Tailor-made Holiday · USA
Florida Keys Island Hopping
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Escape to the enchanting allure of the Florida Keys, a mesmerizing archipelago boasting some of the most captivating tropical islands in the USA. Situated just off the coast of Miami, these islands beckon travelers with their unique charm and rich history.
Each island in the Florida Keys boasts its own distinct ambiance and array of experiences. Whether you're a devoted sun worshipper, an intrepid adventurer, or a passionate cultural enthusiast, you'll find yourself perfectly at home as you traverse these picturesque landscapes.
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Begin your adventure in Key Largo, a gateway to pristine coral reefs and thrilling water sports. Continue to Islamorada, where fascinating history meets natural beauty. Then, venture to Marathon Key, home to sandy beaches and the renowned Turtle Hospital. Finally, explore the vibrant streets of Key West, a fantastic destination particularly for LGBTQ+ travelers.
Immerse yourself in the vibrant tapestry of wildlife that thrives amidst the natural splendor of the Florida Keys. From colorful coral reefs teeming with marine life to graceful dolphins frolicking in azure waters, each encounter promises to create lifelong memories.
Whether you're embarking on a romantic getaway, a family vacation, or a solo expedition, the Florida Keys offer an unparalleled blend of natural beauty, cultural heritage, and boundless adventure. So pack your bags, hit the open road, and let the enchanting allure of the Florida Keys whisk you away on an unforgettable journey of exploration and discovery.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1-2 Miami
On your arrival day you’ll fly into Miami International Airport where you’ll pick up your car hire and drive to your first hotel.
Take some time to relax after your flight in your luxury hotel or go downtown and discover some of Miami’s famous nightlife. Spend your next day at the beach soaking in the sun, stroll around the many hip boutiques in the South Beach area, or go on a sightseeing tour to see some of the most famous sights in Miami such as Little Havana or the Art Deco district.
Day 3-4 Key Largo
Set off in the morning for a leisurely drive down to Key Largo, the most northern point of the Florida Keys. This island is known for being the place to explore the marine wildlife and enjoy water sports.
Take a tour of the Everglades and discover one of the most unique ecosystems in the world via a speedboat tour and see if you can spot alligators amongst the lush vegetation. Hire some snorkeling equipment and discover the creatures that inhabit the blue seas, or take a scenic boat tour at sunset. There’s plenty to do in Key Largo.
Day 5-6 Islamorada
In the morning, set off down to Islamorada. Islamorada encompasses six of the Florida Keys and is known for being a place of natural beauty with its stunning array of coral reefs. It’s a great place to spot marine wildlife such as dolphins and for being a place to learn about the history of the area.
Take a day trip to the Indian Key Historic State Park where you’ll find the ruins of the 19th-century town which was once the heart of the wrecking industry. Go out to sea on a dolphin spotting excursion and get up close with some of the most intelligent mammals in the sea. Alternatively, chill out and relax at spots such as Islamorada Library Beach or Anne’s Beach for some downtime.
Day 7-8 Marathon
In the morning, set off down to Marathon Key – a city comprising of 13 islands known for its sandy beaches, coves, lagoons and wildlife. Take a visit to the Turtle Hospital – a non-profit organization dedicated to rehabilitating endangered sea turtles. See everything from baby turtles to fully grown adults and even get the chance to pet them.
Step back in time and visit Pigeon Key island and discover the homeplace of the workers who built the seven-mile-long bridge that connects the keys to mainland Florida. Or, if you’d prefer to relax, take a visit to Bahia Honda at nearby Big Pine Key for one of the best beaches in the Florida Keys.
Day 9-11 Key West
Set off for Key West, the most famous and friendly of all of the Florida Keys. Key West is definitely the most edgy, luxurious and vibrant of all of the Florida Keys and is home to great museums, beautiful beaches and plenty of amazing bars and restaurants to explore.
If you’re seeking culture take a visit to Hemingway House, the former home of Ernest Hemingway, or the Museum of Art and History where you can spy local art and learn about the history of this area. For a spot of adventure try parasailing over the emerald blue seas or, for something more chilled, try a catamaran champagne cruise at sunset. It is also worth noting the prominent LGBT community in Key West and the many different nightlife offerings there are for the community.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.