San Francisco Romantic Getaway

San Francisco is a city where you can spend your morning wandering through fog-shrouded hills and your evening clinking glasses under glittering chandeliers. When my wife and I arrived for a romantic weekend in early October, the air was warm and the skies were blue in a way that San Francisco is not known for.

Our base for this getaway was The Clift Royal Sonesta Hotel, a property that balances historic elegance with contemporary flair. Just a block from Union Square, it’s a place where you can easily explore on foot yet retreat into quiet comfort at the end of the day. So once we got out of San Francisco traffic, we could relax into the weekend.

Staying at The Clift Royal Sonesta Hotel

The Clift Royal Sonesta Hotel first opened in 1915 for the Panama-Pacific International Exposition, a world’s fair that celebrated both the completion of the Panama Canal and San Francisco’s remarkable recovery from the 1906 earthquake. Designer Philippe Starck reimagined the interiors, mixing sleek modern furniture with touches that nod to the city’s past.

The first thing I noticed when I stepped into the lobby was a gigantic chair. Between the chair and a large painting of a seal with a crown, the lobby set the tone for a hotel that doesn’t take itself too seriously, even as it maintains a sense of luxury.

We had booked a Junior Suite, which faced the interior courtyard. When checking in, the front desk asked whether we preferred a quiet room or one with a city view. We opted for quiet, and the choice paid off. Our suite was comfortable, with plush bedding, a spacious sitting area, and a modern bathroom stocked with luxury amenities, including a makeup table.

The hotel doesn’t have parking on site, but a convenient garage is located on the same block at Mason and O’Farrell. You can also rent or return a car from Enterprise, National, Alamo, or Hertz there. Given the city’s compact size and robust public transit, we left our car there for the weekend and explored on foot. If someplace is too far to walk, you can also try one of the many driverless Waymo cars that you will see navigating the traffic.

The Clift’s location proved ideal for our plans. The theaters of Geary Street were just a short stroll away, as were dozens of restaurants representing every corner of the culinary world. Union Square sparkled with shop windows and buskers, and the Powell Street cable car stop was just down the hill. Everything we needed was within walking distance.

Dining for Two

San Francisco’s dining scene is legendary, and part of the fun of a romantic weekend is choosing the right mix of ambiance, flavor, and neighborhood charm.

We opted for Mexican food at nearby Matador, a lively spot known for its bold flavors and artful cocktails. We were surprised we could get in without a reservation, but the restaurant is larger than it looks. My wife tried the signature margaritas, and we ordered tacos and enchiladas.

We opted for dessert at PLS on Post. The PLS stands for Peace Love Soul, and the ambience is red brick and psychedelic rock posters. The menu has smash burgers, but we stopped for one of the “groovy” shakes that I had seen online. The CHOCO-NUT ($14) features peanut butter, Reese’s peanut butter cups, Reese’s pieces, crushed peanuts, and chocolate syrup. You can also add an optional shot of Skrewball peanut butter whiskey. 

From the hotel, it is about a 15-minute walk to Chinatown’s restaurants or a 20-minute walk to the Italian restaurants of North Beach. 

Il Casaro Pizzaria

A Taste of History: The North Beach Food Tour

To experience North Beach beyond dinner, we joined a North Beach Food Tasting and Cultural Walking Tour booked through Viator. The tour began at 11:00, and our guide immediately set the tone by explaining how the neighborhood became San Francisco’s Little Italy. Immigrants arrived here in waves during the early 20th century, bringing their recipes, traditions, and a sense of community that still shapes the area today.

Over the next few hours, we strolled past Italian bakeries, old churches, and corner cafés that felt like they had stories to tell. At each stop, we sampled something new: fresh focaccia from a family-owned bakery, sandwiches from a renowned deli, Napoli-style pizza, Rome-style pasta, biscotti, and gelato. (See my review of the North Beach Walking Food Tour in San Francisco).

Our guide shared anecdotes about the Beat Generation writers who once filled the bars and coffeehouses with their ideas, and we paused outside City Lights Bookstore, the literary heart of the movement.

The tour wasn’t just about food; it was about understanding how the city’s character evolved through its neighborhoods. At one point, we stood near Saints Peter and Paul Church, where generations of Italian families had celebrated weddings and festivals, including local boy Joe DiMaggio.

Modern murals and boutique cafés hinted at how San Francisco continually reinvents itself without forgetting its past.

By the end of the tour, we were pleasantly full but not so full that we didn’t stop by Stella Pastry for more cookies for later. A food tour is a great date experience, even for a long-married couple like us. Exploring, learning, and eating through a city with new friends is always a good choice.

