With over 70 miles of beautiful beaches, near-perfect weather year round, and recreational opportunities in spades, happiness is calling in San Diego. This Southern Californian destination is characterized by halcyon days basking in the sun and no immediate sense of urgency. The only disruption to the constant state of bliss is the sound of airplanes flying overhead at all hours of the day, due to the very centrally located San Diego airport. Despite being the eighth largest city in the United States, San Diego is more parts suburbia than it is “traditionally” urban. From Little Italy to La Jolla, Ocean Beach to Pacific Beach, the city is made up of tight-knit neighborhoods, operating as microcosms in the greater San Diego macrocosm. Each neighborhood is lovingly acknowledged by retro signs to announce your arrival. On the table, you’ll find the best Mexican food this side of the border, artfully decorated açaí bowls, craft breweries by the dozen, and the freshest catch of Pacific Rim seafood. If you are in the mood for some surf, sea, and vitamin D, look no further than San Diego. 

✱ BALBOA PARK

1,200 acres of recreational area teeming with gardens, restaurants, walking trails, museums, and even the world famous San Diego Zoo await at this favorite local outing. You can watch free concerts at the Spreckels Organ Pavilion, featuring the world’s largest outdoor organ, explore over 2,100 species of plant life at The Botanical Building, and find new home decor at the Spanish Village Art Center.

TIP: Check out the local events calendar. When I visited in March, the annual Cherry Blossom Watch was taking place in the Japanese Friendship Garden.

✱ LA JOLLA

An affluent neighborhood north of downtown San Diego whose most popular residents aren’t human. Check out La Jolla Cove to stand mere inches away from a congregation of sunbathing marine mammals. FYI— the sea lions are the ones who bark, the seals are the ones who wriggle on their bellies. Do not get too close and be careful as the rocks are slippery.

✱ SUNSET CLIFFS NATURAL PARK

The sight of a sinking sun never gets old from the bluffs of Sunset Cliffs Natural Park, believed to be the best place to watch the sunset in all of San Diego. Your Pacific Ocean sunset will be accompanied by the soundtrack of crashing waves. Bring a picnic blanket as the cliffs are dusty and a sweater as it gets chilly.

TIP: Parking is hard to come by, so order a rideshare and aim to get there 45 minutes before sunset.

✱ LITTLE ITALY

With its charming piazzas, bubbling fountains, chic eateries, and patio cafes, the former fishing district is now San Diego’s trendiest neighborhood. Every Saturday from 8 AM to 2 PM, the Little Italy Mercato Farmer’s Market attracts locals and visitors alike, with over 200 vendors selling the freshest produce, local bounty from sea, homemade goods, and artisanal treats.

✱ TORREY PINES STATE RESERVE

Named after the rare Torrey Pine tree that calls this recreational area home, this 1,500-acre reserve offers everything from sweet hiking trails, to sandy swims, and thrilling surf. Of the 279 California State Parks, only 14 are designated with the “reserve” status, meaning they are conservation areas of great importance and higher restrictions. The Sweet River Hiking Trail is one of the reserve’s more beginner walks, while the Ho Chi Minh Trail is a challenging short trail to the infamous nude beach known as Black’s Beach.

HEADS UP: The Ho Chi Minh Trail is extremely dangerous after a rainfall and you will need to be hands free to navigate the more challenging aspects of the trail. Bring a backpack if you are carrying anything, as well as wear good shoes. The trailhead begins between 9872 and 9882 La Jolla Farms Road and is marked by a silver post tagged in stickers.

✱ CORONADO ISLAND

Ride the curve of Coronado Bay Bridge to Coronado, a callback to retro, coastal kitsch. This island city is known for harboring San Diego’s nicest beaches and the Hollywood favorite (and rumored to be haunted) Hotel Del Coronado. Whether you’re there for ghost sightings or a bike ride on the widest stretch of beach front in the city, make sure you stay for sunset.

✱ MISSION BEACH

Attracting a younger crowd, Mission Beach is a weekend playground for volleyballers, bachelor(ette) celebrations, sunbathers, and spring breakers. Here, you’ll find large helpings of fun with beach bars selling hefty margaritas, vacation rentals for every type of tripgoers, and even Belmont Park, an amusement park with a twenties-era wooden roller coaster and arcade games.

