I Left My Heart in San Francisco, Again!
In my twenties, I fell hard for San Francisco. Though I lived across the country in New York, I’d visit multiple times a year to get my fix of laid-back West Coast vibes, the anything-goes spirit of the Castro, and, oh, those views of the Bay. Now in my forties and returning after a long break, I wondered if this would still be my happy place.
For this visit, I mixed city beats with a staycation in the Presidio, a relaxed space on San Francisco’s northern tip that has been part of the National Park Service since 1994. With nearly 1,500 acres—including miles of hiking and biking trails, and eight scenic overlooks—there was a lot of ground to cover, but I never felt rushed. Rather, the Presidio was built to slow you down and help you appreciate your surroundings.
This was super apparent at the impressive Tunnel Tops, a long-term project that began welcoming visitors in 2022. Designed by James Corner Field Operations, the firm behind New York’s High Line, it features sweeping vistas, hundreds of plant species, walking trails, and plenty of places to picnic or lounge. I plopped myself in an Adirondack chair facing the water, a new favorite spot to catch up on my reading. Later, I took an easy walk to Crissy Field, crossing restored wetlands in the process, which became a favorite spot for people and dog watching.
Next, I hopped on the free Presidio GO Shuttle, which runs throughout the park (and connects to downtown), to Baker Beach. It was a bit chilly to partake in one of the beach’s most famous perks—going au naturel—but I happily zoned out watching Pacific waves with the Golden Gate Bridge posing in the background. For a closer look at that iconic orange beauty, I continued along a stretch of the California Coastal Trail, mesmerized by striking vistas.
After a full day on foot, I unwound at my hotel, the historic Lodge at the Presidio. Once military barracks, the 42-room boutique property opened in 2018. It’s the closest hotel to the Golden Gate Bridge, and my room’s sweeping panorama made me swoon. At the evening wine-and-cheese reception, I poured a glass of Sauvignon Blanc and settled into a rocker on the front porch. The night ended with chats with frisbee-tossing locals on the Main Parade Lawn and time by an outdoor fire pit. I hadn’t felt this relaxed in ages.
The Presidio has several great restaurants, too. Dalida is a warm and inviting Mediterranean spot from husband-and-wife duo Laura and Sayat Ozyilmaz, featuring mouthwatering mezes, Middle Eastern pastas, and entrées such as Aleppo half chicken and Cypriot lamb chops.
Colibrí serves Pechuga Rellena, Mole Poblano, and other tasty Mexican dishes best enjoyed on a festive patio with a margarita. You won’t have to go far for museums and entertainment, either. The Walt Disney Family Museum takes you on a journey through the life and achievements of the legendary animator, while the Presidio Theater offers film, performing arts, and special presentations.
After two days driven by nature and relaxation, I headed back to the streets I once adored, spending a night at the Clift Royal Sonesta in Union Square. A highlight was cocktails and a juicy burger at the on-site Redwood Room, an iconic Art Deco–style space with an enormous bar carved from an 800-year-old redwood tree and original artwork from Gustav Klimt.
Nearby, I met my friend Lisa for drinks at Top of the Mark. Walking the city’s steep hills proved far more challenging in my forties, but I huffed and puffed and rewarded myself with cocktails and skyline views. After discussing life, travel, and writing projects, we had a delicious sushi dinner at Nara in Polk Gulch.
It was another neighborhood I’d never really explored, but quickly took to its funky vibe and artistic spirit. After, I hopped on the trolley car toward home. While I resisted famous tourist attractions like Fisherman’s Wharf and Ghirardelli Square this time around, I’ll never say no to the “ding, ding.”
I spent the next three days at the Hyatt Regency San Francisco in the Embarcadero. Designed by brutalist architect John Portman, the recently renovated hotel features 821 rooms, a wedge-shaped design that provides waterfront sightlines, and a 17-story vaulted atrium that holds a Guinness World Record for the largest hotel lobby. While I loved my room, especially the balcony overlooking the bay, the lobby felt like the area’s living room and was a wonderful place to work and chat. Eclipse Restaurant was perfect for a casual meal or drink, while The Regency Club, reopened in 2024, offers one of the best lookout points in town and rotates during select times in the morning and evening.
