America’s story stretches from the Pacific’s fog-kissed bluffs to the glitter of the Atlantic skyline. This 14-day itinerary connects that tapestry: start from Sunnyvale in Silicon Valley, trace the Bay Area’s innovation and Gold Rush past, pause in Chicago for architecture and blues, then end in New York City with Broadway lights, harbor icons, and art-filled afternoons.

You’ll move efficiently—morning flights, centrally located stays, and smart neighborhood clustering—so most hours are spent exploring, not transferring. Expect must-see landmarks (Golden Gate Bridge, The Bean, the Statue of Liberty) balanced with local favorites: neighborhood bakeries, record shops, waterfront walks, and late-night slices.

Practical notes: reserve timed tickets for popular sights (Alcatraz, NYC observation decks). Pack layers—San Francisco’s microclimates can change by the hour; Chicago and NYC are best navigated by transit and on foot. Tipping is customary (18–20% in restaurants). Contactless payments are widely accepted.

San Francisco

San Francisco is a city of hills and ideas—Victorian facades, cable cars, counterculture, and venture capital, all snugged against the Golden Gate. Its neighborhoods read like short stories: North Beach’s espresso bars, the Mission’s murals, the Presidio’s eucalyptus-scented trails.

Starting from Sunnyvale, you’re already in the Bay Area: warm up with a South Bay tech-and-history sampler, then ride north for classic waterfronts, island prisons, and farm-to-table dinners.

Days 1–4: South Bay Warm-Up + San Francisco Icons

• Day 1 (Sunnyvale/South Bay): Visit the Apple Park Visitor Center for the rooftop view of the ring campus and an AR model of Apple Park. Pop to the Computer History Museum in Mountain View to see the evolution from punch cards to smartphones. Coffee at Voyager Craft Coffee (artful pours), then dinner in Palo Alto’s buzzing core—try Zareen’s for Pakistani/Indian comfort plates or Taverna for Greek meze.
• Day 2 (Golden Gate & Waterfront): Cross the Golden Gate Bridge early for fewer crowds; continue to Lands End for cliffside trails and Sutro Baths ruins. Lunch at Hog Island Oyster Co. in the Ferry Building (don’t miss Acme Bread and Humphry Slocombe). Ride a historic cable car at dusk and dine at Zuni Café (roast chicken for two) or State Bird Provisions (inventive American small plates).
• Day 3 (Alcatraz & North Beach): Book a morning ferry to Alcatraz for the award-winning audio tour. Espresso crawl in North Beach (biscotti at Caffe Trieste), climb Telegraph Hill to Coit Tower murals, then Chinatown for hand-pulled noodles. Dinner ideas: House of Prime Rib (classic SF supper) or Rich Table (Californian with flair).
• Day 4 (Mission & Presidio): Breakfast at Tartine Bakery (morning buns), then stroll Clarion Alley murals and grab a Mission burrito at La Taqueria. Afternoon at the Presidio Tunnel Tops and Crissy Field beach views back to the bridge. Cap with cocktails at Tosca or natural wines at Verjus.

Where to stay: Search central neighborhoods like Union Square, Nob Hill, North Beach, or the Marina for transit-friendly bases.

• VRBO options: San Francisco vacation rentals
• Hotels.com picks: San Francisco hotels

Getting in and around: From Sunnyvale, take Caltrain to SF or rideshare (~45–75 minutes depending on traffic). If you’re flying into the region, compare SFO, OAK, and SJC on Trip.com flights or Kiwi.com. Within SF, use Muni, BART, and your feet; buy a day pass if riding often.

Chicago

Chicago rose from the ashes of the Great Fire to become America’s architecture classroom. Steel and glass meet lakefront beaches, and neighborhoods hum with jazz, Polish delis, taquerías, and new-wave bakeries.

It’s a city for art lovers and eaters: the Art Institute’s masterpieces, a river cruise narrated by pros, and deep-dish pizzas best debated slice by slice.

Days 5–9: Fly to Chicago, Architecture, Art, and Eats

• Day 5 (Travel morning + Loop orientation): Morning flight SFO/OAK/SJC → ORD or MDW (~4–4.5 hours; typical one-way $120–$250 booked early). Search on Trip.com flights or Kiwi.com. Afternoon stroll: Millennium Park’s Cloud Gate, the Chicago Cultural Center (stained-glass dome), and the Riverwalk at golden hour.
• Day 6 (Architecture & River): Take a Chicago Architecture Center–style river cruise to decode styles from Art Deco to Postmodern. Lunch at Portillo’s (Italian beef with hot giardiniera) or Eataly (pastas and cannoli). Sunset views from 360 CHICAGO in the John Hancock building; dinner in the West Loop at Girl & the Goat or burger at Au Cheval.
• Day 7 (Art & Neighborhoods): Spend a few hours at the Art Institute of Chicago (Seurat, Hopper, Monet). Coffee at Intelligentsia (Millennium Park) or Sawada (West Loop). Explore Pilsen murals and the National Museum of Mexican Art; dinner at Carnitas Uruapan or modern Mexican at Topo Gigio? For Italian, try Quartino for small plates.
• Day 8 (Baseball or Beaches): Tour Wrigley Field or lounge on North Avenue Beach if it’s warm. Deep-dish showdown: Lou Malnati’s (buttery crust) vs Pequod’s (caramelized edge). Nightcap at Three Dots and a Dash (tiki speakeasy) or The Violet Hour (craft cocktails).
• Day 9 (Museums & Blues): Choose the Museum of Science and Industry or Field Museum. Dinner at The Purple Pig (Mediterranean plates) and finish with live music at a classic blues club in River North.

