San Diego Three Day Itinerary (Including What to Do at Night)

A San Diego native shares her insider tips and touring ideas, meal and dining suggestions along with plans for after sunset in this San Diego three-day itinerary. This diverse sightseeing itinerary is ideal for adults or families with older kids.

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San Diego Three Day Itinerary

With some of the prettiest beaches in the United States, San Diego is full of amazing places to explore. While a visit to La Jolla shores or Del Mar is must-see on another trip, this 3-day San Diego itinerary offers a different look at this sparkling city along the Pacific Ocean. I’ve included dining location suggestions, a day at SeaWorld, Little Italy day trip and options for enjoying the San Diego nightlife. The attractions in this Southern California itinerary can be reached by foot, by taking the trolley, complimentary hotel shuttle or local ridesharing service. With this San Diego three-day itinerary, you won’t need your own vehicle.

SheBuysTravel Tip:  Attraction and restaurant opening dates and times can change without warning. Always check the website before heading out for a visit.

Day 1: Explore the History of Old Town, San Diego

In this San Diego three-day itinerary, I’ve made Old Town San Diego your travel home base. For the first day, you’ll be exploring the Old Town, San Diego area. Old Town offers families plenty in the way of entertainment, shopping and dining. It’s also centrally located with quick public transportation access. There is a San Diego Transit Trolley Station just a short walk away, which allows public transportation access to many San Diego attractions.

Best Western PLUS Hacienda Hotel Old Town

4041 Harney St, San Diego, CA 92110

This lovely hillside hotel in the heart of Old Town San Diego is terraced with patios and lush landscaping. Rooms are spacious with handcrafted Santa Fe-inspired furnishings, and some offer private balconies. The location is ideal for walking to attractions. The hotel offers cooked-to-order breakfasts daily from 6 a.m. to 10 a.m. for a fee.

Book your San Diego vacation package with SheBuysTravel partner Get Away Today. Packages include discounted hotel and attraction tickets.

Old Town

From the hotel, walk southwest on Harney St. toward Calhoun St. Turn right onto Calhoun St. Turn left onto Twiggs St. Turn right onto Calhoun St. Turn left onto Wallace St to arrive at the Robinson-Rose House.

Old Town San Diego is a historical location your kids will actually enjoy! Unlike stuffy museums, Old Town is open-air, with historical buildings, small free-entry museums and areas for kids to play. Start your Old Town San Diego visit at the Robinson-Rose House, which now holds visitor information. From here you’ll be able to walk a loop to see everything.

Step inside the first San Diego Courthouse, Mormon Battalion Historic Site, Seeley Stable and Wells Fargo History Museum. My favorite is the one-room Mason Street schoolhouse where all eight grades were taught together. The adobe La Casa de Estudillo is another must-see, with rooms decorated as they would have been in the 1800s. There’s a garden courtyard here for kids to explore. Kids will also enjoy the various shops including Cousin’s Candy Shop and Miner’s Gems and Minerals, which make fun family vacation souvenirs.

Lunch at Miguel’s Cocina in Old Town

2444 San Diego Avenue
San Diego, CA92110

Walk San Diego Ave, restaurant is on the left (a 4 minute walk from Twigg Ave)

Miguel’s Cocina is a popular lunch location for visitors and locals alike. Start your meal with the must-try freshly made tortilla chips and incredible jalapeño white sauce. Seriously, I find myself wanting to lick the bowl! Dishes are made with handmade tortillas and topped with fresh salsas. Consequently, I’m happy with a “light lunch” of a bowl of chips, white sauce and a margarita.

Presidio Park

2811 Jackson St, San Diego, CA 92110

From Old Town, walk NE on Mason St. Turn left on Jackson St. Continue straight onto Presidio Dr and follow the road.

Take the walk up to the vantage point of Presidio Park (about .6 miles with some hills). The Junípero Serra Museum sits on the site of the first permanent European settlement in what is today the State of California. There are gorgeous views all around and the grassy palm-studded lawn is ideal for photos. Inside an exhibition showcases San Diego’s cultural influences from indigenous Kumeyaay to the early settlers. Admission to the museum is complimentary, with a suggested donation.

SheBuysTravel Tip: If you want to explore more of Presidio Park, keep walking up the hill to reach additional grounds. There are arbors, beautiful views of the city and large grassy areas for play.

