🗽 NYC Birthday Trip

March 26–29, 2026 — Chris turns 40 in New York

🟢 Booked / Locked 🟡 Strong option — needs booking 🔴 Idea — still deciding

👥 Crew

Chris + Amy

Core crew — all 4 days

Andrew & Christie

Brooklyn — Thu night works great

Aadil & Sadaf

Upper Manhattan — Aadil works Thu til 11p. Free Fri day + all Sat

Fonti & Joe

Chicago friends, in town that weekend. Flexible meetup

📅 Day-by-Day

Thursday 3/26 — Arrival

🟡AMFly ORD → NYC

🟡12–1pmCheck into hotel (LES area)

🟢~3pmKatz's Delicatessen — off-peak

1 pastrami, 1 corned beef, fries, Dr. Brown's. Split and enjoy.

🟡EveBonnie's dinner ~9pm w/ Andrew & Christie (Williamsburg)

Cantonese-American. Book on Resy when slots open (~2 wks out). Delphi monitoring.

🔴LateWilliamsburg drinks / LES cocktails

Attaboy (LES), Smalls jazz, or Williamsburg bars depending on energy

Friday 3/27 — Culture Day

🟡8–9amJewish breakfast

Russ & Daughters Cafe (LES), Tompkins Square Bagels, or Apollo Bagels

🟡DayHang with Aadil & Sadaf

Neighborhood walk, Essex Market, bookstores, The Whitney

🟢7pmMaybe Happy Ending — Broadway

Darren Criss & Helen J Shen. Two aging robots fall in love. Tender, gorgeous.

🔴~10pmPost-show drinks near theater district or head downtown

🟢12:30amComedy Cellar — MacDougal St., $25

Late-night Fri show (technically Sat morning). Phone-free. BOOKED ✅

Saturday 3/28 — Birthday 🎂

🔴MorningSleep in (late Comedy Cellar night)

🔴BrunchBirthday brunch — TBD

🔴DayGroup hang if Fonti & Joe available

🔴DinnerBest meal of the trip — THE birthday dinner

Via Carota, L'Artusi, Frenchette, Place des Fêtes, or St. Anselm

🟡EveVillage Vanguard — legendary jazz

Book ahead. THE room for jazz. Perfect birthday closer.

Sunday 3/29 — Recovery (Optional)

🔴MorningBrunch somewhere good

🔴DayBrooklyn Heights Promenade → DUMBO walk

🟡PMFly home

🏨 Hotel Options

Hotel	$/night	Rating	Notes
Hotel 50 Bowery (Hyatt)	$228	4.5⭐	⭐ TOP PICK — rooftop bar, walk to everything
Moxy LES (Marriott)	$263	4.3⭐	Fun vibe, Japanese restaurant, Marriott points
Untitled at 3 Freeman Alley	$202	4.6⭐	Boutique hidden gem, highest rated
Hotel Indigo LES (IHG)	$203	3.9⭐	Solid, has pool
Holiday Inn LES (IHG)	$111	4.1⭐	Budget pick — surprisingly good

🍽️ Restaurant Options

Classic NYC

Katz's Delicatessen GOING
LES — Old-school Jewish deli, pastrami done right
Russ & Daughters Cafe TOP PICK
LES — Smoked fish, bagels, appetizing culture. Best for Fri breakfast.
John's of Bleecker Street
West Village — Coal-oven pizza, worn-in space
Via Carota
West Village — High-level trattoria, local NY aspirational

Neighborhood Gems

Bonnie's THU DINNER
Williamsburg — Cantonese-American, natural wine, critically acclaimed
Sami & Susu
LES — Warm Levantine plates, lively
Cafe Mogador
East Village — Moroccan staple
L'Artusi
West Village — Polished but not stuffy Italian
Wildair
LES — Tiny, sharp, natural wine + inventive plates
Frenchette
Tribeca — Buzzy but actual NY brasserie
Place des Fêtes
Clinton Hill — Intimate, creative, no scene nonsense
St. Anselm
Williamsburg — Unfussy steakhouse alternative

Birthday Dinner Contenders (Sat 3/28)

Via Carota
West Village — The "special but not pretentious" pick
L'Artusi
West Village — Polished date-night energy
Frenchette
Tribeca — Buzzy brasserie, great for groups
Place des Fêtes
Clinton Hill — Intimate, creative
St. Anselm
Williamsburg — Unfussy, great food, local crowd

🎭 Entertainment

Broadway / Shows

Maybe Happy Ending BOOKED — Fri 7pm
Two aging robots fall in love. Darren Criss. Tender, gorgeous, critics obsessed.
Buena Vista Social Club BACKUP
Cuban music/dance, joyful, Tony buzz
Dog Day Afternoon PREVIEWS 3/10
Jon Bernthal + Ebon Moss-Bachrach. Gritty NYC 1972. Very NY.
Death of a Salesman PREVIEWS 3/6
Nathan Lane + Laurie Metcalf. Once-in-a-generation pairing.
Moulin Rouge (w/ Megan Thee Stallion)
Spectacle. Her first week. Show closing July.
Titanique PREVIEWS 3/26
Céline Dion Titanic parody. Hilarious.

Comedy

Comedy Cellar BOOKED — Fri 12:30am
MacDougal St. (OG room), $25. Phone-free. Late-night magic.

Jazz

Village Vanguard SAT NIGHT
THE legendary room. Perfect birthday closer. Book ahead.
Smalls
Raw, intimate, classic downtown jazz. Good Thu alt.
Mezzrow
Calmer, piano-forward vibe

🍸 Cocktail Bars

Attaboy (LES) — No-menu, bartenders build to your mood
Temple Bar (NoHo) — Dark, elegant, grown-up Manhattan
Long Island Bar (Cobble Hill) — Old NY tavern DNA
Maison Premiere (Williamsburg) — Absinthe, old-world Brooklyn
Bar Goto (LES) — Japanese cocktails
PDT (EV) — Speakeasy through Crif Dogs phone booth

🚶 Vibe Walks

West Village → SoHo → LES — Brownstones to cast-iron to grit
Brooklyn Heights → DUMBO — Skyline at dusk
Fort Greene → Clinton Hill — Tree-lined Brooklyn calm
Red Hook afternoon — Industrial waterfront, slower pace

✅ Booking Checklist

☐ Flights: ORD → NYC 3/26, NYC → ORD 3/29
☐ Hotel: Pick and book (Hotel 50 Bowery recommended)
☑ Comedy Cellar: Fri 3/27 12:30am MacDougal St. — BOOKED
☑ Maybe Happy Ending: Fri 3/27 7pm — BOOKED
☐ Bonnie's: Watch Resy ~2 weeks out for Thu 3/26 ~9pm (Delphi monitoring)
☐ Village Vanguard: Book Sat 3/28 evening set
☐ Birthday dinner: Pick and reserve for Sat 3/28
☐ Coordinate with Andrew & Christie (Thu night)
☐ Coordinate with Aadil & Sadaf (Fri day + Sat)
☐ Check with Fonti & Joe (Sat?)

Last updated by Delphi 🔮 — March 2, 2026