If you’re looking to catch a ride halfway to the stars, then here’s the perfect tour to follow in Tony’s footsteps. It turns out that the places where Tony Bennett sang make a decent sightseeing tour of the city.

Did you know that February 14 is Tony Bennett Day in San Francisco? The fabulous crooner, who passed away in 2023 at 96 years old, gave the city a voice with his 1962 song “I Left My Heart in San Francisco.” A lifelong New Yorker who left an indelible mark on SF. Decades of love between Tony Bennett and San Francisco spawned art installations, celebrations and many a rendition of “I Left My Heart…” And now, the song’s lyrics are immortalized on Cable Car No. 53, anointed as the Tony Bennett Cable Car in a recent ceremony on Nob Hill.

This tour brings you closer to the most celebrated “San Franciscan” to never live in San Francisco.

The Fairmont Hotel’s Venetian Room is where in 1961 Tony first performed “I Left My Heart in San Francisco.” Then a relatively unknown tune, Bennett pulled a feeling out of the song that sent the crowd wild.

Fittingly, The Fairmont has seized every opportunity to honor the singer. An eight-foot statue of open-armed Bennett welcomes visitors to the hotel, and a street sign dubs the stretch of Mason Street in front of the hotel, “Tony Bennett Way.” This storied hotel sits atop the crest of Nob Hill, and is quintessential, pedigree San Francisco. Flags of the world adorn the classical entrance, limos navigate the driveway, and cable cars crawl by. Take afternoon tea with honey harvested from the beehives on the hotel’s rooftop garden and don’t miss the legendary Tonga Room & Hurricane Bar.

Perched atop Nob Hill, Top of the Mark has been a San Francisco icon since 1939. During World War II, it became a poignant military tradition for departing servicemen to toast the Golden Gate Bridge, believing it would ensure their safe return. The bar's "Squadron Bottle" ritual, where service members left a bottle for their comrades, endures today. With its 360-degree panoramic views, guests can admire landmarks like the Golden Gate Bridge, Alcatraz, and the city's skyline, making it a timeless blend of history and breathtaking scenery.

If you’ve ever wondered how cable cars work, the nifty (and free) Cable Car Museum explains and demonstrates it all, steps away from the Fairmont. Far more than a museum, it’s the living powerhouse, repair shop, and storage place of the cable car system and is in full operation, complete with exposed machinery that pulls the cables under San Francisco’s streets. You and your kids will become mesmerized by the massive groaning and vibrating winches as they thread the cable that hauls the cars through a huge figure-eight and back into the system using slack-absorbing tension wheels. Afterward, head over to the Musee Mecanique, a spectacular (and also free) penny arcade museum housing one of the largest privately owned collections of antique coin-operated mechanical musical instruments in the world —160 machines dating back from the 1880s through the present (and they still work!). Show the kids how their pre-Wii parents used to entertain themselves with Grand-Ma Fortune Teller and Laughing “Fat Lady” Sal.

Starting from the Fairmont Hotel, catch the Powell–Mason line cable car down the hill, riding from Powell & California to Filbert. Unfortunately, this route won’t get you onto the Tony Bennett-branded cable car (that one is part of the California line fleet). While you’re riding the cables, you can ponder how “I Left My Heart…” cemented cable cars into modern San Francisco’s identity. At least, the city government thought it did. Bennett was a guest of honor at the 1973 Cable Car Centennial, as well as the celebration for the cars’ reopening in 1984 after systemic rebuilding of the network.

According to CBS News, Bennett’s trips to SF always included a stop in North Beach, the city’s historically Italian neighborhood. He was a regular at a few restaurants in the district, dining on the meat ravioli at Piazza Pellegrini and showing up at the seafood-focused Sotto Mare for a birthday dinner.

If you arrive in North Beach at lunchtime, then do like Tony and order some pasta with a glass of red wine. Luckily, there’s no shortage of great Italian food in the neighborhood. Private event?

