The ultimate American East Coast road trip – from NYC to Key West in 10 days

Affirmed by Wu-Tang and Big Poppa himself, the US East Coast will always be the best, regardless of what Tupac and the Californians are saying. The birthplace of hip-hop and LGBT rights, East Coast states may come smaller and more compact than those along the West Coast, but they also helped endow the world with the best rap lyrics and the most liberal ideals! Even the shortest East Coast driving trips allow for diverse perspectives on culture, history and climate, starting in balmy New England and moving down south towards the sun-soaked beaches of the Florida Keys. Join us on our ultimate road trip through 10 of the best vacation spots on the East Coast, from urban hubs to island retreats.

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New York | Photo: Jerome Dominici

1. New York City

Starting in the queen of cities herself, we land at JFK to go head first into a world of Broadway glamour, deli dishes and iconic yellow taxis for days. Regardless of your relationship status or bank balance, the Big Apple has something for everyone, families, singles and gay couples alike. See the skyline from the One World Trade Centre or any of Manhattan’s fancy rooftop bars, coming back down to earth for tours around each distinct borough, from Brooklyn to Staten Island. Though the entire city is very gay friendly – with gay marriage legal since 2011 – make a note to stop by key sites of LGBT history, in the gay areas of Greenwich Village (site of the Stonewall uprising of 1969), Chelsea and Hell’s Kitchen. Read our New York City travel guide for more insights on how to fill your New York itinerary.

2. Philadelphia, Pennsylvania

NYC > Philadelphia – 152 km; 1hr 45 mins (via I-95 S)

Saying goodbye to NYC doesn’t have to be hard as our next stop brings us more grit and Philly cheesesteaks than we can handle in Philadelphia; Pennsylvania’s largest city. As one of America’s great eastern cities, Philadelphia is of course out and proud when it comes to LGBTQ visibility. Founded on the principles of equality and freedom of expression and now known as the ‘City of Brotherly Love’, gay Philadelphia is particularly welcoming, no more so than within its central gaybourhood between 11th and Broad from Chestnut to Pine Street. Here you’ll find a leafy district with cobblestone streets and brick townhouses hosting a range of gay-friendly venues such as bookstores, cafes, bars and clubs, many of which are involved in the annual global Equality Forum and ongoing LGBTQ+ activism.

Outside of the gay district, art and culture lovers are catered for at various museums, galleries and music venues, particularly along the Avenue of the Arts with its array of dining and entertainments as well as the notable Philadelphia Art Museum which holds one of the largest collections in the US. Chow down of hoagies, scrapple, soft pretzels and, yes, cheesesteaks until your arteries complain, finishing up with some constitutional history at the Independence Hall and costumed re-enactments around the Liberty Bell. For more on what to do and where to stay in the city, see our full Philadelphia travel guide.

Philadelphia City Hall | Photo: Leo Serrat

Photo: Tyler Nix

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Continuing southbound, we skip state lines from Pennsylvania into Maryland and wind up in Baltimore, one of the top East Coast vacation spots for its diverse neighbourhoods laid out around a historic harbourside

3. Baltimore, Maryland

Philadelphia > Baltimore – 160 km; 1hr 55 mins (via I-95 S)

Continuing southbound, we skip state lines from Pennsylvania into Maryland and wind up in Baltimore, one of the top East Coast vacation spots for its diverse neighbourhoods laid out around a historic harbourside. The colours here come as fresh as the seafood, jointly showcased at the famous crab market in the city centre. Though the Inner Harbour can keep you busy peeling shellfish, the city’s USS Constellation, National Aquarium and Maryland Science Centre can ensure you’ll learn something too. The Civil War nerds among you will also be pleased to hear that there are as many as 15 maritime museums in the area, while art and literature lovers can split their time between Baltimore Museum of Art, American Visionary Art Museum and Edgar Allen Poe House & Museum.

Founded in 1729, Baltimore’s history is just as easy to discover out on the streets, across charming neighbourhoods and landmarks such as at the Fort McHenry National Monument, as well as on match days when support for the long-running baseball and football teams can also be considered a historical activity. Before the day ends and the party begins, join sunset seekers at the top of Federal Hill where the best skyline views take precedence. Afterwards, it’s the gay nightlife in Mount Vernon that comes calling (particularly during June’s pride festival), with LGBT events laid out helpfully in the two local LGBT papers: Baltimore OutLoud and Baltimore Gay Life. Once you’ve ticked off all the things to do in Baltimore, consider making a stop at the NASA Goddard Space Flight Centre on your way to Washington D.C. to see the Hubble Space Telescope and satisfy your young self’s astronaut aspirations.

