It’s possible to see quite a bit of San Diego in only a weekend when strategically based. That’s exactly what a friend of mine from up north and I did recently on a long-overdue girls’ trip that was a staycation for me, vacation for her.

This girls’ trip was made possible thanks to Wyndham Rewards. With the Wyndham Rewards program, 15,000 points get you a free night at more than 7,800 hotels worldwide—there are 30+ locations right here in San Diego!

Using the Wyndham Rewards mobile app, I was able to redeem my points in a matter of minutes. I’m used to redeeming miles on airlines with much hassle attached, and there was none here. A confirmation landed in my inbox within seconds.

It’s not often that I get to explore downtown San Diego for long stretches of time, so I was excited to play tourist in my own town. Our relaxed itinerary was easy to execute because of  Wyndham San Diego Bayside’s location on the Embarcadero, within walking distance to many of San Diego’s best restaurants, shopping, and attractions in my favorite San Diego neighborhood Little Italy.

My goal was to allow for loads of conversation, a jaunt into my scenic neighborhood, a little bit of sightseeing, as well as plenty of food and wine along the way. I’m sharing what we did below with you as an example of things to do in San Diego when a few days is all you have, and definitely check out @WyndhamRewards on Instagram to see more.

Day 1: Check-in, Dinner in Little Italy, Bay Views for Miles

Sunset view from Wyndham San Diego Bayside

With Wyndham Rewards to spend, I booked the hotel (only 15,000 points per night) in a matter of minutes. I’m used to redeeming miles on airlines with much hassle attached and there was none here. A confirmation landed in my inbox within seconds.

You can reach Wyndham San Diego Bayside from the plane’s door in well less than 30 minutes because it’s only 2.5 miles from San Diego International Airport (there is a free shuttle). I can’t emphasize enough what a good location this is. In addition to Little Italy, Maritime Museum of San Diego, USS Midway Museum (a must-see), cruise port and bayside boardwalk are right below the hotel.

The new Waterfront Park with water features kids can play in, loads of grassy space to kick a ball around and even outdoor movies on select summer nights is here, too. It’s possible to walk to the Gaslamp and even the convention center. Foodies rejoice because this is a prime position for the best eats in San Diego. Yes, we have a flourishing food scene here!

Check-in was a breeze. I’d highly, highly recommend that you opt for a bay view room as there’s nothing like a glass of wine on the balcony at the end of a long day. We’d been upgraded to a suite with a huge sitting room, bar and dining area decked out in pretty contemporary decor that would be great for entertaining so rest assured the hotel has options for those who want more space and luxury.

San Diego is home to almost 100 craft breweries (a few within walking distance), which is a big reason why people come, so the hotel put together a sampler of suds from popular San Diego breweries in addition to a fantastic cheese plate as a thoughtful welcome amenity. What a cool way to kick-off a Friday evening!

I’d made a dinner reservation at one of Little Italy’s popular restaurants that I hadn’t been to yet. It’s about a 10-minute walk to the heart of this fun neighborhood, a former tuna fishing village home to Italian immigrants now an urban hotspot that buzzes with energy on the weekends especially.

As expected, the uber-cool restaurant was packed when we arrived perhaps because of its award-winning seafood, including one of the best lobster rolls I’ve EVER eaten. It’s 1 lb of meat stuffed into a housemade butter brioche. At the server’s recommendation, we both ordered it, in addition to crab cakes and a fresh oyster starter.

With just a tad bit of room left after a lengthy meal, the futuristic build-your-own dessert place we’d passed along the way lured us in. Flavored meringue covering gelato, a layer of cake and some sauce over dry ice made for quite the presentation. Crack the meringue with a spoon and have at it. See what I mean about San Diego being a destination for foodies?

Do you know what else lured us in? A nearby artisan market where we picked up some fantastic wine and snacks for stargazing on the balcony. You see, the boardwalk below the hotel and bay view is full of activity even in the evening with pedicabs decked out in neon lights, boats cruising the harbor and people milling about.

Speaking of markets, the Saturday Farmer’s Market in Little Italy is one of the best in San Diego.

Day 2: A Full Day of Playing Tourist and Dinner In

So, *maybe* we went to bed a little too late because it was a slow-moving morning kickstarted by the fact that I’d booked a tour of downtown via these crazy little car/go-carts that happen to be street-legal as long as you don’t take them on the freeway or exceed 20mph.

