Leslie's 29th ✨ San Francisco

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Bridges, Beaches & Birthday Dinner

Golden Gate views + a stunning dinner at Meski

💰 Estimated Daily Costs (per person)

☕ Hotel lobby coffeeFree

🏖️ Baker BeachFree

🌉 Golden Gate Bridge walkFree

🍷 Eco Terreno wine tasting~$25

🍷 Hotel happy hourFree

🍽️ Meski dinner~$80–100

🚗 Rideshare (2–3 trips)~$40

Daily Total~$145–165/person

* Meski may vary depending on drinks ordered.

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9 AM

🍳 Morning

Hotel Coffee + Wharf Stroll

Grab the free coffee from the lobby — yes, it's included — and just walk. The Embarcadero in the morning is everything. No agenda yet. We just landed in San Francisco, baby.

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11 AM

📍 Must-Do

Baker Beach

Les, I need you to trust me on this one. You've seen the Golden Gate a thousand times in photos — but standing at the water's edge at Baker Beach with the whole bridge right there in front of you? Nothing prepares you for it. This is why we came.

💡 We're ridesharing here — parking is a whole situation. Bring layers, it's windy at the water. Come before noon for the clearest views.

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1 PM

📍 Must-Do

Golden Gate Bridge

Now we actually walk it. The scale doesn't make sense until you're standing next to it — it's one of those things that makes you feel genuinely small in the best way. East side has city views, west side has the ocean. We're doing both.

💡 Free to walk. Bring that jacket — I'm not playing about the wind on this bridge.

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3 PM

🍷 Winery

Eco Terreno Urban Tasting Room

A winery. In the city. With a 4.9 rating and a charcuterie board they've been known to upgrade for free. This is the pre-dinner vibe — organic wines, North Beach energy, good people watching off Columbus Ave. You're going to love it here.

💡 140 Columbus Ave. Open from noon Thu–Sun. Ask for the charcuterie board when you sit down.

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5 PM

🏨 Hotel

Kimpton Happy Hour

Head back to the hotel. Free wine and beer in the lobby from 5–7PM — yes, free. Get cute. We have a dinner reservation tonight and I need you looking fine af. 😏

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7:30 PM

⭐ Reservation

Dinner at Meski

I made this reservation for you. Draymond Green's Afro-Latin and Ethiopian fusion restaurant — honey wine, oxtail pasta, chicken sambusas so good people order them twice in the same sitting. It's electric in there, Les. Dress up. This is your kind of place.

🗓 7:30 PM · Confirmed Reservation

💡 1000 Larkin St. Order the sambusas first — don't wait. And get the honey wine. I mean it.

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🌿

I'm Taking You to Where I Used to Live

My campus, my park, my city — now ours

💰 Estimated Daily Costs (per person)

☕ Arizmendi Bakery breakfast~$12

🎓 USF Campus walkFree

🌸 Japanese Tea Garden entry~$10

🌳 Golden Gate Park strollFree

🫓 Pupusas at Panchita's~$15

🌞 Dolores ParkFree

🎶 Blondie's Bar (drinks + cover)~$35

🚗 Rideshare (2–3 trips)~$35

Daily Total~$107/person

* One of the most affordable days — mostly free attractions.

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9 AM

☕ Breakfast

Arizmendi Bakery — Inner Sunset

This is a worker-owned co-op bakery near campus that I used to go to. The pastries are incredible and the coffee is exactly right. No chains, no tourists — just a real SF neighborhood spot. Welcome to my old world.

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10:30 AM

🎓 Homecoming

University of San Francisco

I went to school here, Baby. 2130 Fulton Street — right across from the park. I want to walk you through it and show you the places that were mine before I knew you. Lone Mountain, the lawns, all of it. This one's personal.

💡 The grounds are open on weekends. The offices aren't, but we don't need them. It's all ours.

