Four Days in San Diego -

San Diego: Not Your Typical 4 Day Itinerary


During July 2018 I went to sunny California to visit my friends who live near San Diego. Rather than paying for a hotel, which can be expensive during the summer months, I chose to stay with them in their RV in Chula Vista. Here’s everything we saw in and around San Diego during my short visit. I rearranged our itinerary a bit so fit what I think (in hindsight) would have been a better order. Since we were staying outside of the city and had to check on a dog during the day, I figured this arrangement will work best for other travelers.

So here it is. My “Not Your Typical Four Day Itinerary” for your stay in San Diego!

San Diego: A Less than Typical 4 Day Itinerary -

Day 1: Hiking and Relaxing Beach-side

Get into the California spirit by spending as much time outdoors as possible. The best way to do this is to spend all day along the coastline, soaking up the sun and taking in the views. Plus, you’ll get in your daily (or weekly) workout!

Hiking Torrey Pines

Hiking Torrey Pines State Natural Reserve - Sand Diego A Less Than Typical 4 Day Itinerary-

Address12600 North Torrey Pines Road, San Diego CA
Hours: 7:15 AM until sunset (exact closing time is posted at South Beach Entrance)
Entrance Fee: High Season/South Beach $15 Mon-Thurs and $20 Fri-Sun; High Season/North Beach $10 Mon-Thurs and $15 Fri-Sun;
Parking: South Beach parking options include beach level parking at the entrance and smaller lots at High Point and near the Visitor’s Center (closest to trails).

You’ll want to arrive at Torrey Pines by no later than 10:00 AM if you want a parking spot and less crowds. Another reason to get there early is the heat. There is little to no shade on this hiking trail, so starting early is a must.

To find out more about Torrey Pines’ trails and the beach, check out my post here!

Important Info to Know: (1) No dogs are allowed anywhere. (2) Only water is allowed on trails. (3) Drones are not permitted on the reserve, including the beach.

Stroll Through Ocean Beach

Ocean Beach (“OB”) is a neighborhood in San Diego offering beach access, restaurants and bars, parks, and a photogenic fishing pier.

Address: Ocean Beach Park, 4726 Santa Monica Ave, San Diego, CA 92107
Parking: Depending on time of year, you’re likely going to spend several minutes driving through the neighborhood looking for street parking. We lucked out with a spot right in front of where we chose to eat lunch.

Things to See:

(1) Ocean Beach Fishing Pier –
The pier is the longest concrete fishing pier on the West Coast, jutting 1,970 feet into the ocean. You will still find several people sitting along the edges with their fishing poles propped up on the railing. It can smell extra fishy depending on how successful they are that day.

Originally named the San Diego Fishing Pier when it was built in 1966, this pier is one of the most visited landmarks in the county so don’t be surprised if its crowded. Make your way to the very end to be free of the crowds and for a great view of the beach. Be sure to stop and watch the surfers below as you make your way down the pier.

(2) Ocean Beach Park –
During summer, the beach will be hard to find underneath all the beachcombers, but if crowds don’t both you, then bring a beach towel and stretch out for some sun and swimming at the ocean. It’s also a popular spot for surfers. (We skipped this beach because it was packed! Crowds are not my thing and I avoid them best I can).

If you’re traveling with your dogs, take them to the Dog Beach, just north of the park. Here they can run off leash along the sandy shore and into the waves.

(3) Tide Pools
Just below the Ocean Pier, is the entrance to the tide pools. Check the tides before you visit to make sure you’re not there at high tide. Not only will you miss the pools, but you will have a difficult time reaching them without getting wet. I had to dodge a few waves and try not to slip on the rocks.

(4) Cow Records – for nostalgic music fans
Address: 5040 Newport Ave, San Diego, CA 92107
If you find yourself walking along Newport Ave for shopping or bar hopping, stop into Cow Records. We spent about 15 minutes perusing the records and the art on the walls. If I had a record player (and room in my suit case) I probably would have left with something.

Plus lots more. You could spend a whole day in this neighborhood. We just did strolled through one afternoon.

Places to Eat & Drink:

(1) OB Surf Lodge – American Eats with an Ocean View
Address: 5083 Santa Monica Ave Suite 1F, San Diego, CA 92107
(2) Pacific Shores – a Dive Bar with an underwater theme along Newport Avenue
Address: 4927 Newport Ave, San Diego, CA 92107

Have any other suggestions? Leave a note in the comments!

