4 Day Itinerary San Diego, California

I absolutely LOVE Southern California (it’s definitely my favorite part of Cali), but I haven’t had a chance to visit San Diego until now! And after this four day trip I can confirm that SoCal is one of my favorite places in the country. Today I’m sharing my exact 4 day Itinerary of San Diego including how to get around and where to stay plus more restaurant, bar and food recommendations I didn’t get a chance to check out! No matter if you’re a first time visitor like me or a San Diego lover, this guide will help you plan your trip!

San Diego is a city on the Pacific coast of California just north of the Mexico-United States border, known for it’s extensive beaches, laid back attitude and near perfect weather year-round. Tourism is a huge industry in San Diego thanks to attractions such as Balboa Park, the San Diego Zoo, SeaWorld San Diego, Old Town San Diego State Historic Park, the local craft brewing industry and more!

4 Day Itinerary San Diego, CA

While you can easily spend an entire week or more visiting San Diego, after reading through my 4 Day Itinerary you’ll see this is a perfect amount of time to explore multiple neighborhoods in this beautiful West Coast city and get a taste of Southern California life!

Day 1 – Hillcrest, Chula Vista & Coronado

I took the 8am flight out of JFK in New York City and arrived at San Diego International Airport at 11:30am, and let me say the airport is San Diego is SO nice and efficient and easy to navigate. My plane pulled up to the gate at 11:30am on the dot and I was off the plane and outside in departures waiting for my friend, Lauren, to pick me up by 11:35am and I’m not even exaggerating!

Hash House a Go Go

Since I was starving we went right to lunch at Hash House a Go Go in the Hillcrest Neighborhood of San Diego and it is definitely the restaurant you want to go to after a long flight because the portions are HUGE (we could’ve easily split one entrée, but we ordered 2 and they didn’t disappoint)! I highly recommend the Crispy Pork Hash with their famous hand hammered pork tenderloin and the HH Famous Flapjacks (we got banana), both were unbelievable!

After lunch we headed down to Chula Vista and checked into our hotel, The Ramber Motel, which was probably one of the most colorful and Instagrammable hotels I’ve ever been to AND in the perfect location for the night we had planned in Coronado.

Coronado

Coronado is a California resort city on a peninsula in San Diego Bay. It’s filled with incredible beaches, lush parks, one-of a kind boutiques and atmospheric dining so I knew it was a must visit on my first trip to the San Diego area. We drove out to Coronado Island, parked on Orange Ave and walked around exploring all the cute little stores! We loved Wild Dove Boutique, so make sure to pop in there.

You can’t visit Coronado without going to the iconic California beach resort, Hotel del Coronado, and to be honest it’s almost impossible to miss it! Built in 1888 it’s one of the last surviving wooden Victorian beach resorts in the world and the second largest such structure in the United States! With majestic Queen-Anne architecture and soaring red turrets this beachfront hotel is a must visit if you’re in the area.

Hotel del Coronado

I highly suggest getting to Hotel del Coronado about an hour before sunset and grabbing a seat at Sun Deck facing the water! With gorgeous front row views of sunset on the West Coast there is no better place to end your day! There are cozy fire pits available to sit at for larger parties and plenty of other bar stools and tables. Get a pitcher of you’re with friends and plan on having a few drinks, we got the Smokey Sunburn (without mezcal) and it was awesome.

The Henry

After sunset we walked over to The Henry for dinner. Highly recommend making a reservation there because the wait for walk-ins was fairly long! And if you’re lucky enough to get an early dinner reservation you can take advantage of their Happy Hour drink specials available to 6pm (even if you’re sitting at a table)! We ordered (and loved) Roasted Artichoke “Rillettes”, Umami Brussels Sprouts, Spicy Tuna & Crispy Rice and Bolognese. And if you have room, the Warm Croissant Bread Pudding for dessert was to die for! If you find yourself in the area during the day, The Henry also serves breakfast and lunch!

Day 2: North Park & Little Italy

We grabbed coffee (which was delicious) at The Rambler Motel Coffee Shop in the lobby before checking out and headed up to North Park! One of the perks of staying at The Rambler Motel is that you get 50% off Rambler Coffee so definitely take advantage!

