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Ultimate 14-Day USA Adventure: New York, Chicago, and San Francisco Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and Broadway Magic

Morning

Start your New York adventure with a classic breakfast at The Perfect Pint, fueling up for a day of exploration. Begin with a skip-the-line visit to the Empire State Building, enjoying panoramic views of the city from the iconic observation deck.

Afternoon

For lunch, head to Mustang Harry's for their famous burgers. Afterward, take a leisurely stroll across the historic Brooklyn Bridge, admiring the skyline as you make your way to Brooklyn.

Evening

Dine at The Penrose, known for its cozy atmosphere and delicious pub fare. Cap off the evening with the award-winning musical, The Lion King Broadway Show, a timeless New York experience.

Bedtime

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4.88
Empire State Building
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4.34
Brooklyn Bridge
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Central Park Serenity and Gourmet Cruising

Morning

Enjoy a morning coffee at Bar Six before embarking on a private horse carriage ride through the enchanting Central Park. Take in the natural beauty and iconic landmarks with a knowledgeable guide.

Afternoon

Savor a gourmet lunch aboard the NYC Gourmet Dinner Cruise with Live Music, cruising along the Hudson River and enjoying the sights of the city from a unique vantage point.

Evening

Experience the vibrant atmosphere of Sel Rrose for dinner, offering a blend of French and American cuisine. Afterward, take a magical holiday lights carriage ride, exploring the festive Dyker Heights neighborhood.

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4.72
Central Park
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3.88
NYC Gourmet Dinner Cruise with Live Music
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Cultural Marvels and Evening Skyline

Morning

Begin with a hearty breakfast at Tiny's & The Bar Upstairs, a hidden gem in the city. Then, immerse yourself in the wonders of the American Museum of Natural History, exploring its fascinating exhibits.

Afternoon

For lunch, visit Bea, a stylish eatery with a menu to match. Spend your afternoon at the Metropolitan Museum of Art, one of the world's largest and finest art museums.

Evening

Dine at Buddha-Bar Restaurant New York, an opulent setting for a memorable meal. Conclude the day with a NYC Skyline and Statue of Liberty Night Cruise, admiring the city's glittering skyline and the Statue of Liberty.

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4.43
American Museum of Natural History
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4.28
Metropolitan Museum of Art
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Historic Tributes and Culinary Delights

Morning

Pay your respects at the 9/11 Memorial & Museum, a poignant start to the day. Follow it with a breakfast at Crompton Ale House, known for its warm ambiance and diverse menu.

Afternoon

Explore the vibrant neighborhood of Harlem, stopping for a soulful lunch at Red Rooster. Afterward, enjoy the uplifting New York City Harlem Gospel Live Music Concert to experience the heart of the city's music scene.

Evening

For dinner, head to Underdog, a popular spot for its innovative dishes. Conclude the evening with a visit to the NYC Harlem Hallelujah! Gospel Wednesday Choir, where you can join in the celebration with the local community.

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4.78
9/11 Memorial & Museum
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4.73
New York City Harlem Gospel Live Music Concert
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Island Explorations and Evening Heights

Morning

Start with a breakfast at St. Pat's Bar & Grill NYC, then catch the ferry to Statue of Liberty & Ellis Island with Ferry. Explore the historic landmarks and enjoy the views of the city skyline.

Afternoon

Have a delightful lunch at Yard House, known for its extensive menu and vibrant atmosphere. Spend your afternoon at the One World Observatory, where you'll witness breathtaking views from the top of the tallest building in the Western Hemisphere.

Evening

Dine at Smith's Bar, a local favorite with a laid-back vibe. Then, visit the Edge Observation Deck, the highest outdoor sky deck in the Western Hemisphere, for a memorable end to the day.

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4.49
Statue of Liberty & Ellis Island with Ferry
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4.65
One World Observatory
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Magnificent Mile and Riverfront Dining

Morning

Begin your Chicago journey with a hearty breakfast at Carragher's, preparing for a day of Windy City wonders. Start with a visit to the Magnificent Mile, where you can indulge in world-class shopping and iconic architecture.

Afternoon

For lunch, enjoy the casual elegance of Club Bar & Grill, conveniently located near the Magnificent Mile. Afterward, take a relaxing Chicago River Architecture Cruise, learning about the city's famous buildings and history.

Evening

Dine at Beacon Tavern, offering a refined dining experience with views of the Chicago River. End the night with a visit to the Second City Comedy Club, where you can enjoy top-notch improv and stand-up comedy.

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4.61
Magnificent Mile
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Cultural Corners and Navy Pier Delights

Morning

Start your day with a classic Chicago breakfast at Underdog, then head to the Art Institute of Chicago, where you can admire masterpieces from around the world.

Afternoon

For lunch, visit The Gage, a gastropub with a diverse menu and a lively atmosphere. Spend your afternoon at Navy Pier, exploring the shops, attractions, and enjoying the stunning views of Lake Michigan.

