San Diego? More like Slay Diego. With year-round sunshine and a breathtaking skyline, this city is the ultimate Summer getaway. Sunny San Diego isn’t just another coastal city – it’s a Navy town with a whole lot of history, adventure and SoCal charm. Whether you’re a foodie, a beach bum – or just here for the ‘Gram: 5 days in San Diego is all you need to fall in love with America’s Finest City.
In my early tweens, I moved continents and ended up living in San Diego for a few years. I can tell you that – without a doubt – there is no place like it. By the time you’ve read this guide, you’ll be wondering if it’s socially acceptable to add “San Diego resident” to your LinkedIn. (Spoiler: It is. Just manifest it.) Let’s dive in!
Best time to visit San Diego
San Diego is basically on permanent vacation mode, but that doesn’t mean every month is created equal. Want to avoid June Gloom (yes, it’s a thing) or dodge the summer tourist stampede?
☀️ Best weather? March – May & September – November. Warm, sunny and basically perfect without the peak-season madness.
🎡 Best for events? July – October is poppin’ with Comic-Con, music festivals and beach parties. It’s chaotic but in a fun, “should I quit my job and move here?” way.
🚫 Worst for crowds? June – August. Tourists. Everywhere. Oh, and say hello to May Gray and June Gloom, San Diego’s version of a seasonal mood swing where the skies look like they haven’t had their morning coffee yet. Clouds tend to clear up around noon, but count on overcast mornings.
Long story short: if you want the best of San Diego without the crowds and overcast mornings, aim for spring or fall.
Check out prices right here:
The Pier 
Sunset in San Diego
Getting around in San Diego
Renting a car
San Diego is like Los Angeles’ chill younger sibling – big enough to have everything you need, but without the traffic-induced existential crisis. Think of it as 120,000 football fields of ocean views, good vibes and a dangerously high chance of you considering a permanent move.
If you’re planning to stay in the Downtown area and just want to hit a few spots, the trolley (yes, that really is what they call the Subway) is a solid option. But let’s be real – San Diego is huge and public transit only goes so far. If you want to explore the beaches, the hidden gems, and all the best views, then renting a car is the way to go.
Pro tip: don’t rent your car at the airport. Instead, check out rental spots closer to the city to save on the airport fees. And if you’re balling on a budget, apps like Turo (Airbnb for cars) can be a game-changer.
Check out prices right here:
Where to park in San Diego
Finding parking in San Diego can be a bit of a mixed bag. You’ll definitely want to avoid the “I’ll just circle the block for 30 minutes” situation, especially in popular areas like the Gaslamp Quarter or Pacific Beach.
Tip #1: Look for metered parking spots (they’re usually not too bad). Download ParkMobile ahead of time so you can pay and extend your time from your phone. It will save you time!
Tip #2: Opt for parking garages near popular attractions to save time, even if it costs a few extra bucks. To really up your parking game, download SpotHero – a lifesaver for booking parking spots in advance.
Tip #3: Most of the spots you’ll check out are located just outside the City Center and have some type of private parking. They’re not always free, but that’s what I call the cost of convenience.
And if all else fails, embrace the San Diego vibe: park a little further out and get your steps in! It’s all part of the adventure.
Where to stay in San Diego
Trying to figure out where to stay in San Diego? Don’t worry, we’ve got you. Here’s the rundown on the best spots to crash, so you can focus on the important stuff: making your friends jealous with your vacation pics.
#1 – Downtown / Gaslamp Quarter: if nightlife, rooftop bars and city vibes are your thing, stay here. The Gaslamp Quarter is home to a buzzing scene with everything from trendy restaurants to nightclubs. You can roll out of bed and straight into the city’s best dining, bars and entertainment. Perfect for first-timers who want to be in the middle of the action, with easy access to museums, shopping and waterfront views
#2 – Mission Beach: If you live for that quintessential SoCal beach vibe, Mission Beach is the place to be. If you’re the type to wake up, hit the beach and just vibe with the ocean breeze, this is for you. Beachy, fun and close to Belmont Park (hello, rollercoaster by the ocean). My personal favorite!
#3 – La Jolla: Bougie but beautiful. This spot has luxe hotels, cliffside views and sea lions that will 100% s(t)eal your heart. It’s the ideal place for a quiet retreat, a sunset beach stroll or indulging in some upscale shopping and dining. Unfortunately, you’ll need a sugar daddy if you want to stay here.
