Your Perfect Five Day San Diego Itinerary NOT CREATED BY CHATGPT
I moved to San Diego in September of 2025, and my brother visited me three months into me living here right after Christmas, and here is an itinerary I created to show my brother around all my favorite spots in San Diego! No, I am not afraid of AI replacing my jobs because I am certain my brain is absolutely irreplaceable by a human, let alone a robot.
If you are visiting San Diego or if you are too lazy to create an itinerary yourself, sit back and relax because I have already done the work for you 😉
Day 1 (assuming you have a morning arrival)
- Lunch: The Lafayette Hotel
- Drop off bags
Old Town
Sunset cliffs beach, sunset cliffs cave,
4pm Sunset at Sunset Cliffs
Froyo at Cup of Yo
Come home to change, chill
Dorothy’s Wine Bar
8:15pm dinner reservations at Born and Raised in Little Italy
When eating at the Lafayette Hotel, be ready to wait a little before you are able to be seated since they are always so crowded. Additionally, you may have to hunt down a waiter right when you get there too
I love parking at Cornish Dr on Sunset Cliffs for accessible parking and easy access to the cliffs!
I have tried to do a walk in at this restaurant and it is simply impossible during those prime time hours, a reservation is still your best bet. You will still have to wait for a while before you are seated even after checking in for your reservation. Regardless, the atmosphere and food is delicious.
Day 2
Breakfast at Relic Bakery (pastries) and ASA bakery (matcha)
Coronado (but not limited to):
- Tidelands Park
- Coronado beach
- Hotel Del Coronado
I love seeing downtown San Diego from here! I love driving across the Coronado bridge but taking the ferry from downtown to Coronado is also fun for your first time. Lots of restaurants and fun little shops to explore on the island. Preppy-ish vibes, but also watch out for jet skiers, they are ruthless on these waters and you might get splashed on the island or when you are on a boat on these waters!
Day 3
Breakfast Charli’s Landing
Walk around then drive around
Olive’s Cafe for coffee
Annie’s Canyon Trail
Del Mar Beach
Powerhouse Park
Sea cliff coastal trail
Nothing like the calm view along the water for breakfast at Charli’s Landing! You can bring your breakfast to go and park somewhere along mission bay as well for a better view of the water.
If you are exploring Pacific Beach (PB), set your destination to Olive Cafe and there is a large parking lot at the end of that street. Olive Cafe’s food and drinks are delicious! When exploring PB during Christmas, look out for the Christmas trees along the beach!
Del Mar beach is my favorite beach due to how nice Del Mar is, and I also love Powerhouse Park, which is a large grassy area right above the beach. I like to relax by the beach and once it hits sunset, I move to the grassy area and love watching the sunset from higher up.
Day 4
Breakfast: Modern Times
10:30am Sunday service at St. Paul’s Church (my brother is Christan Protestant but I am Buddhist. However, I love attending Sunday service with him).
Explore Balboa Park and have lunch there (also where the spanish village art center is located)
La Jolla:
- Coast Walk Trail
- La Jolla’s Cove, Tide Pools
- Sunset at La Jolla
8:45pm dinner reservations at Fleurette
Modern Times is a safe bet food wise with lovely outdoor seating in downtown San Diego. At night, it turns into a fun little bar!
I swear when I say the La Jolla Coastal Walk transports me straight back to Europe! How stunning are these waters?! Make sure to not touch the cute little seals! I love parking on Park Row in La Jolla to escape the parking mayhem.
Day 5
Midway/Maritime Museum
1:30-3:15pm BRING YO BROTHER TO WORK DAY!
Afternoon snack:
Humberto’s Best tacos all around!
Explore Kearny Mesa: Walk down Convoy Street
7:15pm Dinner at Seneca
Seneca has beautiful downtown views and delicious Italian food. Vinarius in Little Italy has the best Italian food in the city, but the atmosphere in Seneca is unmatched.
Might be interesting to link an article about the restaurant such as this one https://sandiegomagazine.com/food-drink/born-raised-cost-6-5-million-to-build/
