Ultimate 3-Week East Coast USA Road Trip Itinerary

Day 1: Historic Boston Exploration

Boston, Massachusetts on May 15, 2025

8:30am

Breakfast at The Paramount

Enjoy a classic American breakfast at this popular spot in Downtown Boston, known for their pancakes and excellent coffee. Open from 7:00am to 3:00pm.
USD20, 1h

9:30am

Freedom Trail Walking Tour

Take a self-guided or guided walk along the famous Freedom Trail to see historic sites like Paul Revere's House and Boston Common. Trails open all day, best in daylight hours.
USD15 (guided tour), 3h

1:00pm

Lunch at Quincy Market

Sample diverse local foods and fresh seafood at Quincy Market's bustling food court within Faneuil Hall Marketplace. Open 10:00am to 9:00pm.
USD25, 1h

2:30pm

Visit Museum of Fine Arts

Explore one of the top art museums in the country featuring American, European, and contemporary art. Open 10:00am to 5:00pm, closed Wednesdays.
USD27, 2h

5:00pm

Relax at Boston Common

Unwind at the oldest public park in the U.S., ideal for a stroll or to people-watch.
Free, 1h

7:00pm

Dinner at Union Oyster House

Dine at the historic Union Oyster House, the oldest continuously operating restaurant in the USA specializing in seafood. Open 11:30am to 10:00pm.
USD50, 1.5h
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Day 2: More Boston & Travel to NYC

Boston, Massachusetts to New York City, New York on May 16, 2025

8:00am

Breakfast at Flour Bakery + Café

Start your day with delicious pastries and strong coffee at this beloved bakery. Open from 7:00am to 6:00pm.
USD15, 1h

9:00am

Visit Harvard University

Cross the Charles River to Cambridge and take a guided tour of one of the world’s most prestigious universities. Tours available 10:00am to 4:00pm.
USD12, 2h

11:30am

Drive to New York City

Begin the roughly 4-hour drive south to New York City with options for scenic stops en route.
USD0 (transport cost varies), 4h

4:00pm

Check in & Rest

Arrive in NYC and check into your hotel to rest before evening activities.
USD0, 1.5h

6:00pm

Dinner at Katz's Delicatessen

Experience iconic New York deli fare like pastrami sandwiches at this legendary eatery. Open till midnight.
USD30, 1h

7:30pm

Evening walk on Brooklyn Bridge

Enjoy stunning skyline views walking the Brooklyn Bridge at sunset and night.
Free, 1.5h
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Day 3: Iconic NYC Sites

New York City, New York on May 17, 2025

7:30am

Breakfast at Buvette

An intimate French café experience in Greenwich Village, known for delicious croissants and coffee. Open 8:00am - 3:00pm.
USD20, 1h

8:30am

Statue of Liberty & Ellis Island Tour

Take an early ferry to visit the Statue of Liberty and Immigration Museum. Ferries start at 8:30am, tickets must be booked in advance.
USD25, 4h

1:00pm

Lunch at Chelsea Market

Explore this indoor food hall with diverse cuisines perfect for casual bites. Open 10:00am to 9:00pm.
USD25, 1h

2:30pm

Visit The Metropolitan Museum of Art

World-renowned art museum with vast collections from ancient to modern times. Open 10:00am - 5:00pm.
USD30, 3h

5:30pm

Stroll in Central Park

Relax and explore the iconic urban park, including Bethesda Terrace and the Bow Bridge.
Free, 1.5h

7:30pm

Dinner at Joe’s Shanghai

Famous for soup dumplings and authentic Chinese cuisine in Chinatown. Open 11:30am - 10:30pm.
USD35, 1.5h
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Day 4: Philadelphia History

Philadelphia, Pennsylvania on May 18, 2025

7:30am

Breakfast at Reading Terminal Market

A vibrant indoor market offering diverse local foods including Amish specialties. Open 8:00am to 6:00pm.
USD15, 1h

9:00am

Drive to Philadelphia

Travel approximately 2 hours from New York City to Philadelphia.
USD0 (transport cost varies), 2h

11:30am

Visit Independence Hall and Liberty Bell

See where the Declaration of Independence was signed and see the iconic Liberty Bell. Independence Hall tours run 9:00am to 5:00pm.
Free (timed tickets required), 2h

1:30pm

Lunch at Jim’s Steaks South Street

Try an authentic Philadelphia cheesesteak at this classic deli.
USD15, 1h

2:30pm

Visit Philadelphia Museum of Art

Famous for the 'Rocky Steps', this museum houses impressive collections of American and European art. Open 10:00am to 5:00pm.
USD25, 2h

5:00pm

Walk along Schuylkill River Trail

Enjoy a scenic riverside walk or bike ride.
Free, 1h

7:00pm

Dinner at Zahav

Award-winning Middle Eastern restaurant offering innovative dishes. Open 5:00pm to 10:00pm.
USD60, 1.5h
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Day 5: Washington, D.C. Monuments

Washington, D.C. on May 19, 2025

7:00am

Breakfast at Founding Farmers

Farm-to-table dining experience serving hearty American breakfasts. Open 7:00am to 10:00pm.
USD20, 1h

8:00am

Drive to Washington, D.C.

