The Best of San Diego in Three Days or Less

This has been, by far, the oddest summer I’ve ever lived through. As the world is still in a pandemic, international and even cross-country vacation plans are at a halt for most Americans. However, taking a day trip or weekend trip somewhere close by is the perfect alternative. The great thing about living in California is that we’re close to so many beautiful cities and coastal towns.

San Diego, my hometown, is the last county after Orange County and just north of the U.S./Mexico border. It’s about a two-hour drive from downtown Los Angeles, making it the ideal day trip or weekend escape. It’s breathtakingly beautiful and the beaches are open, unlike many other cities in Los Angeles. As a San Diego native, here’s my personal guide on how to spend a few day in “American’s Finest City.” You can choose between a three day, two day, or one day trip since they’re broken down by area. I’ve also given a hotel suggestion for each location, but they’re all relatively close by. From morning to night, here’s a list of recommendations of what to do, see, and where to eat.

PS: At the bottom I’ve organized a list of even more recommendations on where to stay, eat, shop, and where to sightsee. Since times are changing, it’s best to call or check the website of any places you plan on visiting.

Day 1 – Downtown San Diego (North Park, Hillcrest + Coronado)

I would recommend your trip starts in downtown San Diego so you can make your way around the city by the end of the weekend.

Where to stay: The first thing to do is to check into your hotel. The Gaslamp Quarter in downtown San Diego has so many hotel options to choose from. One that stands out is the Hotel Indigo as it’s in the city’s heart, so you’re close by a lot of excursions (especially tourist hot-spot Coronado Island). This pet-friendly hotel has gorgeous rooms with a city-scape view, new cleaning procedures for Covid-19 to keep guests safe, and free parking.

Coffee: If you want to grab a takeout coffee before you begin your day, the authentic Italian Caffe Calabria is the place to go. They’re known for their freshly roasted Espresso, so try the Espresso con Panna (the whipped cream is to die for!). Next, head to the trendy (and my favorite) North Park for some breakfast. It should take you about 10-15 minutes by car to get there from the Gaslamp Quarter.

Grab a quick breakfast: Breakfast Republic has a ton of outdoor seating, which is ideal for people-watching in the city. Some of their popular dishes include the chilaquiles, eggs benedict, and the bacon mac and cheese. This is one of my favorite Southern California breakfast chains, and it’s a must-try. Pair your dish with a mimosa and you have the perfect breakfast to start your day.

Explore North Park on foot: Skip hopping in your car or hailing a rideshare and instead, take a walk around the city. You’ll see a ton of insta-worthy murals created by local artists, unique gift shops selling handmade items, as well as microbreweries, coffee shops, cafes and diners, and Craftsman cottages. In fact, Forbes named North Park “one of American’s best hipster neighborhoods.”

Sightsee in a quirky town: Hillcrest is the next place to visit which is about 10 minutes away. This LGBTQ central hub is a fun neighborhood to walk around, take pictures and get a bite to eat. Even though it’s small, it’s vibrant and welcoming.

Have a slice of “New York pizza”: For lunch, I recommend Bronx Pizza—an old-fashioned joint that has the best New York-style pizza in San Diego. The Whitestone Spinach version is mouth-watering and cheese heaven. It’s a white pizza (no sauce) with mozzarella, ricotta, parmesan, spinach, and garlic. I would order it to-go so you can enjoy it down by the water.

Picnic by the water: Take a ride to Waterfront Park (about 10 minutes away) and have a make-shift picnic on the grass while overlooking the picturesque San Diego Bay. Once you’re done you can walk along the port and look at the boats before ending your afternoon.

See the sights of Coronado Island: If you have time before you head back to your hotel to freshen up for dinner, drive over the Coronado Bridge to check out the famous Coronado Island. Coronado Beach is exceptional for taking a quick dip or to take photos in front of the iconic Hotel del Coronado. It’s a cute beach village to explore with so many great spots like the Glorietta Bay and Park.

