Siblings by the Bay

Choose one: Arsicault, Plow, or Hedge

Pastry-first recommendation: Meet Arsicault Mission Bay when it opens at 8:00 for croissants and coffee with Alexis near the OpenAI office. Full-breakfast choice: Be at Plow at 7:00 for a polished sit-down meal; leave if the first-come wait grows. Relaxed backup: Hedge at 7:30 is best only when the priority is lingering over coffee.

Timing: Choose one stop—do not stack Arsicault and Hedge. Leave Arsicault by 8:25, or Plow/Hedge by about 7:50, then continue to the firehouse.

Princess Diaries firehouse

Quick exterior photo at 724 Brazil Avenue before continuing south. The exact arrival follows whichever breakfast option wins.

Go: Head from the chosen breakfast stop to Brazil Avenue, then take I‑280 south. This order avoids backtracking from Daly City.

Target + Tesla Supercharger

Shop at Target Serramonte while the Tesla charges at the same center, 3 Serramonte Center.

Go: Arrive earlier after Plow or Hedge and closer to 9:10 after Arsicault. Finish by about 10:15, then return north via I‑280 so Alexis and the purchases are back at Eddy Street before the airport run.

Drop Alexis + purchases at Eddy Street

This is the necessary Model 3 reset. Colton continues alone, leaving four passenger seats and the car's cargo space available for the three arrivals and their luggage.

Iru works

Iru is unavailable during the airport pickup and luggage drops, then rejoins the group after work.

Colton drives solo to SFO

Leave Eddy Street with an empty passenger cabin and as much open trunk and frunk space as possible. Arriving before the flight lands preserves time for traffic and terminal circulation.

Pick up Christa, Marshal, and Bri

Three guests plus Colton fit without Alexis in the car. After bags, drop Marshal and Bri at Hotel Spero, then take Christa and her bag to Eddy Street. If the luggage is unusually large, order one Uber XL at SFO rather than forcing the load.

Muni + walk to SFMOMA

Leave the Tesla at Eddy Street. The airport group takes the 38/38R eastbound, then walks south through Union Square toward the museum. Iru stays at work and joins everyone for shopping afterward.

Why: The 2026 Pokémon World Championships and PokémonXP run August 28–30 across Moscone North, South, and West. Expect heavy pedestrian traffic and unreliable curb pickups around Howard, 3rd, and 4th; Muni plus walking should be more predictable.

Two-hour SFMOMA visit

Give the museum a real two-hour window without requiring everyone to move at the same pace. The art-focused group stays until 4:25; anyone ready for shopping can leave at 3:35 and walk about 15 minutes to meet Iru in Union Square.

Split: Early shoppers leave at 3:35. Museum lingerers leave by 4:25—well before the 5:00 Friday close—and catch up at Nintendo or POP MART around 4:45.

Staggered meetup · Nintendo + POP MART

Iru meets the early-shopping group around 3:55 for roughly 90 minutes in Union Square. The museum group joins around 4:45 and still gets about 40 minutes to prioritize one or both stores. Nintendo SAN FRANCISCO is at Powell and Geary; POP MART is one block south at 200 Powell.

Pace: Both branches leave Union Square around 5:25 and walk directly to Naadam. Chinatown sightseeing moves to Sunday, so Friday can stay focused on shopping and dinner.

Mongolian dinner at Naadam

Gather all six around traditional Mongolian favorites, with hearty meat dishes and dumplings made for sharing.

Go: Walk downhill through Chinatown. Decide over dinner whether the group wants the optional rooftop or a direct ride home.

Optional · Charmaine’s rooftop

If everyone still has energy, finish with one polished rooftop drink or mocktail at the San Francisco Proper Hotel. It is near Hotel Spero and just beyond the Union Square side of downtown, so it makes a convenient final stop for Marshal and Bri.

Go: This is not a short post-dinner walk; take two Waymos or rideshares. Charmaine’s is open until 11:00 p.m. Friday. Evening reservations for parties of three or more carry a $50-per-person food-and-beverage minimum, so reserve only if the group wants a real rooftop round.