If you're feeling like pizza, then stop by Tony’s Pizza Napoletana (different Tony). Tony's is where 13-time World Pizza Champion Tony Gemignani creates his masterpies. Located in San Francisco's Little Italy, you will most certainly wait to eat here, as “No Reservations. No Exceptions,” is a prominent slogan, but it is worth it. All of the ingredients are imported from Napoli, the “Pizza Capital of the World.” Yes, that's a thing. Order the gold-medal winning Cal Italia — asiago, mozzarella, Italian gorgonzola, Croatian sweet fig preserve, Prosciutto di Parma, parmigiano, balsamic reduction, no sauce — and the signature Negroni. Hours are 12pm to 9pm Monday and Tuesday, 12pm to 10pm Wednesday, Thursday and Sunday, 12pm to 11pm Friday and Saturday. tonyspizzanapoletana.com

You might as well rent out the Tony Bennett room at Original Joe’s. We’ve got a theme to stick to, people! Original Joe’s go-to order is an espresso martini and Joe’s chicken parmigiana but newer menu items such as summer vegetable risotto with seared day boat scallops are so very summer in the city.

For two decades, Bennett’s heart was left in Union Square. That is, a heart sculpture that he painted with the Golden Gate Bridge sat in the square as part of the citywide Hearts in SF public art installation. The heart motif was pulled from Bennett’s hit song.

The Fairmont actually snatched the hand-painted heart from the square via a 2023 purchase (look out for it in the hotel lobby on your first leg of the tour). But rest assured, Union Square is not completely heartless. Two heart statues remain, and eager tourists pose with the sculptures for recognizable photo ops.

Aside from the hearts, Union Square was also a venue for at least one free concert by Bennett. And when the pandemic hit in 2020, he led a citywide singalong from home, while a live stream broadcasted a masked performance at the square from singer Mark Robinson.

Tony Bennett has appeared in more San Francisco World Series than the team’s former shortstop Brandon Crawford. Well, kind of.

Tony first performed for the team at the old Candlestick Park’s 1993 home opener, but we’re not cruel enough to make you go all the way to Candlestick. Instead, we’ll start this story with the singer (slash Giants fan) appearing at AT&T Park, now called Oracle Park, where they play “I Left My Heart…” after every home victory.

For the uninitiated: The SF Giants won three world series in five years, rocking Major League Baseball and drawing Tony Bennett back to the Bay. Singing at Game One of the 2010 World Series, the 2012 victory parade and during the seventh inning stretch at 2014’s Game Three, Bennett was there each year.

When visiting Oracle, you can — naturally — watch a Giants game. If you don’t have time for a whole nine innings, then walk around the park’s bay-facing wall to peek through its free viewing windows. Don’t like baseball? Meander the Embarcadero, or knock down some pins at Lucky Strike bowling alley and bar.

Begin at the Ferry Building Marketplace with a locally roasted coffee in hand, then amble north along the sun-sparkled promenade where historic F-Line streetcars clatter by and piers tempt you to pause for skyline photos or a quick peek inside the Exploratorium. Drift at your own pace—dodging joggers, browsing farm-stand snacks, and inhaling briny bay air—until you reach the iconic Cupid’s Span sculpture or Pier 7’s wooden planks for postcard-perfect views. As twilight settles, savor oysters and a craft cocktail while the Bay Bridge’s LED light show ignites, before hopping a streetcar or scooter back the way you came.

Located in the historic San Francisco Ferry Building, Hog Island Oyster serves up fresh shellfish in front of gorgeous views of the bay. Get a mix of West and East Coast oysters to taste the differences, and follow it up with their clam chowder or delectable ceviche, paired with one of their craft cocktails. The line might be long, but it moves fast, and no matter what time you sit down, you're going to get seafood that's fresh off the boat. Stop for a bite to eat at this popular market. Then head towards Crissy Field, and on your way you'll pass the Fort Mason Center for Arts & Culture and the Marina Green (featured in Mrs. Doubtfire).