Have dinner at barleymash: Only a 6-minute walk away, grab a meal at Instagram-famous barleymash. They have plenty of outdoor seating and it’s located right in the city center. For an appetizer, the Pretzels N’ Dip is a good choice if you’re craving something savory and cheesy. My favorite entree is the Surf N’ Turf beef and lobster burger or the popular The Maine Event lobster mac and cheese. My Instagram and Snapchat stories have featured both these dishes too many times to count. Their cocktails are also amazing, especially the Coconut Margarita and the tropical, Tajin-rimmed Afternoon Delight.

Enjoy an Italian pastry and a scenic city walk: Little Italy, one of the premier spots in San Diego, is just 10 minutes away. Not only are the streets adorned with gorgeous lights and lined with Italian flags, but the desserts here are out of this world.

Buon Appetito has the best Cannoli on the strip and their Tartufo Gelato (chocolate and hazelnut gelato with melted chocolate inside) is a sweet-tooth paradise. They also have all-authentic Italian wines if you want a night-cap.

Stock up on snacks for your hotel room: Before heading back to the hotel, stop at Mona Lisa. This cute grocery store carries authentic Italian snacks and drinks. It’s super old-fashioned, authentic, and literally feels like you’re shopping in a deli in Italy.

Day 2 – Coastal Cities (La Jolla, Pacific Beach, Mission Bay, Ocean Beach + La Playa)

Where to stay: I recommend staying in the stunning La Jolla. This way you can venture around the coastal cities of San Diego. La Valencia has been a famous La Jolla Hotel for celebrities, tourists, and locals since 1926. The all pink, vintage exterior is in the heart of this coastal city and has panoramic views of the Pacific coastline.

Breakfast with an ocean view: Across the street from La Valencia is Cove House. They have outdoor seating with a direct view of the ocean and La Jolla Cove (the next destination). The Wake and Bake is only available on the weekends but it’s one of my favorite breakfast meals in all of California. (Corned beef hash cake, two sunny-side-up eggs, hatch chili gravy, and potatoes.) I always order the pink grapefruit juice which is a refreshing (and tasty) way to start the day.

Take photos of the seals: Across the street you’ll find the beach where you can take a dip at Shell Beach, get some pictures at Seal Rock, lay out at Scripps Park, or head down to the coves. No matter how you choose to spend your day, you’ll have an picture-perfect view of the seals that make this beach so popular. If you decide to explore the coves, be sure to check out the exquisite sea caves. You can also rent snorkeling or scuba gear at Market Outpost (next to Cove House) and view the sea creatures in their natural habitat. (They have new safety regulations for Covid-19.)

Thrift Shop: After venturing around La Jolla, Pacific Beach is a must-see. It’s only about 20 minutes North. Garnet Street is such an exciting street to walk down with many shops and tattoo parlors. Here you’ll find a ton of thrift stores, like Pacific Beach Loan & Jewelry, United Cerebral Palsy Thrift, and Buffalo Exchange. There’s also a Brandy Melville and Urban Outfitters right before you get to the pier for more shopping. Once you walk the entire stretch, you will arrive at the pier and beach. This is a great spot for swimming, flying a kite, or renting a bike. (You can get them at Swings and Things Pacific Beach.)

Lunch at stoner’s paradise: While there are so many joints to choose from for lunch, I highly recommend Cheba Hut. It’s only three blocks away from the pier so you can get takeout and bring it down to the beach. Cheba Hut is entirely cannabis-themed from the decorations inside to the names of the subs and even down to the sub sizes. This place is the epitome of San Diego culture: excellent food, stoner themed, and right at the beach. My favorite is the Kali Mist, which is a foodie’s take on a turkey, bacon, and avocado sandwich. You can’t leave here without getting their signature Rice Krispies Bars (they have every cereal you can think of).

Watch the cliff-jumpers: About 30 minutes from La Valencia is Sunset Cliffs in Ocean Beach. This is a photogenic coastal stop where you can view the caves, walk along the cliffs or watch the cliff-jumpers. About 15 minutes away, head to Mission Bay and stop at Fiesta Island Park. This scenic spot is the ideal place to watch the boats go in and out of the harbor.

