San Diego Weekend Travel Guide

San Diego weekend getaway guide

San Diego Weekend Travel Guide

I’ve been dreaming of visiting San Diego for a very long time. The endless ocean views and laid-back vibe are both things I don’t always get from Chicago living. It’s true what they say, San Diego is SUPER chill. That’s why I fell in love with this place in only a short 4-day stay. San Diego is the perfect city for a weekend getaway. The following blog post is my San Diego weekend travel guide.

About San Diego, California

San Diego is in the very southern part of California right on the Pacific Ocean. It’s known for its beaches, warm weather, and famous attractions. There is plenty to keep you busy during a weekend in San Diego.

san diego weekend travel guide and tips

Best Time to Visit San Diego

The best times to visit San Diego are just before and just after Summer. During the Summer you have more of a crowd because kids aren’t in school and the hot weather is at its peak. I visited in early January and it was still great. There were very little crowds and it was still warm enough during the day to hang at the beach.

Weather in California

The warmest month with the highest average temp is August at around 77 degrees. The month with the lowest average temp is February at around 63 degrees. During my trip, the days were between high 70’s and low 80’s which was great!

I was surprised at how chilly it gets at night once the sun sets though. I would recommend packing a light coat to wear at night especially if you hang out close to the water for sunset. As soon as that sun dips behind the horizon, you’ll be chilly!

Getting to & Getting around San Diego

The San Diego airport is less than 2 miles from downtown which is very convenient if you’re flying in. I had spent a few days in Los Angeles before coming to San Diego, so I drove down. It’s only a 2-hour drive from LA.

Flights from Chicago were way cheaper into LA than they were into San Diego. If you have a flexible travel schedule and want to save a few hundred dollars, you can always fly into LA instead. Then you can also explore some parts of Los Angeles on your way in or out.

I recommend renting a car during your San Diego weekend getaway. The downtown area is pedestrian-friendly and some of the closer beaches are easy to get to with Uber. However, if you want to visit areas just outside of the city like La Jolla, Encinitas, or Carlsbad then you’ll want to drive yourself. Ubers costs could rack up quickly otherwise.

Where to Stay in San Diego

Grand Hyatt Hotel in San Diego California

I stayed at Manchester Grand Hyatt hotel in downtown San Diego. I absolutely loved this hotel! It’s in a central downtown location just a few steps away from the water. The property is HUGE! I could have stayed at the hotel the whole time and still felt like I was on vacation.

There are two towers of rooms, on-site dining options and multiple pools. There’s an adults-only pool on the 3rd floor terrace and an all-ages pool with hot tubs on the 4th floor terrace. I wrote a complete review of my stay at Grand Hyatt HERE.

The rooftop pool at Grand Hyatt Hotel in San Diego California

If you’re looking for an even more laid-back area to stay in, I loved La Jolla and Coronado Island. La Jolla is a cute surf town just over 10 miles north of downtown. Coronado Island is across the bay from downtown San Diego and gives you that charm of a small town without the bustle of downtown.

Neighborhoods to visit in San Diego

There are so many different neighborhoods in San Diego. I could have spent another week here exploring each one a little bit more. Below are some of my favorites for dining, shopping, relaxing or simply to take photos.  

Balboa Park

Balboa Park is one of San Diego’s more popular tourist sites. It’s close to downtown and is filled with 1,200 acres of outdoor urban park space. It’s also home to the famous San Diego Zoo.

Getting into the park is free but the museums inside will cost you money. During my visit in March 2021, some of the museums were still closed due to COVID. Be sure to check online to see the latest list of openings.

You could easily spend a few hours inside Balboa Park. Even if you don’t visit any museums, there are nice photo spots all around the park.

La Jolla

The adorable beach town of La Jolla is almost as well known as San Diego itself. We went here on a mission to find a “secret swing” but stayed to visit other cute parts of town too.

This “secret swing” is a lesser known photo spot in San Diego, but I promise it’s worth a visit. I read about the “secret swing” in La Jolla a few times but have come to find out there are multiple swings in the area. I’m not sure if there’s even an official location name for each swing.