✱ OLD TOWN

You can easily imagine San Diego as a humble Spanish settlement strolling around the district of Old Town. With its fair share of souvenir shops, Mexican restaurants, and historical buildings like the Whaley House (believed to be America’s most haunted house) Old Town is a salute to California’s storied past and Mexican-American heritage.

✱ GASLAMP QUARTER

When native San Diegoans talk about a night out, they’re probably talking about a night out in the Gaslamp Quarter, a 16-block neighborhood named after the 50 gaslamp street lights posted on the sidewalks. The party starts late, so bide your time by catching a bite to eat at one of the many restaurants before hitting up the likes of favorite nightlife spots like Omnia and Atomic.

✱ OCEAN BEACH

This neighborhood of San Diego, known simply as O.B., is the embodiment of San Diego’s surfing soul. The cafes are manned by zen baristas, every establishment is pet friendly, and you’ll find the best homestays in this part of town if you’re highly against big hotel chains.

IF YOU WANT TO KNOW WHAT’S THE BIG DEAL WITH SAN DIEGO’S FISH TACOS

• OSCAR’S MEXICAN SEAFOOD – Fish tacos in San Diego are synonymous to Oscar’s Mexican Food, the most popular proprietor of the Cali-Mex staple. On the menu are two two kinds of fish tacos: a battered fish taco and a smoked fish taco. I came to Oscar’s a fried fish tacos lover and left a fan of smoked fish. While the original Turquoise street location has next-to-no seating, it has way more character than the two other franchise location with its faded mural outside. Order the mixed ceviche (a combo of shrimp and fish) for a refreshing palate cleanser in between each taco, especially if you’re comparing between the smoked and battered fish.
  (703 Turquoise Street in North Pacific Beach)

IF YOU ENJOY AN AL DENTE BOWL OF PASTA

• CESARINA – The first restaurant I visited in San Diego and the last place on my mind. One of Ocean Beach’s newest restaurants, this Italian spot is upscale, yet unpretentious, with jars of fresh citrus and colorful Mediterranean ceramic dinnerware transporting you to the Amalfi coast. The menu is carefully curated and authentically Italian. While there are a number of entrees, the star of the meal was none other than an antipasti, the Polpo Ceci e Rosmarino: lightly seasoned grilled octopus tentacles bursting with so much brightness and depth for such a minimalist dish. The owner is an Italian expat and has successfully brought the simplicity of classic Italian cooking to San Diego .
  (4161 Voltaire Street in Ocean Beach)
• CIVICO 1845 – Sustainability, seasonality, and southern Italian recipes are what you’ll find on the menu at Civico 1845. Everything is made from scratch in house, including the pasta flour, the bread, and even the tomato sauce. Best of all, the restaurant is highly accommodating when it comes to dietary restrictions and serve 100% gluten-free pasta dishes, as well as unrivaled vegan dishes that could convert the staunchest of carnivores. Test that claim by trying the Gnocchi Violetta or the Mushroom “Calamari.”
  (1845 India Street in Little Italy)

IF YOU LOVE A GOOD THEME

• LUCHA LIBRE TACO SHOP – A taco shop dedicated to the infamous masked Mexican wrestlers known as luchadores. The restaurant is exploding with luchador paraphernelia, from figurines to cardboard cutouts, championship belts to eye-catching pop art, all mounted on bubblegum pink walls. This is the very definition of bombastic. They serve both the Cali burrito (ie. a burrito stuffed with french fries) and the regular old burrito we know and love. Pick up a souvenir postcard with a side of horchata.
  (1810 W Washington Street in Old Town)
  
• TRAILER PARK AFTER DARK – A new-ish establishment, this themed bar is glamorizing the trailer life lifestyle. Think: lawn chairs, plastic-covered sofas, milk-crate lighting fixtures, and two airstream trailers you can reserve in advance for a more intimate setting as a party of four or more. While the bar may be slightly insensitive to the mobile home community⁠—waring: if seeing nightly TV dinner specials on the menu will offend you, best skip out⁠—the atmosphere is great for big parties.
  (835 Fifth Ave in Gaslamp Quarter)
  

