How to Make the Most Out of A Quick Trip to San Diego

July 12, 2017


Being from a small town in Virginia, I never thought I would end up living in San Diego — but here I am going on three years! At first, I was hesitant to move 3,000 miles away from home, but I quickly fell in love with this city. With so much to do in San Diego, it’s almost impossible to get bored! I love having my family and friends come visit and really enjoy showing them all the things that make the city so unique.


Usually, visitors are only here for a few days, so I’ve crafted a flexible itinerary that shows them some of the best spots San Diego has to offer in a short amount of time. 


Whether you’re visiting for business or pleasure — there is something for everyone. Here’s how to make the most out of your time in SD:


When to visit — The best times to travel to San Diego are February to April and September to November. During these months the weather is perfect for any outdoor activities. You will want to avoid what the locals call “May Grey” and “June Gloom” because it’s almost always overcast.


What to bring — A light jacket is a must to stay comfortable during chilly nights. With over 100 days of sunshine, don’t forget your sunglasses and sunscreen.


Day 1:


La Jolla Cove — The main attraction of La Jolla Cove, besides the breathtaking views, are the adorable seals. It’s a unique spot where you can see tons of seals sunbathing, sliding into the water and barking at each other.

 A typical scene at La Jolla Cove.

 Be sure to check out Clam's Cave — a massive sea cave you can see from shore.

 Another peek at the seals basking in the sun.

 Along with plenty of seals and sea lions — you'll find lots of kayakers exploring the cove.


After taking in the sights, head over to George’s at the Cove for lunch on their ocean terrace. The restaurant offers delicious food and specialty cocktails with the best view of the La Jolla coastline. Then enjoy a leisurely stroll down the streets, where you will find several unique boutiques and art galleries. Take it easy tonight — tomorrow is a full day!

 The view from George's ocean terrace. 

The streets of La Jolla are full of local boutiques and galleries. 


Tip: Free parking can be hard to find in La Jolla. If you don’t mind a short walk, try parking on one of the residential streets a few blocks away.


Day 2:


Coronado Island — Coronado Island is my favorite place in San Diego — and anytime I take a visitor, they fall in love with the area, too. The island is known for its food, shops and picturesque views. Although it’s not really an island — it’s actually a peninsula, that locals call an island —  it definitely has a laid-back island feel and miles of gorgeous beachfront. There are two main areas to check out while you’re there:


The first is Coronado’s Bayside that looks over to downtown San Diego — giving visitors uninterrupted views of the city skyline. It also boasts several waterfront restaurants and shops that are definitely worth a visit.

 The view of the city skyline from Bayside. 


Next, head over to Hotel Del Coronado — the famous hotel from the movie Some Like it Hot starring Marilyn Monroe. The hotel is absolutely stunning, inside and out, so give yourself plenty of time to explore. There are boutiques and restaurants on-site to check out as well.

Even on an overcast day, Hotel Del Coronado is still stunning.  

You’ll also want to explore Coronado’s main street, Orange Avenue, which is lined with shops, restaurants, galleries and theaters.


Tip: Watch out for rush hour that starts around 9 a.m. and again at 4 p.m — getting to and from the island gets really congested. A great way to avoid the traffic and get around the island is by bike. There are several affordable bike rental places throughout the island.  


Day 3:


Old Town San Diego — Named the “birthplace” of California, Old Town San Diego was the home of the first Spanish settlement. Today, it is a unique state park that embraces and encapsulates its Spanish heritage. The park is designed to represent the town during 1821 to 1872 and is quite a sight to see! Its packed with historic buildings, galleries, museums and exhibits.

 A few of the buildings around Old Town.

 Who knew cactuses could be so beautiful — and not prickly?! 

 You'll find all sorts of trinkets in the local shops.


While in Old Town, you’ll want to eat at one of the many authentic Mexican restaurants — one of the most popular being Cafe Coyote — where they make homemade flour tortillas.


If you enjoy a little spooky history — visit San Diego’s most haunted house, The Whaley House, located in the heart of Old Town. Stories surrounding the estate and resident ghosts vary, but there have been so many paranormal experiences reported at the home, the Travel Channel named it the No. 1 most haunted house in America! If you’re brave enough, check it out for yourself on a tour. 

 From its beautiful exterior you'd never guess this is considered the most haunted place in America.


Tip: Parking can be hard to find around Old Town. If you’re having issues, try parking at Old Town Transit Center — it’s free to park and located just across the street from the park.


Gaslamp Quarter — After exploring Old Town, head down the road to the Gaslamp Quarter in downtown San Diego. This area of the city was developed in the 19th century and originally called “New Town”. During this era, the city installed 50 gaslamp street lights, which led to it eventually being called Gaslamp. While it has a seedy past full of gambling and other shenanigans in the late 1800s to the early 1900s, it’s been completely transformed into a popular destination full of art galleries, boutiques and restaurants!

Restaurants on 5th Avenue in the Gaslamp Quarter. 


While you’re there you’ll definitely want to grab a drink or a bite to eat — you can’t go wrong with any of the restaurants on 5th Avenue. And, if you’re looking for a fun night out — this is the place — it’s very walkable and great for bar hopping. Popular bars include the Tipsy Crow, Shout House, Moonshine Flats and Barley Mash.  


Tip: If it’s baseball season, grab dinner before attending a Padres game at Petco Park. Like any city, parking can be an issue. Use the Gaslamp Quarter’s website to help you find parking.


Day 4:


Brunch in Pacific Beach — Brunch is a big deal here in San Diego — and one of the best areas to get brunch is in Pacific Beach. The main go-to spot for a delicious meal is a restaurant called Crushed where you can get their famous cinnamon swirl pancakes and order a mimosa flight. Yes, you read that correctly, mimosa flights! Be aware that it is a popular spot, so there may be a bit of a wait for a table, but it’s definitely worth it. While you’re waiting, you can walk down Garnett Avenue and check out some of the shops. After brunch, you can walk a couple blocks over and spend the rest of the day on the beach. Some other bars to check out in Pacific Beach are Moonshine Beach, The Local Pacific Beach and Shore Club.


Tip: If you’re craving ice cream, try Baked Bear — it’s a favorite among locals.

 Mimosa flight for the win!

 Crushed is famous for its cinnamon roll pancakes.


Sunset Cliffs — This is what the West Coast is all about — beautiful ocean views! At this national park, you will see coastal bluffs, arches and sea caves. You can walk along the cliffside trails or find a spot to sit and watch the sunset. It’s the perfect place to end your stay in San Diego.


Tip: Bring a blanket and some takeout food to have a picnic on the cliffs as the sun sets. If you walk to the end of Sunset Cliffs, you will see a narrow staircase that goes down to the water.

 Panoramic views of the Pacific from Sunset Cliffs.

The perfect way to end your trip. 


If you end up with a little extra time, here are some other great options to add to your trip:


San Diego Zoo Safari Park — The main attraction at the safari park is the African Tram which explores the African Exhibit, where you will find giraffes, rhinos, antelope and more exotic animals roaming around.  


Balboa Park — With over 17 museums, gardens and trails, Balboa Park offers plenty to see and do.


Harbor Cruise — Whether it’s through the Hornblower Cruise or the Flagship Cruise — a harbor cruise is a great way to spend the day on the water. (Groupon often has deals on San Diego day cruises.)  


Enjoy your time in San Diego — they don’t call it “America’s Finest City” for nothing.

You can read more from today's contributor, Lauren Tipton, on her site, Chasing Life.  

For more snapshots of my recent trip to San Diego to visit Lauren — follow SouthernDeparture on Instagram.


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