Travel approximately 2.5 hours from Philadelphia to Washington, D.C.
USD0 (transport cost varies), 2.5h

11:00am

Visit National Mall and Monuments

Explore iconic landmarks including the Lincoln Memorial, Washington Monument, and World War II Memorial. Open all day.
Free, 3h

2:00pm

Lunch at Union Market

Enjoy a variety of artisanal and international foods at this modern market venue. Open 10:00am to 9:00pm.
USD25, 1h

3:30pm

Smithsonian National Air and Space Museum

Discover historic aircraft and space exploration artifacts. Open 10:00am to 5:30pm.
Free, 2h

6:00pm

Dinner at Old Ebbitt Grill

Historic bar and restaurant serving American cuisine near the White House. Open 11:00am to 10:00pm.
USD40, 1.5h
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Day 6: Travel to Charleston

Charleston, South Carolina on May 20, 2025

7:00am

Breakfast at The Royal

Cozy spot for southern style breakfast with excellent biscuits and grits. Open 7:00am to 2:00pm.
USD18, 1h

8:00am

Fly or Drive to Charleston

Option: Fly (about 1.5 hours) or enjoy a longer scenic 7-8 hour drive down the coast from Washington, D.C. to Charleston.
USD0-100 (flight price varies), 1.5h (flight) or 7-8h (drive)

12:00pm

Check-in and lunch at Fleet Landing Restaurant

Waterfront seafood dining offering fresh local catches. Open 11:00am to 9:00pm.
USD35, 1h

1:30pm

Explore Historic Downtown Charleston

Walk cobblestone streets, see Rainbow Row and the Battery promenade with charming antebellum architecture.
Free, 3h

5:00pm

Visit Charleston City Market

Browse local crafts, food products, and souvenirs. Open until 6:00pm.
Free, 1h

7:00pm

Dinner at Husk

Renowned Southern cuisine restaurant focusing on local ingredients. Reservations recommended. Open 5:00pm to 10:00pm.
USD60, 1.5h
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Day 7: Charleston Culture & Beaches

Charleston, South Carolina on May 21, 2025

8:00am

Breakfast at Callie’s Hot Little Biscuit

Enjoy delicious freshly baked biscuits and coffee. Open 7:30am to 3:30pm.
USD15, 1h

9:00am

Visit Magnolia Plantation and Gardens

Explore historic gardens, a house museum, and wildlife exhibits. Open 9:00am to 5:30pm.
USD27, 3h

12:30pm

Lunch at Page’s Okra Grill

Casual Southern eatery with fresh, local ingredients. Open 11:00am to 3:00pm.
USD25, 1h

2:00pm

Afternoon at Folly Beach

Relax or walk the beach, just a short drive from Charleston’s downtown area.
Free, 3h

6:30pm

Dinner at The Ordinary

Upscale seafood restaurant housed in a historic bank building. Open 5:00pm to 10:00pm.
USD55, 1.5h
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Day 8: Savannah Charm

Savannah, Georgia on May 22, 2025

7:30am

Breakfast at Clary’s Café

Quaint café with hearty southern-style breakfasts. Open 7:00am to 3:00pm.
USD15, 1h

9:00am

Drive to Savannah

Travel about 2 hours south from Charleston to Savannah, Georgia.
USD0 (transport varies), 2h

11:00am

Historic District Walking Tour

Explore scenic squares, architecture, and landmarks such as Forsyth Park and Cathedral of St. John the Baptist.
USD20 (guided), 3h

2:00pm

Lunch at Mrs. Wilkes’ Dining Room

Experience classic southern comfort food served family-style. Open 11:00am to 2:00pm.
USD30, 1h

3:30pm

Visit Bonaventure Cemetery

Beautiful and historic cemetery known for its statuary and scenic nature. Open all day.
Free, 1.5h

6:00pm

Dinner at The Collins Quarter

Trendy café with Australian influences and creative cocktails. Open till 9:00pm.
USD40, 1.5h
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Day 9: Historic St. Augustine

St. Augustine, Florida on May 23, 2025

7:30am

Breakfast at Maple Street Biscuit Company

Southern biscuit sandwiches and coffee, a St. Augustine favorite. Open 7:00am to 3:00pm.
USD15, 1h

9:00am

Drive to St. Augustine

Travel about 3.5 hours from Savannah to historic St. Augustine, Florida.
USD0 (transport varies), 3.5h