Photo: Mitch Kemp

4. Washington D.C.

Baltimore > Washington D.C. – 64 km; 1hr (via Baltimore-Washington Pkwy and New York Ave NE)

A major stopping point on any East Coast America itinerary is to the US capital and independent state of Washington D.C. While you might associate D.C. with political stuffiness and suits, the city actually has a lot more texture, made interesting through fabulous nightlife opportunities and a diverse crowd. Before sundown, make a point of ticking off the Lincoln Memorial, Washington Monument and Vietnam War Memorial, moving onto the Smithsonian Museums for air and space technology and the National Archives for a glimpse at the Declaration of Independence and US Constitution. From there, you’ve still got the US Capitol building to behold, as well as the Kennedy Performing Arts Centre which takes over a prime piece of riverside opposite Theodore Roosevelt Island.

After taking in a hefty amount of neoclassical architecture around the city, the city’s visitors and its thirsty government workers call loudly for decent food and alcohol. DC gladly complies, offering a thriving dining and bar scene that is wholly bipartisan when it comes to fun. To find like-minded souls, head either to the new gay neighbourhood of Logan Circle or to the long-standing Dupont Circle on 17th Street, two areas ever-alive with LGBT bars, eateries and other gay-owned businesses, particularly around June and October when Capital Pride and Dupont Circle High Heel Race respectively take over. For more on how to get down in the capital, see our Washington DC travel guide.

Washington DC

Washington DC | Photo: David Mark

National Gallery of Art, Washington

National Gallery of Art | Photo: Ryan Spencer

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A new day on the road, a new state to see; this time it’s Virginia, the south-eastern state that stretches from the Atlantic Ocean in the east to the Appalachian Mountains in the west

5. Richmond, Virginia

Washington DC > Richmond – 175 km; 2hours (via I-95 S)

A new day on the road, a new state to see; this time it’s Virginia, the south-eastern state that stretches from the Atlantic Ocean in the east to the Appalachian Mountains in the west. Not only is Richmond a significant city within the region, it’s also one of the oldest cities in the US, boasting a treasure trove of historic gems. Home to the White House of the Confederacy during the Civil War and the place where founding father Patrick Henry entreated for liberty or death, Richmond carries some weight. Explore the neighbourhood around Court End to glimpse Federal-style mansions, moving to the Lewis Ginter Botanical Garden and Belle Isle for a touch of classic beauty. Also in the offing is a visit to the Virginia State Capitol and the Virginia Museum of Fine Arts where you’ll find yourself among younger crowds than you might have anticipated.

Politically active they may be but the hip young locals of Richmond (many of them students at VCU) also know how to have a good time. The gay scene itself is thinner than in DC but visitors still have a handful of gay bars to choose from and one majority lesbian bar all based in the area around downtown. As the youthful population makes its mark and the LGBT rights movement continues, Richmond can only get gayer. While you’re waiting, tick off all the top things to do in Richmond, snapping photos of all the street art as set up by the Richmond Mural Project.

Richmond, Virginia | Photo: Bruce Emmerling

6. Richmond to Myrtle Beach, South Carolina

Richmond > Myrtle Beach – 482 km; 5 hours (via I-95 S)

At a journey time of five hours, travelling from Richmond to Myrtle Beach could seem like the waste of a vacation day. On the contrary, however, with so many worthy stop-offs, the trip is a must for all serious East Coast vacations. Two and half hours in, you’ll reach the capital city of Raleigh, North Carolina, a place known for its college life and academic clout, in line with neighbouring cities of Durham and Chapel Hill. While in the vicinity, learn something new at the North Carolina Museum of Natural Sciences, get crazy at the Marbles Kids Museum or go highbrow at the North Carolina Museum of Art. For pinnacle architecture in town, pass by the North Carolina State Capitol in all its 19th century Greek Revival stylings, winding up at Pullen Park for a leisurely sunset thereafter. Other attractions in the area include Fort Bragg military base, Fantasy Lake Water Park, Cape Fear Botanical Garden and the Museum of Cape Fear Historical Complex.

After drooling over Air Force pilots, there’s only one place left to go; gay Myrtle Beach. More than just a fabulous shorefront on the Atlantic, Myrtle Beach is one of South Carolina’s best cities, hosting a number of quaint beach towns and barrier islands on the 96-kilometre coastal stretch from Little River to Georgetown. Popular all year round and especially so in winter, Myrtle Beach is our first taste of southern warmth, allowing for sunbathing, swimming, boating and water sports from here on in. Though the local roads are not the friendliest, the Myrtle Beach gay scene will more than make up for that fact, centred on the beach near 82nd Avenue North. Besides partying with new friends, be sure to soak up Myrtle’s kitsch fairground vibes at the Family King Amusement Park or on the Skyweel Ferris wheel, overlooking long stretches of beachside boardwalks, green space and a Ripley’s Aquarium to boot. Looking to stay in the area? See our guide to the best hotels in Myrtle Beach.

