14 Days of Southern Charm and Island Bliss: A Journey Through Nashville, Birmingham, New Orleans, Houston, and Honolulu

Embark on a 14-day adventure through the heart of the American South and the tropical paradise of Hawaii. From the vibrant music scene of Nashville to the historic streets of New Orleans, the cultural richness of Birmingham, the cosmopolitan allure of Houston, and the breathtaking beauty of Honolulu, this itinerary promises an unforgettable experience.

Welcome to a journey that combines the soulful rhythms of the American South with the serene beauty of the Hawaiian Islands. This 14-day itinerary will take you through five vibrant cities, each offering its own unique charm and attractions. From the country music capital of Nashville to the historic streets of Birmingham, the lively culture of New Orleans, the bustling metropolis of Houston, and the tropical paradise of Honolulu, you'll experience a diverse array of sights, sounds, and flavors.


Each city on this itinerary has its own story to tell. Nashville, known as Music City, is the heart of country music and offers a rich tapestry of live performances, historic venues, and Southern hospitality. Birmingham, a city steeped in civil rights history, invites you to explore its cultural landmarks and vibrant neighborhoods. New Orleans, with its French Quarter and jazz-filled streets, promises a lively and unforgettable experience. Houston, a sprawling metropolis, offers a mix of world-class museums, diverse cuisine, and space exploration. Finally, Honolulu, the gateway to Hawaii, beckons with its stunning beaches, lush landscapes, and rich Polynesian culture.

Throughout this journey, you'll have the opportunity to indulge in local cuisines, from Nashville's hot chicken to New Orleans' beignets, and experience the warmth and hospitality of the South. Whether you're exploring historic sites, enjoying live music, or relaxing on a Hawaiian beach, this itinerary promises a memorable adventure.

Nashville, Tennessee

Day 1: Arrival in Nashville

Arrive in Nashville in the afternoon and settle into your accommodations. For the best places to stay, check out VRBO or Hotels.com. Spend your evening exploring the vibrant Broadway area, known for its honky-tonks and live music venues. Enjoy dinner at Hattie B's Hot Chicken, a local favorite for spicy fried chicken.

Day 2: Exploring Music City

Start your day with a visit to the Country Music Hall of Fame and Museum, where you can learn about the history of country music. In the afternoon, take a guided tour of the historic Ryman Auditorium, known as the "Mother Church of Country Music." For dinner, head to The Southern Steak & Oyster for a taste of Southern cuisine with a modern twist. End your day with a show at the Grand Ole Opry, a must-see for any music lover. Book your tickets here.

Grand Ole Opry Show Admission Ticket in Nashville on Viator

Birmingham, Alabama

Day 3: Travel to Birmingham

In the morning, travel to Birmingham. The best way to get there is by car, which takes about 3 hours. Alternatively, you can book a flight via Trip.com. Upon arrival, check into your hotel. For accommodations, explore options on VRBO or Hotels.com. Spend your afternoon visiting the Birmingham Civil Rights Institute, a powerful museum dedicated to the history of the civil rights movement.


Day 4: Discovering Birmingham

Begin your day with a visit to the 16th Street Baptist Church, a significant site in the civil rights movement. Next, explore the Birmingham Museum of Art, home to an impressive collection of artworks. For lunch, try Saw’s Soul Kitchen, known for its Southern comfort food. In the afternoon, take a walking tour of the historic Five Points South neighborhood. For dinner, head to Highlands Bar & Grill, a James Beard Award-winning restaurant offering French-inspired Southern cuisine.

New Orleans, Louisiana

Day 5: Travel to New Orleans

Travel to New Orleans in the morning. The drive takes about 5 hours, or you can book a flight via Trip.com. Upon arrival, check into your accommodations. For the best places to stay, explore VRBO or Hotels.com. Spend your evening exploring the lively French Quarter, where you can enjoy live jazz music and dine at Café du Monde for their famous beignets.

