The ultimate American Southeast road trip - from New Orleans to Key West

Accelerating from zero to sixty in the front seat of a ford mustang, our all-American road trip of the Southeast begins. Whether its Creole bites or saxophone sounds you want, our first stop, New Orleans, will satiate. But don’t get too comfortable because we soon cross state borders into Florida, with stop-offs at Panama City, Tallahassee, Jacksonville and Fort Lauderdale quenching a thirst for lively beaches, student lifestyles and distinct south eastern flavours. Travelling further south on the peninsula, rub shoulders with Aladdin in Orlando before dressing up for peachy sunsets viewed from Miami’s best rooftop bars. Our final stretch across the Overseas Highway runs through Florida Keys, landing on Key West – America’s gay Elysian Fields. Discover the best New Orleans vacations and beyond with Mr Hudson’s ultimate Southeast US road trip itinerary.

Tailor Made Journey

Let Us Plan
Your Perfect Vacation

Mr Hudson designs unique and luxurious vacations for sophisticated travelers who prioritize beauty and style.

Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson

Oak Alley Plantation, New Orleans | Photo: Dirk Spijkers

Day 1 - New Orleans

New Orleans is home to a great many cross-cultural attractions, thanks to its European colonial past, extensive migrant influence and its global renown as the birthplace of Jazz. Here you’ll find hearty local delicacies such as the Po’ boy sandwich in authentic diners just around the corner from the city’s notable French quarter, a place which firmly celebrates LGBT+ culture in an otherwise conservative Deep South.

Diversity in New Orleans is in good supply, acting as a melting pot for different ethnicities, nationalities and sexual orientations to live, create and unwind. A hub for artists, musicians, literary minds and activists, New Orleans will leave you inspired, with liberty on your mind and Cajun spice on your tongue. Read more about fun things to do in New Orleans for couples as well as the various day trips from New Orleans in Mr Hudson’s dedicated New Orleans travel guide.

French Quarter, New Orleans | Photo: Rosie Kerr

New Orleans | Photo: Samuel Dixon

Day 2 - New Orleans to Panama City

After exploring the many wonders of urban New Orleans, we top up the tank on our shiny convertible and zoom off on our epic journey from New Orleans to Miami, along stunning coastal roads flanking the Gulf of Mexico. We roll up first in Panama City to be greeted with fun-loving beach resorts and ocean action. Within Gay Panama City located on St. Andrews, there’s the marina and all manner of seafood eateries, while across the bay, Panama City Beach treats us to its long white-sand shores and wonderfully trashy amusement parks.

The list of Panama City Florida things to do continues with a call to nature over on Shell Island Peninsula where St. Andrews State Park lays claim to beaches, nature trails and open-water excursions. Pack your binoculars for the opportunity to glimpse dolphins and sea turtles up close!

Panama City Beach | Photo: Jordan Benton

Photo: Deedee86

Mr. Hudson highlight image

After exploring the many wonders of urban New Orleans, we top up the tank on our shiny convertible and zoom off on our epic journey from New Orleans to Miami, along stunning coastal roads flanking the Gulf of Mexico

Day 3 - Panama City to Tallahassee

Next, we venture on to Tallahassee, Florida’s capital city. What Tallahassee lacks in gay bars it makes up for in youth culture, as home to two progressive universities; Florida A&M and Florida State. LGBTQ-friendly and alive with PYTs, Tallahassee’s institutions, cafés and bars host numerous gay-centric events, culminating in the PrideFest each April. For more information on things to do in Tallahassee, the Visit Tallahassee website has got you covered.

Panama City Beach | Photo: Craig Cameron

Day 4 & 5 - Tallahassee to Jacksonville

From Florida’s capital to its largest city, we park up next in the coastal city of Jacksonville, another gay haven with a population of over 1,300,000. Despite its conservative roots, gay culture burgeons in Jacksonville, leaving gay travellers with plenty to smile about. Named among the ‘top 5 emerging cities for gays and lesbians’ by The Advocate, Tallahassee shines, particularly within the up-and-coming neighbourhoods of Avondale, San Marco and Riverside where charming stores and eclectic restaurants benefit from both affordability and endless Florida sunshine. Visit Jacksonville is a worthy bookmark, providing all the best seasonal things to do in Jacksonville.