IF YOU’RE A FAN OF TIKI BARS

• THE GRASS SKIRT – This speakeasy tiki bar pulls all the gimmicky stops (but totally in a good way). The entrance is hidden inside the refrigerator of the faux storefront, Good Time Poke. Once you cross the fake ice cooler threshold, you’ll be led to the main dining room decorated in all things “Polynesian.” The cocktails are as delicious as they are pricey. Unlike other tiki bar restaurants, their food menu actually features Pan Asian sharing plates that are well-prepared and not just Americanized Chinese. Order the Lamb Dan Dan Noodles, you won’t go wrong. Every now and again, the tiki mask backsplash gets flashy with a light show display.
  (910 Grand Ave in Pacific Beach)

IF YOU LOVE KOMBUCHA

• THE TAPSHACK – An actual shack on the corner of Sunset Cliffs and Lotus. There’s an astroturf sitting area (perfect for bringing around pets). The surfboard-shaped menu advertises both kombuchas on tap and cold nitrobrews. There are a number of flavors to choose from that rotate daily, like Guava & Fig and Mango Mojito, so you could easily  try a new flavor every day while on vacation. They also sell Mexican blankets for much cheaper than the souvenir shops on Mission Beach and they are much better quality too. Buy a growler to go and bring it to the beach.
  (2232 Sunset Cliffs Blvd in Ocean Beach)

IF YOU NEED SOMETHING SWEET

• EXTRAORDINARY DESSERTS – When it comes to luxurious desserts, this place takes the cake. Floral flourishes, generous portion sizes, and every dessert you could dream of live in their immaculate display cases. The bakery also has a number of vegan and gluten-free treats that aren’t basic mousses or macarons (the cop outs of the dietary restriction world in my opinion). They even have their own signature chocolate bar line. The lines are out the door every single day so get there right when the shop opens to avoid waiting.
  (1430 Union Street in Little Italy)

IF YOU’RE LOOKING FOR THE FRESHEST FISH

• BLUEWATER BOATHOUSE SEAFOOD GRILL – A stone’s throw away from the Hotel del Coronado is one of San Diego’s finest seafood restaurants, serving classic seafood meals like clam chowder, freshly shucked oysters on ice, and fried calamari. They boast a hyper-local menu and both indoor and outdoor seating, although outdoor seating tends to be reserved well in advance. Don’t worry, you can get gorgeous views of the marina from inside too.
  (1701 Strand Way on Coronado Island)
• FATHOM BISTRO BAIT & TACKLE – Spot the tiny blue outpost on the pier and you’ll know you’ve made it to to Fathom Bistro, the only craft brewery right on the water. The canteen sits no more than 15 patrons at one time (with some outdoor seating) but if its gets too claustrophobic, pop outside for some fresh air. If you enjoy nautical kitsch and sausages, this is the place for you. You can also go fishing right on the pier.
  (1776 Shelter Island Drive in Point Loma)

When it comes to both quality and quantity, San Diego comes out on top as the booziest city in the United States. With over 150 microbreweries to choose from, including the world’s first kombucha bar, there is want for nothing in the alcohol department. Take the guesswork out of the many offerings with this handpicked selection of breweries, beach clubs, and brewpubs.

• JUNESHINE HARD KOMBUCHA – The world’s first hard kombucha bar is in San Diego’s trendy North Park neighborhood serving 6% ABV kombucha. Order up a flight of kombucha to try all their unique flavors like. There are also other breweries in this North Park building. (3052 El Cajon Blvd in North Park)
  
• NOLITA HALL – One of Little Italy’s newest residents, this sophisticated beer hall is European in design, Italian in cuisine, and 100% San Diego in spirit. Don’t let the floor-to-ceiling windows, skylight, and hanging greenery fool you into thinking this place is snobby; they have sports playing on their TVs all day long. (2305 India Street in Little Italy)
  