San Diego: A Less than Typical 4 Day Itinerary -

Day 2: Venture Outside of San Diego

Make the most of your trip to Southern California by visiting another city along the coast. There are several popular destinations within a few hours from San Diego: Laguna Beach, Palm Springs, Carlsbad, even Tijuana. But if you’re looking for a quieter, less crowded city, head to Dana Point.

Day Trip to Dana Point

The city is named for Richard Henry Dana, a man who spent two years as a sailor, traveling around Cape Horn and up to Alta California on the brig The Pilgrim. He recounted his adventures in his memoir “Two Years Before the Mast” which became very popular during the California Gold Rush. He described this harbor, then known as San Juan Bay, as “the only romantic spot on the coast.”

To read more about what to do in Dana Point, check out my blog post here.

(1) Stroll Along Dana Point Bluff

On this short historic trail you can see the Dana Point Arches, the Hide Drogher Statue, and views of the harbor below.

(2) Shop, Eat, and Relax at Dana Point Harbor

There are nearly 30 shops and restaurants to choose from at the marina, several parks, and other activities to entertain yourself with during your stay. Bring your suit, beach towel, picnic, and hiking shoes if you plan to take in all that Dana Point has to offer.

Find a more detailed list here.


If you leave Dana Point in time, you’ll be able to watch the sun set with a cocktail in hand with the historic Hotel Del Coronado behind you.

Sunset at Hotel del Coronado

Hotel del Coronado - San Diego 4 Day Itinerary -

Address: 1500 Orange Ave, Coronado, CA 92118

If you’re an old movies fan, then you’ll recognize this beautiful hotel from the famous Marilyn Monroe film, “Some Like it Hot”! Ever since I saw that movie I have wanted to visit this hotel. Though I didn’t get the chance to walk the halls and see everything the hotel has to offer, just being on the grounds was a great experience. It’s also a great spot to watch the sunset.

The hotel is located on Coronado Island. The town itself is both quaint and touristy, so if you have time to walk around, I suggest doing so. There’s a 1950s style diner, which we didn’t have time to eat at, but we did park near it. It seemed very popular on a summer day, so check it out!

Hotel History

The island’s beauty inspired the hotel’s inception. Elisha Babcock and Hampton Story purchased Coronado Island in 1886 with the plan to build a grand hotel. To support their vision, they planned out an entire city, from parks to railroads. To finance their dream, the founders sold 350 lots around their newly established city, raising $2.25 million at auction. Construction of the all-wooden hotel began in 1887. Hotel Del Coronado began accepting guests in January 1888, but it’s official birthday is celebrated on February 19th, the date the hotel served its first meal. In the 1890’s, due to an economic downturn, the founders decided to sell their share in the Del to Claus Spreckles, a sugar baron.

When the Del first opened, it boasted many technological and modern elements. From electricity to private bathrooms, the hotel offered luxury for its guests. Much of the original design is still on display today, including the interior. Though the Rotunda (main lobby) has changed over the years, and off limits to non-guests, the original elevator is still in use. The Crown Room, an enormous banquet hall, is still used to serve guests.

The Hotel has hosted many notable guests over its 130 year history. In 1920, a banquet was held in the Prince of Wales’ honor. Another banquet celebrated Charles Lindbergh’s trans-Atlantic flight. One well-known guest who spent several months at the Hotel was L. Frank Baum, author of the Wizard of Oz. He wrote three books in the series during his stay. Some noteworthy celebs who chose the Del as a vacation destination are: Douglas Fairbanks, Charlie Chaplin, W.C. Fields, and many more.

Several U.S. Presidents have also visited or stayed at the Hotel Del Coronado. The first was President Benjamin Harrison, followed by President William Howard Taft for the 1915 Panama-California Exhibition. Franklin D. Roosevelt was also a hotel guest during the Exhibition and returned in 1935 as president, accompanied by his wife, Eleanor D. Roosevelt. Several celebs attended President Nixon‘s state dinner held on September 3, 1970. President Jimmy Carter continued the tradition of Presidents visited the Hotel when he frequented the hotel (visiting in 1979, 1989, 2011 and 2012). The last president to stay at the Del was President Gerald Ford (who also made several trips over the following years).