Philz + an unhurried start

Schedule coffee and breakfast delivery to Eddy Street. No one needs to wake at 6:00 or add a café detour before the drive north.

Recommended · pre-booked Uber XL to Larkspur

Leave the Model 3 at home. The pre-booked Uber XL first collects Marshal and Bri at Hotel Spero around 8:25, adds the Eddy Street group around 8:35, then continues north. Allow up to 60 minutes after the second pickup plus the shuttle's required 15-minute check-in buffer.

Transport: One pre-booked Uber XL carries all six with a single intermediate pickup. Confirm the added 923 Eddy Street stop Friday night.

Recommended · later Muir Woods shuttle

Target a 10:00 departure, about 90 minutes beneath the redwoods, and a return shuttle around 12:30. Reserve the closest available pairing rather than defaulting to the first bus of the day.

Important: Download all six tickets before leaving Larkspur; there is no dependable cell service at Muir Woods.

Uber XL to Sausalito + lunch

Sausalito is a small waterfront town across the bay, known for its hillside homes, little art galleries, shops, cafés, and beautiful views of San Francisco. Suzette, a waterfront French café and bistro, is one appealing lunch option, but the plan is to stroll along Bridgeway and choose whatever looks best on the spot.

Pace: Eat from about 1:35–2:20. If the shuttle runs late, order takeaway and preserve the bridge, garden, and getting-ready block.

Uber XL to the Golden Gate Bridge

At the south-side Welcome Center, spend about 30 minutes walking a short way onto the bridge and back, with time for photos, restrooms, and a quick look at the exhibits or souvenirs.

Transport: Rideshare drop-off is allowed during the weekend parking closure. Call a fresh Uber XL after the walk; drivers cannot wait or stage here.

Palace of Fine Arts photo stop

Built for the 1915 Panama-Pacific International Exposition, the Palace of Fine Arts is the fair's only surviving structure on its original grounds. Its grand classical rotunda, curved colonnades, and lagoon make it one of San Francisco's most striking landmarks. Take one Uber XL from the bridge, walk the lagoon for about 20 minutes, and continue.

Uber XL to the Japanese Tea Garden

The Japanese Tea Garden began as a Japanese Village exhibit for San Francisco's 1894 Midwinter Exposition, then landscape architect Makoto Hagiwara helped shape it into a permanent garden. Its winding paths, bridges, ponds, pagodas, and carefully composed plantings offer a peaceful introduction to Japanese garden design. Ride directly from the Palace, enter around 4:25, and explore until about 5:10.

Everyone's Waymo ride to Haight-Ashbury

Waymo is an app-booked, fully autonomous rideshare—the car drives itself with no human driver. Order two Waymos to the same destination and decide who rides together on the spot.

Setup: Use two phones and payment accounts. The first car waits at Haight and Ashbury if arrival times differ.

Brief Haight-Ashbury wander

Haight-Ashbury is the neighborhood around Haight and Ashbury streets, famous as a center of 1960s counterculture and the 1967 Summer of Love. Today it is known for colorful Victorian homes, vintage shops, record stores, murals, and music history. Give the group about 30 minutes for a few photos and one or two shops—not a 75-minute thrift marathon.

Marshal's Gamescape stop · everyone else resets

Marshal takes the 7 bus or a short ride to Gamescape for about 25 minutes, then a Waymo or Uber to Hotel Spero. Everyone else splits into rides back to Eddy Street and Hotel Spero and starts getting ready.

Hard stop: Marshal leaves Gamescape by 6:30. The shop closes at 7:00 and dinner prep matters more than extending the browse.

Protected birthday reset

Shower, change, recharge phones, and leave purchases behind. Eddy Street and Hotel Spero are separate getting-ready bases; Marshal should reach Hotel Spero around 6:40. If the available dinner reservation is later, use the extra time here rather than adding another stop.

Leave for Chotto Matte · tentative

Chotto Matte combines Japanese technique with bold Peruvian flavors—sushi, tiradito, robata, and shareable plates—in a dramatic, mural-filled rooftop space with skyline views and lively DJ energy. It has the biggest birthday-night “wow” of the options, but no reservation has been made yet. The Eddy Street group takes one Waymo or Uber; Marshal and Bri walk about 10–12 minutes from Hotel Spero or take a very short ride.

