14-Day Epic Road Trip from Maine to Florida

Day 1: Exploring Portland

Portland, Maine on March 24, 2025

8:00AM

Breakfast at The Blue Spoon

Start your day with a delicious farm-to-table breakfast featuring locally-sourced ingredients. Try their famous lemon ricotta pancakes!
USD20, 1 hour

9:30AM

Visit Portland Head Light

One of the most photographed lighthouses in the United States, this iconic structure offers stunning coastal views.
FREE, 1 hour

11:00AM

Explore Old Port

Wander through this historic district filled with cobblestone streets, unique shops, and waterfront views.
FREE, 2 hours

1:00PM

Lunch at Eventide Oyster Co.

Savor the freshest seafood at this renowned eatery, especially their lobster roll with a twist.
USD40, 1.5 hours

3:00PM

Museums at Portland

Visit the Portland Museum of Art to admire its collection of American and European artwork.
USD18, 2 hours

5:30PM

Dinner at Fore Street

Enjoy a farm-to-table dinner at one of Portland's best restaurants, known for its wood-fired cuisine.
USD60, 2 hours

8:00PM

Sunset at East Promenade

Relax and watch the sunset over Casco Bay, a perfect end to your first day.
FREE, 1 hour
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Day 2: City Attractions

Boston, Massachusetts on March 25, 2025

8:00AM

Breakfast at Flour Bakery

A local favorite, this bakery offers delicious pastries and breakfast sandwiches. Don't miss their famous sticky buns.
USD15, 1 hour

9:30AM

Freedom Trail Walking Tour

Explore the historical landmarks of Boston on this 2.5-mile-long path through the city.
USD20, 2 hours

12:00PM

Lunch at Quincy Market

Enjoy a variety of food options from clam chowder to Italian sausages in this bustling market.
USD25, 1.5 hours

2:00PM

Visit Boston Common

Relax in the oldest park in the U.S. and enjoy a peaceful break from your sightseeing.
FREE, 1.5 hours

4:00PM

Museum of Fine Arts

Explore this expansive museum with an incredible collection of art from around the world.
USD27, 2 hours

6:30PM

Dinner at Legal Sea Foods

A Boston staple, this restaurant is known for its fresh seafood and clam chowder.
USD45, 2 hours
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Day 3: The Big Apple

New York City, New York on March 26, 2025

8:00AM

Breakfast at Sarabeth's

Enjoy a delightful breakfast in this upscale eatery known for its delicious eggs benedict.
USD30, 1 hour

9:30AM

Visit Central Park

Stroll through this iconic park, enjoy the beautiful landscapes, and soak in the city's ambiance.
FREE, 2 hours

12:00PM

Lunch at Shake Shack

Try this popular burger joint famous for its ShackBurger and crinkle-cut fries.
USD25, 1 hour

1:30PM

Visit the Metropolitan Museum of Art

Spend the afternoon exploring one of the largest and finest art museums in the world.
USD25, 3 hours

5:00PM

Times Square

Experience the vibrant energy of Times Square, famous for its bright lights, shops, and entertainment.
FREE, 1 hour

6:30PM

Dinner at Carmine's

End your day with a hearty Italian meal at this family-style restaurant.
USD70, 2 hours
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Day 4: Historical Discoveries

Philadelphia, Pennsylvania on March 27, 2025

8:00AM

Breakfast at Reading Terminal Market

This bustling market is filled with various food vendors, perfect for a quick and tasty breakfast.
USD15, 1 hour

9:30AM

Liberty Bell and Independence Hall

Visit these iconic symbols of American independence in the historic district.
FREE, 1.5 hours

11:30AM

Visit Philadelphia Museum of Art

Don't forget to run up the 'Rocky Steps' and enjoy the impressive art collection.
USD25, 2 hours

1:30PM

Lunch at Pat's King of Steaks

Experience the famous Philly cheesesteak at one of the city's best spots.
USD20, 1 hour

3:00PM

Elfreth's Alley

Walk through the oldest residential street in America and enjoy its historic charm.
FREE, 1 hour

5:00PM

Dinner at The Capital Grille

Indulge in fine dining with exceptional steak and fresh seafood offerings.
USD80, 2 hours
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Day 5: Capital City Excursion