Some may know this hotel for its ties to the supernatural. The story begins with a young woman by the name of Kate Morgan checking into the hotel, alone, on November 22, 1892. Five days later she was found dead on an exterior staircase leading to the beach. Cause of death was a gunshot to the head. Her ghost supposedly haunts the halls of the hotel. Most notable hauntings occur in the guest room where she stayed for those 5 days.

The hotel was designated a National Historic Landmark in 1977. If you want to learn more about the Hotel’s history, you can reserve a Legendary Tour. Or head down to the Shops at the Del in the tunnels under the hotel to read more about the hotel’s history and see a lot of photos from its debut.

Things to Know:

The lobby and tunnels are open to the public, but everything upstairs is for guests’ eyes only.
Though there are several restaurant choices, if you’re traveling on a budget, I suggest eating before or after your visit.

San Diego: A Less than Typical 4 Day Itinerary -

Day 3: Exploring City Gems

Discover some of the historical parts of town in one day. Balboa Park dates back to 1915 when San Diego hosted the Panama-California Exhibition.

Balboa Park

To read more about what there is to do in this beautiful park, check out my post here!

With 16 museums, several gardens, and the Spanish Arts Village, there is a lot to see in Balboa. You could easily spend a whole day here. If you don’t have a lot of time to devote to this park, check out my guide to help you narrow down what you want to do and see during your visit.

Old Town San Diego

The first settlement of San Diego has become very touristy, but there are some interesting things to do and see in this part of town. My friends and I spent one evening in the heart of San Diego, exploring the Historic Park, eating dinner, and learning some ghost-filled history.

It was packed with people, and we spent several minutes looking for parking. The website (listed below) suggests where visitors can park. Here is a map of parking lots, too.

Since I prefer photos with out strangers in them, I didn’t take that many pictures at Old Town. It was too difficult to avoid people.

Old Town San Diego - 4 Day San Diego Itinerary -

A Little History

Old Town is San Diego’s first settlement. When it was created in 1769 by the Spanish, there was only one mission (Mission San Diego del Alcalá) and fort (El Presidio Reál), one of many being established across California. Like other missions in the United States, they were run by Franciscan padres and used the Indigenous peoples as its workforce. In San Diego, the Kumeyaay lived and worked at the mission.

By 1821 Mexico had won its independence from Spain and the following year a Mexican military command arrived in San Diego. Along with the well-established mission and fort, there was also presidio housing and a busy port. During this period, there were 5 main families who made San Diego their home: Carrillo (and later Fitch), Ruiz, Ybañez, Serrano, and Marron families. But this period ended when the United States declared war with Mexico in 1846. The town was captured by the U.S. and remained American territory after the war was over in 1848.

Then came the Gold Rush. The influx of people moving West to try their luck in gold mining (along with the country’s potential of losing a lot money and the ongoing debate of slavery in new territories…) paved the way for California to achieve statehood.  Good times didn’t last very long, however. As the gold rush dwindled and years of natural disasters hit the area, San Diego shrunk. There was a slight resurgence as New Town was established in 1867 only to be destroyed when another fire struck the town in 1872.

Restoration to buildings in Old Town began in 1907. Interests in the area were renewed with a novel called “Romona”, and by the 1930s the Spanish Village was created. In 1968, Old Town became a State Historic Park. The park recreates life between 1821 and 1871.

(1) Old Town Historic Park

Address: 4002 Wallace St, San Diego, CA 92110
Visitor Center Hours: 10:00 AM – 4:00 PM (closing hour depends on day of week and time of year)

“The core of restored original historic buildings from the interpretive period are complemented by reconstructed sites, along with early twentieth century buildings designed in the same mode. Five original adobe buildings are part of the historic park, which include museums, unique retail shops, and several restaurants. The Historic Plaza remains a special place for gatherings and historic activities. Visitors can also experience a working blacksmith shop, enjoy music, see or touch the park’s burros, and engage in activities that represent early San Diego.”

Learn more about Old Town’s history by touring some of the buildings in the Historic Park. For a list of the historic sites, click here.

(2) Shopping & Eating

There are several shops and restaurants surrounding the Historic Park. I managed to eat at two of them, so I listed those for you. For more restaurants, click here.

