Foodie & Relaxation Rail/Train Road Trip in Florida

Day 1: Beach Day in Miami

Miami, Florida on May 11, 2024

8:00 AM

Breakfast at Versailles Restaurant

Start your day with a delicious Cuban breakfast at Versailles Restaurant, known for its authentic Cuban cuisine and vibrant atmosphere.
Versailles Restaurant is located in Little Havana, easily accessible by public transportation or rideshare from your accommodation.
10 USD, 1 hour

11:00 AM

Relax at South Beach

Head to South Beach to relax on the sandy shores, soak up the sun, and take a refreshing dip in the turquoise waters of the Atlantic Ocean.
South Beach is a short drive or bus ride from Little Havana.
Free, 3 hours

2:00 PM

Lunch at La Camaronera Seafood Joint & Fish Market

Enjoy a casual seafood lunch at La Camaronera, a local favorite known for its fresh fish sandwiches and ceviche.
La Camaronera is located in Little Havana, a convenient stop after your beach visit.
15 USD, 1 hour

5:00 PM

Explore Wynwood Walls

Take a stroll through the vibrant street art murals of Wynwood Walls, a must-see cultural hub in Miami showcasing works by local and international artists.
Wynwood Walls is a short drive or bus ride from Little Havana.
Free, 2 hours

7:00 PM

Dinner at Puerto Sagua

Indulge in classic Cuban comfort food for dinner at Puerto Sagua, a beloved Miami institution known for its hearty dishes and friendly ambiance.
Puerto Sagua is located in South Beach, offering a cozy atmosphere to unwind after a day of exploring.
20 USD, 1.5 hours
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Day 2: Island Adventure in Key West

Key West, Florida on May 12, 2024

8:00 AM

Breakfast at Blue Heaven

Start your day with a unique breakfast experience at Blue Heaven, a charming eatery known for its delicious food, live music, and roaming chickens.
Blue Heaven is located in the heart of Key West's historic district, easily accessible by walking or short taxi ride from your accommodation.
15 USD, 1 hour

10:00 AM

Visit the Southernmost Point Buoy

Make your way to the iconic Southernmost Point Buoy, a must-see landmark marking the southernmost tip of the continental United States.
The Southernmost Point Buoy is a short walk from Blue Heaven, offering picturesque views of the ocean.
Free, 30 minutes

12:00 PM

Lunch at Garbo's Grill

Savor delicious gourmet tacos and sandwiches at Garbo's Grill, a popular food truck known for its innovative flavors and relaxed outdoor seating.
Garbo's Grill can be found at various locations in Key West, check their social media for the daily schedule.
10 USD, 1 hour

2:00 PM

Explore Mallory Square

Immerse yourself in the vibrant atmosphere of Mallory Square, known for its street performers, sunset celebrations, and eclectic shops.
Mallory Square is a short walk from Garbo's Grill, offering plenty of shopping and entertainment options.
Free, 2 hours

5:00 PM

Sunset Sail on a Schooner

Embark on a magical sunset sail aboard a historic schooner, enjoying breathtaking views of the sunset over the Gulf of Mexico.
Various companies offer sunset cruises from Key West Harbor, be sure to book in advance for this memorable experience.
50 USD, 2 hours

7:00 PM

Dinner at Santiago's Bodega

Treat yourself to a tapas feast at Santiago's Bodega, a cozy restaurant offering a wide selection of small plates bursting with flavor.
Santiago's Bodega is located near Mallory Square, providing a perfect spot for a relaxed evening meal.
25 USD, 1.5 hours
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Day 3: Relaxation in Naples

Naples, Florida on May 13, 2024

8:00 AM

Breakfast at Skillets

Start your day with a hearty breakfast at Skillets, a local favorite known for its delicious omelets, pancakes, and breakfast burritos.
Skillets has multiple locations in Naples, choose the one closest to your accommodation for a convenient start to your day.
12 USD, 1 hour

10:00 AM

Beach Day at Lowdermilk Park

Spend a relaxing day at Lowdermilk Park, a beautiful beach spot with calm waters, shady picnic areas, and stunning views of the Gulf of Mexico.
Lowdermilk Park is a short drive or taxi ride from Skillets, providing a serene setting for sunbathing and swimming.
Free, 3 hours

1:00 PM

Lunch at The Dock at Crayton Cove

Enjoy a waterfront lunch at The Dock, a laid-back restaurant offering fresh seafood dishes, tropical cocktails, and panoramic views of the marina.
The Dock is located in Crayton Cove, a scenic area perfect for a leisurely lunch after your beach visit.
20 USD, 1 hour

