San Diego: Where the Great Outdoors Promise the Greatest Escapes

Apr 14, 2021

A blend of breathtaking beaches, hilly terrain and legendarily perfect weather, San Diego is the kind of place where fun-in-the-sun is merely the daily baseline. As for where you take things from there, the sky’s the limit—sometimes literally. Whether you want to propel your adventuring to new heights (picture favorable winds lofting you over the Pacific)—or you’d rather keep things more down to earth—you’ll find no better outdoor rec menu to choose from.

From one of the planet’s prettiest urban hikes to wildlife-rich ocean excursions to flat-out amazing bike rides (emphasis on flat in some cases, for anyone who fears sore quads), alfresco adventures could easily fill up your entire itinerary here. On the other hand, weaving even one or two of them into an otherwise mellow beach vacation will add a whole new level of appreciation for San Diego’s land- and seascapes—to say nothing of the Insta-posting potential. But before you start plotting how you’ll rack up those likes, check out some of our favorite outdoor excursions.

Take a Hike

Between its vast swaths of walkable coastline and varied inland topography, San Diego is a hiker’s happy place. And while the most famous local trails tend to get you out into protected wilderness (more on those in a minute), one of the city’s best kept—and most stunning—secrets is an urban hike called Seven Bridges, aka the Pedestrian Bridge Tour.

Doubling as an intro to the historic enclaves of Balboa Park, Bankers Hill and Hillcrest, this approximately 5.5-mile loop trail begins in the acclaimed Inez Grant Parker Memorial Rose Garden, whose 1600+ flowers dazzle at various points throughout the year, but never more so than in April and May. After a warmup lap around the raised rose beds, you’ll cross the hike’s first bridge toward the San Diego Natural History Museum—and from there, you’ll take in one of the most scenic stretches of Balboa Park: El Prado, home to the famously ornate Spanish Colonial Revival structures built for the 1915 Panama-California Exposition.

Just past the iconic Lily Pond and landmark California Tower, you’ll hit the 1914 Laurel St. Bridge (aka Cabrillo Bridge): the state’s first multiple-arched cantilever bridge, which serves up views of Downtown and the San Diego Zoo as you traverse a wooded canyon. Next comes an astonishing series of historic structures and tucked-away treasures—highlights of which include the 1931 First Avenue Bridge (the city’s lone steel-arch bridge); Maple Canyon (a fairytale-like forested hideout, complete with old wooden houses on stilts); the 1905 wooden trestle Quince Street Bridge (note the sweet Little Free Library at one end); and the 1912 Spruce Street Suspension Bridge (a narrow and gently swaying passage over the dreamy Kate Sessions Canyon).

Eventually, you’ll land on Hillcrest’s buzzing University Avenue, where you may well want to refuel at Bread & Cie’s sidewalk café before you take on the final two bridges: the Vermont Street Bridge, inscribed with quotes that will keep you motivated (“you must do the thing that you think you cannot do,” notes Eleanor Roosevelt, for example) and the 1914 Georgia Street Bridge—a local, state and national landmark with striking perspectives on the North Park neighborhood below.

For a more traditional take on hiking, head to the beloved Torrey Pines State Natural Reserve, a 1,750-acre expanse of surreal wilderness—much of which sits 300 feet above the Pacific along a series of oceanside cliffs. Named for—and dedicated to preserving—the rarest pine species in the US, the reserve is home to 7,000 or so of these (often) wind-sculpted wonders. They live among thousands more indigenous plants here, most notably, the spiky Mojave Yuccas—some of which reach 15 feet, as you’ll find at the appropriately named Yucca Point Overlook (accessible via multiple interlacing trails).

One trail that no floraphile should miss happens to be among the shortest (2/3 mile) and easiest to access: the Guy Fleming Trail, named for the turn-of-the-century naturalist whose work gave rise to the reserve. The loop is adorned with a generous allotment of not only Torrey Pines, but—come peak springtime—some of the area’s showiest wildflowers.

You may well want to take on a series of trails here, because few are longer than a mile, and many intersect. But if you do nothing else, check out the Razor Point Trail (about 1.3 miles out and back) for the sculpted sandstone gorge views and the Beach Trail (about 1.5 miles out and back) for the dramatic, 300-foot descent to the beach. 

