Start at Chelsea Market around 11 a.m. and take your time browsing before lunch. The food hall has plenty of options; plan on roughly $15–$30 per person for a casual meal. Afterward, walk about 15–20 minutes to Little Island.
Your Live with Kelly and Mark tickets are for Day 2, not today, so keep this first day relaxed and don’t plan around a studio arrival. Double-check the ticket confirmation for the Day 2 timing and entry instructions.
Spend about 45 minutes at Little Island, exploring its paths and river overlooks. It’s free, but check the park’s seasonal schedule before you set out; December can be windy along the water, so bring a warm layer.
From there, walk back toward Gansevoort Street to enter the High Line and follow it north toward Hudson Yards. Allow 1–1½ hours at an unhurried pace, with stops for public art and views. The park closes earlier in winter than in summer, so avoid leaving this walk too late.
The High Line ends beside Vessel and Hudson Yards. Take 30–45 minutes to admire Vessel from the plaza; if you want to go inside, check current hours, prices, and reservation requirements in advance, as access rules can change. Finish with a café break or browse the shops at Hudson Yards—a useful chance to warm up before dinner.
Today is the day for your Live with Kelly and Mark tickets. Since you’re arriving from another city, this plan works best if you can reach the Upper West Side in time for the check-in window printed on your ticket; audience members need to follow those instructions, and the taping and check-in can take about 2–3 hours. If your arrival timing won’t allow that, contact the show’s ticket provider about options rather than counting on being admitted late.
After the taping, head downtown to The Battery for the Statue City Cruises ferry to Statue of Liberty and Liberty Island. Buy a timed ticket in advance and allow about 3–4 hours for security, the ferry, and a visit to the island. Check the official operator’s schedule before setting out, especially for the last return ferry. December daylight is limited, so keep the island visit focused if you also want time for the bridge.
Back in Manhattan, make your way to the pedestrian entrance near City Hall and walk the Brooklyn Bridge toward Brooklyn. Allow roughly an hour at a relaxed pace, with extra time for photos; the walk is free, but the bridge can be windy and busy. If the taping or ferry runs behind, shorten the island stop rather than rushing through both experiences.
Take the subway back to Midtown for Times Square, then walk to Lillie’s Victorian Establishment. Budget approximately $30–$60 per person before drinks and tip, and consider reserving ahead. Leave a comfortable buffer to reach your theater for the Broadway show; showtimes vary, and performances commonly run 2–3 hours.
Keep the morning flexible for the separately arranged journey into Manhattan, then head to Bethesda Terrace and Fountain for a relaxed look at the terrace and a brief walk through Central Park. In winter, paths can be slippery, so wear shoes with good grip. Continue south to Wollman Rink; allow 1.5–2 hours for skating, rentals, and possible lines, and check the rink’s current schedule and reservation requirements before you go.
Walk out toward The Plaza to see its holiday display, then take a look at the seasonal windows at Bergdorf Goodman. Both are close to the park’s southeast corner, so this makes an easy transition toward Midtown. Have an early dinner at Oscar Wilde before the show; it’s a short cab ride or roughly a 20-minute walk from the Fifth Avenue area. Allow time for the meal and the trip to Radio City, and budget about $40–$80 per person before tip.
Make Radio City Music Hall the anchor of the day: arrive well before curtain for security and to find your seats, and check your ticket for the exact performance time. The Rockettes’ Christmas Spectacular typically runs around 90 minutes, but show dates and times vary, so confirm the December 9 schedule and book tickets ahead; prices depend on the performance and seat.
After the show, walk over to Rockefeller Center and Saks Fifth Avenue for the tree and holiday lights. It will be busy, especially around the plaza, so leave room to move with the crowds and enjoy the displays at an unhurried pace.
No packing list attached yet.