3:00 PM

Explore Naples Pier

Take a leisurely stroll along Naples Pier, a historic landmark known for its scenic views, fishing opportunities, and dolphin sightings.
Naples Pier is a short walk from The Dock, offering a picturesque setting to enjoy the coastal charm of Naples.
Free, 1 hour

5:00 PM

Relaxing Spa Treatment at The Ritz-Carlton Spa

Indulge in a pampering spa treatment at The Ritz-Carlton Spa, rejuvenating your body and mind with luxurious therapies and serene ambiance.
The Ritz-Carlton Spa is a short drive or taxi ride from Naples Pier, providing a tranquil escape for relaxation.
50 USD, 2 hours

7:00 PM

Dinner at USS Nemo Restaurant

Dine at USS Nemo, a unique submarine-themed restaurant known for its creative seafood dishes, extensive wine selection, and cozy nautical decor.
USS Nemo Restaurant is located near The Ritz-Carlton, offering a memorable dining experience to conclude your day in Naples.
30 USD, 1.5 hours
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Day 4: Beach Day in Clearwater

Clearwater, Florida on May 14, 2024

8:00 AM

Breakfast at Clear Sky Cafe

Start your day with a delicious breakfast at Clear Sky Cafe, a local favorite known for its diverse menu, friendly service, and beachy vibes.
Clear Sky Cafe is located near Clearwater Beach, offering a convenient dining spot before heading to the beach.
15 USD, 1 hour

10:00 AM

Relax at Clearwater Beach

Spend the day relaxing on the powdery white sands of Clearwater Beach, known for its crystal-clear waters, water sports, and stunning sunsets.
Clearwater Beach is within walking distance from Clear Sky Cafe, providing a perfect setting for sunbathing and beach activities.
Free, 3 hours

1:00 PM

Lunch at Frenchy’s Rockaway Grill

Enjoy a casual beachfront lunch at Frenchy’s Rockaway Grill, a popular spot for fresh seafood, tropical drinks, and live music by the sea.
Frenchy’s Rockaway Grill is located directly on Clearwater Beach, offering a laid-back atmosphere to enjoy a meal with ocean views.
20 USD, 1 hour

3:00 PM

Pier 60 Park & Sunset Celebration

Explore Pier 60 Park and experience the daily Sunset Celebration, featuring street performers, local artisans, and breathtaking views of the sunset.
Pier 60 Park is a short walk from Frenchy’s Rockaway Grill, providing entertainment and shopping opportunities along the pier.
Free, 1.5 hours

5:00 PM

Dolphin Watching Cruise

Embark on a dolphin watching cruise from Clearwater Marina, where you can observe playful dolphins in their natural habitat as the sun sets over the Gulf.
Various tour companies offer dolphin cruises from Clearwater Marina, book in advance for this memorable wildlife experience.
40 USD, 2 hours

7:00 PM

Dinner at Palm Pavilion Beachside Grill & Bar

Enjoy a beachfront dinner at Palm Pavilion, a laid-back grill and bar offering fresh seafood, tropical cocktails, and live music right by the ocean.
Palm Pavilion is located on Clearwater Beach, providing a relaxed dining atmosphere to end your beach day in Clearwater.
25 USD, 1.5 hours
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Day 5: Theme Park Fun in Orlando

Orlando, Florida on May 15, 2024

8:00 AM

Breakfast at Keke's Breakfast Cafe

Start your day with a delicious breakfast at Keke's, a popular breakfast spot known for its fluffy pancakes, omelets, and fresh fruit toppings.
Keke's Breakfast Cafe has multiple locations in Orlando, choose the one closest to your accommodation for a convenient start to your theme park day.
12 USD, 1 hour

9:00 AM

Visit Walt Disney World

Embark on a magical adventure at Walt Disney World, exploring the enchanting theme parks, thrilling rides, and beloved characters for a day of fun and excitement.
Take a shuttle or public transportation to Walt Disney World from your accommodation, and be prepared for a full day of entertainment.
100 USD, 8 hours

1:00 PM

Lunch at Satu'li Canteen (Pandora - The World of Avatar)

Enjoy a unique dining experience at Satu'li Canteen in Pandora - The World of Avatar, where you can savor flavorful bowls inspired by the Na'vi culture.
Satu'li Canteen is located within Disney's Animal Kingdom, offering a themed setting for a quick-service lunch.
15 USD, 1 hour