Here are the directions to the secret swing in San Diego:

  • Type in Discovery Way & La Jolla Shores Drive into your GPS
  • Park your car on the right side of La Jolla Shores Drive just East of the sign for Discovery Way
  • Walk back down the hill (walking towards the west/the water) about 20 steps
  • On your left just past Discovery Way, you’ll see a grassy area that you can walk down into
  • Once you fully enter the grassy area you’ll see a giant tree with the swing hanging on it facing the ocean

South Park

I never would have thought to go to this neighborhood if it weren’t for some cute photos I saw on Instagram. As much as I love “doing things” when I travel, I am also a sucker for cute photo ops. I stopped by 2 locations for just that.

The first place I stopped at is called Native Poppy. It’s an adorable flower shop that also sells greeting cards, trinkets and other gifts. You can purchase pre-made flower bouquets or build your own and pay-by-the-stem. I chose the latter and used my $12 bouquet as a photo prop for the rest of the day.

Café Madeleine is a super cute café with Parisian inspired décor on the outside. When I first drove by there were SO many people dining on the patio and standing around. I decided to come back later after it closed to avoid the crowd. When I came by later, they had already taken the tables and chairs inside but I still appreciated the quick photo-op.

Gaslamp Quarter

The gaslamp quarter sign in San diego california

I didn’t spend as much time in this neighborhood as I wanted to. Even though I had never been to San Diego before this trip, I have heard so much about this lively part of downtown.

I didn’t dine or drink out here, but I did walk through to take some photos. I definitely recommend checking it out. The Gaslamp Quarter is in the heart of downtown so chances are you’ll pass through driving at least once.

University Heights

Sitting under the university heights street sign in San diego california

I’ll admit I also came here strictly for the photo ops. I’m always looking for Instagram worthy locations when I visit new cities. When I saw the University Heights & The Boulevard street signs online before my trip, I knew I had to stop by.

I saw tons of restaurants with outdoor seating on the street where the University Heights sign was at. It may be worth stopping by for a longer visit if you’re hungry or want to grab a drink.

The boulevard sign in university heights san diego california

Little Italy

The little italy street sign in san diego

I absolutely loved the Little Italy neighborhood. This multi block area of downtown was only a 15-minute walk from my hotel. I visited this area at least 3 times during my trip. If you’re driving here there is metered parking along the sides of the road and also a few public parking lots.

We had a delicious Italian dinner here one night that you can read more about in the section below. I also thought it was such a charming area for photos. Don’t miss this neighborhood!

Where to Eat in San Diego

Holy Matcha

The pink floral wall at Holy matcha in downtown san diego

Calling all Matcha lovers! This spot is for you! If you’re not a matcha fan but still love a cute café photo op, you need to stop by. They do also sell pastry items if you want to skip the matcha.

There are 2 locations in San Diego and the one you see pictured here is the downtown location. I’ve heard the other location has a little more greens mixed into the pink florals. This café was perfect for my Spring feed on Instagram!

Davanti Enoteca

This Italian spot in Little Italy came at the recommendation of a friend. It did not disappoint! We sat on the back patio outside and the ambiance of the fire pits made our experience wonderful.

My friend and I split each of our dishes because there were so many menu items we wanted to try. We had the roasted brussels sprouts with an egg on top, the cheese stuffed focaccia bread with honeycomb (omg, so good!) and one of the pasta dishes. They were all amazing, but I don’t think you can go wrong with anything on their menu.

Best Ocean Views in San Diego

What’s a San Diego weekend getaway without plenty of beach time? I find so much peace in just staring out at the ocean. I had to include some of my favorite spots along the water in this blog post.

La Jolla Cove

la jolla cove in san diego california

For as long as I’ve known about San Diego, I’ve known about the famous La Jolla Cove. The cove is protected marine reserve property and is famous for the seals and sea lions. Please do not bother or get too close to the animals. This is their home too. The number of people I saw getting way too close for a selfie made me sad. That part aside, this spot was SO fun and I highly recommend you visit.

Sunset Cliffs

watching sunset at sunset cliffs in san diego california

This was by far my favorite coastline view. What I love about San Diego is that literally dozens of people sit and watch sunset together along the water every night. Maybe this is a normal thing for West Coasters, but it made my Midwest heart so surprised & happy. There were tons of people at sunset cliffs the night we went, it was such a vibe.