Evening

Dine at Giordano's, a Chicago institution known for its deep-dish pizza. After dinner, take a ride on the Centennial Wheel at Navy Pier, taking in the city lights from this iconic vantage point.

Bedtime

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Art Institute of Chicago
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3.99
Navy Pier
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Lakeside Serenity and Historic Heights

Morning

Enjoy breakfast at White Horse Tavern - Financial District, then take a morning stroll along the beautiful Chicago Lakefront Trail. Breathe in the fresh air and enjoy the views of Lake Michigan.

Afternoon

Have lunch at T.J. Byrnes Bar & Restaurant, a local favorite with a welcoming atmosphere. Spend your afternoon at the 360 CHICAGO Observation Deck, where you can experience the city from 1,000 feet above the Magnificent Mile.

Evening

Dine at The Signature Room at the 95th [1228], enjoying fine cuisine with a side of stunning city views. Cap off the night with a visit to the Jazz Showcase, where you can listen to world-class jazz performances in an intimate setting.

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4.13
Chicago Lakefront Trail
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4.49
360 CHICAGO Observation Deck
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Golden Gate Wonders and Wharf Delights

Morning

Start your San Francisco journey with breakfast at Mulberry Street Bar, then head to the Golden Gate Bridge for a morning walk or bike ride, taking in the iconic views of the bay and the city.

Afternoon

For lunch, enjoy the seafood at Tadich Grill, the oldest restaurant in California. Afterward, explore the historic Fisherman's Wharf, visiting attractions like Pier 39 and the sea lions.

Evening

Dine at Slanted Door, offering modern Vietnamese cuisine with panoramic views of the bay. End the night with a visit to Alcatraz Island, taking a ferry to the infamous former prison and learning about its history.

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Fisherman's Wharf
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Alcatraz Island
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Urban Parks and Island Escapes

Morning

Have breakfast at St. Pat's Bar & Grill NYC, then spend your morning at Golden Gate Park, visiting attractions like the Japanese Tea Garden and the de Young Museum.

Afternoon

For lunch, head to Yard House, a lively spot with a wide range of dishes. Afterward, take a ferry to Angel Island, where you can hike, bike, or simply relax and enjoy the views of the bay.

Evening

Dine at House of Prime Rib, a San Francisco classic known for its prime rib and old-school charm. After dinner, take a ride on the San Francisco Cable Cars, a unique way to experience the city's hills and neighborhoods.

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Golden Gate Park
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4.59
San Francisco Cable Cars
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City Heights and Island Tranquility

Morning

Start with breakfast at The Penrose, then head to Coit Tower for panoramic views of the city and the bay. Explore the murals inside the tower and learn about San Francisco's history.

Afternoon

For lunch, visit The House, offering Asian fusion cuisine in a stylish setting. Spend your afternoon at Sausalito, a charming waterfront town with art galleries, shops, and beautiful views of the bay.

Evening

Dine at Hog Island Oyster Co., enjoying fresh oysters and other seafood dishes. End the night with a visit to Twin Peaks, where you can see the city lights from one of the highest points in San Francisco.

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Coit Tower
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Sausalito
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Cultural Charms and Bay Breezes

Morning

Enjoy breakfast at Bar Six, then visit the San Francisco Museum of Modern Art (SFMOMA), home to an impressive collection of modern and contemporary art.

Afternoon

For lunch, head to The Slanted Door, a modern Vietnamese restaurant with stunning bay views. Afterward, take a leisurely cruise on the San Francisco Bay, enjoying the sights of the city, the Golden Gate Bridge, and Alcatraz.

Evening

Dine at Prospect, a stylish restaurant serving New American cuisine. Conclude the day with a visit to The Fillmore, a historic music venue known for its great acoustics and memorable performances.

Bedtime

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San Francisco Bay
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The Fillmore
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Urban Elegance and Coastal Escapes

Morning

Start with breakfast at Tiny's & The Bar Upstairs, then spend your morning at The Exploratorium, a hands-on science museum with interactive exhibits for all ages.

Afternoon

For lunch, visit Bea, a stylish eatery with a menu to match. Afterward, take a drive across the Golden Gate Bridge to Muir Woods, where you can walk among the majestic redwood trees.

Evening

Dine at The Progress, a Michelin-starred restaurant offering innovative, globally-inspired cuisine. End the night with a visit to The Independent, a popular music venue showcasing a diverse range of artists.

Bedtime

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Muir Woods
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The Independent
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Farewell to the Bay Area

Morning

Enjoy a final breakfast at White Horse Tavern - Financial District, then take a morning walk along the Lands End Trail, enjoying the rugged coastline and the views of the Golden Gate Bridge.

Afternoon

For lunch, head to The Signature Room at the 95th [1228], enjoying fine cuisine with a side of stunning city views. Spend your afternoon at The Presidio, exploring the park's trails, historic sites, and the Walt Disney Family Museum.

Evening

Dine at The House, offering Asian fusion cuisine in a stylish setting. End your trip with a memorable dinner and reflect on your time in the beautiful city by the bay.

Bedtime

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