I am so excited to finally write this blog post! It has been a full week since I returned from my epic 5 day road trip from Seattle, Washington, to San Diego, California, and I finally feel ready to put it all on paper.
A little back story – a friend of mine was moving from Seattle to Los Angeles, and I decided it would be super fun to fly to Seattle and drove with her down to LA. My little sister is a Freshman at San Diego State University, which is why I continued the trip down to San Diego for a couple of days!
This road trip deserves 7-14 days, truly, but in reality – we both work full-time and were unable to get more than a couple of days off work, so we managed to jam pack our trip into 5 days. I hope this guide is helpful for everyone who wants to do this road trip but doesn’t think they have the time!
Day 1 – Seattle, Washington to Tenmile, Orgeon
I flew from North Carolina and arrived in Seattle at 11:00am. Since my friend had a full work day before we took off for the big move, I hopped on a train, then an Uber, to Pike Place Market. I had about 3 hours to kill and it seemed like the perfect place to kill time given the gloomy, rainy weather. I have been to Seattle before, and when I was first planning my day trip I wanted to visit the Bill and Melinda Gates Foundation, and take a ferry to a small island. My short time frame, in addition to the bitter cold and rainy weather, persuaded me to spend my time indoors eating all the food!
I just want to say – overall, I am incredibly impressed with how well we ate during this trip – one challenge during a road trip is fueling your body with good foods and avoiding the easy to access, quick fast-food options. We never once ate fast food, and enjoyed some of the best meals I’ve had in a while. Just letting you know – all food recommendations I make in this post are FOR REAL great!
Seattle Stops
- Visited Pike Place Market – strolled, sampled foods
- Mac and Cheese at Beecher’s Handmade Cheese
- Moscow Mule at Rachel’s Ginger Beer

THE ROAD TRIP BEGINS
We departed the Seattle area at 4:30pm – and our first stop on the epic 5 day road trip was Portland! Here are a few things we did during our very brief stop in Portland:
- Perused and purchased books at Powell’s – the world’s largest independent bookstore
- Grabbed sandwiches at Lardo – yum!
In no time we were back in the car on our way to our first overnight destination. The idea behind picking Tenmile, Oregon to stop in was that (1) it was a few hours South of Portland, and realistically we weren’t going to make it much further that first night and (2) there was an adorable and affordable chalet (Airbnb) on a vineyard (see below!)

Day 2 – Tenmile, Oregon to Sonoma Valley, California
We had arrived at our chalet around 1:00am (which was really 4:00am for me East Coast time) and within 20 minutes we were asleep in our super comfy bed. We woke up to a bottle of wine, and french press coffee and homemade bread for breakfast (thank you Marc!). We wandered the vineyard in the morning, taking in the beautiful Oregon countryside, but were in the car to start our very full day of driving by 9:00am.

We drove straight to the coast from Tenmile, and the rest of our road trip going forward was down the entire Oregon and California coastline. Our goal was to make it to Sonoma in time for dinner, while enjoying stops along the coastline throughout the day!

The southern coast of Oregon is BREATHTAKING. While we wanted to stop just about everywhere, we tried to limit ourselves to stopping only at some of the best places where we could run along the coast and stretch our legs.
Our first planned stop was at Samuel H. Boardman State Scenic Corridor. This corridor is a stunning 12 mile stretch between Gold Beach and Brookings, Oregon. We were in search of the beautiful vista seen below – the Natural Bridges!

After some epic views, we made our way out of the corridor and into Brookings, Oregon for lunch. I had found this incredible sustainable fishery sushi restaurant called Pacific Sushi and Grill and it did NOT disappoint. Do not be discouraged by the average appearance outside, this was some of the best sushi and service I’ve ever had!
After lunch – we continued our drive to Sonoma Valley by weaving our way down the coastline, stopping for coffee in Crescent City, and then driving all throughout Redwood State Park. Highlight? The Avenue of the Giants.

We continued on into the darkness, and made it to our destination (Glen Ellen, 10 minutes north of Sonoma), around 8:00pm. We were thrilled to be staying at the Olea Hotel – an exquisite boutique hotel in Glen Ellen! I was immensely impressed with their amenities and hospitality, and will be writing in greater detail about the Olea Hotel in a follow-up post! (shout out to their phenomenal 2-course breakfast, photo below)!

After arriving at the Olea Hotel, we were quite exhausted, but we were recommended to visit The Fig Cafe for dinner in downtown Glen Ellen. Dressed in our nicest lounge / road trip clothing, we made our way to The Fig Cafe and enjoyed a wine tasting and arugula fig salad!
Day 3: Sonoma Valley to Monterey
HOORAY – WINE DAY! This was the first day we had minimal driving to do (only 2.5 hours from Sonoma to Monterey), and could truly enjoy wine country! We started with our breakfast at the Olea Hotel (yum!), then made our way to downtown Sonoma for window shopping and wine tastings, eventually taking an Uber to two vineyards within Sonoma County, and then taking an Uber back to downtown Sonoma for dinner – and finally driving to Monterey after dinner.