Windansea Beach

watching sunset at windansea beach in san diego california

This spot was recommended by our hotel concierge. I was looking forward to an epic sunset the day we went but sadly Mother Nature had other plans. Despite the overcast, I was glad we went. Even with the gloomy sky, people still sat out here in their lawn chairs watching the sky turn dark.

Coronado Beach

hotel del coronado on coronado island in san diego

I recommend saving an afternoon to visit Coronado Island. It’s a quick 15-minute drive across the bridge from downtown. I spent about 2 hours on the Island but wish I saved more time. I briefly mentioned Coronado Island earlier in this blog post and how I loved the laid-back vibe.

Hotel del Coronado is an iconic beach resort on the Island. I saw photos of this hotel on Instagram which prompted me to put the Island on my to-see list in the first place. The beach and hotel property were crowded but not surprisingly for how popular this spot is.

Centennial Park

San diego weekend getaway on coronado island

While you’re on Coronado Island you should make a quick pitstop at Centennial Park. This park is on the opposite facing side from Hotel del Coronado and faces downtown San Diego. A friend of mine from Instagram recommended this park for skyline views. You won’t want to miss it!

Seaport Village

sunset over seaport village in san diego

I stumbled into this area on a quest to watch sunset on the first night in town. I was trying to walk to any spot along the water and wound up finding this cute area filled with shops, galleries and restaurants. Some of the dining options also had front row patio seating along the water.

I absolutely loved my time in San Diego. I can’t wait to go back and explore some of these neighborhoods even more. There are also other surf towns even further north of La Jolla I’d like to see as well. I hope this San Diego weekend travel guide helps you plan your next trip!

Have any questions about the places I talked about in this post? Leave them in the comments below or send me a DM on Instagram.


San Diego Weekend Travel Guide
Article Name
San Diego Weekend Travel Guide
This blog post is your ultimate San Diego weekend travel guide. From beaches to cafes and everything in between, this post has you covered.


  1. Taylor
    May 29, 2021 / 9:11 am

    Ah I love San Diego! I almost moved there before I started my travel blog. Such a great city with so much to do. I would have to say I love La Jolla and Coronado the best. Great guide Jen! 🙂

    • ontheroadwithjen
      May 29, 2021 / 1:10 pm

      Wow I didn’t know you almost moved there. Well, it will always be there waiting for you if you decide to move later in life 🙂 I loved La Jolla too, it was such a nice change of pace from the city. Thanks for stopping by!

  2. May 29, 2021 / 10:06 am

    Great guide and photos! I’m from Los Angeles and love visiting San Diego. It’s just a fun, underrated city.

    • ontheroadwithjen
      May 29, 2021 / 1:10 pm

      That is awesome you’re so close – makes a day trip or weekend trip very easy! Thanks for stopping by!

  3. May 29, 2021 / 10:53 am

    San Diego is probably my favorite US city. I love the parks, the proximity to the ocean and there are so many fun things to do there. You definitely captured some of the reasons I loved my time there so much. I definitely didn’t spend enough time in Little Italy so I’m looking forward to going back soon

    • ontheroadwithjen
      May 29, 2021 / 1:11 pm

      It’s such a well rounded city I can really see why people love to visit and live there! Definitely check out Little Italy next time. There are so many great restaurants and the area is very lively.

  4. May 29, 2021 / 1:56 pm

    I would absolutely love to go to San Diego one day! It’s one city in the states that has been on my list for a while, so thanks for sharing all of these tips!

    • ontheroadwithjen
      May 31, 2021 / 8:49 pm

      I hope you can get there soon. It is such a fun city!

  5. May 29, 2021 / 3:06 pm

    This is a great guide to San Diego! I’m from Phoenix, Arizona, so I’ve spent many weekends in San Diego since it’s such a short drive. I’ll actually be there in a few weekends! I’ve never been to Holy Matcha. I’ll have to check it out! You’ve really captured all the best neighborhoods and scenic spots to visit 🙂 Also, your photos are beautiful!

    • ontheroadwithjen
      May 31, 2021 / 8:50 pm

      That’s great you’re so close by! Have fun on your next visit there! 🙂

  6. June 8, 2021 / 3:41 pm

    Loving all the amazing spots! I am so excited to move there soon and will definitely use your guide!

    • ontheroadwithjen
      June 26, 2021 / 1:12 pm

      I still can’t believe San Diego is your new home. You will love it!

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