Here are some of my favorite hotels:
5 Days in San Diego: the Ultimate Itinerary
Let’s Rock & Roll
Day 1: Coastal Vibes & Cliffside Views
Nothing says “Welcome to San Diego” like ocean cliffs, sea caves and adorable sunbathing seals. Today is all about soaking up those coastal vibes and getting your first taste of the city’s natural beauty.
MORNING – LA JOLLA
On your first morning, drive down to La Jolla to visit an upscale Seaside neighborhood in San Diego. First things first, it’s pronounced “La HOY-yah”. Messing this up is almost as bad as dubbing Yosemite “Yo-se-might” instead of “Yo-si-mi-tee”. Don’t be that guy.
With that out of the way, you can start your trip on a literal high. Head to Mt. Soledad for a panoramic view of the entire city (bonus points if you make it for sunrise). This place is more than a viewpoint, as it’s known as the most unique veterans memorial in America – honoring Veterans from the revolutionary war to the current war on terror. And it offers a beautiful 360º panorama view.
Next, cruise down to La Jolla Cove, where you’ll meet some of the cutest locals: the seals and sea lions sunbathing on the rocks at The Children’s Pool. Next, stroll through Scripps Park towards La Jolla Cave Store, where you can walk down into a sea cave straight from the shop.
La Jolla is home to some of the most exclusive dining options. But for a casual, beachside meal with no reservations needed, check out Shore Rider. It’s a laid-back spot with great fish tacos, burgers and a solid selection of drinks.
FIND PARKING
Mt. Soledad: Free Private parking – 6905 La Jolla Blvd, La Jolla
La Jolla Cove: On-street parking near 850 Coast Blvd, La Jolla
AFTERNOON – CABRILLO NATIONAL MONUMENT
After lunch, make your way to Cabrillo National Monument. This spot is a triple threat: epic views, tide pools and a side of naval history. The entrance fee is $20 per vehicle, but included with the must-have America The Beautiful National Park Pass. Just take into account the opening hours: 09:00 AM – 05:00 PM.
Drive all the way to the top to visit the Old Point Loma Lighthouse, a beautifully restored 1850s lighthouse sitting high above the bay. It’s basically a time capsule with a view. On a clear day, you can see all the way to Mexico, but the real flex is watching massive Navy ships and submarines glide through the water below – San Diego’s military presence is no joke.
Next, drive down to the tide pools to see colorful sea anemones, tiny crabs, starfish and maybe even an octopus. Just make sure to check the tide schedule: this place is only magical at low tide, otherwise it’s just a lot of wet rocks. Speaking of wet which, please wear good shoes unless you want to dramatically wipe out in front of strangers.
On your way out, take a quiet moment at Fort Rosecrans National Cemetery, a stunning military cemetery perched on the cliffs. It’s peaceful, humbling and offers a view like no other.
FIND PARKING
Cabrillo National Monument: 1800 Cabrillo Memorial Dr, San Diego
Tide Pools: follow the signs down for free private parking
Fort Rosecrans National Cemetery: free on-street parking
EVENING – FOOD!
For a post-Cabrillo bite, head to Liberty Public Market in Liberty Station. It’s a food hall paradise, meaning you can grab a gourmet burger, tacos, sushi or a craft beer – all in one spot. Bonus: no reservations needed, and everyone in your group can eat whatever they want (because we all have that one indecisive friend).
If you’re feeling fancy but still casual, check out Stone Brewing World Bistro & Gardens, right next door – good beer, good vibes and an outdoor patio that feels like a hidden oasis.
FIND PARKING
Liberty Public Market: free open-air parking – 2820 Historic Decatur Rd, San Diego
Statue of Juan Cabrillo Liberty Public Market Fort Rosecrans Cemetery Cabrillo National Monument
Day 2: Ships, Skylines & Seaport Village
Time to swap the flip-flops for decent walking shoes! From historic ships to waterfront strolls, today is all about experiencing San Diego’s city-meets-sea charm.
MORNING – USS MIDWAY MUSEUM
San Diego is a naval city. The harbor isn’t just a place for tourists to gawk at city views while sipping their lattes. It’s a bustling, real-deal naval hub where ships of all shapes and sizes – from battleships to submarines – regularly cruise by.
With that in mind, it’s time to go full Top Gun. Step aboard the USS Midway, a decommissioned aircraft carrier turned museum. It’s massive, immersive, and totally worth the visit (especially if you love fighter jets).
If you’re curious to find out more, check out our review here!
FIND PARKING
USS Midway Pier: Paid private parking ($ 10) – 910 N. Harbor Drive, San Diego
AFTERNOON – SEAPORT VILLAGE
Lunch with a view? Yes, please. Stroll through Seaport Village, an adorable waterfront spot with boutique shops, live street performers and plenty of spots to grab a bite with an ocean breeze.
