Naples, Florida 12-Day Trip Itinerary

Depart Detroit

Begin your exciting road trip from Detroit, heading south towards Louisville, Kentucky.

Check-in to Hotel

Arrive in Louisville and check into your accommodation.

Hotel suggestions will be provided in the transport section.

Explore NuLu Neighborhood

Discover the 'New Louisville' (NuLu) district, known for its art galleries, antique shops, and local boutiques.

A great blend of historic architecture and modern flair.

Dinner in NuLu

Enjoy a farm-to-table dinner at one of NuLu's acclaimed restaurants, sampling local Kentucky cuisine.

Old Louisville Stroll

Take a morning walk through Old Louisville, admiring the beautiful Victorian mansions and tree-lined streets, a true historic gem.

Drive to Atlanta

Continue your journey south from Louisville to Atlanta, Georgia.

Check-in to Hotel

Arrive in Atlanta and check into your accommodation.

Hotel suggestions will be provided in the transport section.

Ponce City Market & BeltLine

Explore Ponce City Market, a historic building transformed into a vibrant food hall, retail space, and offices.

Afterwards, take a leisurely stroll on the Atlanta BeltLine, enjoying art installations and city views.

Morning in Atlanta

Consider a quick visit to the Martin Luther King Jr.

National Historical Park to reflect on significant Civil Rights history before heading out.

Drive to St. Augustine

Depart Atlanta for the historic city of St.

Augustine, Florida. Enjoy the change of scenery as you head towards the coast.

Check-in to Hotel

Arrive in St.

Augustine and check into your accommodation in the historic district.

Hotel suggestions will be provided in the transport section.

Historic District Stroll

Take an evening stroll through the charming historic streets of St.

Augustine, soaking in the ambiance and discovering early colonial architecture. Find a cozy spot for dinner.

Dinner in St. Augustine

Enjoy dinner at a local restaurant, perhaps one known for its seafood or Spanish-influenced cuisine.

Breakfast in Historic District

Enjoy a leisurely breakfast at a local cafe or bakery.

St. George Street Exploration

Spend your morning strolling down St.

George Street, the pedestrian-only heart of historic St. Augustine. Explore unique boutiques, art galleries, and historic buildings.

Lunch on St. George Street

Grab a casual lunch at one of the many eateries along St.

George Street.

Castillo de San Marcos

Visit the Castillo de San Marcos, the oldest masonry fort in the continental United States.

Explore its history and enjoy views of Matanzas Bay.

Allow plenty of time to explore the fort and its grounds. Check for ranger talks or cannon firings.

Dinner & Evening Entertainment

Enjoy another delightful dinner in St.

Augustine. Afterward, consider a ghost tour, a popular way to experience the city's haunted past, or find a spot with live music.

Ghost tours often require advance booking.

Leisurely Breakfast

Enjoy a final relaxed breakfast in St.

Augustine before heading towards Naples.

Drive to Naples, Florida

Embark on the final leg of your journey to Naples, Florida, leaving the historic charm of St.

Augustine behind for the sun-kissed Gulf Coast.

Condo Check-in & Settle In

Arrive in Naples and check into your condo.

Take some time to unpack and settle into your home away from home.

As per your request, accommodation details for Naples are not included in the daily plan since you have your own condo.

Naples Pier Sunset Walk

Head to the iconic Naples Pier for your first taste of the Gulf Coast.

Enjoy a relaxing walk along the expansive boardwalk and witness a beautiful Florida sunset over the Gulf of Mexico.

Dinner on 5th Avenue South

Enjoy a welcome dinner on Naples' famous 5th Avenue South, known for its upscale dining and vibrant atmosphere.

Settle into Condo

Arrive at your condo in Naples, unpack, and get settled.

Perhaps a quick grocery run for essentials.

Take some time to relax after the drive and familiarize yourselves with the local area.

Naples Pier & Beach Walk

Stroll along the iconic Naples Pier, a perfect spot to take in the breathtaking coastline and catch the stunning Florida sunset over the Gulf of Mexico.

Enjoy a leisurely walk along Naples Beach.

Parking near the pier can be busy, especially around sunset. Allow extra time or consider a short walk. Entry to the pier is free.

Dinner on 5th Avenue South

Enjoy an evening meal at one of the many exquisite restaurants along Naples' renowned 5th Avenue South, offering diverse culinary experiences.

Many restaurants offer outdoor seating, perfect for a pleasant evening. Reservations are recommended for popular spots, especially on a Thursday night.

Naples Botanical Garden

Explore 170 acres of world-class garden paradise, featuring plants and cultures of the tropics and subtropics.

A serene and beautiful escape.

Wear comfortable shoes and bring water. Check their website for any special exhibits or events. Booking online is recommended.

Lunch near Downtown

Grab a casual lunch at a local eatery, perhaps exploring options near the downtown area or 5th Avenue South.

Numerous cafes and restaurants offer lighter fare perfect for a midday break.

Explore 5th Avenue South

Take a leisurely afternoon to explore the boutiques, art galleries, and charming streets of 5th Avenue South.

It's great for window shopping or finding unique souvenirs.

Enjoy the architecture and vibrant atmosphere. Many ice cream parlors and cafes are perfect for a mid-afternoon treat.