(1) Casa de Reyes
Address: Located inside the Historic Park at 2754 Calhoun St, San Diego, CA

(2) Miguel’s Cocina
Address: 2444 San Diego Ave, San Diego, CA

You can find plenty of shopping opportunities within the State Park, from museum gift shops to boutiques specializing in different crafts (we went into a leather shop for example). Another option is to visit the Bazaar del Mundo Shops, an outdoor shopping center. A lot of restaurants and shops line San Diego Ave., if you want to wander around rather than having a set destination.

(3) Ghost Tours

The Whaley House 

Address: 2476 San Diego Avenue, San Diego
Hours: Hours vary depending on day and time of year. Check here. Closed Wednesdays. Evening Tours are Thursday – Sunday only.
Fee: $10 / adult

Since my friends and I arrived in the late afternoon, we made the most of our time in Old Town by taking a nightly tour of one of the allegedly haunted houses, the Whaley House.

Thomas Whaley moved to San Francisco during the gold rush and set up shop selling equipment to miners. In 1851, Whaley moved to San Diego and married Anna Eloise DeLaunay. They had 3 children before having to relocate once again to San Francisco. Whaley built up his fortune and had 3 more children during their time in the Bay Area. After an earthquake in 1868, the family of 8 moved back to San Diego and back into the home he had previously built. The Whaley home was multipurposeful. With a general store on the first floor, a theatre on the second floor, and a courthouse in the former granary. The home stayed in the family until 1960, when it became a museum.

Now you may be wondering why it’s considered haunted…if you want to learn while taking a tour, skip this next portion. Instead check out submitted “ghostly sightings” photos here.

Short version is that a lot of people connected to the home died. The theatre space was ranted to a Mr. Tanner for the Tanner Troupe. Only three months after the troupe’s opening night, Mr. Tanner died. In 1882, two of the daughters (Violet and Anna) had a double wedding. Violet’s marriage ended and she suffered from depression, taking her own life inside the home only 3 years later. In 1913, her sister Anne passed away in the home. The following year, their brother, Francis, also passed away.

Their sister, Lilian, stayed living in the home until her death in 1953. But, the person whose ghost is known to haunt the home died before the home was even built. James (aka Santiago) Robinson  aka “Yankee Jim” was convicted of grand larceny and was sentenced to death by hanging in the gallows where the house now stands. His story is an interesting one and I encourage taking the tour to learn more. The last ghost is of Mr. Thomas Whaley himself.

If you take a tour let me know if you have any ghostly sightings!

The El Campo Santo Cemetery 

Address: 2410 San Diego Ave, San Diego, CA 92110

After taking a tour of the Whaley House, walk down to the small El Campo Santo Cemetery to find the gravesites of Old Town San Diego’s prominent figures, and Yankee Jim (mentioned above). The cemetery was used between 1850 and 1880.  There are signs next to some of the gravesites to provide information about some of the people who are buried there, too. It’s also interesting to see what information was including on the “tombstones” such as “died by the hands of”. You can find haunted tours that include the cemetery, too.

If you’re worried about it being too creepy, go during the summer. There were around 10 other people walking around using their phones as flashlights so it’s not spooky at all. It’s also very small and right off of the main road, so there a lot of light.

Remember, it’s a touristy cemetery, but a cemetery nonetheless. Be respectful of those buried there. Watch where you walk and don’t disturb the sites.

San Diego: A Less than Typical 4 Day Itinerary -

Day 4: Beaches and Views

La Jolla

The best place to see sea lions up close is La Jolla! But there’s more to this neighborhood than these amazing and goofy animals, so spend a morning or longer in La Jolla.

We parked near Prospect Street. This area has a lot of shopping and restaurants with some public parking options.

But First, Coffee

We didn’t do anything fancy for breakfast. Our main goal was to get a bite to eat and coffee quickly so we could start exploring. We accomplished this at Deli-licious (in a cute outdoor shopping center). But if you want to spend a leisurely morning enjoying a good meal or sitting down to drink a cup o’ joe, then there are plenty of options for you!

For a list of Coffee Shops, click here.

Sea Lion Watching at La Jolla Cove

Address: 1100 Coast Blvd, La Jolla, CA 92037

After filling up on cover we strolled over to La Jolla Cove to watch the sea lions. We began our stroll near the La Jolla Bridge Club and followed the path along the cliffs edge towards the Children’s Pool (we didn’t make it all the way there). There is beach access at a few points along the path, including at the Cove (a popular swimming spot) and the Children’s Pool (not a pool but a small beach).

