San Diego, CA - Jim Flynn's BestWeekends

San Diego, CA

San Diego, CA Overview

As the song goes, “It never rains in California…” and that certainly applies to San Diego. On average there are 266 sunny days in the city and rainfall is less than 12 inches per year. Temperatures average 72 degrees year-round with August and September the warmest at 77 and 78 degrees. It is truly a most delightful climate. This is the September weather we wait for all summer in the East. And they have it all year!

With 1.4mm people it is the 8th largest US city and the second largest in California. It is a perennial Top 10 Most Popular Cities to visit. The city is best known for the San Diego Zoo, quite possibly the best in the world, 1,200 acre multi-attraction Balboa Park, Sea World and the USS Midway Museum. The city is also home to professional baseball’s San Diego Padres whose stadium is downtown in the Gaslight District.

The city is divided into distinct areas;
Historic Little Italy is an area with charming restaurants, cultural events, and year-round street festivals. There are water views, live music, a farmer’s market, and even an Italian-style piazza (visit the Food Hall while you are there).
The East Village is a 130 block section of downtown that is home to Petco Stadium where the Padres play. Once a warehouse district, it is now a thriving area filled with restaurants, cafes, bars and music venues.
Coastal towns in San Diego offer the best of nearby urban living, but at the beach. Pacific Beach is just 15-30 minutes from downtown, but miles away in beach amenities. La Jolla is my favorite section of San Diego. It is a Mediterranean-style village with amazing beaches, towering, rocky cliffs, fantastic restaurants and a wonderful cultural scene. It is also home to the Torrey Pines Gold Course.
North County
Located about 25 miles north of downtown, North County is away from the hustle and bustle of the city, but close enough to enjoy its benefits. Encinitas is the classic California surf town. In fact, it was the inspiration for the Beach Boys, “Surfin USA”. On the north end of Encinitas, Leucadia is a rustic beach community known for its surf culture, secluded beaches and mind blowing sunsets. Carlsbad was named one of the “Happiest Places” in the US by National Geographic Magazine.  It has luxury shopping centers, mineral spas and retreats and golf courses.

When To Go

The climate is delightful year round. August and September are the warmest, but even then, less than 80 degrees on average. December-February is the “rainy” season but usually daily chance of rain is less than 20%.

Getting There

San Diego is accessible from virtually anywhere in the U.S and Canada. It is a 2 hour 20 minute drive from Los Angeles.

Getting Around

Uber and Lyft are plentiful for short distances, but you will want to explore beyond that, so you will need a car.

Things To Do


Torrey Pines Golf Course is the star in this part of the country. With majestic views of the Pacific, it hosts the annual Farmer’s Insurance Open and has hosted the 2018 and 2021 U.S. Open. Maderas Golf Club in Poway is a Troon managed course and a Golf Digest 100 Greatest Public Courses. The Tom Fazio designed Grand Golf Club Del Mar is located at the Fairmont Del Mar and is open only to guests of the resort.


Here’s the best places to run/walk and bike:
Convention Center
This run starts at the Convention Center, exploring the Embarcadero North & South, Seaport Village, Seaport Village, and waterfront park. All along the water.
Balboa Park
65 miles of trails through gardens, groves and sights like the Zoo.
Outside City Proper
Ocean Beach/Sunset Cliffs
Waterside, particularly beautiful at sunset.
La Jolla
Beautiful area, gorgeous homes. Along the water.
Torrey Pines
Torrey Pines, five miles north of La Jolla, is a beautiful State Preserve of 2,000 acres, incorporating a maritime chaparral, the rare Torrey pine, miles of unspoiled beaches, and a lagoon that is vital to migrating seabirds.


HM Landing has been running fishing charters since 1935. They even have a “fish count” to show how many fish were caught each day by each boat.