Curtain Call: A Night at the Theatre

Although we didn’t see a show this time, we walked past the historic theaters on Geary Street and made a note to plan ahead next visit. Both A.C.T. (American Conservatory Theater) and The Curran Theatre offer performances that combine top-notch production values with intimate settings. The theaters themselves are part of San Francisco’s heritage, with ornate facades and plush interiors that harken back to the golden age of live performance.

If you do plan to attend, it’s wise to book tickets in advance, especially for weekend performances. Dress codes are flexible, but many locals still treat a night at the theater as an occasion to look their best. After the curtain falls, nearby bars and lounges offer perfect spots for a nightcap.

Cocktails and History in the Redwood Room

The Clift’s own Redwood Room is a fitting choice for ending the evening in style. It was voted #1 by USA Today Ten Best for Best Nightlife in San Francisco.

The redwood paneled walls are made from a single tree, and they exude warmth. The dim lighting seems designed for assignations. We stopped for a classic whiskey cocktail and a glass of wine. After eating through the afternoon, we had a light dinner of some of the appetizers, like the lamb lolipops and the 

Breakfast In

On our second morning, we kept things simple. We ate at Fredericks in the hotel, which is a busy and bright breakfast spot. My wife ordered the waffles while I enjoyed the option of a California Shakshuka. It is not often that I get the option to have this tasty dish that I first discovered in Israel.

Golden Gate Bridge from Baker Beach

Exploring Beyond the Obvious

While our weekend focused on food and culture, San Francisco offers no shortage of romantic diversions. Couples with extra time might consider a walk along Crissy Field, where the Golden Gate Bridge looms majestically over the bay.

Palace of Fine Arts

The Palace of Fine Arts, built for the same 1915 exposition that launched The Clift, provides a serene setting for photos or quiet reflection. As the sun sets, head to Twin Peaks for panoramic views of the city lights, or to Baker Beach for a dramatic sunset framed by the bridge.

If you prefer something more quintessentially San Francisco, hop on a cable car at Powell Street. The ride down to Fisherman’s Wharf is both nostalgic and scenic, clattering over hills that reveal glimpses of the bay. While Fisherman’s Wharf can be crowded, a short detour to Ghirardelli Square rewards you with chocolate, sea views, and a bit of whimsy.

See also:

• Exploring the Presidio of San Francisco: Nature, History, and Adventure at the Edge of the City
• Weekend Getaways in the Bay Area – San Francisco
• San Francisco Hidden Gems – The Other Places to See

author and wife at Union Square

Practical Tips for a Romantic Weekend

When to Go: San Francisco’s mild climate makes it a year-round destination, but September and early October are ideal. The days are warmer, the skies are clearer, and the summer fog often lifts. Spring and fall generally offer pleasant but cool weather, while winter brings fewer crowds but rain.

Getting Around: Parking can be expensive and scarce, so walking, rideshares, and public transit are the easiest options. BART and Caltrain connect you with the rest of the Bay Area. The Muni buses and trolley cars connect major neighborhoods, and cable cars add a nostalgic touch to short trips.

What to Pack: Bring layers. Even in October, the temperature can shift quickly between afternoon warmth and evening chill. Comfortable shoes are essential for navigating the city’s hills, and a light jacket or scarf will keep you comfortable after dark.

Budget Tips: Weekday stays at upscale hotels like The Clift often come with lower rates. Consider catching a matinee performance for a less expensive theater experience, and make restaurant reservations in advance to avoid long waits at popular spots.

Romantic Photo Spots: The Palace of Fine Arts, Alamo Square’s Painted Ladies, and the rooftop at The View Lounge all provide great backdrops. For a quieter moment, visit the Lands End Lookout trail, where ocean waves crash below and the wind carries a hint of salt in the air.

A City That Invites Return Visits

As our weekend came to an end, we packed and headed for home. San Francisco is a city worth exploring. The city has issues for sure, but it also has heart and variety. For couples seeking a romantic escape, it offers the perfect blend of sophistication and adventure.

After almost 44 years of marriage, I still enjoy a weekend away together. The elegance of The Clift, the energy of North Beach, the flavor of shared meals, and the quiet moments all wove together into a memorable experience. There was no need for grand gestures or elaborate plans; the city itself provided the romance.

As we checked out of the hotel and rolled our suitcases toward the car garage at Mason and O’Farrell, I glanced back at the building’s elegant façade and felt that my heart, at least a part of it, would stay behind among the hills and the fog.

Check rates online at Expedia, Booking.com, Agoda.com, or Hotels.com.

Our stay at The Clift Royal Sonesta Hotel was sponsored (paid for) by the hotel. We paid for all other meals and experiences outside the hotel. All opinions expressed are my own.

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