LGBT travel inspiration – 5 days in Florida Keys

LGBT Travel inspiration Florida Keys Key West
Tim Firmager
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We at Vada Magazine recently travelled to Florida Keys and Key West to research inspiration for the best LGBT-friendly travel itineraries. This is the second of a four-part series of articles about how best to spend time there with other articles for ideas for a weekend, 4-day, or 7-day LGBT-friendly travel itinerary.

In this article we give you a perfect 5-day itinerary of fun and sun across Florida Keys. This is intended as a stand-alone trip, ideally flying into Miami and hiring a car, dropping it off in Key West (and flying out of the airport there), or doing this in reverse. We worked with gay-owned, UK-based Huben Travel who helped organise all our travel for our trip – more information on them at the end of the article.

LGBTQ and Florida Keys

Florida Keys, and more specifically Key West has been a gay hotspot for years and continues to celebrate its openness to the LGBTQ community. In 2000 Key West adopted the philosophy ‘One Human Family’, which was soon adopted across the rest of the Florida Keys island chain. And in 2003 the creator of the original Pride Flag, Gilbert Baker, created a 1.25 mile-long pride flag the full length of Duval Street as part of PrideFest Key West (read more about this in our wider article about the history of the pride flag). The point here is that everywhere in Florida Keys and more prominently within Key West is LGBTQ-friendly, even if it isn’t clearly stated. Though walking around Key West visitors will be hard pressed to miss the Duval Street pride crossing or the many pride flags outside of so many of homes, guesthouses and venues. We found the island chain to feel incredibly safe and welcoming.

Itinerary – Day 1 – arrive at Key Largo

Arrive into Miami Airport and collect your rental car. After setting off the drive is relatively straight forward and takes about 1.5 hours from Miami airport to Key Largo, the first stop on this itinerary.

Once you’ve arrived at Key Largo check into your hotel. We recommend Baker’s Cay (a Curio Collection by Hilton) hotel, ensuring your book an ocean view room. We had a 2-queen-bed waterfront view room in the Coconut Wing (number 341). What we loved about the room were plenty of outlets by the beds, very comfy mattresses, and despite their being lots of lights it was easy to switch them all on and off – some hotels you seem to need an instruction manual for the most basic thing. The best feature though was of course the incredible view across the hotels’ private beach onto the ocean. Baker’s Cay also offer re-usable water bottles to encourage guests to use less plastic on site and what they go out for day excursions.

If you’ve arrived before dark, head to Calusa restaurant (above reception) for a complimentary glass of Pink Flamingo sparkling rosé to enjoy watching sunset. We found the food at dinner to be good quality but all the dishes had too many flavours and overly complex. We suggest ordering the simplest items on the menu. That said service was great, staff were friendly, welcoming and went the extra mile. And the next morning there is a delicious a la carte breakfast menu, so do make the most of that – we couldn’t fault anything we ate from it.

Itinerary – Day 2 – Out to sea

After breakfast, we have two choices for Day 2, both involve being out at sea visiting and learning about coral reefs.

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Option 1

For those who enjoy snorkelling, the Coral Restoration Foundation offers a truly unique experience through their diving partners. As well as just snorkelling, on this full-day excursion, travellers are taking making a sustainable holiday option actively participating in coral restoration. The morning is spent at the Coral Restoration Foundation in Key Largo where you learn about the coral and get hands on training for your work in the afternoon. After lunch, you’ll go out as part of a dive to a coral nursery, collect some coral and re-attach (re-home) it in a nearby reef. This goes way beyond other diving adventures just seeing nature, and we highly recommend this of those who can snorkel. Prices from $150 depending on date and dive provider.

Option 2

Those for whom snorkelling isn’t their option, you’ll still be out at sea. Instead, take the Key Largo Princess Glass-bottom boat tour. The cruise takes 2 hours in total, with about 30 mins bobbing gently over Molasses reef (about 6 miles out to sea) . As the name suggest, in the cabin there are two large glass-bottom cutouts to see directly what sea life there is around the coral reef you visit. The staff on board were incredibly knowledgable about the local fish and coral, keeping us highly informed. And we now know how much sand a parrot fish can produce in a year. Ticket prices from $50 per person, and make sure to book in advance.