6:00 PM

Dinner at The Cowfish Sushi Burger Bar

Dine at The Cowfish, a one-of-a-kind restaurant combining gourmet burgers and sushi rolls, offering a creative fusion of flavors and innovative dishes.
The Cowfish is located in Universal CityWalk, providing a vibrant dining experience after your theme park adventures.
30 USD, 1.5 hours
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Day 6: Historical Exploration in St. Augustine

St. Augustine, Florida on May 16, 2024

8:00 AM

Breakfast at The Bunnery Bakery & Cafe

Start your day with a cozy breakfast at The Bunnery, a charming bakery known for its fresh pastries, hearty sandwiches, and artisanal coffee.
The Bunnery is located in the historic district of St. Augustine, a short walk from many attractions in the area.
10 USD, 1 hour

10:00 AM

Explore Castillo de San Marcos

Visit the iconic Castillo de San Marcos, a centuries-old fortress overlooking the Matanzas River, offering a glimpse into St. Augustine's rich history and military heritage.
Castillo de San Marcos is a short walk from The Bunnery, providing a fascinating look at Spanish colonial architecture and defense systems.
15 USD, 1.5 hours

12:00 PM

Lunch at Columbia Restaurant

Indulge in a traditional Spanish lunch at Columbia Restaurant, Florida's oldest restaurant serving authentic cuisine in a historic setting with courtyard dining.
Columbia Restaurant is located near the fortress, offering a cultural dining experience infused with Spanish flavors and charm.
20 USD, 1 hour

2:00 PM

Stroll down St. George Street

Take a leisurely stroll down St. George Street, a pedestrian thoroughfare lined with charming shops, historic buildings, and local artisans showcasing their crafts.
St. George Street is a bustling hub of activity, perfect for leisurely shopping, sightseeing, and soaking in the historic ambiance of St. Augustine.
Free, 2 hours

5:00 PM

Visit the Lightner Museum

Explore the eclectic collections of the Lightner Museum, housed in a historic Gilded Age building filled with art, antiques, and artifacts from the 19th century.
The Lightner Museum is located near St. George Street, offering a glimpse into St. Augustine's elegant past and cultural heritage.
10 USD, 1.5 hours

7:00 PM

Dinner at The Floridian

Dine at The Floridian, a farm-to-table restaurant known for its seasonal menu, Southern comfort food, and cozy atmosphere in the heart of St. Augustine.
The Floridian is located in the historic district, providing a taste of local flavors and hospitality to end your day in St. Augustine.
25 USD, 1.5 hours
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Day 7: Cultural Exploration in Jacksonville

Jacksonville, Florida on May 17, 2024

8:00 AM

Breakfast at Maple Street Biscuit Company

Start your day with a Southern-inspired breakfast at Maple Street Biscuit Company, known for its flaky biscuits, savory toppings, and cozy atmosphere.
Maple Street Biscuit Company has multiple locations in Jacksonville, choose the one nearest to your accommodation for a comforting breakfast.
12 USD, 1 hour

10:00 AM

Visit Cummer Museum of Art & Gardens

Explore the Cummer Museum, home to a diverse collection of art spanning from ancient to contemporary, and stroll through the picturesque gardens overlooking the St. Johns River.
The Cummer Museum is located in the Riverside neighborhood, offering a cultural immersion into art, nature, and history.
15 USD, 2 hours

12:00 PM

Lunch at Hawkers Asian Street Fare

Enjoy a fusion of Asian street food flavors at Hawkers, a popular eatery offering small plates, noodle dishes, and creative cocktails in a lively setting.
Hawkers Asian Street Fare has a location in Riverside, providing a vibrant dining experience to satisfy your cravings.
15 USD, 1 hour

2:00 PM

Walk along Jacksonville Beach

Take a leisurely walk along Jacksonville Beach, breathing in the fresh ocean air, watching surfers ride the waves, and collecting seashells along the sandy shore.
Jacksonville Beach is a short drive or taxi ride from Riverside, offering a relaxing escape by the sea.
Free, 1.5 hours

4:00 PM

Explore Riverside Arts Market

Discover local art, crafts, and fresh produce at the Riverside Arts Market, a vibrant open-air market showcasing the creativity and community spirit of Jacksonville.
The Riverside Arts Market is a weekend market held under the Fuller Warren Bridge, providing a lively atmosphere for shopping and entertainment.
Free, 1 hour

6:00 PM

Dinner at Black Sheep Restaurant

Savor a farm-to-table dinner at Black Sheep, a trendy restaurant known for its innovative cuisine, rooftop bar, and panoramic views of downtown Jacksonville.
Black Sheep Restaurant is located in the historic Five Points district, offering a culinary experience with a modern twist.
30 USD, 1.5 hours
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