Where to stay: Base in the Loop, River North, or West Loop for easy L-train access.

• VRBO options: Chicago vacation rentals
• Hotels.com picks: Chicago hotels

Transit tips: Buy a Ventra pass for CTA trains/buses. Rideshares are plentiful. Consider the lakeshore trail for scenic bike rides.

New York City

New York is an atlas stacked vertically—each block its own country. Neighborhoods flip from old-world bakeries to neon ramen joints in a blink, museums rival palaces, and the skyline is both backdrop and protagonist.

In five days, mix iconic musts (Central Park, the Met, Broadway) with lived-in corners: a bodega breakfast, a neighborhood jazz bar, a ferry at sunset. Book the big-ticket views in advance.

Days 10–14: Fly to NYC, Neighborhoods, Museums, and Skyline Nights

• Day 10 (Travel morning + Midtown): ORD/MDW → JFK/LGA/EWR (~2–2.5 hours; typical one-way $80–$180). Compare on Trip.com flights or Kiwi.com. Stretch your legs along Fifth Avenue, step into Bryant Park, and see Grand Central’s celestial ceiling. Early dinner at Joe’s Pizza (fold, don’t fuss) or ramen at Ippudo.
• Day 11 (Downtown history & harbor): Walk the Brooklyn Bridge to DUMBO for skyline photos under the Manhattan Bridge. Grab a slice at Juliana’s or coffee at Butler. Ferry back to lower Manhattan for the 9/11 Memorial and cobblestone lanes of Stone Street.
• Day 12 (Museums & Central Park): Morning in The Met (start with the Temple of Dendur), then picnic on the Great Lawn. Late afternoon shopping/people-watching on Madison Avenue; dinner at Via Carota (West Village) or L’Artusi (pastas done right). Dessert: Levain cookies.
• Day 13 (Neighborhood flavors): Bagels at Ess-a-Bagel or smoked fish at Russ & Daughters. Explore SoHo galleries, Chinatown dumplings, and Little Italy pastries. Evening cocktails at Dante or The Long Island Bar, then a jazz set on the Lower East Side.
• Day 14 (Views + Broadway): Hit an observation deck by day, browse MoMA in the afternoon, then a Broadway show at night. Late supper at Los Tacos No. 1 or Korean BBQ in Koreatown.

Where to stay: Choose Midtown for convenience, the Village for dining/nightlife, or the Upper West Side for park access.

• VRBO options: New York City vacation rentals
• Hotels.com picks: New York City hotels

NYC Viator experiences to prebook:

• New York in One Day Guided Sightseeing Tour — a comprehensive, guide-led overview perfect for your first full day. Book here.

  

• SUMMIT One Vanderbilt Experience Ticket — immersive art-meets-observation deck with wild reflections and Midtown views. Book here.

  

• Statue of Liberty and Ellis Island Tour: All Options — reserve-access ferries and storytelling that bring immigrant history to life. Book here.

  

• Manhattan Architecture Yacht Cruise — a refined, narrated loop around Manhattan’s shoreline with postcard vistas. Book here.

  

Coffee, breakfast, lunch, dinner picks:

• Coffee/breakfast: Joe Coffee (balanced espresso), Devoción (Colombian beans, greenhouse vibe), Ess-a-Bagel (hefty, classic NYC bagels).
• Lunch: Los Tacos No. 1 (adobada), Katz’s Delicatessen (hand-carved pastrami), Prince Street Pizza (spicy square slice).
• Dinner: Via Carota (tender pastas, seasonal veg), L’Artusi (signature garganelli), Ippudo (porky tonkotsu), or splurge on a steakhouse night at Keens (mutton chop).
• Drinks: Dante (Negroni variations), Westlight in Williamsburg (rooftop panoramas), The Dead Rabbit (Irish pub downstairs, cocktail bar upstairs).

Local tips: Use OMNY or a reloadable MetroCard for subways/buses; walk crosstown through Bryant Park to Times Square in the evening when the LEDs are in full chorus. For theater, look for same-day tickets at TKTS or rush/lotteries—plan dinner after the show to dodge pre-theater crowds.

Getting Between Cities (assume morning departures)

• Sunnyvale → San Francisco: Caltrain (~1–1.5 hours) or rideshare (~45–75 minutes).
• San Francisco (SFO/OAK/SJC) → Chicago (ORD/MDW): Flight ~4–4.5 hours; expect $120–$250 one-way with advance purchase. Search and compare on Trip.com flights and Kiwi.com.
• Chicago (ORD/MDW) → New York (JFK/LGA/EWR): Flight ~2–2.5 hours; typical $80–$180 one-way. Search on Trip.com flights or Kiwi.com.
• Scenic alternative (optional): If you have extra time, consider Amtrak’s California Zephyr/Capitol Limited segments for epic scenery; total transit is long but unforgettable.

From Pacific bridges to Manhattan bridges, this route gives you the USA’s greatest hits with plenty of neighborhood texture. You’ll finish in New York with your camera roll full and your appetite trained for the next coast-to-coast adventure.

Safe travels—and bring comfortable shoes. The best stories here are a few city blocks past where most people stop.