Dinner at Casa Guadalajara

4105 Taylor St, San Diego, CA 92110

From Presidio Park, head north on Jackson St. toward Presidio Dr. Turn left onto Presidio Dr. Turn left onto Taylor St. (restaurant is on the left). Approximately 5 minutes. 

In the mood for Mexican food? This hot spot has the tacos, burritos and fajitas you’ve been craving without having to visit Mexico. Casa Guadalajara is located in the Bazaar Del Mundo section of Old Town. This festive spot has fun shopping, all with a Mexican flair. The restaurant is bright and colorful, with both indoor and courtyard dining. Kids enjoy the live mariachi music. Platters are large, so consider sharing but save room for dessert because the deep-fried ice cream and sopapillas are worth the calories.

Whaley House Museum

To return to the hotel, walk southwest on Taylor St. toward Juan St. Turn left onto Juan St. Turn right onto Harney St. (approximately 7 minutes).

To reach the Whaley House, continue walking toward Calhoun St. Turn left onto San Diego Ave. (one minute more).

While you can certainly tour the Whaley House during the day, the late night ghost hunting tours are the hot ticket. The Whaley House has been called the “Most Haunted House in America.” During the 90-minute tour you’ll hear history behind the legendary spirits that haunt the house. Attendance for the ghost hunting tours is limited to just 20 guests (ages 6+ only). Tickets are sold on a walk up, first-come first-served basis so if this is a must-do, make a stop here earlier in the day to get your tickets.

SheBuysTravel Tip: Scaredy cat? You can still tour the Whaley House during daylight hours on a self-guided tour. This museum and some tours have a fee.

Day 2: Making a Splash at SeaWorld San Diego

Breakfast at Old Town Mexican Cafe

2489 San Diego Ave, San Diego, CA 92110

From the hotel, walk southwest on Harney St. toward Calhoun St. Turn left onto San Diego Ave. 

The hearty breakfast options at Old Town Mexican Cafe will kick-start your morning! Choose Grande Breakfast Burritos, Pork Carnitas Hash, Spanish omelets or my personal favorite, Chilaquiles. And if you just want breakfast without the Mexican influence, choose pancakes instead of tortillas. But I don’t know why you’d want to do that – the Old Town Mexican Cafe serves amazing handmade tortillas.

SeaWorld San Diego

500 Sea World Dr, San Diego, CA 92109

The Best Western Plus Hacienda Hotel Old Town offers a complimentary area shuttle. Check at the desk to see when they’ll be driving to SeaWorld. Or drive your own car (parking at SeaWorld is $25 per vehicle).

SeaWorld is definitely an all-day theme park. With a variety of activities, rides, shows and attractions, you’ll have no problem filling your day with fun and learning. I do recommend arriving when the park opens, especially on weekends. If rides are important, get to those first thing before the lines get too long.

Check the guide for show times as many of the times overlap during the busy summer season. The new Orca Encounter is where you’ll see the beautiful killer whales. Sea Lions Live is a silly favorite for the kids.

The dining options at SeaWorld are better than most theme parks. I highly recommend the Dine With Orcas buffet lunch with killer whale encounters while you eat. Fill in the rest of the day by visiting the aquariums, touch pools and animal exhibits.

SheBuysTravel Tip: Plan your visit to SeaWorld San Diego during one of the exceptional special events. There are events for Lunar New Year, Seven Seas Food Festival, Halloween Spooktacular and SeaWorld’s Christmas Celebration.

Looking to save money on tickets and food? Purchase discount tickets for SeaWorld San Diego with the All-Day Dining package via our partner Get Away Today.

Dinner at Island’s Restaurant in Mission Valley

Day 3: Little Italy and Downtown San Diego

Walk to Old Town Transit Center. From hotel, walk southwest on Harney St toward Calhoun St. Turn right onto San Diego Ave. Continue onto Wallace St. Turn left onto Taylor St (approximately 8 minutes’ walk).

At the station, take the GREEN line towards downtown, hopping off at County Center/Little Italy (just three quick stops).

Harbor Breakfast

Little Italy Mercato Farmer’s Market (Saturday only)

519 W Cedar St, San Diego, CA 92101

Short two-minute walk from restaurant. Head north on India St. toward W Cedar St. Turn right onto W Cedar St.

