San Diego Trip Planner for You San Diego Vacation

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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.

San Diego

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’d done that.” If you want to get right to it, see our post on the top things to do in San Diego.

» Looking for more travel inspiration in the United States? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit. Here are a few more fabulous U.S. Cities to visit.

Tips for Planning a Trip to San Diego

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 hot spots 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.

San Diego makes a great addition to a California road trip, which is perfect for spring or fall.

However, if you prefer smaller crowds and a more “local” experience, there is nothing wrong with traveling to San Diego in the off season. 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.

Find a great hotel in San Diego on

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.

Tour you may enjoy: Tequila, Tacos and Tombstones Culinary Tour of San Diego

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.

There are 219+ breweries and tasting rooms in San Diego. 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

Tour you may enjoy: San Diego Brewery Tour

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

Top San Diego Attractions


Tourist attractions in San Diego are excellent and include many superb beaches, which make San Diego the perfect holiday destination for all ages. Facilities include a number of notable buildings, museums and art galleries, countless must-see sights and family attractions, and a number of large parklands and gardens.

Top attractions include Mission Beach and Pacific Beach, which both offer a range of water sports and coastal walks. Also worth a visit in the city are:

  • The world-famous San Diego Zoo
  • SeaWorld San Diego
  • Museum of San Diego History
  • Museum of Art
  • Cathedral of the Basilica San Diego de Alcala
  • Knott’s Soak water park
  • Legoland California

Also a popular excursion from San Diego is the city of Anaheim, home to the spectacular Disneyland Resort, which can be reached by car, with the journey lasting around 90 minutes.

If you have a few more days to spend, check out these great weekend trips from San Deigo that are also just a short drive away.

Balboa Park

Balboa Park
Balboa Park

San Diego is quite popular for its Balboa Park. The park is spread in 1200 acres and nestles the globally acclaimed Zoo and some wonderful and eminent museums. Balboa Park is also the cultural center of the city. It parades an incredible variety of flora that mesmerizes each and every visitor.

The San Diego Zoo in the park is a home for more than 4000 animals of various species. It is a habitat for some of the most exclusive or rare species of birds and animals on earth.

Besides this Balboa Park is swarming with people because of its fantastic museums. These museums are variously devoted to San Diego’s history, science, art, cars, railroads, mankind etc.

For instance, the San Diego Museum of Art is the largest museum of San Diego that displays the magnum opus of great artists.

While the San Diego Natural history museum presents an exclusive collection of environmental habitats such as desert, ocean and shore habitats.

Beautiful and sparkling gems and minerals can also be seen here.  Apart from these a visit to the Reuben H. Fleet Space Theater and Science Center and the San Diego Aerospace Museum in the Balboa Park is also extremely informative.

For all the aqua lovers the Mission Bay area near the Pacific Ocean is an ideal place. The bay includes 27 miles of Bay Shore beaches and 17 miles of ocean front beaches. It is an amazing picnic spot for the residents as well as the visitors.

Tour you may enjoy: Private Balboa Park Segway Tour

Hiking in San Diego

San Diego hiking trail

The first of the treks worth your time is the beach hike. It is relaxing, easy and will remind you why it is great to visit San Diego. You can start and stop just about anywhere. 

A personal favorite is to head north starting at the beach in front of restaurant row in Cardiff. Depending on how far you want to go, you can just cruise up past Swami’s through Encinitas and up into relaxing Leucadia. The really great thing is you can just pop up off the beach and take in lunch on a patio whenever you feel like it. 

If you are looking more for a hiker’s hike, there are plenty to fit the bill. A trip up the San Diego River, particularly in spring, is candy for the eyes. No, I am not talking about the section of the river down in the city.

Instead, we are looking at the area out by Ramona. This is a 10 mile hike that takes 10 hours or so. It begins at the Inaja Picnic Area or Ramona Oaks Road on the other end. The hike is 10 miles one way, so you either need to have two cars or turn around at some point.

Regardless, you will see waterfalls, hike through canyons, groves of oaks, granite grottos and do some boulder hopping. You will have to exert yourself on this trail, so be warned.

The Gaslamp Quarter

The Gaslamp Quarter in San Diego gives the feel of the 18th century and is occupied by restaurants, clubs and bars. People, who are used to the modern nightlife, will have a unique experience here in the backdrop of 18th century architecture.

La Jolla
La Jolla

La Jolla

From the long white sand of La Jolla Shores to the quiet and relaxing beach off Marine Street, you’ll have plenty to enjoy and find your very own piece of paradise.

La Jolla restaurants are world class, playing host to some of the finest chefs and coming chefs in the entire country.  With its year round growing  season, these chefs have some of the finest products to work their collective magic with – creating some of the best meals you’ll ever taste.


Within the first few seconds of looking out over the Pacific, you’ll know you made the right choice visiting San Diego. The most dangerous part of vacationing in San Diego is you won’t ever want to leave.

>> Find other great United States cities to visit.

Pit it for later!

San Diego Trip Planner
San Diego Trip Planner for You San Diego Vacation

4 thoughts on “San Diego Trip Planner for You 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.

    • Gregg Lorenz says:

      Here are some more ideas for SD. A trip to Ocean Beach to enjoy the eclectic vibes of the “60’s”. Get a burger at Hodad’s or enjoy one of the great local Mexican eateries in OB.

      Go to Sunset Cliffs on Point Loma for a sunset and out to the Point on Point Loma. Take a ride up to the top of Mount Soledad where you can park and view the coastline from above. It’s a beautiful view. Walk Harbor Island in the evening. The lights of the city are amazing on San Diego Bay from there. Park at the ferry landing on Orange Ave in Coronado with some local coffee and watch the boats go by. You get a great view of the city from the ferry landing, which until 1969, was how you got across the bay to Coronado.

      Take a ride on the Horn Blower. It’s a tour of San Diego Bay and wear a canvas brimmed hat. The sun is bright and that one, or two hour ride, will give you a sunburn if you’re uncovered.

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