Jacksonville | Photo: Lance Asper

Mr. Hudson highlight image

In addition to classy jazz joints like the Bösendorfer Lounge, one of the best gay clubs Orlando has on offer is Southern Nights Orlando

Day 5 & 6 - Jacksonville to Orlando

Hold onto your Minnie Mouse ears for the next drive south because we now make our way to the hometown of Mr Mouse himself. A guilty pleasure, Orlando is much loved by gays worldwide for its over-the-top Walt Disney sensibilities and its prime position in the market of gay weddings. In addition to the countless amusement parks, Orlando is surprisingly cosmopolitan and bustling, most notably down by the beachfront where Gay Orlando thrives.

Voted the tenth gayest city in the US, Orlando has a fine selection of gay nightlife choices. In addition to classy jazz joints like the Bösendorfer Lounge, one of the best gay clubs Orlando has on offer is Southern Nights Orlando. Fusing queer and ‘LatinX’ cultures, Orlando keeps visitors dancing to dawn with its endless run of gay events, including the LGBTQ-oriented Disney Gay Days, Come Out With Pride and Orlando Pride festival. In the wake of the Pulse Nightclub Tragedy, the city has rallied, becoming more committed to inclusivity and togetherness than ever before. For more things to do in Orlando Florida, see our guide to the best gay bars in Orlando.

Photo: Sherrold Valentin

Photo: Julie Tupas

Day 7 & 8: Orlando to Fort Lauderdale

As we traverse the entire stretch of Florida it would be remiss of us not to stop in Fort Lauderdale, another gay mecca home to an ever-growing number of sun-seeking gays! Not surprising, due to its endless beach views, South Florida climate and relaxed culture, Fort Lauderdale’s LGBT population soar, outnumbering the straight population in certain areas. Find out the must-see spots with our dedicated Fort Lauderdale City Guide.

While the whole city is gay-friendly, if you’re looking for the gayest places to stay, Wilton Manors gaybourhood is a magenta on the gay-scale, closely followed by the area surrounding San Sebastian Gay Beach. Both quirky and luxurious, Fort Lauderdale is packed with classy resorts, bars and restaurants with the added interest of artsy suburbs and a chocka-block gay events calendar. When the time comes for a tipple in like-minded company, you’re going to want to make your way to one of the 5 best gay bars in Fort Lauderdale.

Photo: StockSnap

Day 9 & 10: Fort Lauderdale to Miami

From the azure shores of South Beach to the Cuban-spiced neighbourhood of Little Havana, our next stop in Miami is bound to please. Where the sun reigns all year round and glitz is a way of life, Miami is the perfect penultimate stop-off. In between taking in the talent at 12th Street Beach (a proudly gay gathering spot signposted by rainbow flags) and partying in the best Miami gay clubs, spare some time to explore across the causeway, where Art-Deco pastel buildings provide a stunning backdrop to the city’s exciting foodie movement and a buzzing art scene. See our Miami travel guide for all the trending ins and outs of this sun-kissed urban beauty.

Miami | Photo: Jason Briscoe

Photo: Karina

Day 11 & 12: Miami to Key West

Ending on a high, we make the spectacular journey down to Key West, one of the best known US destinations for queer travellers since the 1970s, an LGBT safe haven founded amidst picture-perfect beaches and rugged coastal landscapes. Offering gay-friendly guest houses and a magnificent gay culture centred on Duval Street, Key West reaches its peak during the summer months when annual events such as Tropical Heat, Fantasyfest and Womenfest draw international crowds. For more things to do in Key West year-round, see our guide of the top 10 things to do in gay Key West.

Photo: Gautier Salles

Want to simplify luxury travel planning?

Whether you want a resort vacation, wildlife safari, city break, luxury cruise, wellness retreat, honeymoon, once-in-a-lifetime adventure or weekend escape, the trip curation experts at Mr Hudson make travel planning a breeze. Find out how we can handle the finer details of vacationing in style.

Photo: Michelle Maria

Subscribe to our newsletter

You can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing.

Sign up for exclusive insider promotions