12:30pm

Lunch at The Floridian

Modern southern cuisine focusing on fresh, local ingredients. Open 11:30am to 9:00pm.
USD30, 1h

2:00pm

Explore Castillo de San Marcos

Visit the oldest masonry fort in the continental US with impressive views of the waterfront. Open 9:00am to 5:00pm.
USD15, 2h

4:30pm

Walk Historic Downtown

Stroll along cobblestone streets to explore shops, galleries, and historic landmarks.
Free, 2h

7:00pm

Dinner at Columbia Restaurant

Historic Spanish restaurant known for paella and Cuban sandwiches. Open 11:00am to 9:00pm.
USD45, 1.5h
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Day 10: Orlando Theme Parks

Orlando, Florida on May 24, 2025

7:00am

Breakfast at Keke’s Breakfast Café

Popular breakfast spot with waffles and omelets. Open 7:00am to 3:00pm.
USD15, 1h

8:00am

Drive to Orlando

Travel about 2 hours from St. Augustine to Orlando for theme park adventures.
USD0 (transport varies), 2h

10:00am

Visit Universal Studios Florida

Experience exciting rides, shows, and movie-themed attractions. Open 9:00am to 9:00pm.
USD110, 8h

6:30pm

Dinner at The Toothsome Chocolate Emporium

Steampunk-themed restaurant known for inventive desserts and varied menu. Open 11:30am to 10:00pm.
USD40, 1.5h
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Day 11: Disney Magic

Orlando, Florida on May 25, 2025

7:00am

Breakfast at Hotel or Starbucks

Quick breakfast to start a long day at the parks.
USD15, 1h

8:00am

Visit Magic Kingdom Park

Classic Disney park with iconic Cinderella Castle and family-friendly rides. Open 9:00am to 9:00pm.
USD130, 10h

8:00pm

Return to Hotel

Rest and relax after a magical day at Disney.
Free, —
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Day 12: Miami Beach & Culture

Miami, Florida on May 26, 2025

7:00am

Breakfast at Big Pink

Miami Beach diner famous for large portions and eclectic menu. Open 7:00am to 3:00am.
USD20, 1h

8:00am

Drive to Miami

Travel about 3.5-4 hours south from Orlando to Miami Beach.
USD0 (transport varies), 4h

12:30pm

Lunch at Versailles Cuban Restaurant

Iconic Cuban eatery in Little Havana offering authentic dishes. Open 8:00am to 11:00pm.
USD25, 1h

2:00pm

Explore Wynwood Walls

Check out vibrant outdoor street art gallery showcasing local and international artists. Open 10:00am to 11:00pm.
USD12, 2h

4:30pm

Relax on Miami Beach

Enjoy the white sands and warm ocean along the famous Miami Beach.
Free, 2h

7:00pm

Dinner at Joe’s Stone Crab

Seasonal seafood institution known for stone crab claws and key lime pie. Open 11:30am to 10:00pm.
USD60, 1.5h
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Day 13: Key West Adventure

Key West, Florida on May 27, 2025

7:30am

Breakfast at Blue Heaven

Iconic quirky café with outdoor seating and island vibe. Open 7:30am to 3:00pm.
USD20, 1h

8:30am

Drive to Key West

Scenic 3.5 hour drive via the Overseas Highway offering spectacular ocean views.
USD0 (transport varies), 3.5h

12:00pm

Lunch at Hog’s Breath Saloon

Lively bar and eatery serving fresh seafood and island specialties. Open 11:00am to 9:00pm.
USD25, 1h

1:30pm

Visit Ernest Hemingway Home and Museum

Tour the former residence of the famous American author with beautiful gardens and cats. Open 9:00am to 5:00pm.
USD17, 1.5h

3:30pm

Explore Duval Street

Walk and shop along the vibrant main street with unique shops, bars, and galleries.
Free, 2h

6:30pm

Dinner at Latitudes

Upscale waterfront dining on Sunset Key, reservations needed. Open 5:00pm to 9:00pm.
USD70, 2h
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Day 14: Explore Key West & Departure

Key West, Florida on May 28, 2025

8:00am

Breakfast at Sarabeth’s

Chic spot with a refined menu of breakfast classics. Open 7:00am to 3:00pm.
USD20, 1h

9:00am

Kayaking or Snorkeling in Key West

Enjoy 2-3 hour guided kayak or snorkeling tours to see marine life and beautiful reefs. Tours start from 9:00am.
USD60, 3h

12:30pm

Lunch at Louie’s Backyard

Elegant waterfront dining with Caribbean-inspired cuisine. Open 11:30am to 9:00pm.
USD50, 1h

2:00pm

Visit Southernmost Point Buoy

Iconic photo spot marking the southernmost point of continental USA.
Free, 30m

3:00pm

Departure or rest

Depending on travel plans, prepare to return from Key West or continue your journey south.
—, —
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