PSA – please keep a safe distance (50 yards) from the Sea Lions, especially in the spring and summer months when they are with their pups. If you want close up pics, I suggest bringing a zoom lens. I used my 85 mm lens. We saw way too many people standing a few feet away from the babies trying to take close up photos. Not only is this rude (I wouldn’t want strangers doing this to me) but it can be dangerous. Moms and male sea lions will charge if they feel threatened. They are known for aggressively protecting their young. If you see an injured sea lion, click here, and find a number to call.

And More! 

Kayaking – for those looking for more adventure, consider signing up for a kayaking tour. For more information about this option, click here.

La Jolla Cove – The Cove offers plenty of water sports and other activities if you’re looking for more to do in La Jolla. Some options are Snorkeling, Swimming, and Scuba Diving. Or you can enter the La Jolla Cave! To descend into the tunnel and sea cave, check out the Sea Cave Store. It’s open from 9am – 5pm and costs $5 per adult. You can also rent snorkeling gear from the Store.

Museum of Contemporary Art – If art museums are more your jam, check out the Museum of Contemporary Art of San Diego at 700 Prospect St. (At the time of this post, the Museum is closed for renovations, so check before you go!). Visit the website for more information to plan your visit.

Tidepools –  There are two tide pool spots. One is at La Jolla Cove. The other is south of the Children’s Pool and La Jolla Beach.

Galaxy Taco for lunch! This is where we ate before driving to our next destination, Mount Soledad.

Mount Soledad

Address: 6905 La Jolla Scenic Dr S, La Jolla, CA 92037
Memorial Hours: 10 am to 7 pm daily

Within the La Jolla limits, Mount Soledad is the perfect stop in-between visiting La Jolla and Pacific Beach. Mount Soledad offers the best 360 degree views of San Diego and is worth visiting, especially on a clear day.

The 822-foot hill is a prominent landmark in the city and best known for the Mount Soledad cross and veterans monument atop the hill. The memorial contains around 3,400 plaques with names, stories, and sometimes photos of veterans. The cross was erected in 1913, before the veterans memorial was built. It’s presence is still controversial (mixing of religion and government) and may one day be removed.

Learn more about the memorial here.

Pacific Beach

Address: 4500 Ocean Blvd, San Diego, CA 92109 (the pier is in the center so use this address as a guide)

The Beach

Your most likely came to California to get in as much sun and beach time as possible, right? So why not stop by one more beach before you head back home? Pacific Beach is much larger than most of the beaches and very popular among locals and tourists alike. It’s definitely the party beach (though no alcohol allowed). There are restrooms and showers available, too.

If you decide to do Sunset Cliffs (below) on a different stay, stick around in PB to watch the sunset over the ocean.

The Boardwalk

A big draw for this beach is its 3 1/2 mile Boardwalk. No cars are allowed so its great for runners, cyclists, and pedestrians. Restaurants and bars line the boardwalk, most of which having an ocean view. Since we we’re interested in swimming and had other plans for sunset, we settled for having a drink with a view at the Waterbar.

The Crystal Pier

Pacific Beach has its own Pier (much like Ocean Beach, though not as long) where you can fish or take a stroll. On top of the pier are cottages for rent. If that sounds like fun to you, click here. There isn’t much else, but it makes for a nice walk.

When it was first built in the 1920’s there was an amusement park  located on the pier. Now, only the Crystal Pier Hotel remains.

Address: 4500 Ocean Blvd, San Diego, CA 92109

Sunset Cliffs

Address: 705 Cornish Dr, San Diego, CA 92107 (Natural Park Address)
Parking: The Natural Park has a small, dirt parking lot, but you can park anywhere along Sunset Blvd.

End your day watching sunset over the pacific ocean at Sunset Beach. But get there early to find parking and a spot because its a popular spot for locals, tourists, and couples having their photo taken. My friend and I saw several people hiking further down, sitting on picnic blankets, or walking along the beach.

Aside from the Sunset Cliffs Natural Park, there is also the Sunset Cliffs Cave and Luscomb’s Point further up the coast (800-898 Sunset Cliffs Blvd). There is limited parking along Sunset Blvd so you can watch from your car or get out and find a nearby bench.


Have you been to San Diego? What was your favorite place or attraction?

San Diego Not Your Typical 4 Day Itinerary -


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