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12 PM

📍 Must-Do

Golden Gate Park + Japanese Tea Garden

Over 1,000 acres and my campus literally faces it. The Japanese Tea Garden is a whole different world — koi ponds, arched bridges, traditional tea. Give it time. Then we stroll and explore however we feel. There's no wrong direction in this park.

💡 Tea Garden entry is ~$10. Bike rentals are available inside if you want to cover more ground. Plan for 2–3 hours at minimum.

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3 PM

🫓 Late Lunch

Pupusas at Panchita's — The Mission

Babe. These are the best pupusas I've ever had in my life. 3091 16th St. Cheese, beef, jalapeño-sausage — order at least three kinds and get the curtido slaw on top. Sometimes there's live mariachi inside. You're going to want to come back before we leave.

💡 Rated 4.5 stars, 2,000+ reviews. Do not take them to-go — eat them fresh while the cheese is still melted. Get there before 5PM.

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4:30 PM

🌮 Explore

Mission District Wander

Walk 24th Street with me. The murals on these walls are extraordinary — real art, real community. This is the heart of Latino San Francisco and it shows in every block. Valencia Street has boutiques and good coffee if you want to browse. No rush, just us walking.

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6 PM

🌞 Must-Do

Dolores Park Golden Hour

We're going to lay in the grass with the whole SF skyline behind us, palm trees overhead, and a paleta from the cart vendor in hand. This is the moment I've been picturing since I started planning this trip. Just be here with me.

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9 PM

🎶 Live Music

Blondie's Bar — Valencia St

Right off Dolores Park. This is a Mission institution — incredible music, vibey mixed crowd, and a DJ that actually knows what they're doing. I want you dancing tonight, Les. Check their Friday lineup on Instagram before we go so we know what we're walking into.

💡 540 Valencia St. Get there by 9PM. Check their Instagram page during the week for the Friday night schedule.

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🪩

Thrift Queen Energy, Victorian Houses & The Castro

I planned this day specifically for you, Les 👑

💰 Estimated Daily Costs (per person)

🍳 Brunch on Haight~$20

👗 Thrifting (Held Over + shops)~$30–60

🏡 Painted Ladies / Alamo SquareFree

🏔️ Twin Peaks viewpointFree

🍽️ Dinner in the Castro~$45–60

👑 Beaux drag show (cover + drinks)~$40

🚗 Rideshare (3 trips)~$40

Daily Total~$175–220/person

* Thrifting budget varies by how much you find 😄

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10 AM

🍳 Brunch

Brunch on Haight Street

Pork Store Café is a legendary SF brunch spot — very neighborhood, very real. Or we grab coffee at Flywheel and start browsing early. Either way, we fuel up before I unleash you on the thrift stores. You're going to need your energy.

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11 AM

👗 Must-Do

Thrifting on Haight-Ashbury

I know you, Les. This is your block. Held Over at 1543 Haight is the one — curated vintage leather, bell bottoms, coats, and it's actually priced right. Then we hit Wasteland and Piedmont Boutique down the strip. Take your time. We have nowhere to be.

💡 Held Over opens at noon — plan around that. Budget at least 2 hours for the full Haight strip. Slow is the move here.

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2 PM

📍 Must-Do

The Painted Ladies

A short walk from Haight and I promise you it hits different in person. The iconic Victorian row at Alamo Square Park — we're sitting in the grass with snacks and taking the photo. I want to see your face when you actually see them for the first time.

💡 Don't stand across the street for the photo — walk to the TOP of the park. Houses and the whole skyline behind them in one frame. That's the shot.

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4 PM

🏔️ Must-Do

Twin Peaks at Sunset

We're Ubering up here before the sun goes down. 360 degrees of San Francisco — the bay, both bridges, the ocean, the whole skyline at once. Les, I've been here before and it still took my breath away. This is THE moment of the trip. Jacket on. Eyes up.

💡 501 Twin Peaks Blvd. Sunset is around 8PM in May — let's be up there by 7:30PM. It's windy and cold and absolutely worth it.

