San Diego Trip Planner: Your Guide to the Perfect San Diego Vacation

Ah, San Diego.

Known as “America’s Finest City,” the year-round warm weather, laid-back beach atmosphere, and picturesque ocean views make San Diego a tourist Mecca of the United States. Planning an extended vacation to this magnificent city must be done very carefully in order to get the most out of your stay. If this is your first time in San Diego, you’ll quickly learn that all the options for food, entertainment, accommodations, and everything in between can make your head spin. Regardless of how long you stay, it’s nearly impossible to cover everything.

However, if you plan it out right with our San Diego trip planner, you can experience the best of San Diego and avoid thoughts of; “I wish we did this” or “It would have been nice to see that.”

Here are 5 critical tips to help plan out the perfect long vacation in San Diego.

⇒ Check out these other great vacation destinations in the United States
San Diego sunset
San Diego sunset

1) Consider the Timing

San Diego is one of the most popular tourist destinations in the United States. During the summer months, the streets, beaches, hotels, bars, restaurants, and all the hotspots are going to be packed to the gills. If you don’t mind the crowds or paying top dollar for travel expenses, by all means, plan your stay between May and September. You will be treated to the quintessential Southern California vibes, warm beaches, all sorts of events and festivals, and much, much more.

However, if you prefer smaller crowds and a more “local” experience, there is nothing wrong with traveling to San Diego in the offseason. After all, the weather is sunny and beautiful all year long. Many experts will tell you that the best times to visit San Diego are from March through May or September through October. Travel rates are lower, there are less people, and the weather is great.

In general, wherever you choose to vacation, there are typically two lenses you can choose to see the destination through: the local or the tourist. The time of year is a primary factor differentiating the two. When you are planning, take your time and choose which one you want to see San Diego through.

2) Bring Warm Clothing

One of the biggest mistakes San Diego tourists make is assuming that the weather is always 75 degrees and sunny. While this is more or less true during the daytime, it’s important to remember that San Diego is located on the edge of a desert. This means the temperature will change drastically once the sun goes down. In general, you should plan for a 20 to 30-degree difference in temperature after sunset.

Regardless of what time of year you visit, be sure to pack a sweatshirt/jacket and pants. If you travel in the offseason, the nights are guaranteed to get chilly. Pack your clothing accordingly.

San Diego's downtown
San Diego’s downtown

3) Book Centrally-Located Accommodations

San Diego is huge. This is both a blessing and a curse, depending on how you look at it. There are nearly 3.5 million people in San Diego and the county is spread across 4,526 square miles.

On the bright side, the area is so spread out that there are very few places that are overwhelming in terms of crowds or hustle-and-bustle. The down side is that getting just about anywhere will require a bit of a drive.

When you’re planning out your stay in San Diego, whether you’re staying in a hotel, Airbnb, resort, or anything else, be sure to find accommodations that are near the middle of what your itinerary includes. Unless, of course, you like spending lots of time in the car.

If you want to hit the essential San Diego tourist spots in the city, but also want to check out some fun hikes up North, booking a room in places like Pacific/Mission Beach, Del Mar, or La Jolla are great central locations where you won’t have to worry about airport parking and proximity, long car rides, being far from bars/restaurants, or missing out on any precious beach time.

In San Diego, the location of your accommodation will play a key role in how your trip pans out. While this is true for just about any vacation, it applies to San Diego more than most.


4) Research the Food Scene Beforehand

The United States is widely considered the melting pot of the world. San Diego, is very much a “melting pot” of America. People from all over the country move to America’s Finest City to avoid snowy winters, get a fresh start, or simply live the SoCal lifestyle. As a result, the food scene is one of the best along the west coast.

In addition to a seemingly endless amount of authentic Mexican places, there are all kinds of options for Asian food, Central American, South American, pizza, seafood, BBQ, and much more. You are smart to do your research beforehand and have a handful of eateries picked out before you arrive.

While a list of the best food in San Diego is an article for another day, there are several spots that deserve a mention. If you love seafood, The Fish Market on North Harbor Drive is a must. This San Diego staple is located next to the USS Midway Museum and overlooks the Bay.

In terms of Mexican food, you will likely get a different answer from anyone you talk to. However, one of the best kept secrets is Mariza’s Mexican Food in the Clairemont neighborhood. This small mom and pop eatery has some of the best carne asada in the city. Additionally, their caramel-filled churros are second to none.

For Asian food, definitely take a trip down Convoy Street. There are all kinds of options for authentic Vietnamese, Korean, Chinese, and more.

Awesome food is around every corner in San Diego. Do yourself a favor and conduct some prior research.

San Diego breweries
San Diego breweries

5) Check Out the Many Breweries

No trip to San Diego would be complete without a brewery trip or two. With one of the best craft beer scenes in the country, it would almost be a crime not to try something new. As of 2017, San Diego broke the 200 mark for the number of craft breweries and tasting rooms. This number is on a steady climb and has no signs of slowing down.

If this is your first time in San Diego, there are a handful of breweries that should be on your absolute list. This includes Ballast Point, Stone, Green Flash, Coronado Brewing Company, and Karl Straus. Now, this is just a starting off point; there are MANY more that could be named on this list.

Regardless of how long your San Diego vacation is; you likely won’t be able to try the entire catalogue. However, experiencing the craft beer culture is a must

⇒ Other great craft beer cities to visit are Portland and Seattle

Your Turn

San Diego is a place unlike anywhere else. Within the first few seconds of looking out over the Pacific, you’ll know you made the right choice. The most dangerous part of vacationing in San Diego is you won’t ever want to leave. This is probably why the city is considered a melting pot of the United States.

If a trip to America’s Finest City is in the cards, keep these San Diego trip planner tips in mind to ensure your time here is the best it can possibly be.



Mattie Elsner is a passionate globetrotter and travel writer by profession. When she isn’t on site at exotic locations you can find her blogging for sites like – a leading reservation network and directory for travelers. Learn more about travel and join the fun. ​

San Diego Trip Planner: Your Guide to the Perfect San Diego Vacation

2 thoughts on “San Diego Trip Planner: Your Guide to the Perfect San Diego Vacation

  1. Ryan Biddulph says:

    I would dive into that foodie scene research wise Mattie before heading to SD. I would definitely trip to La Jolla for a little bit. Looks gorgeous and my cousin took a 2 week holiday to that area every year with his fam when he lived in Maricopa, AZ. Fab post.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.