hit the road

How to take the ultimate Miami to Key West road trip

Two men lounge near the EAST Miami pool
Photo via EAST Miami’s Instagram

Miami and Key West are two of the best LGBTQ+ travel destinations in the country. With only miles on Route 1 between them, you could easily make the trek in one day. But you’d be doing yourself a disservice by missing what South Miami-Dade and the upper Florida Keys offer.

Here at GayCities, we’ve put together our ultimate Miami to Key West road trip. Below is an itinerary with three days of outdoor adventures, yummy food, and luxurious stays. After all, it’s all about the journey.

Whether you just flew in, or are finishing up a wild stay in South Beach, you’ll need a good night’s sleep before hitting the road to paradise. Check out our favorite South Miami hotel off Route 1.

EAST Miami

This Brickell hotel, close to the City Centre, is everything you expect from a luxury Miami high-rise. Sleek high-rises surround the stylish pool area, and every room has a city view out its floor-to-ceiling windows.

Once you leave your contemporary haven, you’ll be zen and ready to start your adventure, but not on an empty stomach. Luckily, if it’s Saturday or Sunday, we know the perfect brunch spot just two blocks south of EAST.

Road to Paradise Day 1

Dolores But You Can Call Me Lolita

Photo via the Dolores But You Can Call Me Lolita website

Anytime you go to Dolores Lolita, with a bar, restaurant, rooftop, and dance floor, will be a good one. On weekends, they serve a stunning brunch, with dishes including chicken and waffles, tuna poke bowl, and burrata, salmon, and guacamole toast. This Instagram-worthy and filling brunch is sure to satisfy you before a day in and out of the car.

Once you’ve eaten smoked fish or steak and eggs, our next stop is only a 10-minute drive away.

Vizcaya Museum & Gardens 

Photo courtesy of Vizcaya Museum and Gardens

While it’s not technically confirmed that the original owner of this 1914 mansion was gay, the wealthy industrial tycoon was never married and loved to throw parties with his male decorator. Either way, these two knew how to put together a space – and the house and gardens are now a stunning museum open for you to explore. 

The Last Carrot

Photo via The Last Carrot’s Instagram

Keep the plant vibes going with this longstanding Coral Gables plant-based restaurant between Vizcaya and our next stop

Whether you’re Paleo, vegan, vegetarian, or omnivore, their smoothies, melts, and salads will satisfy your taste buds. This down-to-earth spot has been family-owned, woman-owned, and vegan-friendly since 1975.

The Kampong National Tropical Botanical Garden

Via the National Tropical Botanical Garden website

I know what you’re thinking. Another garden? Trust me, it’s worth it.

This lush botanical garden houses exotic plants and tropical fruit trees. Walk the property and enjoy the zen vibes in this unique habitat. You might even catch some manatees in the water if you’re lucky.

Key Biscayne National Park

Photo via National Park Services

We’ve seen the local flora above ground; now it’s time to dive below the surface.

For those looking for a more adventurous activity before hitting the cape, swing by Key Biscayne National Park. The park is 95% underwater, so gearing up and jumping in is the best way to experience its magic. One of the best spots to snorkel or scuba dive is the Maritime Heritage Trail, which takes you through real shipwrecks off the coast. 

It’s been a long day, and you’ve earned a drink (or five). Luckily, we’ve got the perfect place for you to get your drink on and spend the night.

Gilbert’s Resort

photo via Gilbert’s Resort

The Tiki Bar at Gilbert’s Resort is a favorite for guests and locals alike. This beachside bar serves up tropical drinks, and often hosts live music. Unwind or go wild, the choice is yours, either way the view is great.

Make sure you get some rest. You’ll want it for Key Largo.

Road to Paradise Day 2


Photo via GRATI Cafe on Instagram

It’s road trip day two, and you’ll want to start it with a quality breakfast. This cute little cafe specializes in juices, acai bowls, and gratitude. No matter how many texts you sent last night or how bad your hangover is this morning, you’ll leave this place feeling better. 

Enjoy your GRATI meal outside and take in the beauty of the keys. Then, head a couple of blocks down the street to see the art it inspired.

