Gay Key West & Florida Keys Adventure Tour

zach moses poses with a kayak paddle on a rocky beach in the florida keys

 2019  November 16 to 25

A Gay Travel Florida Keys Adventure Tour


Physical Challenge:

From the bustling gay nightlife of Miami Beach, across the gorgeous islands of the Florida Keys, our multi-sport adventure will put you on the water, on your bike, and in the sky. Enjoy excellent food & hospitality on the way to fabulous, sunny, friendly Gay Key West. Read more about the development of the tour on our Gay Travel Blog or hear from one of our team members on their first visit to Key West here.


  • Explore gay South Beach, enjoying the public art, architecture, & eye-candy of this trendy, gay-friendly island city.
  • Delve into the delicious tropical flavors of the local fruits and specialty wines of southern Florida.
  • Zip through the unique Everglades ecosystem on an airboat.
  • Scuba or snorkel to see Christ of the Abyss, a bronze statue submerged in the crystal clear water off of Key Largo.
  • Kayak through quiet tunnels of mangroves and underneath the bridge to nearby Indian Key.
  • Bicycle southwest along the Overseas Highway, through areas of native plant life as well as immaculately landscaped subtropical gardens.
  • Marvel at the expanse of shallow, shimmering water dotted with hundreds of islands and mangrove stands from the tiptop of the Seven Mile Bridge.
  • See endangered Key Deer in their native habitat (just a few of the thousands of islands host this rare species).
  • Wind your way through back-country scenery on a paddleboard.
  • Experience one of Key West’s famous drag shows and dive into the gay club scene with a guide who can introduce you to everybody!
  • Live it up aboard a catamaran which sets sail for an all-day adventure full of jet skiing, parasailing, snorkeling, and just goofing off in the water.
  • Eat, play, and stay at gay-owned and gay-friendly restaurants, bars, and businesses throughout the tour. The Keys and especially Key West are tremendously welcoming of gay visitors who come from around the world to enjoy the warm, accepting atmosphere in addition to the amazing natural beauty of the island.
  • For those who’d like to spend another day in paradise, we are offering an optional extension to visit Dry Tortugas National Park, a pristine island 70 miles west of Key West, and site of 19th century Fort Jefferson. See details under Extension.

An Adventure Tour of the Fabulous Florida Keys and Gay Key West!

Our multi-sport gay Key West tour begins with a tour of South Beach (the southern section of Miami Beach) and the Florida Keys. We will soak in the thriving gay nightlife of South Beach, then work our way through the Everglades, Key Largo, Islamorada, Big Pine Key, and dozens of smaller islands on our way to the historic town of Key West. We work our way down the Keys (Florida’s tropical islands) HE Travel style, with our usual off-the-beaten-path destinations. Enjoy fabulous handpicked restaurants showcasing the excellent local seafood and cuisine of this Cuban- and Caribbean-influenced region. In Gay Key West we will enjoy water sports, a drag show, and much more. Key West is home to colorful and fun locals; a city whose official motto is “One Human Family.” Gay Key West is also known for being “Close to Perfect, Far From Normal.”



Day 1: Gay South Beach!

tropical foliage poolside on the HE Travel gay key west adventure tour

Guests should fly into the Miami or Ft. Lauderdale airports, for a transfer to our lovely hotel in chic, trendy South Beach (the southern portion of Miami Beach). Those arriving early may want to stroll along the waterfront Art Deco district, meander past the gardens and fountains of the pedestrian shopping plaza, or simply enjoy a coffee and pastry under the palm trees while feeling the buzz of this bustling island city.

After a 6 pm orientation together at our hotel, we will head to a local gay-friendly restaurant for our welcome dinner. Afterward, we’ll discover some of the dazzling gay nightlife that South Beach has to offer!


