New York Trip Itinerary — Five Days Plus a Wedding Weekend (Sep 29 – Oct 8, 2026)
This is a day-by-day New York City itinerary built for a first week in the city, anchored around a Saturday morning wedding at the Church of the Transfiguration. Every stop is geocoded on an interactive Leaflet/OpenStreetMap map with points connected in visit order (straight lines, not navigable walking or subway paths), transit notes, sunset times and reservation status. The page also works as an editor: click any item to change the time, address, cost or note, and your changes are saved locally in your browser.
The five itinerary days
- Day 1 — Marriage license + park south + Midtown: overnight at Casa Blanca Hotel Brooklyn, 143 Park Avenue, Fort Greene (a 23-minute walk from the clerk). Marriage license at the Brooklyn City Clerk's Office, 210 Joralemon Street, Room 205, at 10:30 (arrive 10:00 for building prescreening). Then the 4/5 to Grand Central to leave bags at Hyatt Grand Central (check-in is not a timed appointment). Grand Central ceiling and the New York Public Library are next door. Afternoon in Central Park south: The Plaza, Delacorte Clock, Conservatory Water, Bethesda Fountain and the Annie Hall terrace benches. Dusk at The Plaza and Paris Theater across 58th Street, Times Square, Joe’s Pizza on Broadway, then back along 42nd Street.
- Day 2 — Guggenheim + Chelsea + Bow Bridge: Two booked Guggenheim admissions at 10:30 on Oct 1; public transit to Chelsea Market for lunch and shopping, walk south to Carrie's 66 Perry St and West Village, then transit back uptown for Bow Bridge sunset. Bemelmans Bar follows; leave by 20:15 for The Smith Midtown, 956 Second Avenue, booked for 21:00 (table for six). The Met remains on Oct 5.
- Day 3 — Villages + Dowling's dinner: from Hyatt to an optional Empire State Building morning visit, then southwest to Olio e Più lunch, Washington Square Arch, the 2019 World’s Best Bar Dante for an optional cocktail, Strand Bookstore, SoHo Broadway/Prince and Orchard Street; Bowery Hotel exterior becomes an optional detour. Chelsea and Carrie moved to Oct 1. Then head to the Carlyle for the booked Dowling's dinner at 19:00; buy OTC items or supplements at the 24-hour CVS beside Hyatt on the way back (the pharmacy counter has separate hours). The Smith booking is on Oct 1 at 21:00 instead.
- Wedding day: take luggage from Hyatt directly to Sheraton New York Times Square Hotel, 811 Seventh Avenue at 53rd Street, and leave it with the bell desk before the 10:00 ceremony at The Church of the Transfiguration, 1 East 29th Street; lunch by the church in NoMad; on the way north ask the Richard Rodgers Theatre whether Hamilton standing room is available, then Sheraton bag check and Top of the Rock timed 16:30. Hamilton 19:00 conflicts with lingering at Rockefeller for sunset, so it is not a confirmed show.
- Day 4 — Statue + Brooklyn: Statue City Cruises pedestal at 09:00 from Castle Clinton, Wall Street, Trinity Church and the 9/11 Memorial as pass-bys, eat lunch in the Financial District, walk the Brooklyn Bridge into DUMBO for Jane's Carousel, then take the separate NYC Ferry East River A from DUMBO to North Williamsburg (B62 bus as backup) for the waterfront at night. This afternoon ferry is not part of the booked Statue City Cruises ticket.
- Day 5 — The Met half-day + sunset tram: From Sheraton take public transit to The Met on Oct 5 for 10:00–15:00, then head south to Midtown Fifth Avenue, optionally stop at Valerie, ride the Roosevelt Island Tram near sunset and, if a table is available, visit Ophelia rooftop bar for skyline views on the Manhattan return route instead of the optional Queensbridge Park benches. Neither bar is booked. Departure morning Oct 6 covers Lincoln Center and a shorter MoMA visit before JFK.
Booked and confirmed details
Flights: DL26 Seoul (ICN) to Atlanta, DL520 Atlanta to New York LaGuardia on Sep 29; DL688 New York JFK to Seattle and DL281 Seattle to Shanghai Pudong on Oct 6–8. Lodging: Casa Blanca Hotel Brooklyn, 143 Park Avenue, one night Sep 29; Hyatt Grand Central New York, 109 East 42nd Street, three nights Sep 30 to Oct 3; Sheraton New York Times Square Hotel, 811 Seventh Avenue, three nights Oct 3 to Oct 6. Wedding: 10:00 am, Saturday Oct 3, 2026 at The Church of the Transfiguration, 1 East 29th Street. Rockefeller Center admission is 16:30 that afternoon. Statue of Liberty pedestal sailing is 09:00 on Oct 4, boarding 08:30. Passport numbers, ticket numbers and booking references are deliberately not published here.
How to use this page
Left panel: pick a day (Sep 29 to Oct 8) — each row shows that day’s theme and how many eating, playing, transit and lodging stops it holds, with a trip brief underneath. Centre: geocoded stops connected by straight visit-order lines for the selected day, not turn-by-turn routes; switch to All days for the whole-trip overview. Right: that day laid out on a 15-minute grid, from the first timed stop to the last, including free gaps, the sunset tick and items with no fixed time; click any item to edit every field, or use the Trip info tab to edit the overview, flights and per-day plans
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