San Diego, California

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We had originally planned this trip for early February to celebrate our one-year wedding anniversary, we booked flights on 6/2 and then we found out I was expecting on 6/17 and due in February LOL…. so that’s why you buy changeable/refundable tickets, friends! Changing gears we looked at our calendar and decided early November would be a fun time to visit and about the only free weekend, we had left where I’d still feel comfortable traveling.

Day 1:

We changed our flights, booked a hotel (Paradise Point Resort & Spa), and started planning our visit. We left Cleveland Friday morning, arriving in San Diego around 1 pm with a connection in Denver. When we arrived at the hotel we gave our luggage to the bellman and headed to the onsite lunch spot, Barefoot Bar & Grill, since check-in was not until 4 pm. We loved getting to sit outside in the sunshine bay side and enjoyed a delicious lunch. After lunch with time to kill we headed to sit by the pool, and then eventually made our way back to the lobby to get checked in. Annoyingly, we weren’t given our room until 4:40 pm - and sitting in the lobby allowed us to watch people arrive for the first time and check in right away ahead of us…. but we eventually made our way to the room and got settled in and then headed out for dinner.

I made a reservation at Tahona Bar because I read reservations were suggested and it was highly recommended. They also had mocktails on their menu! This was probably my favorite meal of the trip - the tacos were awesome and the atmosphere was great. Our server was super knowledgeable and you could tell the whole place had a huge respect for the chef and bar manager. After dinner, we walked around Old Town a bit and then headed back to the hotel because I was ready for bed!

I wanted to mention, we debated between renting a car and just ride-sharing everywhere, and we decided to go with ride-share because our hotel had a $40/day parking fee. I put together a whole spreadsheet of our uber charges including tips alongside the price of a car rental, one tank of gas, and parking at the hotel and we saved $140!! by not renting a car. That would also assume we’d have found free parking everywhere we drove, which I don’t think would be true. Our ubers included: 2 airport rides, 3 breakfast trips, 4 dinner trips, one golf round trip (to Torrey Pines), and one site seeing trip. 18 seperate rides in total.

Day 2:

We decided to head towards La Jolla, starting at a coffee shop that opened early enough for our East Coast selves to have something to do in the morning, Bird Rock Coffee Roasters. I hated my coffee, lol… but not sure why. We then headed down a few blocks to a bakery I had on my list, Wayfarer Bread & Pastry, (read more about my lists here), and there was already a line forming so I knew it was going to be good. We got four pastries: kouign-amann, cinnamon roll, an apple cider scone, and a chocolate chip cookie. The cookie was by far my favorite though it was also good - not necessarily worth a trip on its own though. Our morning Uber driver on the way was super helpful and suggested we check out La Jolla Cove, so we grabbed another Uber to head further into downtown La Jolla. We thoroughly enjoyed a stroll along the cliffside sidewalk in La Jolla, spending time watching the sea lions and the surfers. It was a gorgeous morning! From there we walked into town for brunch, picking a popular spot with a 40-minute wait. At this point, we’d realized we had both incorrectly packed for this trip…. high 70’s with low 50s means the weather feels more like 65 the entire day, save for a seat in the direct sunshine… and we’d packed for Florida 75s. SO, we happened (fate, Drew radar, we’ll never know) to find a Lululemon and a Vuori shop in town and we both added one more item of clothing to our wardrobe for the trip.

Enjoy four days of us in Drew’s new sweatshirt below, hahah!

We headed back to brunch, nothing to write home about, and then made our plan for the rest of the day, which involved some time by the pool and exploring the resort grounds. We originally had a reservation for dinner at the property but our Uber driver said it wasn’t anything special and that we should picnic in Ocean Beach for the sunset instead.

We thought about picnic-ing but eventually decided to give another recommended spot a try, Hodad’s, and our Uber driver (who was a lifelong resident) was impressed with our choice, a win for me. We enjoyed a massive chocolate shake, a Diners Drive in’s and Dives-inspired burger and a regular menu burger. The spot was super cool and authentic but the burgers weren’t anything crazy exciting. The most excitement we got was the show out front of some drunk ladies trying to fight a man sitting inside the restaurant. From Hodad’s we walked down to the pier, and then around the cliffs to a spot perfect for sunset.

After sunset, we walked to Kilowatt Brewing which was definitely a local spot. The interior was awesome, see below, and Drew enjoyed his beer. They had a ton of large games to play so it would be a great group hangout spot. At this point, the area was clearly turning into a hot nightlife spot and we decided to call it a night. I think we would’ve stayed longer and gone to a few more of the brewery spots if I had been drinking.

Day 3:

I found this website that allows influencers to book specific hotels for a discounted rate in exchange for content and that was why we stayed at Paradise Point Resort & Spa. I was a bit worried about the location but we found it to be a great central location from which to explore all of San Diego. Because of booking through this app, we had to book two separate reservations and were not able to keep our original room for the whole stay. We planned on spending Sunday by the pool waiting for our new room to be ready but were excited when the front desk attendant was able to get us into an open room ASAP. We packed up and moved and man was that great!! I would say our original room (Lanai Garden Guestroom) definitely made me understand some of the worse reviews on Tripadvisor, it was dated and had some noticeable water damage, plus our sheets were like cardboard. Our new room was a Garden Bungalow and was bigger, with less noticeable wear and tear. Plus our sheets were hotel soft this time, lol. With a newfound morning to enjoy, we headed to Mission Beach for coffee and breakfast.