North Park Neighborhood

The North Park Neighborhood in San Diego located east of downtown bordering Balboa Park, is filled with coffee shops, craft beer bars, brunch spots, upscale pubs and more! We headed to Dunedin New Zealand Eats, a New Zealand themed spot in a funky space for brunch and it didn’t disappoint. They serve brunch daily and I highly recommend The Cure & Chilaquiles + they do $2 Mimosas & $4 Specialty Mimosas on Saturday & Sunday from 9am-12pm.

After brunch we explored North Park and all the cool stores on University Ave. If you’re in the area you MUST stop in Verbatim Books. It’s San Diego’s largest independent bookstore filled with a curated selection of used and rare books in the coolest space!

Then we spent the rest of the afternoon brewery hopping! I didn’t know it before visiting, but San Diego has the best craft beer scene in the country with 150+ breweries (if you’re looking for it’s East Coast beer loving counterpart I suggest visiting Portland, ME)! We ended up going to Mike Hess (I loved the Grazias Amber Ale, Raspberry Hop Cloud & Lager Del Sur) & Belching Beaver Brewery (I loved the Peanut Butter Milk Stout, PB&J Blonde, Blueberry Muffin Stout & Fall of Troy on Nitro), but so many were recommended to us! If you’re visiting and really in local, craft beer consider spending more time here and visiting some of these, but no matter what brewery (or breweries) you end up at I guarantee you’ll have a great time!

Best Craft Breweries in San Diego:

Little Italy

We checked into our second hotel – Hampton Inn San Diego Downtown (if you’re looking for an inexpensive hotel in San Diego in the best location this is it!) and got ready for dinner in the Little Italy Neighborhood of San Diego. Little Italy is located in the northwest end of Downtown, with India Street running through the heart of it. It’s a chic, pedestrian friendly neighborhood filled with trendy cocktail bars, brewpubs and restaurants. If you were to stay anywhere in San Diego, Little Italy is my recommendation because it’s highly walkable, has so much there and boarders the waterfront.

We had dinner reservations at Barbusa, a Modern Sicilian restaurant in San Diego’s Little Italy. The menu was a mix of pizzas, handmade pastas and seafood dishes plus they had amazing Italian cocktails! The overall vibe of the restaurant was great and it was the perfect place to spend a weekend night. I highly recommend the Sicilian Mule to drink, then the Sicilian Meatballs, Chopped Salad, Gnocchi with Pistachio Pesto & Dolce e Picante Pizza!

After dinner we walked over to Craft & Commerce, a hip gastropub with taxidermy and old books lining the walls and antlers as beer taps. We were lucky enough to grab seats at the bar for an after dinner drink, but you can also make a reservation to eat here. The decor alone makes it worth visiting, but the drinks were also amazing – I got the Rocky Mountain High. But quite possibly the coolest part of this restaurant is the secret tiki bar in the back of it! False Idol is a trendy tiki bar located inside the walk in cooler of Craft & Commerce and 100% worth going to if you can get in! You can make a reservation in advance or put your name on the list at the hostess stand inside Craft & Commerce.

Day 3: Little Italy, Balboa Park & Gaslamp

We started with brunch at Nolita Hall, also in the Little Italy section of San Diego and it was definitely one of the coolest restaurants we went to! They describe themselves as an airy industrial beer hall and with floor to ceiling windows and a huge skylight spanning the entire restaurant that’s a perfect description. They are also located directly under the landing route for San Diego airport and at the bar they have a huge split flap display that announces real time flight information of the planes flying over you which was honestly so cool! We loved the Roasted Broccolini, Egg White Hash & Vanh’s Breakfast (the potato latkes are a must!)

After brunch we walked over to Balboa Park because it’s not a trip to San Diego without visiting it! Balboa Park is a 1200 acre historic urban cultural park just minutes from downtown San Diego that is home to 17 museums, gardens galore and the world-famous San Diego Zoo!

After walking around the park, we headed over to Extraordinary Desserts, a bakery/restaurant created by pastry chef Karen Krasne. We went to their Bankers Hill location just outside of Balboa Park and had the HARDEST TIME choosing what to order because everything looked so amazing. We ended up with a slice of the Gianduia cake and a Cocada and we were not disappointed! This place was highly recommended and if you’re visiting San Diego add it to your must visit list!

