18 Days Across America: San Diego to NYC Family Trip

Day 1 - Fri, Sep 11

San Diego, San Francisco

Fly from San Diego to San Francisco

09:00 AM

San Diego International Airport

Take BART from SFO into downtown San Francisco

12:00 PM

San Francisco International Airport

Casual lunch near Yerba Buena

01:15 PM

Yerba Buena / SoMa

Stretch out in Yerba Buena Gardens

02:30 PM

Yerba Buena Gardens

Explore SFMOMA in the late afternoon

03:15 PM

SFMOMA

Budget dinner in SoMa or Chinatown

06:30 PM

San Francisco

Day 2 - Sat, Sep 12

San Francisco

Morning ferry to Alcatraz Island

09:00 AM

Pier 33 Alcatraz Landing

Seafood or chowder lunch around Fisherman's Wharf

12:30 PM

Fisherman's Wharf

Ride a historic cable car

02:00 PM

Powell-Hyde or Powell-Mason line

Browse Chinatown and Portsmouth Square

03:00 PM

Chinatown

Golden Gate view break at Aquatic Park or Marina Green

04:30 PM

Aquatic Park / Marina

Dinner back near the hotel

06:30 PM

Downtown San Francisco

Day 3 - Sun, Sep 13

San Francisco

California Academy of Sciences

10:00 AM

Golden Gate Park

Play and snack break in Golden Gate Park

12:30 PM

Golden Gate Park

Budget lunch around the park or Inner Sunset

01:15 PM

Inner Sunset

Late afternoon at Crissy Field for bridge views

03:00 PM

Crissy Field

Early dinner in the Marina

05:30 PM

Marina District

Pack and prep for Chicago

07:30 PM

Hotel in San Francisco

Day 4 - Mon, Sep 14

San Francisco, Chicago

Transfer to SFO by BART

07:30 AM

Downtown San Francisco

Fly from San Francisco to Chicago

10:30 AM

San Francisco International Airport

Check in and settle near the Loop

05:30 PM

Chicago Loop

Easy walk through Millennium Park

06:30 PM

Millennium Park

See Cloud Gate and the park plaza

07:00 PM

Millennium Park

Casual dinner in the Loop

07:45 PM

Chicago Loop

Day 5 - Tue, Sep 15

Chicago

Chicago Architecture Center River Cruise

10:00 AM

Chicago Riverwalk

Lunch on the Riverwalk

12:30 PM

Chicago Riverwalk

Visit Millennium Park and nearby public art

02:00 PM

Millennium Park

Art Institute of Chicago exterior and quick museum option

03:30 PM

Art Institute of Chicago

Downtime at Maggie Daley Park

05:00 PM

Maggie Daley Park

Deep-dish or casual Chicago dinner

06:30 PM

Loop / River North

Day 6 - Wed, Sep 16

Chicago

Morning at Navy Pier

10:00 AM

Navy Pier

Budget lunch near Streeterville

12:30 PM

Streeterville

Walk the Magnificent Mile

02:00 PM

North Michigan Avenue

Chicago River or lakefront pause

03:30 PM

DuSable Bridge / lakefront

Early dinner in River North

05:30 PM

River North

Return to hotel and pack for Washington

07:00 PM

Chicago Loop

Day 7 - Thu, Sep 17

Chicago, Washington DC

Head to the airport from downtown Chicago

07:30 AM

Chicago Loop

Fly from Chicago to Washington, DC

10:30 AM

Chicago O'Hare International Airport

Check in near the National Mall or Metro

02:30 PM

Washington, DC

Easy first walk on the National Mall

04:00 PM

National Mall

Lincoln Memorial and Reflecting Pool at sunset

05:00 PM

Lincoln Memorial

Dinner near Foggy Bottom or downtown

07:00 PM

Foggy Bottom / Downtown DC

Day 8 - Fri, Sep 18

Washington DC

Smithsonian National Museum of Natural History

10:00 AM

National Mall

Lunch break on or near the Mall

12:30 PM

National Mall

National Air and Space Museum

01:45 PM

National Mall

Capitol grounds and Mall stroll

04:15 PM

US Capitol area

Dinner in Penn Quarter

06:00 PM

Penn Quarter

Return early to hotel

07:45 PM

Washington, DC

Day 9 - Sat, Sep 19

Washington DC

Washington Monument area in the morning

09:30 AM

Washington Monument

World War II Memorial

11:00 AM

National Mall

Lunch break downtown

12:30 PM

Downtown DC

Martin Luther King Jr. Memorial and Tidal Basin area

02:00 PM

West Potomac Park

Jefferson Memorial

03:15 PM

Tidal Basin

Dinner in Capitol Hill or The Wharf