Day 2: Florida Everglades and Local Tropical Flavor

zach moses handles a snake on the HE Travel gay key west adventure tour

We will have breakfast at the hotel this morning before departing for an airboat tour of the Everglades, as well as a kitschy, informative presentation on alligators, crocodiles, and snakes native to this unique habitat.

a large alligator basks in the sun in the florida keys

Lunch today will be at a restaurant which makes great use of the abundant local produce from the acres of farmland in southern Florida. After lunch, we will visit Schnebly Winery and Brewery, the southernmost winery in the continental United States. We’ll taste an assortment of wines made from tropical fruits (such as lychee, guava, and starfruit) grown on Schnebly’s property.

tropical wine tasting on the HE Travel gay key west adventure tour

We may also swing into “Robert is Here”, a fruit stand where shoppers can find strange and exotic fruits grown nearby, some of which are never found in mainstream grocery stores. Visitors may want to enjoy a starfruit, sapodilla, or dragonfruit smoothie; pick up a jar of passionfruit preserves or a guava pastry; or grab a stick of alligator jerky for the road.

We’ll leave the mainland this afternoon and travel a short portion of the Overseas Highway. This famous 127-mile road has 42 bridges that connect dozens of islands all the way to our final destination, fabulous Key West.

a group watches a gorgeous sunset in the florida keys

Dinner will be on our own tonight after checking into our lovely Key Largo hotel.


Day 3: Snorkeling in Turquoise Water

christ of the abyss statue on the HE Travel gay key west adventure tour

After breakfast at our hotel, we will spend a portion of our day snorkeling in the aquamarine waters off Key Largo. Weather permitting, we will visit the famous bronze statue Christ of the Abyss (submerged under the crystal clear water) and explore the wildlife and beauty of the coral formations at Dry Rocks.

coral at the bottom of a vibrantly blue ocean floor in the florida keys

We’ll eat lunch together today and later enjoy happy hour at the Tiki Bar. Dinner tonight is at Key Largo’s best Thai and sushi restaurant, where the ambiance is intimate and the cuisine, delicious. We’ll return to our Key Largo Hotel.


Day 4: Kayaking Through Mangroves; Experience Native Keys Flora and Fauna

kayaking in the verdant and beautiful mangroves of the florida keys

The Overseas Highway has many dedicated sections of bike lanes and bridges, or wide shoulders for bicyclists to truly take in the spectacular seascapes. The dappled turquoise and aqua waters of the Atlantic Ocean to the south and the Gulf of Mexico to the north can be as gentle as any lake. You may occasionally see whitecaps in the distance, but the “surf” here is generally very calm, which makes for perfect kayaking conditions.

In fact, let’s do that today! We’ll take a short ride from our hotel, stow our bikes at Robbie’s Marina, and pick up our paddles to explore the mangrove tunnels nearby. We may get to see one of the wild (and endangered) American crocodiles who call this mangrove stand their home, as well as native birds who relax among the exposed roots. At low tide, tiny crabs can be seen overhead in the tree branches, and purple sea sponges can be spotted just below the waterline. If time and weather permits, we will paddle under the bridge, south-east to Indian Key, an 11-acre island that still has streets and ruins from its 19th-century town.

tarpon feeding on dock in islamorada included in gay florida keys tour

At Robbie’s, we’ll certainly meet the pelicans who loiter at the docks, waiting for a treat from the fishing boats that launch daily. Tarpon are massive game fish (growing up to 8 ft long) native to the area, and the dock has a feeding enclosure where guests get to see them (and the smaller, faster Jacks) up close.

After lunch together, guests have the afternoon free to explore nearby islands or beaches, or simply relax with a cocktail near the pool, with dinner on our own tonight. Restaurants in the Keys are well-known for preparing fresh, locally caught fish such as snapper, grouper, and dolphin. (Visitors can get pretty concerned about this until they learn that dolphin fish is another name for mahi-mahi!). We’ll tonight in one of Islamorada’s lovely beachfront hotels.


Day 5: Surrounded by Sparkling Water

zach moses and another cyclist in the florida keys

Breakfast is at the hotel this morning, and bags will be transferred to our next lodging. We have a long and beautiful bike ride today, with cyclists able to stop and visit various suggested scenic spots, beaches, cafes, and restaurants at their own speed along the way. On the many bridges, cyclists can stop and peer into the pristine water, where we might see sea turtles and schools of fish feeding near the pylons. After checking in to our Marathon hotel, We’ll plan to regroup for dinner together tonight at one of the island’s excellent local restaurants, and share our stories from the day.


