Your Ultimate East Coast Gay Road Trip Guide
Get ready for 1,600 miles of queer memories.
The perfect road trip includes landscapes and flavors that change dramatically en route and stopovers that aren’t too far apart. Even better? If you can gay it up at queer bookstores, galleries, nightclubs, and queer-owned restaurants along the way. The East Coast, with its smaller states and more compact cities, offers an ideal route — mostly on I-95, including worthwhile easy detours to cities like Savannah and Raleigh — with ample stopping-point options and ever-changing terrain, architecture, climate, and cuisine. From port cities in New England to historic hubs like Philadelphia and the rainbow-clad grand finale in Miami, we’ve done all the hard work of mapping out a route for you.
Start on a lobster high in Portland, Maine
For a truly epic East Coast voyage, start in Maine’s largest city, a seaside haven for culture, seafood, art, and the LGBTQIA+ community. This “other” Portland has a lot of the same progressive politics and indie charm of its Oregonian counterpart, but with fewer than 100,000 residents, it feels more like a big, liberal city masquerading as an unpretentious small town. It’s really the best of both worlds, meaning you can kick off your road trip with a round of pool at Blackstones, the oldest gay bar in town, and follow with chic cocktails at Jewel Box, a sparkly cocktail bar that seems perpetually dressed for prom — fit with twinkly lights and pops of pink. Then cap the night off on the dance floor at queer-friendly Bubba’s Sulky Lounge. Before you head out, pick up coffee (and a slice of banana black sesame cake for the road) from the impossibly cool Tandem Coffee + Bakery, and a brown butter lobster roll from wildly popular Eventide Oyster Co.
Spill the tea while restaurant-hopping in Boston
Any city known for a tea party is one worth visiting on your LGBTQIA-centric road trip. A lot has changed in Boston since that infamous event, which of course was more of a protest than a dainty afternoon of petit fours, but now you can spill your own tea in the state that became the first to legalize same-sex marriage in 2004. Lined with cobblestone streets and home to tons of historical places and dazzling new-school restaurants, Boston is a city that seamlessly mixes the old with the new, all with an eye towards progressive thinking and inclusion. A stint here can be as pastoral or as hustle-bustle as you’d like, whether that means a romantic picnic in America’s oldest public park, Boston Common, or a visit to queer-centric Gallery 263 for an out-and-proud exhibit. You can also visit queer-friendly Trident Booksellers for a cup of tea and some road trip reading material — or some literature on how to topple the patriarchy. As it’s such a foodie town, you’d be remiss not to restaurant- and bar-hop a bit. We suggest gay sports bar Cathedral Station for pineapple martinis and fish; and chips or swordfish rice and torched hamachi crudo at LGBTQIA-owned Tiger Mama. Or there's always a cheese tray and rosé all day at Rebel Rebel, a Bow Market wine bar whose website perfectly and proudly proclaims: “Leave your misogyny, your homophobia, your racism, your classism, your ableism, your patriarchy, your gender bias, and all your other bullshit at the door, 'cause that shit will get you kicked out real quick.”
Pair queer history and happy hour in New York City
Home to copious gay bars, LGBTQIA-owned restaurants, queer galleries, and gayborhoods so widespread that the entire metropolis is one big rainbow-hued blur, New York City is a must-visit mecca on any gay pilgrimage. The itinerary options are endless throughout the five boroughs, so it just depends on the ratio of history/art/culture you’re looking to mix with nightlife, drag shows, and Carrie Bradshaw-approved Cosmos. If you’re passing through and scratching the surface, your queer agenda might include a stop at SoHo’s Leslie-Lohman Museum, a stimulating showcase for queer artists and blatantly gay artwork, while brunch could include New Mexican burritos at queer-owned Ursula, a vibrant Brooklyn cafe known for hosting queer brunch events. For an afternoon snack, satisfy your sweet tooth with a key lime pie-inspired mermaid sundae from Big Gay Ice Cream before taking in some important history at the New York City AIDS Memorial and Stonewall National Monument — the latter of which is a stone’s throw from Cubbyhole, a “straight-friendly” lesbian bar with a bangin’ happy hour. For dinner, wind down in classic Italian style at another queer-owned restaurant, the homey and cozy Via Carota, where serious advanced planning or waiting should be expected, and canoodle over plates of fritto misto and pappardelle.
