LGBT travel inspiration – 4 days in Key West

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, 5-day, or 7-day LGBT-friendly travel itinerary.

In this article we give you a perfect 4-day (3-night) itinerary of fun and sun in and around Key West. This could be as part of a wider trip being planned to America. 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 – afternoon arrival

We anticipate you arrive early-to-mid-afternoon into Key West. Either drive a rental car, from Miami airport will take about 4 hours with good traffic, or fly directly into Key West International Airport – there are direct flights from cities all down the US east coast. If you arrive by car, 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, 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.

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Itinerary – Day 2 – 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 3 – enjoying nature

Start day 3 early with Honest Eco’s Dolphin Watch and Snorkel Tour. We admit that we were slightly (very) hungover the morning we tried this, despite this we found the tour an invigorating, incredible experience. The Honest Eco team use their electric-battery operated boat, SQUID for this tour, which is charged overnight for the engine power and has rooftop solar panels to power the instrumentation throughout the tour. Our female team (captain Sarah and marine biologist, Rachel) were super friendly, passionate and keen to make sure everyone got as much from the experience as they want. When we say ‘everyone’ here, the tours are intentionally small groups on SQUID – our tour had 8 people in total. Over the 4 hours, you will spend a leisurely outbound and return journey spotting whales, with the destination being a shallow coral reef where we snorkelled for up to an hour. Our Honest Eco team were great, educating everyone on how to snorkel (so it’s perfectly OK to go as a first timer). Prices from $109 per person.

Alternatively if snorkelling isn’t for you, we suggest a morning kayaking – ask at the hotel for a recommendation on a tour operator – there are so many all around the perimeter Key West

Once back at the marina, have a look around try to spot a manatee in the water, they are attracted to the fresh water outlets, so are regularly found swimming around between the boats.

For lunch, we’d recommend Half Shell Raw Bar, which is found about 90 seconds walk from where Honest Eco’s SQUID is moored. They specialise in fresh and raw sea food, but we craved their open sandwiches, which was ideal to cure the hangover and to fill us up from snorkelling. We’d recommend the BBQ Chicken sandwich or Strip o’boy sandwich, which is fried golden battered prawns topped with Muenster cheese, served with French fries.

For a quieter afternoon, visit the Key West Tropical Forest and Botanical Garden. This is actually on the next Key, Stock Island, so is as instance where you’ll need your hire car (or take an Uber/Lyft) for the 10 minute drive. Key West Tropical Forest and Botanical Garden focuses on provided a space to allow the native flora of the Keys to flourish, which in turn will help rehabilitate the diminishing local butterfly species. We’d suggest a good hour to 90 minutes to stroll around the walkways, sit, and watch out the iguanas who are in fact an invasive species so follow the signs and please don’t feed them. Look out for Lignum Vitae, which has blue flowers in Spring. This plant was used as a cure for Syphilis, and interestingly its bark is self-lubricating. Need we say more. There are also a few erect prickly pear cacti and a golden shower tree (which is actually used as a very strong laxative).

For a drink with a mid-afternoon snack, try nearby Sloppy Joe’s where diners can sit on the terrace overlooking the marina. We had great frozen cocktails (Key Lime Colada anyone), a small (sharing snack plate) of Smoked Wahoo Fish Dip, and great views over the marina.

In the evening, either have a relaxed evening in, or as another way to enjoy seeing the sun set over the ocean, head back to Mallory Square (close to where you caught the boats from day 2 of the itinerary) for Sunset Celebration. This is a nightly festival with arts and crafts exhibitors, street performers, food carts and even psychics. The event usually pulls a big crowd as the views of sunset are sublime.

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Itinerary – Day 4 – 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 your onward travel, whether that be driving back to Miami airport or getting a taxi to Key West International Airport.

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.