San Diego Zoo -Considered by many to be the best zoo in the world. A “must see”
Balboa Park – A 1,200 acre urban oasis with gardens, walking paths, theaters and museums. Also visit Balboa Park Explorer for Park passes.
Sea World –  Animal theme park, oceanarium, outside aquarium and marine mammal park
USS Midway – Historical naval aircraft carrier


Another Side of San Diego offers a host of tours from City Tours to Segway Tours, to Bike Tours. Trip Advisor Hall of Fame.
Highly rated Secret Food Tours explores the culinary world of downtown SD.
Adventure RIB (Rigid Inflatable Boats) Rides. Considered the best whale/dolphin watching tour in SD.
Everyday California – La Jolla Sea Cave Kayak Tour. Explore the Seven Sea Caves and paddle through the La Jolla Ecological Reserve in a 90 minute paddling adventure.
Paddle Pub is a 16 passenger, pedal-powered pontoon boat for the ultimate party on the water in Mission Bay. Equipped with a sound system, 12 pedaling stations, a large backbench and party lighting. Tours are 2 hours long, BYOB, and run seven days a week.
The Crazy Tourist recently ran a post called “15 Best SD Beer, Wine and Tequila Tours.

Water Sports

Adventure Water Sports. Mission Bay. Jet skis, boat rentals, kayaks, paddle boards.

Professional Sports

Petco Park in the downtown Gaslight District is home to MLB’s the San Diego Padres.
Want to tour the park? Click here.


The Del Mar Racetrack is one of the great thoroughbred race courses in the country and has hosted the Breeder’s Cup. Season is mid-July-early September and then again in November.


San Diego Theaters (Balboa Theater and Civic Theater) are host to most of the plays, musicals and dance events in San Diego.


Maritime Museum – One of the world’s finest collections of historic sea vessels
San Diego Air & Space Museum – History of flight, from the days of hot-air balloons to the Spirit of St. Louis to today’s space shuttles.
Museum of Contemporary Art San Diego – The region’s foremost forum devoted to the exploration and presentation of the art of our time, presenting works across all media created since 1950.

Art Galleries

Arts District is a unique location filled with nearly 145 galleries, museums, artists, music groups, dance companies, makers, creators, and distinctive dining experiences


There is live music at many of the Gaslight Districts pubs. Here’s a list.
Dizzy’s. This is the place for live jazz in san Diego in an unpretentious and comfortable venue.
Tin Roof- Weeknights feature a mix of acoustic sets, full bands, local & national acts, and more. Weekend nights showcase the country’s best bands.
House of Blues. Part of the 11 venue national chain offering local and national acts in a state-of-the-art facility. Gospel brunch.
Historic Copley Symphony Hall is home to the San Diego Symphony.  Built in 1929, it is regarded as one of the finest music venues on the West Coast
The Rady Shell at Jacob’s Park is the San Diego Symphony’s new $85mm outdoor venue featuring all kinds of music.
San Diego Theater is an independent guide to concerts and musical events of all genres


Here’s a link to the many gambling casinos in San Diego county.


Gator by the Bay – May
San Diego Restaurant Week – January and September
KABOO – Mid September
San Diego International Film Festival – Mid October
Art San Diego – Late October
San Diego Beer Week – Early November
San Diego Bay Food & Wine Festival – Early November
San Diego Jazz Fest – Late November

The Best Of...


Of course, all hotels offer some type of breakfast service, but if you want to branch out, these are great. Morning Glory. Gotta love a place that serves cocktails at breakfast. German pancakes, Souffle pancakes, Born & Raised (steakhouse) Dry Aged Steak and Eggs, Tableside Lobster Omelet and more. Broken Yoke Cafe with multiple locations throughout the area. Betty’s Biscuits and Gravy, Monte Cristo, Hash Skillet, Cali Breakfast Burrito are some of the favorites. Cody’s La Jolla serves a Chicken Biscuit Sandy that is a cheddar scallion biscuit, fried egg, fried chicken, arugula and sausage gravy that is to die for. Also serves cocktails. Try the Lemon-Thyme Spritzer.


One of my favorite lunch spots is Mr. A’s on Fridays. The restaurant sits at the top of a downtown office building and the views from the patio are breathtaking. Last time enjoyed a wonderful Pork Schnitzel with lemon, capers and brown butter. Monello
is a wonderful Italian restaurant with homemade pasta tossed in  a 60lb cheese wheel. Coasterra is a modern Mexican restaurant that sits on the Bay with wonderful views. Jimmy’s American Tavern has indoor and outdoor seating with marina views and offers a casual, tavern menu. George’s at the Cove in La Jolla has stunning views of the cove. Almost doesn’t matter what’s on the menu.