With its terrific downtown location, it was an easy walk to the Ferry Building for pastries and a latte, Market Street for shopping, and the San Francisco Museum of Modern Art. Chinatown, City Lights Bookstore, and the Italian restaurants of North Beach were also nearby. Having a BART and MUNI station just steps away made it easy to ride to neighborhoods like the Castro.
Ah, the Castro. If there was one place that made me choke up with nostalgia, this was it. While I wasn’t lucky enough to snag tickets to a show at the Castro Theatre, I was treated to a backstage tour of the newly reopened space, and it was a real beauty.
I was joined by my friend Tom, and we caught up over drinks at Twin Peaks Tavern and Lookout. I hadn’t been bar-hopping in a long time, but the ease of chatting with strangers and one drink casually turning into another as the sun began to fade instantly transported me back to my twenties. That feeling continued with a solo night a few days later at 440 Castro. As an introvert, going out alone can be a challenge, but it happened to be underwear night (I wasn’t complaining), and everyone was in a friendly mood. I’d only intended to stay for an hour, but ended up dancing and chatting with strangers until 1:30 a.m. More than trying to relive the past, I realized I was reconnecting with a part of myself that San Francisco had always embraced.
Of course, one of the greatest things about travel is the people you meet along the way. I was introduced to Per Sia, a first-generation trans Mexican American and the city’s second drag laureate. For nearly two hours, we talked about San Francisco’s progress and challenges, her dedication to performing and connecting with audiences, and her work in the arts and education, which includes co-founding the city’s Drag Story Hour. We also spoke about our journeys to come out and accept ourselves as we are. By the end of the conversation, we’d both shed a tear or two.
“There are people out there trying to erase us, but we’ve always been here, and we’re always going to be here. San Francisco is such a supportive place, and we’ve made so much progress, but there’s always more work to be done. I want to educate but also bring people joy, and the best way to do both is by being visible and vocal,” she told me.
It was also wonderful to meet Kate Bove, Associate Director of Programs for Frameline, a nonprofit media arts organization dedicated to LGBTQ+ cinema and independent queer media. Frameline hosts the San Francisco International LGBTQ+ Film Festival, which celebrates its 50th anniversary this year as the longest-running, largest, and most widely recognized queer film exhibition in the world. Her enthusiasm for amplifying queer voices was contagious, and she spoke about the festival with such warmth and detail that I could almost hear the theater buzzing with crowds, laughter, and shared emotion. I left knowing I needed to come back and experience it fully.
To my delight, this trip felt like reuniting with an old friend—familiar and welcoming, yet somehow even better with time. As I headed for the airport, I was ready to leave my heart in San Francisco once again.
Love is Blooming with Presidio’s Romance Package
Most visits to San Francisco begin with a checklist. But, for couples who really want to connect, the Presidio has designed a getaway unlike any other city adventure.
Presidio Lodging’s (any night) Romance Package transforms the Presidio into a secluded and intimate retreat in the heart of the city. Think crackling fireplaces, sweeping bay views, nightly wine receptions, and sunrise walks beneath towering cypress trees. Here, the usual city itinerary gives way to something slower, quieter, and far more memorable. Days begin with coffee and misty trails. Evenings end with sunset views over the Golden Gate and sparkling wine by the firepit. And, for the culinary-curious, both of the boutique hotels are just a hand-in-hand stroll away from world-class dining, including Dalida, Colibri, and the (coming soon) Mess Hall.
The (evergreen) Romance Package includes:
• Deluxe King accommodations at the Inn or Lodge
• A bottle of sparkling wine to enjoy in-room or beside the outdoor firepit
• Artisan chocolate truffles
• Nightly wine & cheese reception
• Daily European-style continental breakfast
• Complimentary overnight parking
• Late checkout
Learn more about the Presidio Lodging packages here.