After lunch, take a short walk over to the Unconditional Surrender Statue (aka the Kissing Statue). This massive sculpture recreates the famous V-J Day kiss photo and is perfect for a quick photo op.
Bonus: The adjacent waterfront area offers incredible views of the bay, and you might even spot some Navy ships passing by.
FIND PARKING
Keep your car parked at the USS Midway lot!
EVENING – SAN DIEGO SKYLINE
For a chef’s kiss skyline shot, take the ferry to Centennial Park in Coronado. The ferry leaves from Broadway Pier right next to the USS Midway and costs around $7 each way. It’s only a 15-minute boat ride but way more fun than sitting in traffic. If you’re driving, the Coronado Bridge gets you there in style, with sweeping views of the city and the navy base below.
Once you’re on the Coronado side, Centennial Park is the perfect place to sit back, relax and watch the city lights dance on the water. Bring a blanket, grab a snack and enjoy a chill night with one of the best views in town. I used to come here all the time after dark and it might just be one of my favorite places in town. This is the move for a dreamy end to your day.
FIND PARKING
Centennial Park: Private parking near 1400-1598 Marine Way, Coronado
Seaport Village The Ferry Landing Centennial Park Seaport Village
Day 3: Animals & Ghosts
Ready for a little bit of everything? From world-famous pandas to a ghost-filled historic district, today is a San Diego sampler platter – with extra tacos on the side.
MORNING & AFTERNOON – SAN DIEGO ZOO
One of the best zoos on the planet (and actually the second-largest in the world). Get there early to see the animals while they’re active. Pro tip: Wear comfy shoes – the zoo is HUGE and you’ll be walking a lot.
Take the free Skyfari Aerial Tram for epic views and to save yourself some steps. If you’re a wildlife fan, consider the backstage tour options to get up close with some of the animals.
FIND PARKING
San Diego Zoo: Free private parking – 2920 Zoo Dr, San Diego
EVENING – OLD TOWN
Ghost stories, Mexican roots, and some A-tier tacos and margaritas. I know we all want to be asleep by 10:00 PM, but this place is worth staying up for.
Old Town is one of the most historic parts of San Diego, with preserved 19th-century buildings, live mariachi bands and endless delicious Mexican food spots. Hit up Café Coyote for massive margaritas and handmade tortillas or Casa De Reyes for live music and a fun athmosphere.
If you’re into spooky vibes, check out the Whaley House, one of the most haunted houses in America.
FIND PARKING
Old Town San Diego: Free private parking (Parking A or Parking F) – Congress St, San Diego
Skyfari at San Diego Zoo Penguin Casa De Reyes Old Town San Diego Sign
Day 4: Beach, baby!
Nothing says “San Diego” like a day of sun, sand and surf. Whether you’re catching waves, catching deals or just catching up on your tan, today is all about embracing your inner beach bum.
MORNING – MORNING SHOPPING
If you’ve got extra room in your suitcase (or just believe in the power of an emergency carry-on), Fashion Valley Mall is your spot. This isn’t your basic mall – it’s an open-air, palm-tree-lined paradise packed with everything from high-end designer stores (Gucci, Prada & Louis Vuitton) to staple SoCal brands (Free People, Vans & Quiksilver).
AFTERNOON – MISSION BEACH
San Diego without a beach day? Absolutely not. Mission Beach is where it’s at – a buzzing boardwalk and plenty of ways to get your feet wet. If you’ve always wanted to channel your inner surfer, there’s no better place. Book a lesson with Pacific Surf School and prepare to wipe out gracefully (or not).
Not a surfer? No problem. This beachfront amusement park has a vintage wooden rollercoaster (the Giant Dipper, built in 1925), carnival games and an oceanfront boardwalk that scream summer nostalgia.
FIND PARKING
Mission Beach: Free private parking next to Belmont Park – Ocean Front Walk, San Diego
EVENING – BONFIRE!
Because nothing says “perfect San Diego day” like ending it with s’mores by the bay #cringe. Mission Bay Park has designated fire pits where you can roast marshmallows, sip on (discreetly hidden) drinks and chill under the stars.
Where to set up:
- Ventura Cove Park: a little park tucked along Mission Bay. It’s more protected from the wind, has a laid-back feel and is perfect if you want a more intimate setting without the big crowds.
- Ski Beach Park: great views, but get there early to claim a pit. Plenty of picnic tables and a large bathroom.