Evening at Artis-Naples (Optional)

Consider attending a performance or event at Artis-Naples, the premier destination for visual and performing arts in Southwest Florida, if there's something that interests you.

Check their schedule in advance for concerts, shows, or art exhibitions. Booking is essential for performances.

Paddle Board Rentals

Experience the beautiful waters of Naples by renting paddle boards.

Suitable for all skill levels, it's a fantastic way to explore the calm bay waters or even try the gulf if conditions are right.

Book in advance, especially for weekend rentals. Lessons are often available for beginners. Bring sunscreen and a hat.

Beachfront Lunch

Enjoy a casual lunch at a restaurant with views of the Gulf, savoring fresh seafood or other local delights.

Many options available along the beach or a short walk from it.

Relaxation at Naples Beach

Spend a leisurely afternoon soaking up the Florida sunshine, swimming in the calm Gulf waters, or simply reading a book on Naples Beach.

Bring beach towels, sunscreen, and perhaps a good book. Many public access points are available.

Naples Tiki Fun Tour

Embark on a unique tiki boat tour on Naples Bay, offering a relaxing way to see the beautiful waterfront homes and potentially spot wildlife during a sunset cruise.

Book well in advance as these tours are popular, especially for sunset slots. Bring a light jacket as it can get breezy on the water. Check-in at The Boathouse Restaurant.

Naples Depot Museum

Discover Naples' history, particularly its railway heritage, at the Naples Depot Museum.

Learn about how the railroads transformed this once-remote area.

This museum offers a glimpse into local history and is usually free to enter. Check opening hours before visiting, especially on a Sunday.

Lunch in East Naples

Enjoy lunch at a local restaurant or cafe in the area around the Depot Museum before heading to the park.

Plenty of casual dining options nearby.

Relax at Cambier Park

Spend a relaxed afternoon at Cambier Park, a beautiful urban green space.

Enjoy a leisurely stroll, watch a game of tennis, or simply sit and people-watch.

The park often hosts outdoor concerts or art shows, especially on weekends. Check local listings for events.

Afternoon Relaxation

Head back to your condo for some downtime, perhaps enjoying the pool, reading, or just unwinding after a day of exploration.

A good opportunity to recharge before your final full day in Naples.

Naples Fishing Charter

Embark on a private fishing charter to experience the abundant waters around Naples.

Whether you're an experienced angler or a novice, enjoy a few hours on the water with a local captain.

Book well in advance to secure your preferred date and time. Charters usually include equipment and licenses. Bring sun protection and any snacks/drinks you desire.

Fresh Seafood Lunch

Indulge in a fresh seafood lunch, perhaps enjoying your catch from the morning charter (if allowed and prepared by a local restaurant) or dining at a top-rated seafood spot.

Ask your charter captain for recommendations for restaurants that can cook your catch, or choose from many excellent local seafood establishments.

Last Naples Beach Time

Enjoy a final afternoon at Naples Beach, taking in the serene Gulf views, collecting shells, or simply relaxing by the water before preparing for your journey home.

A perfect opportunity for some last-minute photos and memories of your beautiful Florida getaway.

Farewell Dinner in Naples

Savor a memorable farewell dinner at one of Naples' upscale or charming local restaurants, reflecting on your wonderful trip.

Consider a restaurant with waterfront dining for a special last evening.

Breakfast in Naples

Enjoy a final relaxed breakfast at your condo or a local cafe in Naples before beginning your journey north.

Scenic Drive to Nashville

Embark on the first leg of your return journey, driving from sunny Naples, Florida, through several states to reach the Music City, Nashville, Tennessee. Enjoy the changing landscapes.

Remember to account for fuel stops, restroom breaks, and meals. There is a time zone change from Eastern to Central Time when you enter Tennessee, so you'll gain an hour.

Hotel Check-in & Freshen Up

Arrive in Nashville, check into your hotel, and take some time to relax and freshen up after your drive.

Dinner in Downtown Nashville

Savor some classic Southern comfort food or explore Nashville's diverse culinary scene.

Consider options in The Gulch or downtown.

Live Music on Honky Tonk Row

Experience Nashville's legendary live music scene with a stroll down Honky Tonk Highway on Broadway, where bars feature live bands playing country, rock, and blues from morning until late night.

Most bars don't have a cover charge, but tips for the bands are highly encouraged and expected. Grab a drink and enjoy the atmosphere!

Breakfast in Nashville

Enjoy breakfast at your hotel or a local Nashville cafe, perhaps trying some local specialties like biscuits and gravy.

Morning Stroll in Downtown Nashville

Take a leisurely morning walk to soak in some of Nashville's atmosphere.

You could pass by the Ryman Auditorium, the Country Music Hall of Fame (from outside), or explore some of the historic streets.

This is a great opportunity for some last-minute photos or to grab a coffee before hitting the road.

Drive from Nashville to Detroit

Begin the final leg of your road trip, driving north from Nashville, Tennessee, back to Detroit, Michigan.

Enjoy the journey as you reflect on your Florida adventures.

Plan for stops for lunch, gas, and stretching. You'll cross back into Eastern Time as you approach Ohio, so you'll lose an hour.

Arrival back in Detroit

Arrive safely back in Detroit, marking the end of your memorable road trip.