Myrtle Beach | Photo: Hannah Busing

Myrtle Beach | Photo: Hannah Busing

7. Savannah, Georgia

Myrtle Beach > Charleston – 158.2 km; 1 h 59 min  (via US-17 S)

Charleston > Savannah – 173.6 km; 1 h 54 min (via US-17 S and I-95 S)

Two more East Coast road trip stops come up on the drive from South Carolina to Georgia; first at the old port city of Charleston and second at Savannah, both sure to charm in equal measure. Charleston woos first with horse-drawn carriage rides through cobblestone streets, giving views of Antebellum-style architecture as well as Civil War era builds within the French Quarter. Spend the rest of the day moseying along the water’s edge, passing by Waterfront Park, Battery Promenade and the Fort Sumter National Monument before driving ways out to the grand Boone Hall Plantation. A sassy mix of European styles and Southern charms, Charleston is ever-popular among the gay community, offering up romantic scenes and authentic Lowcountry fare as well as a whole host of other things to do.

Not too dissimilar to Charleston, Savannah also lies along the Atlantic coast with Antebellum aesthetics and horse-drawn carriages centred on a pretty historic district filled with elegant 18th and 19th-century residences. Quintessentially southern oak trees covered in Spanish moss make for the perfect picnic shelter in Forsyth Park, but the town’s endless stream of museums can also keep you busy. Learn of the region’s slave history at Wormsloe Historic Site, Mercer Williams House Museum, Telfair Museums and more, stopping by haunted graveyards and Civil War sites for added emphasis. While there is no official gay neighbourhood in Savannah, the whole town has an inclusive vibe, best demonstrated on River Street where the majority of gay-owned boutiques, galleries and eateries (as well as the town’s best nightlife) can be found.

Savannah | Photo: Philip Arambula

Savannah, Georgia | Photo: Ashley Knedler

8. Orlando, Florida

Savannah > Orlando: 450 km; 4 hr 20 min (via I-95 S)

And finally, we arrive in Florida, the home state of the Kennedy Space Centre, Disneyland and Gatorland! With so much diverse action, it’s difficult to know how to split your time; either opting for family adventures in Universal Studios and myriad theme parks, fast thrills at the Daytona Speedway or wildlife retreats over on Canaveral National Seashore. Whatever you choose, be sure to go beyond the hype to find Orlando’s authentic side, finding over 100 lakes and 100 more parks, many of which offer weekend entertainment and live music events throughout the year. Despite there being no official gay neighbourhood in the city, there are plenty of great gay bars in Orlando scattered around. However, every June, gay convergence does happen (in crowds of upwards 100,000 gays, lesbians, queers and advocates) for Gay Days Orlando at Walt Disney World – the perfect excuse to don your Minnie Mouse ears and go rollercoastering.

Orlando | Photo: Colin Lloyd

Photo: Tyler Nix

9. Miami

Orlando > Miami – 378 km; 4 hours (via Florida’s Turnpike)

Florida’s next big-time city comes about 4 hours’ drive south down the Atlantic Coast. It is of course Miami, a cosmopolitan melting pot of beach-ready Barbie and Ken Dolls with a reputation for partying. Known as the Gay Riviera, Miami is wholly welcoming to gay travellers, particularly in the gaybourhood of South Beach (or SoBe if you will), as well as the gay beach near Ocean Drive. Have fun in the sand with tan bodies, moving the fun inwards after sundown for sexy gay bars and clubs alongside a range of gay-friendly accommodations and restaurants. Though Coconut Grove has had to hand over its gay crown to South Beach in recent years, the grove area still has a lot to offer, such as the famed White Party at Vizcaya Museum and Gardens. Also on our radar is Coral Gables, a slightly more muted gay area with trendy boutiques, restaurants and a few gay nightclubs thrown in. Discover more ways to fill your itinerary in our full Miami travel guide.

Miami Beach | Photo: Denys Kostyuchenko

10. Key West

Miami > Key West: 265 km; 3 hr 30 min (via US-1 S)

Moving from the US mainland and into island mode, we travel via the Overseas Highway to the very end of the Florida Keys to perhaps the best gay Mecca of them all. At less than 20 square kilometres in size, Key West is a tiny slice of heaven with aquamarine waters on all sides to rival the Caribbean beaches that lie some 140 kilometres south off the coast. Besides pristine landscapes of sand, sea and tropical greenery, Key West also offers one of most inclusive communities in the US, bearing the motto ‘One Human Family’. Be totally at ease within a town led by openly gay and lesbian elected officials, walking through the centre in the footsteps of Tennessee Williams who lived here for decades. Owing to the open-minded and artistic residents and politicians, Key West caters fully to the LGBT community, hosting a great many gay-oriented guesthouses and LGBTQ resorts as well as far-out private villas to appeal to introverted travellers. Extroverts meanwhile can go all out on Key West’s many clothing-optional beaches, turning inland a little for gay-owned cafes and restaurants, followed by drag shows and gay pool parties that run late into the night. Bear in mind that driving and parking on Key West can get pricey so the best bet is to park up at your residence and rent bikes to get around the compact city. Tired of gazing out at the perfect ocean views? Discover our list of the top 10 things to do in gay Key West.

Florida | Photo: Taryn Elliott

Photo: Melissa Walker Horn

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Miami | Photo: Ryan Spencer

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