For hardcore hikers and/or ‘grammers, however, arguably the bucket-listiest of all local trails is tucked into the inland enclave of Lake Poway. Starting lakeside, then working your way up Mt. Woodson, you’ll traverse nearly four miles of steep, mostly unshaded trail to Potato Chip Rock  (a landmark that isn’t mentioned by name on the signage, so when in doubt, ask along the trail). And while you can take shorter routes to the same spot, none is for the faint of heart or fearful of heights. If you want the iconic shot—that is, of a chip-thin rock jutting out over an abyss while doubling as your pedestal—you’ll need to hop onto (or shimmy up the side of) this fabled ledge sans guardrails.

Thanks to a trick of perspective, most Insta posts would seem to suggest that the “potato chip” is suspended thousands of feet in the air, but in reality, the drop is estimated to be more like 40 feet. Even so, do your loved ones a favor and don’t attempt any of the dangling-off-the-edge poses. Just standing there is impressive enough. And though the hike’s wide-open, boulder-strewn vistas are stunning throughout, the truth is, you’ll appreciate them more on the way back—bucket list item duly checked off, and normal heart rate restored.

Ride the wave

By some accounts, surfing took hold in San Diego when Duke Kahanamoku—widely considered the modern father of the sport—captivated crowds with his 1916 Hawaiian Week promotional demos. Other reports have his fellow Oahuan, George Freeth, dropping into waves before awestruck San Diegans even earlier in the 1900s. Either way, this city has loved the idea of hopping on a board and paddling out into the Pacific for more than a century, and visitors tend to want in on the fun.

Of course, these days, the board-curious have various options—with stand-up paddling offering the lowest possible barrier to entry. If you’re brand new to the SUP scene, consider a lesson on Mission Bay, where you’ll glide across protected, wave-free waters, undisturbed by anything but the occasional duck flotilla. Perhaps unsurprisingly—given such serene conditions—Mission Bay has also become a SUP yoga hotspot (check out Aqua Adventures, for one), so sign up for a session if you’d like to try a whole new take on your downward dog.

Then again, if it’s your actual dog you’d like to see on a board, head to Del Mar’s Dog Beach, where—yes—four-legged-friends are known to accompany their humans, whether for flat-water paddling, or SUP-surfing at the confluence of the San Dieguito River and the Pacific. Either way, newbies both human and canine should do fine.

Beginners who’d rather stick to straight-up surfing, however, should consider La Jolla Shores, where certain breaks are so conducive to learning, you’ll find plenty of instructors in the neighborhood—not least, at the famed Surf Divas.

Another spot in La Jolla—Windansea—is legendary among surfers with more experience, and fans of SoCal surf lore (so much so that Andy Warhol set his San Diego Surf here in 1968). On a side note, if you wonder why the celebrated local surfboard maker Tim Bessell has an entire Warhol-themed body of work, the connection goes all the way back to that film shoot. Point is, Windansea has serious OG cred, with a decades-old eponymous Surf Club, a historic landmark surf shack—and palpable respect for seasoned veterans, both in and out of the occasionally 10-foot waves.

Rock the boat

When you want to get out on the water without actually getting in it, San Diego is just as happy to oblige—for starters, with epic kayaking. The area is teeming with hotspots, but the one not to miss is the La Jolla Ecological Reserve—the ultimate intersection of biodiversity and beauty—where kayak companies such as Everyday California run guided tours for visitors of any experience level (even zero).

After a brief lesson on the beach, where you’ll learn (or re-learn) the basics of kayaking, most of these tours will incorporate the greatest hits of this marine protected area, home to one of the highest concentrations of sea life in the state. Among those you’re likeliest to encounter are the neon orange Garibaldi that dart visibly beneath the surface, pop-up dolphins that love the waves and—come summer—famously docile little leopard sharks that congregate here annually. Don’t be surprised if the odd cormorant or pelican dive-bombs the water alongside you.  

But the star of the show, at least geologically, is the series of seven sea caves that you’ll visit (and maybe even enter, conditions permitting). But whether or not you go in, just paddling past these gorgeous grottos—and hearing about some of the characters and treasures they’ve harbored over the years—is amazing. Go back millennia, and the archeological evidence points to all manner of indigenous activity inside. Go back a century or so, and everyone from bootleggers to cliff divers felt the caves’ pull.

