A Long Weekend in San Francisco and Napa Valley

Travel
Written By Mark Dean Guillermo

Just got back from a short but full trip to San Francisco and Napa Valley. The goal was to relax, recharge, and sneak in a few good eats and wine tastings. Mission accomplished. Here’s how it all went down.

Mark photographing his reflection with a Fujifilm camera in a mirrored chrome sculpture in Hayes Valley

Day 1: Wheels Up

We flew out of HNL on Southwest and landed in SFO by evening. We kept it simple with a quick overnight stay at the AC Marriott Oyster Point. It’s right near the airport and perfect for travelers who just need a solid place to rest before the real trip begins.

Colorful mural of Hawaiian alii in feather cloaks above gates E8 to E10 at Honolulu airport
Southwest Airlines jet being loaded at gate E7 on a sunny airport tarmac

Day 2: SF Detour and Napa Arrival

Before diving into wine country, we made a slight detour into the city. First stop was Philz Coffee in the Castro for the Mint Mojito Iced Coffee. You can’t get it in Hawaii, and I’d been craving it since planning the trip.

We wandered around the Castro, popped into a few random shops, and people-watched along the way. The weather was perfect, so we made our way to Dolores Park and just soaked it in for a bit.

A friend holding an iced coffee on the overlook at Mission Dolores Park, statue and palms behind
Castro Theatre marquee sign beside a rainbow flag banner against a bright sky
Vintage orange F-line streetcar rounding a sunny Castro intersection as a pedestrian crosses
Man sitting on the grass at Dolores Park with the San Francisco skyline in the distance
Smiling man holding coffee in a doorway beneath a Castro Tattoo neon sign

Then it was back in the car for the drive up to Napa. We checked into Senza Hotel, which turned out to be beautiful. The room was spacious and peaceful, tucked right between rows of vineyards. We even walked through the vines to get to Ashes & Diamonds winery next door for our first tasting. The walk was calm and quiet, and the wine hit the spot.

Vineyard rows in front of a Napa winery building with a wooden water tower
A friend peeking from behind the giant yellow pivot door at a Napa winery tasting room
Two Ashes & Diamonds Napa Valley white wine bottles flanked by glasses of chardonnay

Day 3: Castles, Cabernets, and Poolside Vibes

We kicked off the day with a wine tasting at Castello di Amorosa, an actual castle surrounded by vineyards. Our wine guide Paolo walked us through a lineup of reds and whites. Afterwards, we explored the grounds and took in the medieval-meets-Napa scenery.

Fresco-covered great hall at Castello di Amorosa set with long wine tasting tables
Two friends flashing peace signs below the stone towers of Castello di Amorosa
Two smiling friends posing at a stone turret overlooking Napa Valley hills

Later that afternoon, we relaxed by the pool at Senza and recharged before dinner. That night’s reservation was at Press Restaurant, one of Napa’s best spots for upscale food and a massive wine list. It lived up to the hype.

PRESS restaurant cocktail and beer menu printed on paper atop a wooden table
Table of small plates including a mini lobster roll, tartare and crudo at a Napa restaurant
Three friends running toward the camera from the Welcome to Napa Valley sign at sunset

Day 4: One Last Bite Before Home

For our last morning, we had a late breakfast at Hog Island Oyster Co. inside Oxbow Market. Oysters, eggs, and strong coffee made for a surprisingly great combo.

Before heading to the airport, we met up with my old design buddy Jeff in Hayes Valley. He took us to Chez Maman, a cozy French restaurant with sidewalk seating and good vibes. We walked around the neighborhood, admired some very stylish dogs, and wrapped up the trip on a mellow note.

Plate of escargots in green garlic-herb butter with a small fork on a doily
Two designers posing arm in arm in front of a colorful bathtub mural on a sidewalk

Highlights

  • Best coffee: Mint Mojito from Philz

  • Favorite tasting: Castello di Amorosa with Paolo

  • Most relaxing spot: Poolside at Senza Hotel

  • Don’t skip: Chez Maman in Hayes Valley

If you’re planning a short escape from Hawaii, this route hits all the right notes—city, nature, wine, and friends. Already thinking about the next time.

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Black and white portrait of Mark Dean Guillermo Mark Dean Guillermo https://inmydna.com
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