Key Largo Art Gallery

Photo via Key Largo Art Gallery on Facebook

This gallery showcases work from some of the best local artists on the Keys. The islands inspire most, if not all, of the pieces here. Get a sneak peek of wildlife you might see during your trip, and get a feel for the local color. 

We hope the ocean paintings inspired you because it’s time to get on the water!

Aquaholic Adventures

Photo via the Aquaholic Adventures website

Go on a tour through the mangroves on a stand-up paddleboard or kayak to get an up-close look at the aquatic life in the Keys. Expect to see some of the area’s most elusive wildlife, like dolphins, sharks, and manatees.

Sharkey’s Sharkbite Grill

Photo by Jackie O’Brien

After making friends with the manatees, grab lunch across the dock at our favorite rainbow-painted dive bar and grill.

Don’t miss this hidden gem on the docks, known for its great food at an affordable price. Sharkey’s is a classic dive bar on the inside, with a rainbow cornucopia on the outside deck and rooftop.

Cheeca Lodge & Spa

Photo via Cheeca Lodge on Instagram

After a day on the water, you deserve to relax, so we recommend this spot for the night.

This Islamorada resort sits on the water, with a private beach and massive pool. You can treat yourself at the spa or relax in your room.

Lorelei Restaurant & Cabana Bar

Photo via Lorelei’s website

If you’re not eating at one of Cheeca’s top-notch dining options, we have the perfect spot for dinner.

Grab some seasonal local seafood at this beachside favorite. The gulf-facing views and live entertainment make Lorelei the perfect spot to watch those famous Florida Keys sunsets.

Road to Paradise Day 3

Midway Cafe & Coffee Bar

Photo via Midway Cafe’s website

This adorable multi-colored coffee shop is exactly halfway between Miami and Key West. Breakfast here is the perfect place to start the final day of roadtripping. Whether you want a classic breakfast, sandwich, or pastry, they’ve got you covered.

Then, enjoy the quick, beautiful drive to Marathon for our first adventure of the day. 

Dolphin Research Center 

Photo courtesy of the Dolphin Research Center

If you haven’t swum with dolphins, you must. If you have, we both know you want to do it again. The knowledgeable trainers at the Dolphin Research Center will teach you about these majestic creatures as you enter their world. Also, dolphins are known to sometimes be gay, so you might have something in common.

Before the next stop, you’ll cross the famous seven-mile bridge connecting Marathon to the Lower Keys. The bridge is exactly what it sounds like—seven miles long—but this one might be over the prettiest water in the world. Watch out for local icon Fred, the tree growing out of the pedestrian bridge!

Bahia Honda State Park

Photo via Florida State Parks

Once you hit the shore at Bahia Honda, you’ll see why this collection of beaches is a state park. During your stop, take in the pristine waters and miles of soft beaches.

You’re bound to be hungry by now, and we have the perfect spot to fill you up before our final adventure.

Kiki’s Sandbar Bar & Grille

Photo via the Kiki’s Sandbar website

This low-key pub on the beach is a local favorite. It serves a mix of bar food and seafood dishes. Sit in the sand, watch the waves, and relax. You’ll need it for what’s next…

Skydive Key West

Photo via Skydive Key West on Instagram

Get ready for the ultimate Key West arrival. We know these pictures will convince you even if you’re afraid to try. Plus, customers rave about this company’s safety and friendliness.

Your adrenaline’s high now. Let’s grab some snacks before settling into your Key West digs.

Baby’s Coffee

Photo via Baby’s Coffee on Instagram

Known for its stellar coffee roasted in-house and amazing bagels, the quirky market is a great place to grab food, coffee, and wine (the essentials) before getting to the guesthouse.

Alexander’s Guesthouse

Photo via the Alexander’s Guesthouse website

You’ll be happy you did that. Once you’ve settled into Alexander’s, it’ll be hard to leave.

This is our favorite LGBTQ+ guesthouse in Key West because while most are men-only, Alexander’s is not gendered. But it is upscale, made for the queers, and close to Duval Street.

Check out the Key West city guide for all our recommendations of the best bars, restaurants, hotels, and beaches.

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