- Crown Point Park: a 5-minute drive from Belmont Park. Tons of fire pits, restrooms and picnic tables. Visually less stunning as the grass is usually very dried out here. But after dark, just as nice!
Pro tip: pick up firewood at Ralphs or Vons beforehand and bring blankets – it gets surprisingly chilly at night! Other essentials include marshmallows, Hershey’s chocolate bars, skewers and Graham crackers.
FIND PARKING
Each of these places have their own, free private parking lot. Just enter their names into your GPS.
Mission Beach Bonfire Mission Bay Hot Coals
Day 5: Borderlands
Your last day in San Diego is a mix of culture, retail therapy and a truly unique spot where the U.S. meets Mexico – literally.
MORNING – BALBOA PARK
Wander through Balboa Park, with its stunning Spanish architecture, museums, and dreamy gardens. It’s giving Europe, but with SoCal weather. If museums are your thing, check out the San Diego Museum of Art or the Natural History Museum.
Not into museums? Check out the Botanical Garden or sit and chill near the fountain. Just strolling around the gorgeous outdoor spaces is worth it. This place isn’t big, but it’s a vibe.
FIND PARKING
Balboa Park: Free private parking – just enter “Balboa Park” into your GPS and follow the signs.
AFTERNOON – LAS AMERICAS OUTLETS
Time to shop ‘til you drop! Las Americas Premium Outlets, located right next to the USA – Mexico border, is the perfect place to score major deals on brands like Nike, Levi’s, and Coach. Prices here tend to be lower than other outlet malls in California, so if you’ve been eyeing a new fit, now’s your chance. Plus, even if you’re not in full shopping mode, it’s a fun place to walk around and people-watch.
FIND PARKING
Free private parking – 4211 Camino De La Plaza, San Diego
LATE AFTERNOON – BORDER FIELD STATE PARK
For a thought-provoking and truly unique end to your trip, visit Friendship Park, where the USA – Mexico border fence extends right into the Pacific Ocean. Located within Border Field State Park, this spot has a deep history: it was originally intended as a place where families separated by the border could meet, talk and even hold hands through the fence.
Today, the area is mostly symbolic, with murals and messages of unity painted across. It’s a powerful way to wrap up your trip, reminding you just how unique and diverse San Diego truly is.
Border Field State Park is constantly patrolled by Border Patrol Officers. If you get to close to the fence, they will intervene. No, you won’t end up in jail but be mindful of their instructions. They’re just doing their job so show them the respect they deserve.
FIND PARKING
Enter “Border Field State Park” and follow the signs.
Balboa Park The US – Mexico Border Spanish Village (Balboa Park)
Day 6 – 7: let’s keep the fun rolling!
If five days just aren’t enough, here are two extra days of adventure. Whether you’re an animal lover or just a big kid at heart, these bonus days will keep the good times going.
DAY 6 – SEAWORLD SAN DIEGO
Before I get cancelled promoting SeaWorld, hear me out. The past decade, laws have gotten much stricter. The shows now focus more on educating visitors of the park instead of relying solely on the animal shows. Of course, you’ll still see dolphins do all sorts of crazy tricks, but in general the animals get a lot more downtime.
Plus, SeaWorld isn’t just about adorable dolphins and massive killer whales anymore – it’s also home to some of San Diego’s best rollercoasters. Start your day with Emperor, California’s tallest and fastest dive coaster, then cool off with a splash-filled ride on Shipwreck Rapids.
DAY 7 – SESAME PLACE (A FUN WATERPARK)
Sesame Place San Diego isn’t just for the little ones – there are actually some solid thrill rides for adrenaline seekers too. If you’re looking to take it easy, Big Bird’s Rambling River is the perfect lazy river to float your worries away. If you want to turn things up a notch, Bert’s Topsy Turvy Tunnels is where it’s at. This enclosed water coaster sends you twisting and splashing through dark tunnels before a final splashdown, making it one of the most thrilling rides in the park. And let’s be real—just because this place is designed for kids doesn’t mean adults can’t have a blast.
FIND PARKING
Mt. Soledad: Free Private parking – 6905 La Jolla Blvd, La Jolla
La Jolla Cove: On-street parking near 850 Coast Blvd, La Jolla
5 Days in San Diego
San Diego serves everything – beaches, city lights, culture, history, and nature all wrapped up in that perfect SoCal package. Whether you’re here for 3, 5 or 7 days, this itinerary makes sure you’ll hit all the right spots.
Now go book that trip!
Ben Voyage, Movie Stars!