Washington, D.C. on March 28, 2025

8:00AM

Breakfast at Founding Farmers

A popular eatery serving hearty breakfast with a farm-to-table concept.
USD25, 1 hour

9:30AM

Visit the National Mall

Explore the iconic monuments, including the Lincoln Memorial and Washington Monument.
FREE, 3 hours

12:30PM

Lunch at Old Ebbitt Grill

Dine at this historic restaurant, known for its oysters and American cuisine.
USD35, 1.5 hours

2:00PM

Smithsonian Museums

Choose from several world-class museums, all offering free admission.
FREE, 3 hours

5:30PM

Dinner at The Hamilton

Enjoy a diverse menu and vibrant atmosphere right near the National Mall.
USD35, 1.5 hours
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Day 6: Southern Charm

Richmond, Virginia on March 29, 2025

8:00AM

Breakfast at The Brunch

Savor a delightful brunch with a Southern twist at this popular local spot.
USD20, 1 hour

9:30AM

Virginia State Capitol

Visit this historic building and take a tour to learn about Virginia's history.
FREE, 1.5 hours

11:00AM

Explore Monument Avenue

Wander down this historic boulevard known for its beautiful statues and architecture.
FREE, 1 hour

12:30PM

Lunch at Mama J's Kitchen

Enjoy some authentic Southern comfort food at this beloved local restaurant.
USD25, 1.5 hours

2:00PM

Visit the American Civil War Museum

Explore exhibits that tell the complex stories of the Civil War and its impact.
USD15, 2 hours

5:00PM

Dinner at The Roosevelt

A chic restaurant offering farm-fresh ingredients and an intimate atmosphere.
USD55, 2 hours
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Day 7: Tar Heel State

Raleigh, North Carolina on March 30, 2025

8:00AM

Breakfast at Biscuit Head

Known for its creative biscuit dishes and house-made jams, this place is a must-visit.
USD15, 1 hour

9:30AM

Visit North Carolina Museum of Natural Sciences

Explore exhibits showcasing the state's natural history and biodiversity.
FREE, 2 hours

12:00PM

Lunch at Beasley's Chicken + Honey

Enjoy a delicious meal featuring fried chicken served with local honey.
USD20, 1.5 hours

2:00PM

Explore Pullen Park

Relax in this lovely park with a historic carousel and lovely walking trails.
FREE, 2 hours

4:30PM

Dinner at Capital Club 16

Enjoy upscale comfort food and craft cocktails in a casual setting.
USD30, 1.5 hours
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Day 8: South Carolina Vibes

Charleston, South Carolina on March 31, 2025

8:00AM

Breakfast at Callie's Hot Little Biscuit

Indulge in Southern-style biscuits, served with various toppings, in this popular spot.
USD10, 1 hour

9:30AM

Historic District Tour

Take a guided tour through Charleston's historic district featuring picturesque streets and antebellum architecture.
USD25, 2 hours

12:00PM

Lunch at Husk

Experience farm-to-table dining at this acclaimed restaurant focusing on Southern cuisine.
USD40, 1.5 hours

2:00PM

Visit Fort Sumter

Take a boat ride to this historic site where the Civil War began.
USD20, 3 hours

5:30PM

Dinner at The Ordinary

Savor seafood in a beautiful setting in this renowned oyster bar.
USD50, 2 hours
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Day 9: Historic Savannah

Savannah, Georgia on April 1, 2025

8:00AM

Breakfast at The Collins Quarter

Enjoy a unique Australian-style breakfast with delicious coffee in this charming café.
USD20, 1 hour

9:30AM

Savannah Historic District Walking Tour

Explore this beautifully preserved area filled with historic homes, squares, and parks.
USD25, 2 hours

12:00PM

Lunch at Mrs. Wilkes' Dining Room

Experience Southern home-cooked meals served family style in this beloved establishment.
USD25, 1.5 hours

2:30PM

Visit Forsyth Park

Wander through this iconic park known for its fountains and beauty.
FREE, 1.5 hours

