Zeitrip Agency

East Coast Friends Trip: NYC Nightlife & DC History

May 15 - 25, 2026

The ultimate 10-day East Coast road trip for friends. From the electric nightlife of NYC to the monumental history of DC and the gritty charm of Philadelphia. This high-energy itinerary is packed with rooftop drinks, legendary food spots, and cultural landmarks, optimized for group fun and easy expense sharing.

Thursday, May 14(Day 1)
LHR → JFK
08:30 → 11:15British Airways BA117

New York City · The Moxy NYC Times Square (2x Double Rooms)

May 14 → May 195 nights
Thursday, May 14(Day 1)
Times Square Check-in + Orientation Walk
16:00 - 18:00
Drop your bags at the hotel and dive straight into the chaos. Times Square is intense, but seeing it for the first time is a rite of passage. Perfect for that first group selfie.
Koreatown Dinner + Noraebang (Karaoke)
19:30 - 23:30
Head to Jongro strictly for the meats. It’s loud, it’s fun, and the galbi is top-tier. Afterwards, hit a private karaoke room to belt out terrible renditions of 2000s hits.
Friday, May 15(Day 2)
Statue of Liberty + Ellis Island
08:30 - 13:00
Book the very first ferry to beat the crowds. If you reserved Crown Access, get ready for a tight squeeze and a lot of stairs, but the view is iconic.
Wall Street + 9/11 Memorial
14:00 - 17:00
Snap a photo with the Charging Bull (rub the nose for good luck?) and then take a quiet moment at the 9/11 Memorial pools. It's a powerful and necessary contrast.
Brooklyn Bridge Walk + DUMBO Sunset
18:00 - 20:30
Walk across the bridge from Manhattan to Brooklyn at sunset. Once in DUMBO, grab a coal-fired pizza at Juliana's—often less of a wait than Grimaldi's and just as good.
Rooftop Drinks at Westlight
21:30 - 00:30
Head up to the 22nd floor for the best panoramic views of the Manhattan skyline. The cocktails are pricey but worth every penny for the backdrop.
Saturday, May 16(Day 3)
Central Park Morning Run/Walk
07:30 - 09:30
Join the locals for a morning loop around the Reservoir (1.58 miles). It’s flat, scenic, and offers one of the classic skyline views found in every movie.
MoMA (Museum of Modern Art)
10:30 - 13:30
Home to 'Starry Night' and 'Les Demoiselles d'Avignon'. It’s huge, so pick a few galleries to focus on rather than trying to see it all.
Top of the Rock Sunset
18:30 - 20:00
The best observation deck because you can actually *see* the Empire State Building. Sunset slots book up fast, so reserve well in advance.
Comedy Show at Comedy Cellar
21:30 - 23:30
The absolute mecca of stand-up. Phones go in bags. You never know who might drop in—Chappelle, Rock, Seinfeld. Reserve online immediately when tickets drop.
Sunday, May 17(Day 4)
High Line + Chelsea Market
10:00 - 13:00
Walk this elevated rail-line-turned-park from Hudson Yards down to Chelsea. It gets crowded, so go early. Finish with a food crawl through Chelsea Market.
Yankees Game at Yankee Stadium
14:00 - 18:00
Take the subway to the Bronx. It’s not just a game; it’s an atmosphere. Grab a hot dog, a large beer, and soak in the energy of the Bleacher Creatures.
Harlem Jazz at Minton's Playhouse
21:00
Minton's is legendary—the birthplace of Bebop. Dress sharp, order some soul food, and enjoy world-class jazz in a sophisticated, historic setting.
Monday, May 18(Day 5)
Chinatown Dim Sum Brunch
10:30 - 12:30
Jing Fong is an experience—massive banquet hall, carts flying by. Don't wait for a menu, just point at what looks good on the carts and dig in.
SoHo Shopping + Little Italy
13:00 - 17:00
Wander the cobblestone streets for world-class shopping. Check out the cast-iron architecture. Grab a cannoli at Ferrara if you wander into Little Italy.
East Village Bar Crawl
20:00 - 02:00
The ultimate bar crawl neighborhood. Start at McSorley's (cash only, only two beer options: light or dark) then hunt for the phone booth entrance to PDT.
Tuesday, May 19(Day 6)
Acela to DC + Check-in
08:00 - 12:00
You upgraded to business class? Nice. The train ride is smooth. Grab a coffee and watch the Jersey scenery fade into Maryland suburbs.
Tuesday, May 19(Day 6)
Penn Station, NYC → Union Station, DC
08:00 → 10:50Acela Express 2151