Show some love to the City of Brotherly Love in Philadelphia
If the traffic angels are with you, it’s only a couple hours from New York City to your next stop in another queer haven: Philadelphia. Like Boston and NYC, Philly is a city steeped in history and rich with progressive LGBTQIA-friendly politics, nightlife, businesses, and gayborhoods, like its most famous enclave, Washington Square West. Located on the southeast side of downtown, this is where most of the annual Pride festivities take place, and where the densest collection of queer-owned businesses reside. While most of the city is staunchly liberal and queer-friendly, a brief sojourn in the City of Brotherly Love should focus on downtown’s gayest alcove, where you can relax in the six-acre Washington Square Park or admire the magnolias on the lush grounds outside the historic Pine Building. Take a leisurely stroll along Philly’s “Mural Mile,” a stretch of 13th Street lined with striking street art, or join an LGBTQIA+ walking tour with Beyond the Bell Tours, which includes a stop at Giovanni’s Room, the oldest LGBTQIA bookstore in the US. When all that leisurely strolling has built up an appetite, wind down at any number of Washington Square West restaurants, like Double Knot for Japanese small plates and cocktails, or wood-oven pizza at LGBTQIA-owned Barbuzzo.
Get outside with pride in Richmond, Virginia
Keeping in the theme of historic American cities lined with brick buildings and cute cobblestone streets, Richmond is more of an underrated gem — especially as a gay destination. Though small in population compared to other East Coast metropolises, with under 250,000 residents, Richmond is an urban hub for queer festivities, bars, art, shopping, and good eats, all in an environment that’s much more mellow than your previous stopovers (i.e., you can easily find street parking, or ride a bike around town without inciting road rage). This is the kind of city that offers something for everyone, be it shopping for rainbow prints and lesbian stickers at Lady Street Studios; drinking in the history (and the Poe-inspired cocktails) at historic Linden Row Inn, a former Edgar Allen Poe haunt-turned-LGBTQIA-friendly mainstay; eating “Gay-Fil-A” chicken sandwiches from Cobra Cabana, with proceeds going to support Virginia’s queer youth; or taking the outdoorsy route with a tranquil hike on the Buttermilk Trail and a dip in the James River. If you’re looking for more adrenaline, you’re in luck, because this is one of the few American cities where you can go white water rafting under a city skyline.
Dine on Southern fare in Raleigh, North Carolina
From Richmond, it’s a hop, skip, and a three-hour jump to Raleigh, a metropolitan area that’s rapidly rising up the ranks of best places to live in the US. The state capitol of North Carolina, home to just under 500,000 people, is an up-and-coming metropolis that has undergone some massive changes in recent years. Nowadays, it’s home to gay-friendly hotels like the Raleigh Marriott City Center, which offers Pride and Joy couples packages, and iconic queer shops, like The Green Monkey, a quirky queer-owned store with kitschy wares, beer on tap, and drag shows. The LGBT Center downtown is a welcoming gathering place for events, readings, health resources, and a library, while nearby Humble Pie is a regular LGBT Center donor renowned for its Sunday brunch spreads of cornmeal waffles and shrimp & grits (we’re officially in the South, y’all). A foodie trip to Raleigh wouldn’t be complete without a pimiento cheese-filled meal at Poole’s Diner, a local icon owned by Ashley Christensen, who famously stood up to the “bathroom bill” by re-labeling her bathrooms as “People Rooms.” Then dance off the pimiento with a night under the disco ball at Legends Nightclub, the city’s oldest gay bar.