After a quick grab-and-go breakfast at the Wyndham San Diego Bayside morning coffee stand, we were off. Pick up point for the car was also about a 10-minute walk from the hotel. Let’s just say this tour made for a ton of laughs… at us, too. It was super fun to drive!

Take a tour of downtown San Diego in a crazy yellow car!

The car provides directions and fun facts about local sights through its radio. We chose the Gaslamp tour which wound from Little Italy, around the Embarcadero, passed the Convention Center and Petco Park and through the Gaslamp to Banker’s Hill over the course of about an hour though you can stop and linger if you like.

Alternatively—which I think we’ll do next time—there are mini speed boats you can drive in the bay and see some of the same sights from the water. How cool is that? Plus, you can rent bikes and Segways at the hotel.

After returning the car, it was time to head to Seaport Village and its new shopping and entertainment zone called The Headquarters, named so because it’s a converted jail.

Seaport Village borders the bay and, yes, it’s scenic though a little touristy. I think it’s a must-visit if you’re based nearby because there are cute shops, street performers, good places to eat (we choose an old-school seafood spot), a carousel and an upbeat vibe. We even had a hilarious caricature drawn.

The "Unconditional Surrender" statue in San Diego

Walking back to Wyndham San Diego Bayside along the water from here is incredibly scenic, passing famous points of interest like our gigantic Unconditional Surrender statue, the USS Midway Museum (once the largest aircraft carrier in the US Navy), street performers (including an epic Tom Cruise impersonator dressed up in Top Gun garb and Chewbacca), great spots to stop and have a drink and the cruise port.

Feeling the ramifications of a late-night, a power nap came next which morphed into, “Why don’t we take advantage of this beautiful room and order in?” This is also why a location next to Little Italy is key… you can dial up some of the city’s best pizza in a jiffy (and wine through room service). Unbeknownst to us, a Little Italy-themed amenity, a perfect happy hour snack, was on its way.

We even lucked out with a viewing of two separate fireworks shows straight from the comfort of the hotel balcony.

Day 3: Fish Tacos, La Jolla Cove and Departure

San Diego has 70 miles of coastline that one must take advantage of in any season. La Jolla is home to a marine-rich underwater park, a reason why many kayak, snorkel, SUP, and dive here. Want to learn to surf? La Jolla Shores beach is the place.

My favorite spot for lunch is in La Jolla — George’s Ocean Terrace. It represents everything about the San Diego lifestyle that I love with a giant open-air patio, spectacular ocean views over La Jolla Cove, great drinks, and some of the city’s best fish tacos, a dish we’re famous for.

We took a leisurely walk on the beach below—where the resident La Jolla seals and sea lions are mesmerizing to watch play, nap, swim, and snuggle up with each other—is always recommended.

You could spend a whole day in La Jolla, browsing shops in the Village, hitting the modern art museum and enjoying al fresco cocktails. That’s pretty much how we ended the trip after a quick stop at my house for a drink with my husband.

Before we knew it, my friend needed to head back to the airport. Time flies when you’re having fun. Life gets busy and it’s so nice to catch up with old friends without the distraction of work, kids and errands.

I truly believe that San Diego is the perfect place to spend a weekend for any type of traveler. We have adventure sports, more water activities than you can handle in one vacation, world-class theme parks, fantastic cuisine, some of the world’s best craft beer and year-round sunshine.

What would you do with 48 hours in San Diego?

When strategically-based, it's possible to see quite a bit of San Diego in just a weekend.
When strategically-based, it's possible to see quite a bit of San Diego in just a weekend.

Katie Dillon is the managing editor of La Jolla Mom. She helps readers plan San Diego vacations through her hotel expertise (that stems from living in a Four Seasons hotel) and local connections. Readers have access to exclusive discounts on theme park tickets (like Disneyland and San Diego Zoo) and perks at luxury hotels worldwide through her. She also shares insider tips for visiting major cities worldwide, like Hong Kong, London, Paris, and Shanghai, that her family has either lived in or visits regularly (or both).

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  1. I’m glad that you were able to squeeze in those activities during your 48 hours stay in San Diego! Good job.

    1. In Little Italy, we went to Ironside and in La Jolla it was George’s Ocean Terrace. I would highly recommend both. In Little Italy, we also like Bracero, Crack Shack (very casual… order at a window), Juniper and Ivy. In La Jolla, I would also recommend Whisknladle, NINE-TEN, Marine Room and Brockton Villa (breakfast).