4:30PM

Dinner at The Grey

Dine in a restored 1960s Greyhound bus station, serving modern Southern cuisine in a chic environment.
USD60, 2 hours
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Day 10: Family Fun

Orlando, Florida on April 2, 2025

8:00AM

Breakfast at K restaurant

Enjoy fresh and seasonal breakfast items at this farm-to-table restaurant known for its innovative dishes.
USD25, 1 hour

10:00AM

Visit Walt Disney World

Spend an exciting day at the most famous theme park in the world, full of attractions and magic.
USD120, 8 hours

7:00PM

Dinner at Ohana

Experience a Polynesian feast with family-style dining at this well-loved Disney restaurant.
USD50, 2 hours
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Day 11: Beach Vibes

Miami, Florida on April 3, 2025

8:00AM

Breakfast at Big Pink

Start your day at this lively diner serving big portions of American favorites.
USD20, 1 hour

9:30AM

Visit South Beach

Relax on the famous sandy shores of South Beach and soak in the sun.
FREE, 3 hours

12:00PM

Lunch at Joe's Stone Crab

Indulge in fresh seafood and the city's famous stone crab claws at this iconic restaurant.
USD60, 1.5 hours

2:00PM

Art Deco District Tour

Take a guided walking tour of the Art Deco buildings that define Miami Beach's unique architectural style.
USD30, 2 hours

5:00PM

Dinner at The Forge

Dine in an upscale atmosphere with fine dining and an extensive wine list.
USD80, 2 hours
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Day 12: Island Adventure

Key West, Florida on April 4, 2025

8:00AM

Breakfast at Blue Heaven

Enjoy breakfast in a quirky setting with delicious pancakes and fresh key lime pie.
USD25, 1 hour

9:30AM

Visit Duval Street

Stroll along this famous street filled with shops, bars, and restaurants.
FREE, 1.5 hours

11:00AM

Ernest Hemingway Home and Museum

Tour the home of the famous author and see the six-toed cats that roam the property.
USD14, 1.5 hours

1:00PM

Lunch at Louie's Backyard

Dine in a beachfront setting with Caribbean-inspired dishes and refreshing cocktails.
USD35, 1.5 hours

3:00PM

Relax at Fort Zachary Taylor State Park

Spend the afternoon at the beach, swimming and enjoying the beautiful scenery.
USD8, 3 hours

6:30PM

Dinner at A&B Lobster House

Savor seafood dishes while enjoying stunning waterfront views.
USD70, 2 hours
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Day 13: Relaxing Retreat

Naples, Florida on April 5, 2025

8:00AM

Breakfast at Jane's Cafe on 3rd

Start your day at this cozy café known for its delicious breakfast options and friendly atmosphere.
USD20, 1 hour

9:30AM

Visit Naples Botanical Garden

Explore the beautiful gardens and diverse plant collections in this tropical paradise.
USD20, 2.5 hours

12:00PM

Lunch at The Continental

Enjoy a casual lunch featuring an array of delicious dishes in a laid-back setting.
USD30, 1.5 hours

2:00PM

Relax at Clam Pass Park

Spend the afternoon at this beautiful park with a lovely beach and scenic boardwalk.
FREE, 3 hours

5:30PM

Dinner at Campiello

End your day with dinner at this upscale Italian restaurant known for its exquisite pasta.
USD50, 2 hours
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Day 14: Heart of Florida

Tampa, Florida on April 6, 2025

8:00AM

Breakfast at Oxford Exchange

Start your day at this stylish café and restaurant offering inventive breakfast dishes and great coffee.
USD20, 1 hour

9:30AM

Visit Tampa's Riverwalk

Stroll along the scenic waterfront with beautiful views, parks, and shops.
FREE, 2 hours

12:00PM

Lunch at Ulele

Taste delicious Floridian dishes made with local ingredients at this popular restaurant.
USD30, 1.5 hours

2:00PM

Visit the Florida Aquarium

Explore the diverse aquatic life and interactive exhibits at this family-friendly venue.
USD30, 2 hours

5:00PM

Dinner at Bern's Steak House

Treat yourself to an upscale dining experience at one of Tampa's most celebrated steakhouses.
USD100, 2 hours
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