp massage) & Ryan headed to the golf course (played the ocean course). The spa was nice - had an indoor jacuzzi tub with a fireplace, sauna and steam room - 30 minutes before my appointment was plenty of time at the spa. I then met Ryan on hole 14 and rode with him the rest of the way. The views from these last holes were incredible and worth it! It was definitely cooler than I was expecting - I’d recommend jeans & sweater/jacket if going in September.


After he finished on the golf course we ate lunch on the Ocean Terrace which was fabulous - the views alone made it worth it. We got the crab dip (insane), guacamole & fries - plus espresso martinis. Alabama played (and it was a damn shame) so we watched that for a little while then got ready for dinner.

We went into HMB for dinner and ate at It’s Italia - such a cute restaurant. Definitely recommend sitting on the back patio - the breeze mixed with the music & fire lanterns was magical. The Burrata and Bolognese were delish! After dinner we got a cocktail from the bar and sat by the fire pits outside right on the ocean - also magical!

Day 3: Half Moon Bay to Pebble Beach to Carmel
We ate breakfast at the Conservatory (same menu as room service) and then packed up to head to Carmel by the Sea!

We stopped in Davenport along the way for some scenic pics - the traffic after Davenport was rough & it ended up taking around 3 hours to drive to Pebble Beach for lunch (so plan accordingly if making this trip). The views along the way were lovely, though! Shark Finn Cove was right off Hwy 1 (below).

We ate at Roy’s at the Inn at Spanish Bay (Pebble Beach) and had sushi & drinks on the back patio with direct ocean views. It was warmer here vs. HMB so no jacket needed!

From here we headed on to Carmel and checked into La Playa hotel - such a quaint, charming spot! Our room had the best views of the sea and the pool’s hotel - and there was a wedding right below our room in the courtyard.


We checked out Carmel and sat by the pool for the afternoon! For dinner we headed to La Bicyclette and split a margherita pizza - the wine was excellent (beer & wine only)

Day 4: Carmel-by-the-Sea
We started off the morning by walking along scenic road along Carmel Beach and took in the beautiful scenery + eclectic homes along the coast.

We went into Carmel and shopped around then had lunch at Stationary - avocado toast + steak & eggs. The town of Carmel is precious - so many cute shops - we got a ton of gifts for the kids and I could have done some damage but decided against it 😉

We stopped by Mission Ranch for a pre-dinner drink (cosmo was great) and then headed back into town for dinner (it was foggy while we were there so scenery wasn’t the best but cool background). We ate at Casanova and it’s the cutest little Italian restaurant - Ryan got the cannelloni and I had a burrata salad + risotto - delish and great ambiance on the back courtyard.


Day 5: Carmel-by-the-Sea to Pebble Beach to Carmel Valley
We started the day off with an epic champagne brunch at the hotel (La playa) and then headed out to pebble beach!

We had a quick bite at the Bench (right on the 18th hole) before Ryan golfed Pebble Beach and I went to the spa for a massage - epic day! The spa is lovely (reminds me a lot of Sea Island) - there's a quiet/relaxation room called the Sanctuary (lounge chairs with cozy blankets around a simmering firepit), an outdoor pool, steam room/sauna, cold plunge tubs (I couldn't bring myself to do this, although I'm sure it would have been worth it) and an ionization room. In regards to golf, there's a 3-night minimum stay at PB resorts to be able to reserve a tee time on Pebble Beach Golf Links. We were able to reserve a tee time on one of the other 2 courses (Spyglass and Links at Spanish Bay) with a 1-night stay and were told if you call 24 hours in advance, you can reserve PB Golf Links if there is availability - we lucked out! Ryan called at 7 AM the morning prior to us checking in and was able to switch over from Spyglass.


Once we finished golf/spa we headed back into Carmel Valley for dinner at Valley Kitchen (the sunset views were insane)! I had the beet salad + burger (fried egg on top, ofc) and Ryan had the veal pappardelle. He says this is his favorite meal of the trip!

Day 6: Big Sur
We left Pebble Beach for Big Sur! We stopped at Pacific’s Edge restaurant right outside of Carmel for breakfast - the panoramic views were insane & the food was delish! We had to make a stop by Celeste’s house from Big Little Lies, ofc 😆, and decided to skip Point Lobos (heard the China grove is pretty with emerald green water) because it was a cloudy morning so assumed the views wouldn’t be great.

We continued along highway 1 and stopped at a few scenic spots:
1-calla Lilly valley: pretty views of the coast but the flowers weren’t in bloom this time of the year so maybe skip this if it’s not Spring. It’s a short trail (about 0.5 miles) to a hidden canyon full of wild calla lilies when in bloom!

2-notley’s landing: pretty pit stop to pull over on side of the hwy and check out - It’s a historic pullout along the cliffs with panoramic ocean views.

3-bixby bridge: iconic spot from big little lies - views coming in from Carmel to Big Sur are the best (we stopped on either side)

4- Pfeiffer beach: really pretty beach - if you’re with kids, this would be a fun stop (maybe pack a picnic to eat lunch out there). It was really windy & chilly, though! Apparently the views are best at sunset (there’s some purple sand on the north side). It’s a slight detour down Sycamore Canyon Road (unmarked, narrow road-watch for the sign after Big Sur Station).