If you plan your visit to Little Italy on a Saturday, you’ll have the opportunity to experience this award-winning Mercato. California certified farmers & ranchers sell flowers, cheeses, eggs, honey and nuts. Other vendors supply fresh-baked breads, jams, dips, sauces, and snacks. The perfect San Diego souvenir is to be found along the five long blocks. Lots of tasty food samples along the way too!

Additional Little Italy Itinerary

If you’re visiting on any day other than Saturday, there are still many things to see in Little Italy. Boutique shopping and historical spots abound. Read my day trip itinerary for Little Italy including recommendations for a self-guided walking tour (and free smart phone app).

Little Italy Pizza Tour for Lunch (Saturday only)

555 W Beech St Suite 101, San Diego, CA 92101

From Farmer’s Market area, head east on W Cedar St toward Columbia St. Turn right onto Columbia St. Turn right onto W Beech St.

When in Rome…eat pizza! The perfect combination of history, pizza and walking is provided on this entertaining Little Italy Pizza Tour. You’ll have the chance to visit multiple eateries in the Little Italy district, sampling a variety of pizzas. I took this tour with a friend and it was delightful. I still can’t decide which pizza was my favorite, but I sure did enjoy trying them all!

Additional Little Italy Dining Suggestions

If your visit brings you to Little Italy on a day other than Saturday, I highly recommend the following restaurants.

• For upscale dining, make a reservation for Civico 1845.
• Filipi’s Pizza Grotto offers the classic pizza experience.
• For casual dining and craft beers, choose Ballast Point Brewing.

Waterfront Park & Maritime Museum

Heading towards the water, walk down W. Grape, W. Cedar, W. Beech or W. Ash (Do not walk down either W. Fir or W. Date, as both will dead-end). 

Waterfront Park is a perfect place for free play because of the expansive grassy lawns and large playground. Families are welcome to cool off in the spray fountains on a warm day.

The Maritime Museum, Star of India and U.S.S. Midway are also located along N. Embarcadero. Discount tickets can be purchased from our partner Get Away Today.

Additional Downtown Itinerary Suggestions

• If you’re looking for more downtown San Diego ideas, consider a 20-minute walk along N. Embarcado to Seaport Village. The USS Midway aircraft carrier museum is along the harbor.
• Visit Coronado Island across the bay, home to the beautiful Hotel Del Coronado. See my one-day San Diego itinerary for more information about taking a harbor ride to the island.
• A trip to Balboa Park can include a day at the world famous San Diego Zoo, museums, hiking or picnicking.

Downtown San Diego After Dark in the Gaslamp Quarter

Walk back to County Center/Little Italy trolley station and take the GREEN line to the Gaslamp Quarter. 

When night falls in San Diego, the Gaslamp Quarter really shines. This happening Gaslamp district offers a diverse range of activities.

• If it’s baseball season, take in an evening Padres game at Petco Park.
• Happy hour is happening at pubs and bars all over the Gaslamp. Try the Tipsy Crow or Stone Brewing Tap Room.
• Live music can be found in many of the coffee houses and pubs. Try The House of Blues for a large venue, The Shout! House for dueling pianos or Prohibition Lounge with a 1920s vibe.
• Dinner options are plentiful. For upscale, try Lionfish Modern Coastal Cuisine. Kids love The Old Spaghetti Factory or Sugar Factory for dinner and dessert.
• Dance the night away at one of the many nightclubs like Onyx Room or Oxford Social Club.

SheBuysTravel Tip: Many of the venues in the Gaslamp are 21+. Be sure to check the websites ahead of time for age limits before taking the kids.

San Diego City Lights Night Tour

470 Kettner Blvd., Seaport Village, San Diego

See San Diego in a whole new light on this evening tour of the city at night. Guests on this Old Town Trolley Tour will see the the historic Gaslamp Quarter, Balboa Park, the view atop of the Coronado Bridge and Embarcadero’s bayfront views. You’ll disembark the tour in Coronado for a 20-minute stop at the Ferry Landing. This spot allows for a spectacular view of the twinkling nighttime city skyline. The photo you take here will be the ideal San Diego souvenir!

Discounted tickets for Old Town Trolley Tours are available through our partner Get Away Today.

Find More Places to Stay Near San Diego, California

There are lots of options for hotel stays near San Diego, including vacation rentals. Use this interactive map to help you find a place to stay in the area.

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