Ballast Point Brewery Tasting Room

We stopped by Ballast Point Brewery Tasting Room in Little Italy on the way back to the hotel. There were a bunch of games on and we had time to kill before dinner! I love Ballast Point Sculpin. However, I wanted to try beers that weren’t as easy to get on the East Coast. I ended up loving the Calico Amber, Belgian Bobtail Ring, Blood Orange IPA and High West Victory at Sea Imperial Porter.

Gaslamp Quarter

For dinner, we walked down to the Gaslamp Quarter, a lively downtown neighborhood known for it’s nightlife. We ended up at Rustic Root, a restaurant and rooftop bar with New American Comfort food. So, we were there on a Sunday night. It wasn’t that lively, if you’re looking for more of a party scene in the Gaslamp make sure to go on a Friday or Saturday night. Also, we loved the Firecracker Shrimp, Heirloom Tomato Burrata, Kale Caesar Salad, Charred Broccolini and Mary’s Roasted Half Chicken.

Day 4: La Jolla/Sunset Cliffs

We checked out of the hotel and walked over to Morning Glory, an Instagrammable pink hued eatery, for breakfast. They don’t take reservations. So I suggest getting there early or going during the week. I can confirm the food is definitely worth the wait and just as tasty as it is aesthetic! You MUST order their signature Soufflé Pancakes and we also got the Veggie Benny & Veggie Scramble.

La Jolla

After breakfast we drove up to La Jolla. It’s a hilly seaside area of San Diego County known for it’s rugged coastline. Also, one of the top beach destinations in the world. La Jolla Cove is a small beach surrounded by cliffs and home to hundreds (maybe thousands) of seals, sea lions and other animals!

After getting our fill of seals and sea lions, we walked around the Village of La Jolla before driving down the coast through Pacific Beach and Mission Beach to our final destination, Sunset Cliffs and Point Loma!

Sunset Cliffs

If you’re looking for the best place in San Diego to watch the sunset – Sunset Cliffs is it! Sunset Cliffs is a coastal community in the Point Loma community of San Diego. It’s home to Sunset Cliffs Natural Park. It features dramatic cliff formations and caves and expansive Pacific Ocean views.

And I couldn’t leave Southern California without tacos. Hence, I ended my trips at La Perla Cocina Mexicana before heading to the airport for my red eye flight back to NY. By way of Boston because apparently there’s no longer a red eye to NY).

Recommended Restaurants/Bars in San Diego:

Where to Stay in San Diego

The rambler Motel

• Located in Chula Vista, right off of I-5, so if you plan on being in the car exploring a large portion of San Diego County this is a great option!
• Extremely affordable!!
• Perks include a swimming pool, fire pits, free parking, retro arcade and 50% off at the Rambler Coffee Shop & Snack Bar.
• Very aesethic and Instagrammable!
• We stayed here during a portion of this trip!

Pendry San Diego

• It’s a 5-star boutique hotel located in the Gaslamp district of San Diego. It’s just blocks from the San Diego Convention Center and Petco Park.
• Amenities include rooftop pool with private cabanas, 6 restaurants and bars, 24 hour fitness center, full service spa and more!

Hotel del Coronado

• A Curio Collection by Hilton hotel!
• Quite possibly the most historic hotel in all of Southern California, located on beautiful Coronado Island.
• If you’re looking for more of a laid back, beach vacation this is where you want to stay!

Marriott Marquis San Diego Marina

• Waterfront hotel overlooking in downtown San Diego connected to the convention center.
• Every hotel room has a view of their private marina in San Diego Bay or the city!
• Amenities include a day spa, 24 hour gym and outdoor pool.

Hampton Inn San Diego Downtown

• It is located in the heart of downtown San Diego in the Little Italy neighborhood. It is just a block away from Waterfront Park.
• Free daily breakfast!
• We stayed here during a portion of this trip and I highly suggest staying in the Little Italy area of San Diego if you’re following this guide! It was my favorite area of the city.

PIN my 4 Day Itinerary San Diego, California for LATER:

Looking for more travel itineraries? Check out:

• 2 Days in Boston | What to Do, See & Eat
• 3 Day Itinerary Savannah, GA
• First Time in Chicago: The Perfect 3 Day Itinerary
• A First Timer’s Guide to 3 Colorful Days in Charleston
• Travel Guide: 48 Hours in Newport, Rhode Island