Brockton Villa in La Jolla has sweeping views of the Cove and their Coast Toast, a fluffy, souffle-like French toast with orange zest notes and house-made, beer-brined corned beef with eggs and chive horseradish creme fraiche are worth the visit alone. Snooze has multiple locations and offers 6 types of Bloody Mary, 9 types of “bubbles” and an array of other cocktails. Select from 8 types of “bennies.” breakfast pot pies, killer corned beef hash and all your other favorites. Madison Park is a bit different with a Mediterranean bent to it. How about cinnamon and sugar coated waffle pieces with cream cheese sauce and jalapeno blackberry jam? Or a Blue Dream Mimosa, blue-green spirulina, cold pressed lemonade and ginger?


Michele Parente of the San Diego Union-Tribune literally tried hundreds of burgers in the San Diego area and she declared the In-n-Haut at Juniper & Ivy (get the homage to the famous California fast food chain In-n-Out?) as the best. The burger at Bankers Hill Bar + Restaurant gets strong marks as well.


City Tacos, a fast casual chain, has multiple locations and excellent food. Death by Tequila offers Baja cuisine and a killer tequila bar. It is run by Top Chef Angelo Sosa. Lola 55 is a beautiful taqueria that can be good for a mid-week lunch or a celebration dinner.

Fried Chicken

Fried chicken isn’t something we usually recommend, but the Crack Shack is no usual restaurant. Multiple locations, always a line. Their signature Jidori fried chicken, served with choice of sauces, is not to be missed.


Lots to like at Born & Raised from the stylish main dining room with leather booths and lots of brass to the rooftop, open air bar and dining room to the dry aged steaks and solid, albeit expensive wine list. But what I really loved was the Steak Diane and Beef Wellington, two items not seen on most steakhouse menus.

Oyster Bar

I love the look and feel of Ironside Fish & Oyster in little Italy. Good clam chowder and their Lobster Roll is made with brown butter mayo, chives and crispy shallots. Yum!

Wine Bar

Village Vino! has a nice selection of wines and cheeses, charcuterie, flatbreads and more. Vin de Syrah is a wonderful  subterranean spot in the Gaslamp and Solterra in Leucadia who makes their own wines with grapes from all over California and Valle de Guadalupe, Mexico. They age all of their red wines in predominately French oak barrels for a minimum of 14-24 months depending on the varietal and style of wine that they are looking to produce. Most of their fermentations are done in small open-top fermenters with a variety of hand-selected yeasts that bring complexity to the wines. Currently, in barrel and bottle they have 14 different red varietals, 3 whites, rose’, port, and late harvest wines. Fun place.


When it’s time for cocktails in San Diego, we’re partial to those with a view Like George’s at the Cove in La Jolla or Altitude Sky Lounge in the Gaslamp. There are also great views at Mister A’s and Born & Raised. The Nolan has a rooftop and patio and fire pits. The Pony Room patio at the Rancho Valencia Resort is a wonderful place for drinks and at the end of the day you’re likely to see hot air balloons passing by.

To enjoy the real art of mixology, try Polite Provisions, “Manufacturers of Local Tonics, Elixirs and Cures” and Realm of the 52 Remedies, a true speakeasy with a hidden entrance. Starlight is another favorite that also has good food. Youngblood offers a unique cocktail experience like we’ve never seen before. Reservations are a must at this plush and intimate hideaway where you will enjoy a customized, multi-course cocktail experience.

Craft Beer Bars

San Diego enjoys a well deserved reputation as one of the premier beer producing cities in the country with over 200 breweries and brew pubs. Too many to mention all the good ones, but this will get you started. Encinitas Ale House features 350+ bottles of every type of beer you could want, in addition to 32 beers on tap. Great burgers, too. Blind Lady Ale House has been named to Draft Magazine’s “100 Best Beer Bars in America” list every year since it opened its doors. Fantastic pizza, too. Barrel Republic is the nation’s first self-service craft beer bar. You get a bracelet, pour your own beer and are charged by the ounce. 44 electronic taps. Click here for a guide to all San Diego Craft Beers.

After Dinner Fun

Certainly the above wine and beer bars are an after dinner option. You can also cruise the Gaslamp where virtually every bar has some music.

Other choices: The National Comedy Theatre is an association of theaters that host improv comedy performances from professional and up-and-coming comedians. Started in San Diego. The San Diego House of Blues is a bar and restaurant that serves Southern comfort food with live music and folk art. The Belly Up Tavern in Solana Beach is a great live music venue for known and up and coming performers.

Special Things

Grab a bottle of wine, some cheese and the makings for a campfire. Head to San Elijos State Park and enjoy a glorious sunset. After the sun goes down you are permitted to build a campfire on the beach. Perfect end to a day in San Diego.

