San Diego, California

Looking for the best chillin in San Diego? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around San Diego. The detailed guides, photos, and reviews are all submitted by the Outbound community.

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Top Chillin Spots in and near San Diego

  • San Diego, California

    Catch a Sunset at Sunset Cliffs

    4.8
    Sunset Cliffs Natural Park area is a 68-acre park on the western edge of Point Loma. The cliffs overlook the Pacific, creating a great spot to take in the sunset. If you head to the parking lot off of Sunset Cliffs, you can get a great view from Pappy's Point. Try to get there a bit before the su...
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  • San Diego, California

    Picnic at Sunset Cliffs in San Diego

    5.0
    San Diego has so much outdoor adventure to offer! After exploring and playing all day head over to Ocean Beach to catch the sunset with a packed picnic at Sunset Cliffs. The cliffs are pretty vast, but filled with lots of spectators. It can be a bit trafficy getting in and out around sunset so gi...
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  • San Diego, California

    Sunset Cliffs Open Ceiling Cave

    0.5 mi
    Starting from you parking spot on the street you will see it right away. Then look to the right in the small bay--to the right of it you'll see a small place to climb down. There is no rope so be careful when scaling it. Walk south until you hit the reef wall and walk along it until you get aroun...
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  • San Diego, California

    Beach Trail

    5.0
    1.43 mi / 259 ft gain
    I'm stoked for those of you to find this adventure! Torrey Pines is home to a species of tree that is one of the most rare native pines in the United States. Below I have directions on how to get to the trailhead as well as the parking lot to park for the hike. There is a charge to get into the...
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  • Coronado, California

    Explore Bayview Park

    5.0
    Even though I am quite familiar with this spot, I doubt that most San Diegans have sat in the benches at this little park to take in the sunset, sunrise, or spectacular views of downtown San Diego. I'm absolutely positive that most out-of-towners have no idea that this little gem exists. I want t...
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  • La Mesa, California

    Lake Murray Reservoir

    5.0
    6.07 mi / 164 ft gain
    Lake Murray Reservoir provides drinking water to parts of San Diego, and thus is a no swimming lake. This is one of the reasons it is such a great place to photograph!  If you are shooting the sunset, use your weather app to check the time the sun sets, and get to the lake at least 30 minutes pr...
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  • San Diego, California

    Los Penasquitos Canyon Loop

    3.3
    6.77 mi / 131 ft gain
    Los Penasquitos Canyon Loop After about a five minute hike on the trail you will start to enter into Los Penasquitos Canyon. Every section of the trail is different, one minute you are walking next to a stream with trees arching over the trail and another minute you are walking through an open f...
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  • Santee, California

    Cowles Mountain via Big Rock Road

    4.3
    4.32 mi / 1109 ft gain
    Start by plugging 8125 Arlette St, Santee, CA into your GPS. This takes you to Big Rock Park, a convenient parking spot for the Cowles Hike. From here you want to walk through the park, and around the right side of the tennis court. This will take you to the fenced entrance to the hike. Head sout...
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  • Coronado, California

    Coronado Central Beach

    5.0
    Coronado Central Beach in San Diego is a 1.5-mile-long, wide sandy beach set against the backdrop of the iconic Hotel del Coronado. It’s popular for swimming, surfing, sunbathing, and beachcombing. The flat terrain is ideal for skimboarding and walking, attracting families who often spend the ent...
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  • Santee, California

    Cowles Mountain via Big Rock Trail

    4.0
    4.86 mi / 1207 ft gain
    Starting somewhat near sea-level, Cowles Mountain via the Big Rock Trail climbs about 1000 ft in elevation.  This trail is about 5 miles total, out and back.  Arrive at Big Rock park which has good parking.  At the park you will walk to the left of the tennis courts past the limits (the fence) of...
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  • Coronado, California

    Coronado Beach

    4.6
    Photograph the iconic and historic Hotel Del and Coronado Beach on Coronado Island. The Del is a beautiful Victorian resort, which is the second-largest wooden structure in the United States. The Del offers amazing photo opportunities during sunset and during sunrise when it is beautifully backli...
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  • Del Mar, California

    Sunset Seat in Del Mar

    3.8
    Sunset Seat: Del Mar's Iconic Carved Tree Bench & Sunset Destination One of the most picturesque locations to watch a sunset in San Diego is Sunset Seat in Del Mar. An old Torrey Pine has been carved into an artistic bench to sit on while watching the sunset. The cliffs and railroad that run...
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  • San Diego, California

    Explore Chambers Hidden Dam and Waterfall

    4.3
    0.5 mi
    Once you get off on Poway road, turn right onto Sabre Springs Parkway. Take your immediate left onto Creekbridge Road and park right there on the hill. Walk straight down towards the black gate and go down the hill. Turn right on the trail and walk down 1/4 mile to the dam, and another 500 yards ...
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  • San Diego, California

    Cabrillo Sea Cave (CLOSED)

    3.4
    From the park entrance, follow the park road down to the tide pools parking area. From the parking area, follow the trail down to the cliffs, and head north. If it is high tide, this route will be inaccessible, so be sure that you are visiting this area at low tide. Follow the cliff as it wraps a...
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  • San Diego, California

    Explore Cabrillo National Monument

    4.8
    Cabrillo National Monument is named after Juan Rodriguez Cabrillo, the first European explorer to reach America's Wet Coast. There are many knowledgable rangers in the park who are eager to share interesting historical facts.  Activities in the park include hiking: the Bayside Trail offers 2 mile...
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  • San Diego, California

    Bayside Trail

    4.5
    1.99 mi / 397 ft gain
    The Bayside Trail features beautiful spring wild flowers and is accessible year-round. The trail is wide with a few rest stops and benches along the way. The trail is breezy, much cooler than many trails inland, featuring ocean views throughout the duration.  This monument commemorates the landi...
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