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7 PM

🍽️ Dinner

Dinner in the Castro

We're eating in the neighborhood tonight. Frances is incredible if we can get a table — if not, Anchor Oyster Bar is a Castro classic. Or we graze multiple spots on Castro Street and make a night of it. Your call, I'm with you either way.

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9:30 PM

👑 Drag Show

Beaux Bar — The Castro

This is the one I planned for us. The Castro's most iconic bar — drag shows, themed nights, performers who actually put on a show. The energy in this room on a Saturday night is something else. Wear something you feel good in, because we're going to have the time of our lives.

💡 2344 Market St. Check their Instagram for the Saturday night lineup — they post it mid-week. Get there by 9PM and find your spot.

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🎂

Happy Birthday, Les. Today Is All Yours. 🥂

29 in San Francisco — I planned every detail of this day for you

💰 Estimated Daily Costs (per person)

🦀 Wharf sourdough bowl breakfast~$20

🦭 Sea lions at Pier 39Free

🚋 Cable car ride~$8

🌾 Ferry Building market bites~$20

☕ North Beach espresso + bookstore~$15

🎂 Birthday dinner for Leslie 🥰~$60–80

🚗 Rideshare to SFO (Mon 3AM)~$45

Daily Total~$168–188/person

* Tell every restaurant it's her birthday — SF spots usually do something special 🎂

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9 AM

🎂 Birthday Morning

Sourdough Breakfast at the Wharf

Good morning, birthday girl. Your first meal of 29 is from Boudin Bakery — right outside our hotel door. Dungeness crab is on the menu. I think you deserve it.

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10 AM

🦭 Explore

Sea Lions at Pier 39

These sea lions took over Pier 39 after the 1989 earthquake and the city literally just said — okay, they can stay. They're loud, they're chaotic, and they are absolutely the energy I want for your birthday morning. Free admission, all attitude.

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11 AM

🚋 Iconic

Cable Car Ride

It's a National Historic Landmark and it's genuinely fun. We're riding the Powell-Hyde line from the Wharf up through Nob Hill — one last slow, beautiful look at this city on your birthday. Hold on and look around. This is San Francisco.

💡 ~$8 single fare, buy it at the booth. Ride all the way to the top of Nob Hill and just take in the view.

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1 PM

🌾 Birthday Lunch

Ferry Building Sunday Farmers Market

Sunday market runs 10AM–2PM right on the water. Local oysters, Cowgirl Creamery cheese, stone fruit, vendors from all over the Bay. We graze, we walk the Embarcadero, and we enjoy your birthday afternoon in the sun with the bay in front of us. Slow and perfect.

💡 Get the oysters — it's your birthday. Walk toward the Bay Bridge after for the view. This is a no-rush stop.

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3 PM

🇮🇹 Afternoon Stroll

North Beach + City Lights Bookstore

SF's old Italian neighborhood for your birthday afternoon. City Lights is a legendary Beat Generation bookstore — we're browsing it together. Then an espresso at Caffe Trieste and a sit in Washington Square Park. Just us, the city, and your last afternoon at 28. Soak it in.

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6 PM

🎂 Birthday Dinner

Birthday Dinner — Your Pick, Les

Tonight is yours. Sotto Mare in North Beach has the best cioppino in San Francisco — or we go somewhere completely new that feels right in the moment. Whatever you want. Tell them it's your birthday. You deserve the full experience. 29 looks good on you. 🥂

💡 SF restaurants love a birthday — tell them when you walk in. You might just get something special.

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Pack + Sleep

⚠️ Early Flight Alert

Pack Tonight — We Leave at 3:15AM

I know, I know. But our flight is WN 2318 at 5:15AM Monday and BART doesn't run at 3AM so we're Ubering. Pack everything tonight so we can just roll out the door. Set multiple alarms. Sleep on the plane. Every single second of this trip was worth it.

💡 Leave the hotel by 3:15AM → ~30 min to SFO with no traffic → arrive by 3:45AM. Plenty of time. ✈️

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Leslie's 29thBirthday Trip

Leslie's 29th
Birthday Trip