Historic and haunted: End the day by dining in Old Town, San Diego. Miguel’s Cocina, one of my favorite Mexican restaurants, is only 10 minutes from Mission Bay. What makes Miguel’s so special is their insanely addictive chips and queso dip that come free of charge. The number one thing to share on the menu is the surf and turf burrito which is a 1 pound take on the classic California burrito. It’s gigantic and so delicious. Their fried ice cream is also epic. Once you’ve finished, take a stroll around the festively adorned streets of Old Town. Some of the rumored haunted places are the Whaley House Museum, Cosmopolitan Hotel & Restaurant, and El Campo Santo Cemetery.

Day 3 – North County (Encinitas, Cardiff, Solana Beach, Del Mar + Torrey Pines)

Where to stay: In the heart of Del Mar is L’Auberge. It features stunning rooms with an ocean view with private stairs to the local beach, and it’s pet-friendly. This destination is about 25 minutes up the coast from La Jolla.

A walk along the beach: On your last day in San Diego, end it by visiting one of the best beaches in the country. North County (my hometown) is a chill, relaxing, and immaculate location that’s often missed when people vacation in San Diego. Get a head start by waking up early (before the beaches get crowded) and take a stroll along the beach in the picture-perfect town of Del Mar.

Breakfast and coffee: 10 minutes away in Solana Beach is a great breakfast spot, called Claire’s on Cedros. They have outdoor seating and most of their dishes include locally sourced ingredients from San Diego county. For example, their coffee comes from Caffe Calabria, the spot I mentioned in North Park. I recommend, for your drink and morning fuel, the lavender honey cortado paired with their beach bowl, which is a fruit-filled acai bowl.

Have a beach day: Once you’ve eaten, you can take a walk down the Cedros strip where there are tons of stores, like Muttropolis (a boutique pet supply store) or Pink Lagoon (women’s clothing). Sightsee at Fletcher Cove which is a 7-minute walk away. This beach is the landmark of Solana Beach and a superb place to take some photos or suntan.

Soar above the coast while paragliding: The next stop is Torrey Pines, right outside of Del Mar, and only about 20 minutes from Solana Beach.

Check out the Torrey Pines Gliderport which will give you a panoramic view of San Diego and you can learn to paraglide or take a tandem flight with an expert. People come from all over to fly here, especially since you’re gliding over a premier part of the California coast.

Take a hike to the beach: Black’s Beach in Torrey Pines is one of my favorite beaches in all of San Diego because of the scenic view of La Jolla from here. You can get your exercise for the day by hiking down the Ho Chi Minh Trail (La Jolla Trail on Google Maps) which will lead you down to the beach. You climb through the cliffs with a full, gorgeous view of the coast. It’s safe and not too difficult of a trek.

Order a sandwich to-go: Board & Brew is the ultimate local spot for some top tier sandwiches. If you’re like me and obsessed with all things avocado, you will be obsessed with the Turkado sub. It is avocado heaven and their special sauce makes it even better. You can take this to-go to eat right down 11th Street where you can overlook the ocean at the train tracks.

Watch the sunset: The grassy viewpoint on top of Swami’s beach is perfect for watching the sun set behind the horizon. If you walk along the shore, you can also see the reefs and look at the sea anemones and little crabs that habitat there.

The 101 strip: Explore Encinitas from Cardiff to Leucadia via the 101. There are a ton of stores like my go-to spiritual home goods boutique, SoulScape. A little further down is my favorite vintage and resale shop, Flashbacks.

Authentic Italian food: Trattoria I Trulli is a couple of blocks down from Swamis on the 101. I’ve still never eaten better Italian food stateside than here. I recommend the Fritto Misto as an appetizer (calamari), the Farfalle alla Vodka con Salmone for your entrée (the best pasta I’ve ever had), and the Strawberry Napoleon for dessert. They decorate the entire restaurant with wine shelves and even wine on the ceilings, so drink as much as your heart desires.

End the night continuing your walk down the 101. You can walk down any cross street, like E Street or F Street, to find the perfect beach viewing point.