First (1st stop)
- Olea Hotel – breakfast!
Second
- Pangloss Winery – Downtown Sonoma -wine tasting (the best red wine by far that we had all day, The Optimist, try it)
Third
- Gloria Ferrer Vineyard – 10 minutes from downtown Sonoma – did a complete wine tasting and paired with a hummus plate. Has all of those dreamy views (see below)

Fourth
- Gundlach Bandschu Vineyard (aka Gun Bun) – 5 minutes from Gloria Ferrer – very cool, laid back atmosphere – everyone brought their dogs, music was playing, it was such a great environment (and the wine was great)
Fifth (last stop)
- The Girl and The Fig – late lunch after a lot of wine, gave us time to prepare to drive to Monterey! Everyone recommended this place for lunch / dinner and it was so delicious – we split the mussels, and then I got the quiche and my friend got the seared tuna!

We got to Monterey around 9:00pm, and after a long day of drinking wine and eating delicious food, we were exhausted! We hung out at our hotel, and fell asleep early, very big day tomorrow!
Day 4: Monterey to Los Angeles
Unfortunately – the AT&T Pebble Beach Pro-Am golf tournament was taking place in Monterey during our visit. Meaning finding a place to stay felt nearly impossible… and also that the 17-mile drive was CLOSED to the public. UGH! This was a huge bummer, but with so much still to see in the area, and a long day of driving down the California coast to Los Angeles, we moved forward with our plans!
We got up early and got breakfast at Crema in Pacific Grove – it was recommended by a friend and YUM that avocado toast and latte did NOT disappoint!

After breakfast we parked by Cannery Row and walked around, listened to the ocean, and jumped back in the car to head to downtown Carmel. Carmel is absolutely adorable – we spent 2 hours shopping and roaming the town center, and then back in the car! We were very ready to drive through Big Sur and down the California coast!
Oh – the dreamy, dreamy coast of Northern California. Again, we found ourselves wanting to stop every 20 minutes, but we limited ourselves the best we could! First stop – Bixby Creek Bridge!

Not sure if you watch Big Little Lies, but even if you haven’t – you are likely to recognize this iconic bridge just South of Monterey and North of Big Sur. It was so beautiful in person – we spent about 30 minutes taking photos and enjoying watching the onslaught of tourists braving the cliff side to get the best shot.

I have about 35 photos of this bridge and this part of the coastline I want to share with you all – but we must move on.
We drove 25 minutes and stopped at a highly recommended restaurant for great cocktails and views – Nepenthe. We waited for a seat overlooking the ocean – I ordered a margarita and a cup of chili, and after a quick bite and drink, we were back on the road!

I’ll be honest – we didn’t stop anywhere else for longer than a few minutes from here to Los Angeles. At this point it was already about 3pm and we still had 5.5 hours of coastline to drive. The drive was epic – winding around the tight corners on the cliff side was an adrenaline rush on it’s own.
We had an absolute blast listening to music and throwing our hands out the windows for HOURS.
We arrived in LA with every intention on going out and partying – but (1) truth be told, we were so tired at the end of every long driving day (see photo evidence below), and (2) it had rained in LA that day, which is rare, so very few people were going out anyway. To bed we went.

Day 5 – Los Angeles to San Diego
After a pretty epic 4 days, I had to leave my friend behind in her new home in LA, grab a rental car, and drive to San Diego to visit my sister! But first, we went to breakfast at Kreation and strolled the Santa Monica Pier.
I drove the 2 hours to San Diego and picked my sister up – we had a pretty epic 48 hours, and instead of boring you with the details, I am going to bullet point the highlights below with photos!
- I stayed at one of my favorite Airbnb’s ever – a loft style apartment in Little Italy, San Diego


- We went to one of my favorite San Diego beaches – Coronado

- Dinner at Craft and Commerce – beautiful atmosphere, delicious food – HIGHLY recommend. Lucky us – it was right across the street from our loft in Little Italy
- Breakfast at Lofty Coffee – one of the best Acai bowls I’ve ever had (which is saying a lot … I eat a lot of Acai bowls)

- Basketball game at San Diego State University – UNDEFEATED STILL!

After an undeniably spectacular week, it was time for me to head back to North Carolina! This year bring about a lot of travel and a lot of change – I’m thankful you are all here on this journey with me!
Up next – Madagascar for the month of March, then France for the first two weeks of April!