Washington DC · The Line DC (2x Twin Rooms)

May 19 → May 223 nights
Tuesday, May 19(Day 6)
National Mall Walking Tour
14:00 - 18:00
It's a lot of walking. Start at the Capitol (don't miss the Library of Congress underground tunnel) and work your way west to Lincoln.
Lincoln Memorial at Night
21:00 - 22:30
Lincoln Memorial is majestic during the day, but at night it's spiritual. Sit on the steps and just take it in. The reflection in the pool is perfect.
Wednesday, May 20(Day 7)
Smithsonian Air & Space Museum
09:30 - 12:30
Touch the moon rock near the entrance. See the Spirit of St. Louis. It's crowded with school groups, but totally worth it.
National Gallery of Art
13:30 - 16:00
The only Da Vinci in the Americas is here (Ginevra de' Benci). The walkway between the East and West buildings is a trippy light show.
Georgetown Evening + Waterfront
17:30 - 22:00
Cobblestone streets, expensive boutiques, and the 'Exorcist Steps' (36th & Prospect). Walk down to the waterfront for dinner.
Thursday, May 21(Day 8)
Arlington National Cemetery
09:00 - 12:00
Humbling and vast. The Changing of the Guard at the Tomb of the Unknown Soldier happens every hour on the hour (every half hour in summer). Respectful silence is key.
Library of Congress
13:30 - 15:30
The Great Hall is jaw-dropping. It's arguably the most beautiful interior in DC. Show your library card if you want to access the reading room.
U Street Corridor Night Out
20:00 - 01:00
Black Broadway. Stop by Ben's Chili Bowl for a half-smoke (it's a spicy sausage, not a hot dog). Then hit 9:30 Club or any bar on U St.
Friday, May 22(Day 9)
Train to Philly + Pat's vs Geno's
10:00 - 13:30
Take the train to 30th St Station. Then head straight to the intersection of 9th & Passyunk. Pat's or Geno's? Try half of each and decide the winner.
Friday, May 22(Day 9)
Union Station, DC → 30th Street Station, Philly
10:00 → 11:45Regional 172

Philadelphia · Hotel Monaco Philadelphia (2x Queen Rooms)

May 22 → May 242 nights
Friday, May 22(Day 9)
Independence Hall + Liberty Bell
14:30 - 17:00
You're standing in the room where the country started. The Liberty Bell is right across the street. It's smaller than you think, but still cool.
Philadelphia Museum of Art (Rocky Steps)
17:30 - 19:00
Yes, you have to run up them. Yes, play the song on your phone. At the top, turn around for one of the best views of the Benjamin Franklin Parkway.
Fishtown Bar Hopping
21:00 - 02:00
Frankford Avenue is the spot. Hit up Barcade, Garage, or just wander. It's cleaner and hipper than South Street.
Saturday, May 23(Day 10)
Reading Terminal Market Brunch
09:30 - 11:30
Get there early. DiNic's Roast Pork is better than a cheesesteak (fight me). For dessert, get a fresh Amish donut from Beiler's.
Eastern State Penitentiary
12:30 - 15:00
Audio tour narrated by Steve Buscemi. It's eerie, damp, and fascinating. The crumbling cellblocks are a photographer's dream.
South Street + Magic Gardens
16:00 - 18:30
Eclectic, gritty, and fun. Philadelphia's Magic Gardens is a mosaic masterpiece that covers an entire block. You need a timed ticket.
Final Dinner at Zahav
20:00 - 22:30
If you managed to get a reservation, you won the lottery. The pomegranate lamb shoulder is life-changing. If not, try Laser Wolf (same owners).
Sunday, May 24(Day 11)
Airport + Final Cheesesteak
14:00 - 18:35
One last cheesesteak at the airport? Why not. Give yourself plenty of time for security, PHL can be unpredictable.
Sunday, May 24(Day 11)
PHL → LHR
18:45 → 06:50 (May 24 - May 25)British Airways BA066

Ready to plan your trip?

Customize this itinerary to handle logistics, bookings, and collaboration in one place.