San Diego had long been on our wish lists, so we were beyond excited to get the chance to visit this past Memorial Day weekend. Initially, we had dreamed of a relaxing beach vacation spending our days sunning on the beach, drinking cocktails & soaking up those rays of sunshine California is so famous for.
However, when we began packing for the trip, we ruled out beach time when we learned the temperatures were only going reach the low 70’s. If you are thinking that’s a bit strange, you’re probably not from the Deep South where it’s not considered the perfect beach day unless the temperatures are at least in the mid-80’s! So, we revamped our itinerary and packing list.
Upon arriving in San Diego, it was nearly midnight. We wearily grabbed our bags from baggage claim and found our way to the exit where we took a taxi to our downtown hotel. We commented to our driver about the chill in the air and were promptly told that the forecasted temperatures and overcast skies were completely normal for the May/June time frame. We even learned the weather pattern had names – “May Gray and June Gloom”.
Where We Stayed:
While many people choose to stay in the Gaslamp district, we decided to stay in the downtown area also known as the “Centre City” at the Westin San Diego. It was the perfect location because it put us within easy walking distance to Little Italy, the Gaslamp district, Broadway Pier and public transportation.
Day 1: Shopping, Food and a Ferry Ride!
We began our first full day a little late as we had a late arrival the night before. When we were ready to leave the hotel, we headed to a nearby coffee shop to grab a cup of coffee and a quick snack. We figured this would hold us over until our lunch we had planned for later. We needed to make a stop in a nearby CVS in Westfield Horton Plaza to pick up a few things we had forgotten to bring. As we arrived, the bold colors and architecture of the indoor/outdoor mall, amazed us. We had not planned to spend much time there, but once we realized there were over 100 stores on various levels set up like a maze, we spent a few hours window shopping and taking in the scenery.
When we decided our bank accounts were done with the mall. Since we were already in the trendy Gaslamp Quarter, we set off to find the 94 restored Victorian era buildings the area is famous for. When it was founded in the 1850’s, it was well known for gambling halls and brothels before cleaning up its act during the 1980’s. It is now a thriving district offering eclectic dining and shopping options. After spending some time window shopping, the smells coming from the surrounding restaurants had made it impossible to ignore our hunger. We headed to Little Italy, where we found the restaurant that had been recommended to us, Filippi’s Pizza.
We were advised to check out this location because it is the original and operates as both a grocery and a restaurant. Even if you aren’t hungry, it is worth stopping by to check out the ceiling covered with wine bottles. Our waitress told us we should not miss their famous homemade meatballs, so we choose to put her recommendation to the test. We agree, it was delicious!
After we finished lunch, we headed to Broadway Pier. We bought ferry passes for $4.75 , and took the 15 minute Coronado Ferry to Coronado Island. We choose to take the ferry because it gave us time to take water pictures of the picturesque area and was the first US ferry we had the chance to take since we were children.

We enjoyed some time relaxing on the beach. It was too cold to get in, but the views were great.
It had been really cloudy for most of the day, so we did not have high hopes for a good sunset. However, we got lucky because the sun made an appearance as it got later and cleared the fog to reveal a stunning sunset. This was a great way to end our evening on Coronado Island.

After the sunset, we took the return ferry back to Broadway Pier where we walked the few blocks back to our hotel. We had an early activity planned for day 2 -a Whale and Dolphin tour that we were really looking forward to and decided called it a night.
The hubs and I have been thinking of going to San Diego when winter comes so this is great. Gives me more ideas of where to go and where to stay.
I’m glad you were able to get some ideas for your trip from our post! It really is a fun city to visit!
That’s an ideal San Diego day… or two. Time on Coronado is a must. Walking through the neighborhood is just as awesome as the beach and the Del.
It was a really fun day. The Del was definitely a highlight of our entire trip.
Great experience, the ferry ride appears to be a great experience, What amazing views of the city skyline.The sunset especially is magical.
The ferry ride is just relaxing. We definitely did luck out on the sunset!
The whole place looks so beautiful, including the food too! We also love that one place is called the Little Italy, such a cute idea.
The wine bottles on the ceiling gave the place its unique charm. The pizza was super good too, so it turned out to be a good find.
sounds like a big day of shopping and eating and exploring great way to spend a day
It was definitely a fun day!
Great article and I love the sunset photo. A great way to spend time with family 🙂
Thanks, it was a fantastic sunset!
Great article! Love the sunset photo. Also what a great way to spend time with your family. 🙂
Looks like you guys saw quite a bit in a day! What a great adventure!
We only had a few days and we managed to fit in quite a lot. It was fun!