Where To Stay

Estancia La Jolla, La Jolla CA

OVERVIEW of Estancia La Jolla

Just north of San Diego lies the upscale enclave of La Jolla (pronounced hoy-a), and within it, Estancia La Jolla Hotel & Spa, a peaceful refuge from the bustle of the city. The impeccably manicured grounds are designed in Spanish hacienda…

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Fairmont Grand Del Mar, Del Mar CA

OVERVIEW of the Fairmont Grand Del Mar

The magnificent 249-room luxury San Diego resort, Fairmont Grand Del Mar,  captures the elegance and comfort of an old-world Mediterranean estate with an enviable Southern California locale. Its design honors the indelible style of visionary architect Addison Mizner (1872-1933)…

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Grand Colonial La Jolla

OVERVIEW of the Grand Colonial La Jolla

La Jolla is our favorite part of San Diego and The Grand Colonial is the ideal base for your activities in the area. The hotel is a wonderful and warm European style boutique hotel steeped in history, but perfectly…

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Lodge at Torrey Pines, La Jolla CA

OVERVIEW of The Lodge at Torrey Pines

Set on 6 1/2 acres beside the famed Torrey Pines Golf Course and overlooking the Pacific Ocean, the Lodge at Torrey Pines is one of the most dramatic settings for a resort in the country. The beautiful Torrey Pines State Park with its beaches,…

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Pendry San Diego

OVERVIEW of Pendry San Diego

In 2017, we stayed at a new hotel called the Sagamore Pendry in Baltimore. It was a new brand of the Montage luxury group of properties. We immediately became big fans because Pendry offered many of the same amenities, same level of…

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Rancho Bernardo, San Diego CA

OVERVIEW of Rancho Bernardo

Nestled amidst the sprawling neighborhoods of San Diego’s coastal mountains, Rancho Bernardo has been awarded the AAA Four Diamond award for 33 years running and has earned the Award of Excellence from Wine Spectator Magazine. It is a cozy and intimate respite just 30 minutes from downtown…

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Rancho Valencia Resort, San Diego CA

OVERVIEW of Rancho Valencia Resort

Set on 45 acres of lush gardens and olive groves, the Mediterranean-inspired Rancho Valencia,  is an all-suite property and recently completed a $30 million renovation including remodeled guest casitas, a brand new restaurant and new bar, completely remodeled meeting space, as…

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Where To Eat

A.R. Valentien

A.R. Valentien was a talented 20th century California artist and is the namesake for the signature restaurant at the Lodge at Torrey Pines in La Jolla. Many of the artist’s works are displayed throughout the restaurant. Serving regional San Diego cuisine, the timbered and elegant restaurant features both indoor and patio dining with views of…

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Addison, at the Fairmont Del Mar Resort, is San Diego’s most acclaimed restaurant earning two Michelin stars, AAA Five Diamond and Forbes Five Star Awards and Wine Spectator’s Grand Award. Chef William Bradley is a Grand Chef of Relais & Chateau and was the winner of the Culinary Master Competition. The formal dining room is…

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Born & Raised

Born & Raised is a fantastic steakhouse opened in 2017 in Little Italy. The $6.5mm project created a 10,000 square foot restaurant with 250 seats that pays homage to the mid-century and art deco eras. Downstairs is classic steakhouse décor with leather booths, wood paneled walls, green marble table tops and lots of brass. Makes…

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George’s at the Cove

I never miss an opportunity to visit George’s at the Cove in La Jolla when I am in San Diego. It’s cliffside location with views of the ocean is nothing short of spectacular. It’s a great spot for lunch, for drinks or for dinner. George’s is actually three restaurants in one, all have great ocean…

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Mister A’s

Wow, inadequately describes the view from Mister A's 12th floor restaurant overlooking the in downtown SD. You’re so high up, planes are actually landing below you at the airport. Whether you are there for lunch (Fridays) or Brunch (Sundays) and sitting on the delightful patio, or for dining in the evening with the City all…

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The Marine Room

Since opening in 1941, The Marine Room in La Jolla, has become renowned for its beachfront location, spectacular sunsets and high tide surf that creates incredible activity right outside your window. In fact, when the tides are right the restaurant offers special High Tide Dinners. All tables are positioned to take advantage of the remarkable…

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