Back on terra firma, very close to the Coral Reef Foundation, is the perfect lunch spot: Key Largo Fisheries Backyard Cafe. The food is quite pricey here but you’ll be hard-pressed to be disappointed with anything your order. Our lobster Mac n cheese, and deep fried Mahi Mahi were both delicious. From this spot next to a small marina, spot the wildlife and sea life before you – we saw basking sharks very casually swimming around as we ate. And pelicans become so commonplace, they are akin to seeing seagulls in English season towns – ten-a-penny.

In the afternoon head back to where the Key Largo Princess is moored, and next to her is the African Queen. She is a much smaller boat from the film of the same name, made famous by Henry Bogart and Katherine Hepburn. This is a very gentle, calm tour, staying broadly within the canals. There’s so much information to absorb about Katherine Hepburn on this tour, but perhaps the most fascinating is that she published a book about her experience of making it, something rarely seen today, so it must have truly left a mark on her. Prices from $59 per person.

In the evening, head to The Fish House for dinner, a 10-15 mins drive from Baker’s Cay hotel. This has all the hustle and bustle of a city diner and this restaurant is overflowing with kitsch and camp décor. Moreover, the fish dishes are all simple, enhancing the flavour of the fish and delicious. Try your fish either Hemingway or Matecumbe style. And don’t forget dessert – the slices of pie are generously portioned and exactly what you’d imagine.

Itinerary – Day 3 – Seven Mile Bridge then on to Key West

Aim to set off about 9am for the drive down to Key West, this is to give you enough time to take a break for a bike ride along Seven Mile Bridge, get some exercise and just appreciate the views and turquoise waters. There are several bike rental companies on Marathon Key (where you’ll need to stop), we used Bike Marathon Bike Rental. The stretch of Old Seven Mile Bridge that is open (for cyclists and pedestrians only) is about 2 miles long, plus a further 3 mile-round trip from the bike hire to the start point. This is a leisurely flat, ride.

Grab some lunch before you do the second half of the day’s drive. We suggest some Conch fritters at Keys Fisheries.

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Continue the drive for another 1 hour 15 mins until you reach Key West. Once you’ve parked up, you will not need your car for the rest of the weekend to get around Key West, it is easily walkable. Check-in at your hotel. We recommend the historic and well-know Island House, a clothing-optional hotel for gay men. We loved the relaxed and fun atmosphere here, which works particularly well for couples or small groups of friends. On arrival they’ll give first-timers a tour of the facilities, with most open 24×7 (including the well-equipped gym, pool, indoor and outdoor jacuzzi, sauna, steam room, and the ‘red room’). Sun-beds are most popular around the pool but these are often taken during the morning, so there is an ‘upper deck’ with more space upstairs. We loved the bar because of the 5:00 – 6:30pm daily happy hour where up to four drinks are free for every guest. Depending on when you arrive, try to make use of this to kick-start your weekend. Note there are huge variety of room categories, as the hotel is like a mini-maze depending on what your want your door to open on to. We stayed in a deluxe double queen (room number 216), which was on the upper deck overlooking the pool area.
Other LGBT accommodation options we recommend are Equator Resort or Alexander’s Guesthouse.

For night dinner head down to Mangoes on Duval Street. We highly recommend ordering the Conch fritters as a starter (only if you want them twice in one day, after lunch earlier), and trying the stuffed brioche bun with lobster or some of the Key West Pink Shrimp scampi as a main course. For those who want to indulge in a dessert, try either the Peanut Butter Pie or the Key Lime Pie.

Just across the street from Mangoes is Aqua, where there is a daily drag show. Book in advance (from $25) for the 9pm show and make sure you arrive a couple of minutes ahead of time to be seated – or prepare to be read for arriving late and interrupting the opening number. Get your $1s and $5s ready for resident queens – on our visit we were highly entertained by Epiphany Jessica Devereaux, and Elle Taylor. Enjoy the show!

After the show, if you’re in the mood to stay out later, try either Side Bar or 801 Bourbon Bar.