06:00 PM

Washington, DC

Day 10 - Sun, Sep 20

Washington DC

Slow morning and neighborhood breakfast

09:00 AM

Washington, DC

Choose one extra Smithsonian or family free-choice stop

11:00 AM

National Mall area

Lunch near the Mall

01:00 PM

National Mall area

Afternoon park time or hotel break

02:30 PM

Washington, DC

Early dinner and prep for New York transfer

05:30 PM

Washington, DC

Pack for train to New York City

07:00 PM

Hotel in Washington, DC

Day 11 - Mon, Sep 21

Washington DC, New York City

Train from Washington Union Station to New York Penn Station

09:00 AM

Washington Union Station

Check in at Manhattan hotel

01:30 PM

Midtown Manhattan

Late lunch near the hotel

02:15 PM

Midtown Manhattan

Empire State Building area and Midtown walk

03:30 PM

Midtown Manhattan

Bryant Park pause

05:00 PM

Bryant Park

Dinner in Koreatown or Midtown

06:30 PM

Koreatown / Midtown

Day 12 - Tue, Sep 22

New York City

Statue of Liberty and Ellis Island ferry

09:00 AM

Battery Park

Lunch in the Financial District

01:00 PM

Financial District

Walk Wall Street and the Charging Bull area

02:15 PM

Lower Manhattan

Explore the 9/11 Memorial exterior plaza

03:30 PM

World Trade Center

Sunset waterfront pause at Battery or Brookfield Place area

05:30 PM

Lower Manhattan

Dinner back in Midtown

07:00 PM

Midtown Manhattan

Day 13 - Wed, Sep 23

New York City

Morning in Central Park

09:30 AM

Central Park

American Museum of Natural History

11:00 AM

Upper West Side

Lunch near the museum or inside if convenient

01:30 PM

Upper West Side

More Central Park time at the Great Lawn or nearby playgrounds

03:00 PM

Central Park

Early dinner on the Upper West Side

05:30 PM

Upper West Side

Quiet evening back at the hotel

07:30 PM

Midtown Manhattan

Day 14 - Thu, Sep 24

New York City

Walk the High Line area

10:00 AM

Chelsea

Lunch at Chelsea Market or nearby casual spot

12:00 PM

Chelsea

Explore Greenwich Village streets

01:30 PM

Greenwich Village

Times Square for a short look, not a long stay

04:00 PM

Times Square

Dinner in Hell's Kitchen

05:30 PM

Hell's Kitchen

Optional evening view from Midtown streets

07:00 PM

Midtown Manhattan

Day 15 - Fri, Sep 25

New York City

Slow breakfast and laundry/reset time

09:00 AM

Midtown Manhattan

Optional second museum or neighborhood choice

11:00 AM

New York City

Lunch wherever the family chooses

01:00 PM

New York City

Brooklyn Bridge or DUMBO-style skyline option

03:00 PM

Lower Manhattan / Brooklyn

Casual dinner with skyline views or back in Manhattan

06:00 PM

DUMBO or Manhattan

Return to hotel for rest

08:00 PM

Midtown Manhattan

Day 16 - Sat, Sep 26

New York City

Family choice morning in Central Park or playground time

10:00 AM

Central Park

Brunch nearby

11:30 AM

Upper West Side or Midtown

Rockefeller Center and Fifth Avenue walk

01:30 PM

Midtown Manhattan

New York Public Library and Bryant Park exterior stop

03:00 PM

Bryant Park

Dinner in Midtown East or Koreatown

05:30 PM

Midtown Manhattan

Optional evening lights walk

07:00 PM

Midtown Manhattan

Day 17 - Sun, Sep 27

New York City

Free morning for souvenirs or favorite repeat stop

09:30 AM

New York City

Relaxed brunch

11:00 AM

New York City

One last classic neighborhood walk

01:00 PM

SoHo / West Village

Afternoon hotel break and packing

03:30 PM

Midtown Manhattan

Farewell dinner

06:00 PM

Midtown Manhattan

Final evening stroll

07:30 PM

Bryant Park or nearby streets

Day 18 - Mon, Sep 28

New York City

Breakfast and hotel checkout

08:30 AM

Midtown Manhattan

Transfer to airport

10:30 AM

New York City

Fly home from New York City

01:30 PM

New York City airport

Airport lunch if needed

11:45 AM

New York City airport

Wrap-up and departure

12:30 PM

Departure gate

Trip ends

05:00 PM

Home destination