Day 6: Exploring the Big Easy

Start your day with a visit to the historic St. Louis Cathedral and Jackson Square. In the afternoon, take a guided tour of the Garden District, known for its stunning antebellum mansions. For lunch, try Commander’s Palace, a New Orleans institution offering Creole cuisine. In the evening, embark on a Steamboat Natchez Evening Jazz Cruise for a unique dining experience on the Mississippi River.

Steamboat Natchez Evening Jazz Cruise with Dinner Option on Viator

Houston, Texas

Day 7: Travel to Houston

Travel to Houston in the morning. The drive takes about 5 hours, or you can book a flight via Trip.com. Upon arrival, check into your accommodations. For the best places to stay, explore VRBO or Hotels.com. Spend your afternoon visiting the Space Center Houston, where you can learn about NASA’s space exploration efforts. Book your tickets here.

Space Center Houston Admission Ticket on Viator

Day 8: Discovering Houston

Begin your day with a visit to the Houston Museum of Natural Science, home to fascinating exhibits on dinosaurs, gems, and more. For lunch, head to The Pit Room for some authentic Texas barbecue. In the afternoon, explore the Museum District, where you can visit the Museum of Fine Arts or the Contemporary Arts Museum. For dinner, try Xochi, a restaurant offering innovative Oaxacan cuisine. End your day with a stroll through the vibrant Montrose neighborhood, known for its eclectic shops and lively nightlife.


Honolulu, Hawaii

Day 9: Travel to Honolulu

Fly to Honolulu in the morning. Book your flight via Trip.com. Upon arrival, check into your accommodations. For the best places to stay, explore VRBO or Hotels.com. Spend your afternoon relaxing on Waikiki Beach, where you can soak up the sun and enjoy the stunning ocean views.

Day 10: Exploring Oahu

Start your day with a visit to Pearl Harbor, where you can explore the USS Arizona Memorial and learn about the events of World War II. Book your tickets here. In the afternoon, take a scenic drive along the North Shore, known for its beautiful beaches and surf spots. For lunch, stop at Giovanni’s Shrimp Truck for some delicious garlic shrimp. In the evening, enjoy a traditional Hawaiian luau at Paradise Cove, where you can experience Polynesian music, dance, and cuisine.

Pearl Harbor USS Arizona Memorial & Battleship Missouri on Viator

Day 11: Adventure and Relaxation

Spend your morning hiking to the top of Diamond Head, where you’ll be rewarded with panoramic views of Honolulu and the Pacific Ocean. In the afternoon, explore the lush landscapes of the Manoa Valley, where you can take a leisurely hike to Manoa Falls. For dinner, head to Alan Wong’s, a renowned restaurant offering innovative Hawaiian cuisine. End your day with a sunset sail along the coast, where you can enjoy breathtaking views of the island.

Day 12: Cultural Immersion

Begin your day with a visit to the Bishop Museum, where you can learn about the history and culture of Hawaii. In the afternoon, explore the vibrant neighborhood of Chinatown, known for its eclectic shops and delicious food. For lunch, try The Pig and the Lady, a popular restaurant offering Vietnamese-inspired dishes. In the evening, attend a performance at the Hawaii Theatre, a beautifully restored historic venue offering a variety of shows and concerts.

Day 13: Island Exploration

Spend your day exploring the island of Oahu. Visit the Dole Plantation, where you can learn about Hawaii’s pineapple industry and enjoy a refreshing Dole Whip. Next, head to the Polynesian Cultural Center, where you can experience the diverse cultures of the Pacific Islands through interactive exhibits and performances. For dinner, try Roy’s Waikiki, a restaurant offering a fusion of Hawaiian and international flavors.


Day 14: Departure

Spend your morning relaxing on the beach or doing some last-minute shopping in Waikiki. In the afternoon, head to the airport for your flight home, taking with you unforgettable memories of your journey through the American South and the Hawaiian Islands.

This 14-day itinerary offers a perfect blend of culture, history, and relaxation. From the vibrant cities of the American South to the tropical paradise of Hawaii, you'll experience the best of both worlds. Whether you're a music lover, history buff, or beach enthusiast, this journey promises an unforgettable adventure.

Ready to book your trip?

Search Hotels
Search Homes

Traveling somewhere else?

Generate a custom itinerary