Itinerary – Day 4 – relaxed day followed by sailing and sumptuous dinner

Take a leisurely morning after the previous night out. This may include a dip in the pool and sauna, and breakfast/brunch either order at your hotel or head out to a nearby eatery. Then head out for a midday stroll along Duval Street to explore the shops and boutiques. We suggest a pause at Cuban Coffee Queen on Key Lime Square to rehydrate with some incredible coffee or smoothies. Them amble back to your hotel, leaving time for a quick lay by the pool before getting ready for Saturday evening.

As Key West is as much as about enjoying the incredible waters (not just water sports) as on-land fun, we recommend taking the Wind & Wine Sunset Sail run by Danger Charters. Ignore any connotations from the company name, this is a thoroughly relaxing 2 hour sailboat tour where the crew will both sail about 30 guests around waters close to the marina with a stunning view back towards Key West, Sunset Key, and of course of the sunset itself. All the while they’ll serve keep your glasses generously topped up with a selection of wines and canapés (there are beer and non-alcoholic options too). We found this a truly unique way to enjoy sunset. Prices from $109 per person.

Once you’re back on dry land, walk over to the ferry point for Sunset Key, which is about 20 yards away. The ferry shuttles back and forth between Key West and the private island of Sunset Key where Latitudes Restaurant is located. Book as far in advance as you can, request a table on the beach, and time it so that your dinner is about 45 minutes after your return from the previous sunset sail. The ferry is completely free and on arrival (about 5 minutes after departure) on Sunset Key, everyone is directed to Latitudes and checked in for dinner. If you table isn’t ready there is plenty of space at the bar to have a drink and wait. The logistics really are very easy.
Latitudes itself is the big splurge item of this weekend trip – a truly romantic setting, dressed for dinner (no casual wear) and expect to pay London prices. But with that comes great service and we were impressed by everything we tried from the menu – we’d recommend the octopus starter, and salmon and chicken mains. And if you have room for dessert the warm churros will go down a treat.

At the end of the night, take the next ferry back to the Key West, where you can walk back to the hotel (burning off a few calories perhaps). If staying at Island House, you may want to indulge in a late night swim or fun in the jacuzzi before you round off the evening.

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Itinerary – Day 5 – cultural morning, lunchtime departure

For your last morning, depending on how much time you have left, we suggest a visit to the Ernest Hemingway Home and Museum. The house is open from 9am in the morning and does get busy so we suggest an early arrival and allow for 1.5 hours there. On arrival guests can sign up for the next available tour around the house or self-guide through the house and then grounds. Expect to learn about Hemingway’s home and where he grew up, but also about his second legacy (after his accomplished written works) i.e. the descendants of his 6-toed cats, all of whom are kept at the house. In fact the house is the cats’ permanent home, who have on-site vets and staff who come into feed and look after them throughout the day.

Then collect your bags from your hotel and make your way to Key West International Airport for your onward travel.

Huben Travel

Huben Travel is a gay-owned travel agent (by couple Hugh and Ben), who we used to help book our flights to/from Miami International Airport are car hire for our trip to Florida Keys. They have fabulous customer service, understand their clients needs really well and were able to tolerate our many tweaks and questions. What we really liked is how they checked in regularly in the few days before and during our trip to make sure we had everything sorted. And they’re very easy to get in touch with via email or WhatsApp.

As a sample package, Huben offer seven nights in the Florida Keys and Key West from £2,026 pp including Heathrow flights, car hire and seven nights room-only accommodation (two nights at Baker’s Cay, Key Largo; three nights at the Island House, Key West; and two nights at Tranquility Bay Beach House Resort, Marathon). For more information visit or give them a call on 020 3443 8969.

More about Florida Keys and Key West

We’ve outlined our recommendation for a weekend itinerary but there is so much more to see and do in Florida Keys and Key West. Visit the Florida Keys website to explore even more ideas. Or while in Key West drop into the Gay Key West Visitors Centre for a map & directory of gay friendly Key West businesses, discount coupons and information.

About Tim Firmager

Tim divides his time being a Digital Consultant in The City and as a food and travel writer across the globe. When he's not working as one of the Lifestyle Editors here at Vada, he's planning his next trip, or on the lookout for the latest food crazes or unusual foods in London's markets.