A San Diego Itinerary for Five Days in the Sun

Five days is, in our opinion, just about enough time to take in the sights and sunshine at the coastal Cali city of San Diego. With our high standards and refined tastes (read: we’re a bit snobby) you know you can trust Plum Guide to create a superb San Diego itinerary to take you through the highlights of the city.

Explore our homes in San Diego.

We think the first day of a holiday should set the tone for the rest, so we’re recommending you start your itinerary in San Diego with a visit to the city’s legendary Balboa Park. It’s one of San Diego’s most famous attractions, and probably the most scenic; no wonder the views from this Plum home on the outskirts of the park are so good. These sprawling gardens cover over 1200 acres and contain 16 museums (at last count) so get your coffee to go from Cafe Bassam and get walking. Discover some prickly characters in the Old Cactus Garden, check out some masterpieces in the San Diego Museum of Art, and read the secrets of strangers in the unusual and intriguing Museum of Us.

For dinner head on to delicious small plates at Little Italy’s Juniper & Ivy, where the ever-changing menu guarantees you’ll be back for a second visit. Finish your first day on your San Diego itinerary with a cocktail on the Fairweather Rooftop Bar as you watch the sun go down over the city skyline.

Explore our homes near Balboa Park.

Feeling peckish? You’re in luck. San Diego is overflowing with trendy street food trucks, stylish pop-ups and chic restaurants, and day two is all about exploring the best of it. Start with a leisurely brunch at Breakfast Republic, a bacon Bloody Mary providing the perfect rocket fuel for an afternoon wandering North Park. This eclectic neighbourhood is filled with bars, cafes and unusual shops – browse for vintage vinyl at the fantastic FIVESPACE or pick up some surf-inspired vintage shirts at The Girl Can’t Help It (which, contrary to the name, sells men’s clothes as well). Indulge your sweet tooth as you walk around with a Nomad Donut, with their daily menu often including unusual flavours like blueberry lavender. But make sure you save room for dinner; the industrial chic interiors of Underbelly might not look particularly comforting, but the steaming bowls of traditional ramen served up here definitely are.

If you love a good chat about hops, San Diego also has a bustling, and very friendly, microbrewery scene. One of the best things to do in San Diego is to try the sheer variety of beers on offer, which have led to the county being dubbed the Capital of Craft. Try the latest release at Modern Times’s Lomaland Fermentorium, which is the archetypal brick-walled hipster microbrewery, or enjoy a sunny afternoon in the beer garden of Border X Brewing sipping on one of their Mexican-influenced beers.

Explore our apartments in San Diego.

After a few days in the city, you’ll be ready to escape to the other must-do on a San Diego itinerary – the beach. There’s plenty of coastline to choose from, but we’d recommend heading up to La Jolla. Spend the morning lounging on Windansea beach – it’s where Andy Warhol shot his film San Diego Surf and though a lot has changed since the 1960s, you can still see plenty of the surfers riding the waves and even have a go yourself, if you think you’ve got the bravery or the balance. Once the grumbling of your stomach starts to rival the noise of the ocean, head towards chic, and cheekily named, The Promiscuous Fork for burgers and quesadillas before you set off for an afternoon of exploration. La Jolla Cove is surrounded by rocky outposts and secretive beaches, and the nearby tide pools are perfect for a quick dip – if you watch out for the crabs, of course. With so much shoreline to take in, we wouldn’t blame you if you can’t tear yourself away as the sun goes down. Luckily, we at Plum have sourced a lofty seaside home or a stunning ocean-view hideaway for you to stay the night. Don’t say we’re not prepared.

Explore our homes in La Jolla.

San Diego is steeped in history, and there’s no better (or easier) way to discover the city’s intriguing past than to put your feet up and let one of the iconic trolleys ferry you from sight to sight. Let the rattling Trolley Tours take you from the (allegedly) haunted Whaley House mansion to the Victorian style streets of the Gaslamp Quarter, with frequent stops throughout the historic Old Town to see where the Spanish settlers first landed on the West Coast.

If all that history has worked up an appetite, hop off at University Avenue and head to local favourite Tacos Libertad for – what else – tacos. These are no ordinary tacos, though; you’ll find fillings like duck confit and octopus among more traditional favourites and best of all, the restaurant donates 100% of the profits to local charities – so you can feel righteous rather than guilty as you order a second helping.

Explore our homes near the Old Town.

If you don’t go to a kitsch boardwalk or a cheesy theme park, is it really even a beach holiday? We say no, and we’re the experts after all. Therefore we give you a free pass to use one day of your San Diego itinerary soaking up the extremely high-brow culture on offer at Belmont Park. This quirky funfair has been here since the Fourth of July in 1925, and the celebratory spirit hasn’t been dulled in the decades since. The Giant Dipper roller coaster is a marvel of engineering – or at least it was when it was first built in (you’ve guessed it) 1925. We’ve got to admit it’s an exhilarating experience, but the faint of heart and queasy of stomach may prefer the gentler delights of the antique reproduction Liberty Carousel or the miniature railway. Finish the afternoon with a stroll on the beach, pop back to your accommodation to freshen up and, if you’re staying in this Plum home, a pre-dinner drink with a view of the ocean. Then it’s off for your final night in San Diego; we think that the local swordfish, charred pork belly and innovative cocktails that put upscale eatery Herb & Wood on the map are just the thing to soothe the bitterness of departure.

Explore our homes in San Diego.

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