Coffee was from Better Buzz a local chain I’d compare to Rising Star in Cleveland (mainly because I liked it just as much). The staff was super friendly and the coffee was excellent. We walked down to breakfast at The Mission - Mission Beach, and enjoyed a filling breakfast.

After breakfast, we decided to walk along the beach, and eventually, I suggested we just walk the whole way back to the hotel because it was such a nice day and an easy walk. It ended up being about 2 miles.

After our walk back, we were ready to change and hang out on the property. They have a ton to do and the whole resort is SO family-friendly. We checked out paddles and played pickleball, and then decided to play the on-site mini golf, too. The mini-golf was pretty basic (and they didn’t provide a scorecard) but we still had fun. We went back to Barefoot Bar & Grill, for lunch because we had enjoyed it so much the first day and it was just as good this time.

I decided to sit by the pool for the remainder of the afternoon and found another mini-golf spot near our planned dinner, so we decided to head there early to check it out. The Loma Club is hands down worth a visit. They have two mini-golf 9-hole courses plus a “pitch + putt” par three course on site. Everything, Yes even golf, is dog friendly, and they have beer, cocktails, and NA options to enjoy. We loved it and would love to see something like that around home!

We enjoyed cocktails at Moniker General and then dinner at Officine Bueno Forchetta. Both were great!

Day 4:

When we picked San Diego, Drew knew he was going to play Torrey Pines. I decided to join him and ended up riding along the whole course in the cart. Sometimes I just stay in the lobby/restaurant and read, but I didn’t want to miss the views. His tee time was at 7:30, so we grabbed a quick breakfast on-site at The Lodge and then got started. Here is where you can read about Drew’s round.

After the round, the weather was cool and a bit cloudy, so we decided we should just take his clubs back to The Loma Club and play the bigger course. Something I could actually play - haha! So, we took a detour to the food hall located near The Loma Club for some snacks and then headed out for another round of golf. It was SO much fun, you could see directly into downtown and on the airport runway. We had fun watching the planes take off during the round.

After lunch and golf, we headed back to the hotel and tried to decide if we could possibly eat any more food, eventually deciding to grab some apps along the boardwalk in Pacific Beach. This was probably our least favorite neighborhood. It was definitely out of season, which didn’t help, but it seemed very alcohol and party-focused and most of the places we passed were more about their mega margs than the food. We did have some great Lobster Taquitos at Baja Beach Cafe, but since we both were drinking we did not fit in with the crowd. We tried one more spot and had a mediocre taco and decided to call it a night. AFTER I got my ice cream cookie sandwich at The Baked Bear (which was a highlight for me).

Day 5:

Departure day and the weather wasn’t looking great. We took an uber back to Better Buzz in Mission Beach so Drew could take a call, and then we walked down to The Funky Lemon for one of the best Acai bowls I’ve ever enjoyed. From there, once again we decided to walk back to the hotel. While walking we got a notification that our departing flight was delayed and I knew we wouldn’t make our tight O’Hare connection. Once we got back to the hotel we just finished packing and headed to the airport to see what they could do about changing our flights. If you have the opportunity to do this, I highly suggest it because it was SO efficient and the staff was knowledgeable and helpful, much better than sitting on the phone.

They ended up getting us on a flight through Denver that was boarding in the next 20 minutes, so thankfully we have TSA Pre-check! We arrived at the gate just as boarding started and ended up getting home 2.5 hours earlier than planned. A nice win for the day.


San Diego has a bunch of distinct neighborhoods and we tried to visit a bunch during our trip.

Mission Beach:

Things to do:

  • Stroll the beach along the bay

  • Visit Belmont Park, featuring amusement park rides, mini-golf, arcade games and more

  • Get out on the bay, rent a boat or kayak

  • Play Golf at the Mission Bay Golf Course

Places to Eat:

Where to stay:

La Jolla:

Things to do:

Places to Eat:

Where to stay:

Ocean Beach:

Things to do:

  • Walk the streets and explore the Murals Of OB

  • Walk long Newport Avenue Beach

  • Catch the sunset at Sunset Cliffs Natural Park

  • Head to the OB Farmers Market (Every Wednesday 4-8pm on the 4900 block of Newport Ave. between Cable and Bacon Streets in Ocean Beach)

Places to Eat:

Drinks:

Liberty Station:

Liberty Station was a historic Naval hub that’s been turned into a hub for things to eat and do!

Things to do:

  • The Loma Club

    • Includes a par three 9-hole course, and two 9-hole mini golf courses

    • family-friendly & dog-friendly

  • Corvette Diner

    • The Gamers Garage features 64 games including Air Hockey, Pinball, Skee Ball, Gold Fishin', Snocross, The Big Bass Wheel, and Fruit Ninja.

  • First Friday Arts District

    • Meet working artists, discover outdoor public art installations, wander and explore all that the arts district has to offer

Places to Eat:


Additional Recommendations:

Places to Eat:

Things to do:

Where to Stay:


Haley

Haley has always loved reviewing locations and being in the know about the best neighborhoods, restaurants, and events. This passion fuels each guide and article she creates for Our Great Bucket List. She hopes you enjoy her stories and guides and get inspired to create an adventure of your own!

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