• MIKKELLER LITTLE ITALY – A cozy and intimate tasting room with no more than ten tables, hailed for its minimalism and collaborations with other local brewers. (2021 India Street in Little Italy)
  

• EPPIG BREWING WATERFRONT BIERGARTEN – Point Loma’s only waterfront biergarten by way of Brooklyn. The Eppig family has been brewing craft beers since 1866, but were forced to close shop during the prohibition. The family business was reborn on the other side of the country 150 years later. Heads up – there is no onsite parking. (2817 Dickens Street in Point Loma)
  
• PACIFIC BEACH SHORE CLUB – The kind of place you love to hate/hate to love. This beachside bar is home to unbeatable drink deals, drawing in a fairly young and raucous crowd so don’t be surprised when you’re battling for a seat out on the deck with fresh-faced collegiates. But if you secure a coveted spot on the patio, soak in the view with a red bull vodka slushie in hand. (4343 Ocean Blvd in Pacfic Beach)
  
• MAVERICKS BEACH CLUB – If you’re looking for an upgrade from PB Shore Club, head to Maverick’s for a good time that isn’t drowned out by blaring music. They have fairly decent brunches, but expect extremely long lines on the weekends. (860 Garnet Ave in Pacific beach)
  
• THE TIN ROOF – The plain jane shotgun shack bar is a rowdy music venue with live acts, as well as a dancefloor powered by American Top 40s hits. Keep the hangover at bay with some tasty bar bites that are served until 11 pm. (401 G St in Gaslamp Quarter)
  
• LA PUERTA – If you’re looking for a chill bite to eat before the party begins in the Gaslamp Quarter, check out La Puerto for margaritas and tacos while admiring a larger-than-life ofrenda dedicated to the 27 Club, famous celebrities who all passed at the age of 27. (560 Fourth Ave in Gaslamp Quarter)
  
• CORONADO BREWING COMPANY – For over twenty years, the Chapman brothers have been serving up their hoppy coastal ales to adoring locals. In the wake of their success, four kid-friendly brewpubs have opened up. But for the original location, head to Coronado Island for solid American grub paired with award-winning beers. (170 Orange Ave on Coronado Island)

Here is a map of all the places mentioned on this guide!

Stay Alfred offers modern apartment rentals in downtown San Diego that are pretty affordable during the off-season, and are all within a walking distance from popular attractions like Little Italy and the Gaslamp Quarter. Some rentals even have their own fitness centers and rooftop lounges. (Rooms starting at $50 per night.)

Found San Diego is a three-star bed and breakfast in Little Italy with 24 private rooms, economy rooms with shared bathrooms, and even shared bunk rooms. While the location is unbeatable, the hotel is also close to freeway and it can get very noisy. They also serve a light breakfast of bread, yogurt, coffee, tea, and juice. (Shared dorms starting at $35, private rooms starting at $70.)

Hotel Z is a fully renovated, 96-room boutique hotel embracing the retro style of the StayPineapple hotel franchise. Keeping on brand, their most popular amenities include free pineapple cupcakes and bright yellow beach cruisers to ride around the Gaslamp Quarter, a great activity if you’re traveling with kids. Guests also cannot stop talking about how comfortable the beds are. (Rooms starting at $140 per night.)

Kimpton Hotel Palomar is a 211-room trendy hotel tower right in the heart of downtown San Diego with a rooftop pool, luxe guest rooms with rainforest showers, and sweeping views of the city skyline in select suites. At their Mexican street food restaurant, Curadero, guests can play vintage arcade games and even order tacos from a late-night drunchies window (drunchies = drunk munchies). And couples take note: they have a special “couples only” soaking tub at their full service spa. (Rooms starting at $209 per night.)

The Pearl Hotel in Point Loma, built in the 1960s, has kept its vintage appeal with its Palm Springs-esque glamour and energy. On-site, you’ll find the award-winning restaurant, Charles + Dinorah, hailed for its contemporary Californian fare, as well as an oyster-shaped salt water pool surrounded by open air cabanas, an outdoor rain shower, and hammocks. They also host poolside movie nights weekly. (Rooms starting at $160 per night)