Timing: A 7:45 table is the planning target, not a confirmed reservation. If availability is later, shift this departure and extend the getting-ready block by the same amount. If another restaurant wins, replace only this final route.

Morning coffee

Philz is a San Francisco-born coffee shop known for customized, hand-poured drinks such as the minty Mint Mojito. Schedule delivery to Eddy Street or pre-order a quick pickup before leaving for Pier 33.

Alcatraz Day Tour

Alcatraz is the rocky island in San Francisco Bay that became one of America's most famous federal prisons, once holding inmates including Al Capone. The visit includes a ferry ride, sweeping bay views, and an audio-guided walk through the historic Cellhouse. Be at Pier 33 by 8:10.

Pier 39 sea lions

A large colony of California sea lions gathers on the floating docks beside Pier 39, where they can be watched barking, swimming, and sunning themselves. Walk there along the waterfront after returning from the island.

Boudin Bakery lunch

Boudin is San Francisco's historic sourdough bakery, known for its tangy loaves and clam chowder served in hollowed-out bread bowls. Choose soup, sandwiches, or a bread bowl at the 160 Jefferson Street bakery and café.

One-hour Pier 45 split

USS Pampanito is a restored World War II submarine that visitors can explore from its cramped torpedo rooms to its crew quarters. Nearby, Musée Mécanique is a hands-on collection of antique arcade games, mechanical amusements, and coin-operated curiosities. Split the hour between the two experiences.

Vintage F streetcar to the Ferry Building

The F line uses colorful historic streetcars from cities around the world, running along the waterfront and Market Street as part of regular Muni service. Board near Fisherman's Wharf and ride to the Ferry Building at Market and Drumm.

Ferry Building Marketplace

Opened in 1898 as San Francisco's grand ferry gateway, the clock-towered Ferry Building now contains a skylit marketplace of local food shops and artisan producers. Browse the hall, step outside for Bay Bridge views, and keep this to about 35 minutes.

California cable car + Cable Car Museum

Ride the California line from its downtown terminal toward Mason Street, then walk to the free Cable Car Museum. The museum occupies the working Washington-Mason powerhouse, where the giant moving cables that pull the cars can be seen beneath historic cars and mechanical displays.

Pace: Explore until about 4:25, then walk downhill to Ross Alley. The museum closes at 5:00 p.m. Sunday.

Ross Alley + Fortune Cookie Factory

Ross Alley is one of Chinatown's oldest lanes and home to the tiny Golden Gate Fortune Cookie Factory, where cookies have been folded by hand since 1962. Watch them being made, try a sample, and buy a bag before the short walk to dinner.

Pace: Leave Ross Alley around 5:00. Z & Y is only a few minutes away, so this preserves the dinner arrival buffer.

Z & Y dinner for six

Finish with a seated, family-style Sichuan dinner: chili-oil fish, dumplings, peppercorn heat, and plenty of dishes to pass around. It is more comfortable for all six than balancing street pizza outdoors.

Go: Walk the few minutes from Ross Alley to Jackson Street. Reserve a table for six; Sunday dinner service begins before the planned arrival.

Choose the finale

If skies are clear, take an Uber XL to Twin Peaks for sunset. If it is foggy, choose The View for skyline drinks or Bourbon & Branch for a speakeasy nightcap before going home to pack.

Colton drives Alexis + Christa to SFO

Both leave from Eddy Street in the Tesla for a 4:00–4:15 airport arrival. Caltrans has intermittent US‑101 lane and ramp closures through 5:00 a.m.; charge Sunday and check roads before bed and again before leaving.

Fallback: If US‑101 shows active work or a ramp closure, route via I‑280 south → I‑380 east. Follow live navigation rather than forcing 101.

Marshal + Bri Uber to SFO

Be checked out and waiting with bags at Hotel Spero before the car arrives. A direct ride avoids an extra pre-dawn stop for Colton.

Marshal + Bri reach SFO

Target a 5:20–5:30 arrival, preserving a buffer even if overnight lane work slows the trip.