SF May 23-26 itinerary guidance

Question

Traveling to CA for family trip this May and SF is the first leg. Myself and my two adult kids, ages 24 & 21, will fly into SFO May 23 (could make this May 22 if necessary). We will not rent a car until the day we are leaving SF for the next parts of our trip so will rely on walking when possible, public transportation, and rideshare. Looking at Hotel Riu FW, Hotel Zoe, Courtyard FW, or Marriott FW but really wanting help ensuring that we'll have time to do/see the following:

FW (yes, I know it's touristy! Won't need much time there.), Pier 39, Embarcadero: can we explore these areas and have time to do an Alcatraz night tour same day?

Daughter wants to see Painted Ladies (won't need much time here either)

Son wants to see Yoda Fountain

Musee Mechanique

Ghiradelli Square and possibly factory tour (is it worth the time?)

Ferry Building, Little Italy/North Beach area

This is the list of what we've come up with so far -- we really like local bookstores so will likely go to City Lights. Would love other suggestions. Also open to local game/video game stores.

Daughter is vegetarian and GF so would love suggestions on restaurant recommendations.

I appreciate any feedback, including how to group our activities together in ways that make the most sense. Thank you!

Answer

Great plan — you’ve picked a compact, walkable set of neighborhoods that fit together well. Below is a practical, grouped, and time-smart plan for May 23–26 that uses public transit / walking / rideshare, plus quick notes on the specific places you listed and a few food + bookstore + game-store suggestions for your group.

Quick overview / big-picture

Base yourself near Fisherman’s Wharf / Pier 39 (Hotel Riu FW, Hotel Zoe, Courtyard Fisherman’s Wharf, Marriott Fisherman’s Wharf all put you in the same general area). That location makes Pier 39, Musee Mécanique, Ghirardelli Square, and the Alcatraz ferry very easy to reach on foot and gives straightforward transit to the Embarcadero and North Beach.
Do Alcatraz Night Tour on one evening (they run evening/night departures during spring–summer and are a different — quieter — experience than daytime ferries). Try to book in advance.
Group the North Beach / City Lights / Coit Tower / Ferry Building / Embarcadero sights into one day since they’re compact and easy to connect by foot or short rides. City Lights is right in North Beach.

Suggested day-by-day plan

Arrival day — Friday (May 23)

Check into your hotel near Fisherman’s Wharf (quick freshen-up).
Explore Pier 39, do a leisurely walk along the Embarcadero toward the Ferry Building if time/energy allows. Pier 39 + shopping + sea lions is classic tourist fun and close by.
Visit Musée Mécanique (old-school coin-op arcade museum on Pier 45) — short fun stop for all ages. Plan ~30–60 minutes.
If you booked an Alcatraz Night Tour for the same night, head to the Alcatraz ferry terminal with plenty of time — night tours have evening departures (they run on select nights spring–fall, so check days/times and reserve tickets early). Night tours depart in the evening and are about 2½ hours total.

Full day — Saturday (May 24)

Morning: Take transit/rideshare to Alamo Square to see the Painted Ladies (quick photo stop — 15–30 minutes) then head toward the Haight/Golden Gate Park if you want a short walk through that area.
Midday: Return toward North Beach — stroll Columbus Ave, have lunch, visit City Lights Bookstore (great local bookstore and short visit). City Lights is centrally located in North Beach.
Afternoon: Walk up to Coit Tower area or head down to the Ferry Building / Embarcadero (farmers, food stalls, and views). The Ferry Building has a cluster of vendors that are fun to explore for snacks or dinner. Consider a late-afternoon stroll along the Embarcadero so you don’t feel rushed.
Evening: Dinner in North Beach or the Embarcadero. If you want a chocolate stop, Ghirardelli Square is very near Pier 39 and is a short evening detour (it’s mostly a shopping/ice-cream/restaurant area).

Half day — Sunday (May 25)

Morning: If your son wants the Yoda Fountain, plan a short rideshare trip to the Presidio / Letterman Digital Arts Center courtyard — it’s quick and makes a nice outdoor stop (lobby access can be limited, but the fountain outside is a public photo spot).
Another morning option: Walk closer to Fisherman’s Wharf and visit Ghirardelli Square and the nearby waterfront again, or pick up souvenirs.
Afternoon: If you haven’t done the Ferry Building market or want more book-shopping, revisit City Lights or explore local neighborhood shops. If you want gaming stores, ask your hotel front desk for a nearby game store recommendation — there are small hobby/game stores dispersed around the city (they’re easy to reach by rideshare).
Evening: Pick a relaxed neighborhood dinner (see vegetarian / gluten-free notes below).

Notes on doing Alcatraz + Wharf same day

Yes — you can explore Pier 39/Fisherman’s Wharf in the afternoon and still do an Alcatraz Night Tour that evening. Night tours depart in the evening and are designed to be combined with earlier-day sightseeing — just leave ample time to be at the ferry terminal 30–45 minutes before departure. Book the night tour early — they sell out.

Your specific items — quick facts & tips

Pier 39 & Embarcadero: Walkable from your hotels; lots of tourist shops, sea lions, and casual restaurants. Evening strolls are scenic.
Alcatraz Night Tour: Evening departures are offered (book early). Night tour is quieter and has a different atmosphere than daytime ferries.
City Lights: Located in North Beach (Columbus/Broadway area); a must for bookstore lovers.
Yoda Fountain: Small bronze Yoda fountain outside the Lucasfilm/ILM area in the Presidio (good quick photo stop; lobby access may be restricted).
Musée Mécanique: Classic coin-operated arcade museum on Pier 45 — fun for all ages and right at Fisherman’s Wharf.
Ghirardelli Square: Short walk from Pier 39; mostly shops/restaurants and a Ghirardelli store/ice-cream experience (the “factory tour” is not a large factory tour like some chocolate factories — it’s primarily a visitor experience and shop).

Vegetarian + gluten-free dining suggestions

San Francisco is very friendly to vegetarian and gluten-free diets. A few reliable options (mix of casual and sit-down) that are centrally located or easy to reach:

Greens Restaurant (Fort Mason) — long-running vegetarian spot with seasonal menu (more of a short ride from North Beach but excellent if you want a sit-down, vegetable-forward dinner).
Ferry Building vendors — several stalls and small restaurants offer vegetarian and GF-friendly options (easy for lunch or grazing). (Ferry Building is on the Embarcadero.)
North Beach options: Lots of Italian spots can accommodate GF pasta/pizza requests — Tony’s Pizza Napoletana is famous and offers GF options (call ahead if needed).
If you prefer dedicated vegetarian/vegan or gluten-free places, let me know and I’ll tailor a short list by neighborhood.

Bookstores & gaming stores

City Lights — priority visit; great poetry and lit sections.
For video / hobby game stores: there are several local hobby and game shops around the city; they’re compact and easy to reach by rideshare from Fisherman’s Wharf — I can list a few by name if you want one focused on video games vs tabletop.

Transport tips

Walking + short rideshares is perfect for your plan. San Francisco’s hills are concentrated — moving between North Beach, Embarcadero, and Fisherman’s Wharf is mostly flat or short uphill sections.
MUNI / F-Line streetcar along the Embarcadero is a scenic and useful option between Fisherman’s Wharf and the Ferry Building.
Reserve Alcatraz night tickets in advance — they often sell out for weekend evenings.

Quick practical reminders

Book Alcatraz early.
Carry layers and a windproof jacket — evenings on the water get chilly even in May.
For vegetarian/GF dinners, call ahead for Tuesday–Saturday dinner reservations for popular spots, especially on weekends.

SF May 23-26 itinerary guidance

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