5- mcway falls: pull off on side of the hwy and stop for a pic! The water and landscaping is gorgeous. The waterfall is tiny, though 😆

We then ate lunch at Nepenthe (I had a caprese salad & fries & Ryan got the burger) which was gorgeous - to get the best seats outside you need to try to be there at 1130 right when it opens because it filled up quickly! It’s a legendary cliffside restaurant with sweeping ocean views.

Then we headed to Post Ranch Inn for our last night! Wow - this resort is so magical. You feel like you’re in the clouds and all of the different rooms/houses are so neat. We booked the butterfly room but were upgraded to a mountain house - the wood burning fireplace & bathtub/jacuzzi were 👌🏼 and the view from our back deck was so serene. They stock your fridge with complimentary drinks & snacks which was a nice change from the other resorts.

Since we only had the afternoon to spend here, we checked out both of the infinity pools (the meditation pool was right outside of our room and we had the pool to ourselves) and the jade pool is the bigger/main pool right next to the restaurant. They were both heated to ~95/100 and so relaxing.


We ate dinner at Sierra Mar (the resort’s restaurant) and the sunset views were unreal. I had the Stracciatella app (delish) and the pasta and Ryan had the guinea hen 🤔 - our female server was a little rude but otherwise the service/staff at the resort were all so nice & accommodating.

DAY 7: Big Sur to Home!
Breakfast is complimentary at Sierra Mar for resort guests which was v nice after 6 days in Cali 🤣 we checked out and headed to the airport! We flew out of Monterey airport which was about an hour drive from Big Sur.
NOTES:
Things to pack:
-Athletic clothes for any long walks / scenic days … not cute clothes like I did 😂 the trails are steep & lots of dirt so your shoes will be gross & it gets hot!
-Jackets! The weather along the coast is wild! Literally could be foggy/chilly one stop and then sunny & warmer 5 minutes later. The beaches were all really windy & chilly so pack layers to wear for these (scenic road along Carmel Beach, Pfeiffer Beach). I really wish I had packed a big, plush jacket for these chilly stops!
-Mace??? OK, maybe I’m being a little paranoid but I wish we had brought some mace or something as a weapon 🤣some of the tourist spots were trails in the middle of nowhere selfie with zero cell service .. the amount of times I turned my rings around 🤣 (leave your nice jewelry at home). We skipped Monterey after talking with some people who said it’s dirty & sketchy (lots of homeless people) - we did stop at a gas station before flying out of Monterey, and I’ll say that this was another instance where I wished I had mace with me 😆
-Selfie stick! If you want good pictures, at least. I hated having to ask someone to take our picture all of the time - and noticed a lot of tourists had their own selfie sticks or tripods, ha!
-Air tags in your checked suitcases if you are traveling to multiple locations! We had flight issues and very well could have lost our luggage which would have been difficult to track down with changing hotels every few days!
Things I could have left at home:
-shampoo/conditioner/body wash (all resorts had full sized bottles of nice products)
-hair dryer
-robe/slippers
-heels! Everyone dresses super casual for the most part and I never saw anyone wearing heels
Weather:
We went end of August/early September (Labor Day weekend) and the temperature ranged from 60-70s during the day and 50-60s at night (generally). We lucked out with our weather (only one day was cloudy) so the sunny days felt great (warm enough to sit by pool in Carmel & was actually hot at lunch at the Inn at Spanish Bay) but it was definitely chilly when cloudy!
SHOP:
Clothes/shoes/accessories I packed: https://shopmy.us/shop/collections/2163554
Skincare/haircare/bodycare I packed: https://shopmy.us/shop/collections/2285206
Makeup I packed: https://shopmy.us/shop/collections/2290476
WHAT WE HAD PLANNED FOR NAPA:
We planned to fly into Sonoma ~1130 AM and pick up a rental car at the airport. We planned to arrive to our first vineyard by 1 PM.
Vineyards:
-Alpha Omega 1 PM
-Cliff Lede 230 PM
-Far Niente 345 PM
Dinner:
-Bouchon (in Yountville - 10 minutes from Far Niente)
and then we would have driven to Half Moon Bay from there! Sad we didn't get to do this part of the trip, but even more reason to plan a trip back!
OTHER NAPA RECS:
I asked for help with suggestions for planning this trip on my Instagram page earlier in the year and got some great ones! I planned the trip myself so I took into consideration everyone’s suggestions and compiled lists of the top recommended places/restaurants, which I’ll include below.
Other Vineyards: Amizetta, Barnett, Cade (amazing views), Caymus (great scenery and great vibes), Chandon or Domaine Carneros (for bubbles), Davis Estates (lunch + tasting with pretty views), Del Dotto (cave tour), Frank Family (chill vibe), Frog’s Leap (beautiful garden), Nickel & Nickel (beautiful property, service and intimacy), Paradigm (small & cozy), Quintessa (amazing tasting experience and great vibes: do quintessential tasting), Schramsburg (cave tasting but sparkling, hands down best tour), Scribe (in Sonoma-limited to members but will make exceptions)
Restaurants: Auberge (for lunch in Napa)
We had a wonderful trip and I hope you find this helpful for your future travel planning!
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