San Diego’s Road Trips

San Diego’s Most Scenic Road Trips

San Diego is a city brimming with stunning destinations. Our miles of breathtaking coastline, unique neighborhoods and can’t-miss attractions often mean it can be tough for prospective sightseers to know where to begin. But sometimes, a journey can be just as appealing as an end point. So if you’re down for a road trip, we have some suggestions for some of the most scenic drives in San Diego.   

The 59-Mile Scenic Drive 

(Photo: @sdsunsetchasers)

The famous 59-Mile Scenic Drive is the jaunt that inspired this post. As one of the most stunning day trips in the city, this route offers drivers glistening coasts and lush landscapes, allowing anyone who navigates it to experience the most magnificent views in San Diego. Whether you have a day or a week to undertake this trek, you won’t want to miss out on the opportunity to experience this adventure — it’s quite possibly the best way to see all of San Diego’s most impressive sights. And if you get lost? Just follow the blue-and-yellow seagull signs that mark each quarter mile! If you are interested in taking the entire trip, here’s a good guide. Otherwise, read on for the highlights. 


Point Loma

(Photo: @anmat_foto)

Start your journey through San Diego’s southern edge — the peninsula known as Point Loma. A variety of unique sights will reveal themselves here, from beach vistas to city scenery. Head to the very tip of Point Loma (a.k.a., the southwestern-most point of the continental U.S.) and watch the gray whale migration during the winter months. While there, make sure to pass through Harbor Island for incredible views of the San Diego Bay, Shelter Island for the docked sport-fishing fleet in the marina (and to pay us a visit at Humphreys SoCAL Dining & Music!), and the famous Cabrillo National Monument


Ocean Beach

(Photo: @crisgarciaphotos)

Head north along the coast from Point Loma and you’ll hit Ocean Beach. On your drive, you’ll pass the stunning Sunset Cliffs. If you have the time, make a pit stop to see them from up close. Once in OB, take some time to walk the pier and enjoy a variety of activities including fishing and birdwatching. If you’re passing through mid-week, don’t miss the Ocean Beach Farmers Market — it’s one of the best in the entire state. 


Mission Bay Park

(Photo: @mbaquaticcenter)

Just a few miles up the shore in shore in Mission Bay, you’ll discover the Mission Bay Aquatic Center. The park features 4,600 acres of water and shoreline and is your one-stop shop for adventure on the Pacific. Spend a few hours here and enjoy water sports including paddleboarding, waterskiing, and kayaking. The area is also one of the most beautiful spots in a city overflowing with them, so grab a few postcard-worthy snapshots before you go. 


Pacific Beach

(Photo: @pacific__beach)

The laid-back community of Pacific Beach is the epitome of SoCal culture, and the ultimate San Diego destination for surfing and sunbathing. In addition to fantastic shopping destinations, world-class dining and a lively nightlife scene, visitors will enjoy impressively memorable ocean views. So slow down, and enjoy the visual splendor. 


La Jolla

(Photo: @joeguayguy)

As “the jewel” of the San Diego metro’s coastline, La Jolla is among the most vibrant communities in the state. La Jolla brings together a mix of fun local color, unique experiences and stunning coastal views. It can be hard to narrow down the top things to do in this area, but you won’t want to miss Mount Soledad, the University of California San Diego campus, or La Jolla Cove.


Old Town 

(Photo: @oldtownsandiego)

Old Town is located on the site of the first European settlement in the state of California, dating back to the late 1700s. Today, Old Town is a fun and eclectic mix of fantastic restaurants, historical locations, park space, shopping, entertainment, and area tours. If you’re feeling peckish, you’ll want to check out our post on can’t-miss dining and drinking destinations in Old Town. Presidio Park — where early missionaries established some of the country’s first churches — is a lush and gorgeous green space that’s the ideal spot for a family picnic.



(Photo: @hillcrestsandiego)

Hillcrest is the center of the LGBTQIA+ community in San Diego and is absolutely overflowing with incredible nightlife. If you want to dance, then you simply need to open your ears and follow the beat. You’ll find a world-class farmers market here, as well as outstanding fashion retail. In need of a little refreshment? Stop in at Hillcrest Brewing Company — “The First Gay Brewery in the World” — and hoist a pint of craft beer. 



(Photo: @markd_avid91)

The perfect place to end your scenic tour of San Diego, the Embarcadero is a hub for maritime history and nautical sights. As you pass through, you’ll see the large bay filled with aircraft carriers, cruise ships, sailboats, and yachts. If you have time to stop and explore, pay a visit to the Maritime Museum of San Diego, the nearby Balboa Park, or make a pit stop at the idyllic beaches of Coronado Island


Humphreys Is the Perfect Road Trip Home Base

Every great road trip needs an origin point, and Humphreys Half Moon Inn is the perfect pin to put in the map. Our great rates, lovely locale and legendarily spot-on service all make us the starting spot of choice for savvy travelers. Check out our Special Offers page to select the San Diego travel package that’s right for you, and we’ll see you soon!