Once you’ve had your fill of the caves, you’ll likely have a chance to swim (in fact, if the water is warm enough as spring gives way to summer, you may well want to consider one of the tours that pairs kayaking with snorkeling among the legendary leopard sharks). And for a final dose of adventure, there’s typically a kayak-surfing primer so you can power your boat back onto the sand. But whether or not you’ve opted to swim or snorkel, you will get wet on these kayaks. So you may want to BYO wetsuit, or rent one from one from your tour operator.

Of course, as even the casual observer might guess from the multitudes of masts around, there’s another kind of boating adventure that’s at least as beloved in San Diego: sailing. Whether you want to spend a weekend learning the basics of the sport, or you already know what you’re doing and you want to captain your own boat, or you’d rather kick back and let someone else take the helm, options abound.

One perennial favorite? Zipping around on Stars & Stripes, i.e., the racing yacht of America’s Cup fame. The fastest sailing tour on San Diego Bay, this three-hour adventure will have you doing everything from grinding winches to raising sails. And yes, you can even take a turn at the helm. If you prefer something slower—and decidedly more romantic—there’s no better city for a guided sunset sail.

Experience the wheel deal

Seeing San Diego from the seat of a bike is one of the most immersive (and inexpensive) experiences to be had here. With countless bike rental and share services around, ever more specialized cycles—from hybrids to electric fat tire scooters—and dozens of gorgeous trails, you’ll never want for variety. But you can’t go wrong with a couple of top spots.

Beginners (as in many sports) should proceed directly to Mission Bay, where 12 miles of flat, mellow and scenic trail await. The route connects no fewer than 10 parks and two wildlife reserves, where the birdlife is particularly epic.  Another fun and easy option in the neighborhood: biking along the Mission Beach boardwalk, where Belmont Park adds a layer of old-timey seaside amusement park vibes to the experience.

If you’re looking for something longer, consider another local favorite: the Bayshore Bikeway, a 24-mile circuit that strings together car-free paths and designated bike lanes across a series of iconic backdrops, not least, the Hotel Del Coronado, where presidents, royals and Hollywood A-Listers have been stealing away since 1888.

Finishing up in downtown San Diego, you’ll have ample opportunity to explore the age-old love between bikers and breweries. Consider Mission Brewery, where the Shipwrecked Double IPA feels extra-celebratory, or Karl Strauss, where—in addition to whatever’s on tap—the beer pretzels are always a good post-ride idea).

Take to the skies

Where prevailing westerly winds meet towering oceanside cliffs, aerial magic ensues—as the legendary Torrey Pines Gliderport has demonstrated for nearly a century. With all manner of historic flight firsts having taken place here, including the 1947 debut of the Pacific Coast Soaring Championship, the site has drawn everyone from Charles Lindbergh to Buddy the Hang-Gliding Dog (of CNN, Animal Planet and People fame). But almost anyone can learn to fly on the spot here, thanks to the gliderport’s paragliding and hang gliding instructional tandem flights. And of course, even if all you want to do is sit back and let the pro do everything for you after the 10-minute, pre-flight 101 course, that’s cool, too. Either way, you’ll soar over this devastatingly beautiful, bluff-bordered stretch of the Pacific for nearly half an hour.

Of course, everything depends on the winds, which come with daily variations, so you can’t ever reserve. Instead, call the office between 9:30 and 10 on the day of your choosing, and the staff will let you know the best time to show up. If there’s anyone in your travel party who’d prefer not to jump off a 350-foot bluff, know that the outdoor Cliff Hanger Café comes with unreal views of the coastline—and some people go just to nosh and spectate as a rainbow of paragliding chutes takes to the skies.

If you’d rather float in a hot air balloon, the skies over Del Mar are the place to go, especially at sunset, when the Pacific, the coastal canyons and pretty much all else looks extra magical in the shimmering light. But beyond all that beauty, the sheer breadth of San Diego's natural playground becomes clear from that vantage point—as does the range of outings it offers.  

One minute, kayakers or surfers may be paddling into view; the next, hikers and bikers may be catching the waning rays from the trails. Point is, this is the kind of place so full of outdoorsy opps, no one—including you—will want to waste a moment of them.

Ready for your own great escape? Check out more outdoor activities and things to do when you visit San Diego.

Editor's note: Funded in part by City of San Diego Tourism Marketing District Assessment Funds. Be sure to check websites of the attractions and businesses listed here prior to your visit to ensure you have the latest information on ways to visit safely.

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