Eat dinner in a pink mansion in Savannah, Georgia
Draped in Spanish moss and filled with historic architecture, cobblestone streets, and coastal cuisine, Savannah is a singular American city oozing innate romance and charm. And for any LGBTQIA+ couple who has yet to spend time in this beautiful Southern city (in America’s newest blue state, no less!), it deserves top priority on your road trip itinerary. Along with the larger Georgian metropolis of Atlanta, this is a city that’s been at the forefront of progress and inclusion in the Deep South, and while it lacks the multitude of gay bars found in ATL (save for the must-visit Club One), what you’ll find is a more widespread and cohesive sense of warmth and welcome. Thanks to its gothic architecture and open-container laws, it’s got the feel of a calmer and cleaner Charleston or New Orleans, with lots of date night-worthy restaurants, like The Grey for salted fish croquettes and butter bean falafel, or The Olde Pink House, a modern Southern mainstay set inside a stunning 18th century Colonial mansion, where aphrodisiacs take the form of cornbread fried oysters. Rest your head at the JW Marriott, located on the always-bustling — and particularly queer-appealing — River Street corridor. Not only is Marriott International one of the most vocally LGBTQIA-friendly hotel brands in the world, but this one is loaded with so many dining and drinking options, from Electric Moon Skytop Lounge and Graffito pizzeria, to African-inspired Baobab Lounge and District Seafood, that you hardly need to leave the property. Outdoors enthusiasts have plenty to do as well, from a picture-perfect beach day on nearby Tybee Island to tours of Fort Pulaski National Monument. As you make your way further south, Georgia is dotted with breathtaking barrier islands fit for exploration, like Cumberland Island with its wild horses and miles of undeveloped seashore, and Jekyll Island, a pastoral paradise that’s home to honeymoon-worthy hotels like Jekyll Island Club Resort, where in-room massages, dolphin cruises, and fried green tomatoes await.
Experience the magic and waffles of Orlando, Florida
As you enter your final state of Florida, it’s time for a little magic. After the long drive, you deserve waffles shaped like Mickey Mouse and cocktails garnished with mini marshmallows. Orlando is the ultimate road trip stopover, with endless gay-friendly things to do in Disney World, a global pioneer of inclusivity and merriment that’s been championing LGBTQIA+ rights for decades by hosting events like Gay Days Orlando and overloading its gift shops with Pride merch. Plus, this is the only place in the country where anyone can comfortably wear pink caps that say “But Daddy I Love Him” and not feel like you’re suiting up for Bear Week (I speak from first-hand experience). Beyond the honeymoon-level thrills from all the attractions, romantic resort dinners, and Disney princess sightings, the city of Orlando itself is a haven for LGBTQIA+ travelers. Orlando was named as the first ever “City of the Year” by GayCities.com in 2016, due partly to the strong sense of community and pride felt in the wake of the Pulse Nightclub tragedy. Today, Orlando is filled with gay bars and clubs for dancing — Southern Nights and SAVOY are star attractions — or you can keep it quaint with a romantic scenic boat cruise through Winter Park’s canals, and brunch at LGBTQIA-owned Se7en Bites where the pearl sugar waffles may not be Mickey-shaped, but they’re still magical.
Finish Miami-style with drag shows, art, and clubs
1,600 miles later, there’s no better place to cap off an epic road trip than Miami, a veritable Oz of gay bars and drag queens. The Magic City, in all its vibrant queerness and omnipresent art, is the perfect end point, and an ideal setting in which to reset and recharge — assuming your method of resetting involves over-the-top drag brunches, pool parties, and gay nightclubs that stay pumping until 5 am. If you prefer the sand and up-all-night antics of South Beach, there’s plenty to see and do, from strolling the pastel-hued Art Deco district to taking in a drag show at Palace. To stay, AxelBeach Miami on South Beach is so queer-centric that their tagline is “We Are Hetero-Friendly,” with a stunning Art Deco facade, a pool, outdoor dance floor, and rooms tastefully stocked with condoms. For something a bit calmer, Miami’s sheer size ensures you’ll find comfort and inclusion anywhere, from the queer artist murals at Wynwood Walls to the immersive and colorful photo ops at Superblue and the Latin beats at gay nightclub Azucar near Coral Gables. It's a gay road trip wrapped up right.