Day 6: The Highest Vista on the Overseas Highway

seven mile bridge on the HE Travel gay key west adventure tour

After a hearty breakfast, cyclists will prepare to cross one of the prettiest (and certainly the most famous) stretches in the Keys, the Seven Mile Bridge. The topmost spot on the bridge provides one of the most breathtaking ocean views in the Keys.

Lunch is on our own today, and those with time may choose to detour on Big Pine Key or No Name Key, home to the tiny, endangered (and adorable) Key Deer who are native only to this very small area. For a bit of casual, southern Florida fun at the half-way point, stop at the local mini-golf course. This themed golf course is landscaped with lush sub-tropical foliage and flamboyant winter-flowering plants and could be a fun break from the saddle.

We’ll reach Key West this evening and check into our charming gay-friendly lodging. New visitors to Key West are pleasantly surprised at how gay the town really is, and not just in the number of clubs, but also in how free couples feel to walk around town holding hands, sunning together at the beach, or sharing a cozy dinner at any restaurant in town.

a drag queen puts on a fantastic show in key west

Tonight we’ll dine together at one of Key West’s best restaurants (it’s so hard to choose!), and we’ll take in a drag show at one of the many gay hotspots in town.


Day 7: Gay Key West

Sailboat on the ocean infront of a warm Key West sunset.

Enjoy your free morning by sleeping in or you can head out for some paddleboarding!

We’ll have lunch together today, and then give you the afternoon and evening to explore this unique, colorful, gay-friendly town. We have some great suggestions for touristy sights worth seeing, and we’ll give you the 411 on the hottest gay destinations for visitors and locals alike.


Day 8: Watersports!

parasailing on the HE Travel gay key west adventure tour

We will spend the last day of our gay Florida Keys adventure playing in the water! Take an all-day watersport-cruise and experience the thrill of jet skiing, take in breathtaking views while parasailing, snorkel at the coral reef, and sunbathe on the deck of the catamaran. Breakfast, lunch, and drinks are included during the tour. Bring your sunscreen, towel, and a waterproof camera!

rainbow flag at gay key west house party venue


Day 9: More Fun in Key West

handsome nude trio on the HE Travel gay key west adventure tour

The continued fun is on today! For our male guests, you will receive day passes to the Island House, world-famous gay men’s resort, for their famous clothing-optional Pool Party. Lunch is on your own today; many will choose to dine in at Island House’s full-service restaurant and bar. After the party, take a short disco nap or just rinse and repeat before meeting with the group for our farewell dinner!

two gentlemen excited to see food on the table at a tapas restaurant in key west florida

After dinner, we’ll go out tonight for drinks at one of the many gay establishments in town!


Day 10: Departure or Begin Optional Extension

sea bird on dock during weekend of gay key west house party

We love having visitors in our town! We hate to say goodbye! But today is the day….Unless you stay just one more day. See the Extension tab for more info about a trip to Dry Tortugas National Park.

Excursion to the Dry Tortugas

aerial view of the dry tortugas on the HE Travel gay key west adventure tour


Day 10: A Quick Flight

Sea plane unloading at the Dry Tortugas National Park.

In the morning, we will provide a transfer to board a seaplane flight (40 minutes duration) out to Dry Tortugas National Park (70 miles west of Key West). We will spend time snorkeling the pristine, crystal clear water; exploring 19th-century Fort Jefferson; and sunning on the beach. Boxed lunch and snacks will be provided.

two gentlemen gear up to go snorkeling in the beautiful dry tortugas off of key west in the florida keys

We will return to our hotel in the afternoon and enjoy an afternoon at leisure. Enjoy dinner together at another of Key West’s intimate local restaurants, before retiring (or not!) for the evening.


Day 11: Departure

Breakfast is at your leisure this morning, with many convenient flights departing throughout the day.

See the Price Includes Tab for more details.


South Beach to Key West Adventure

Price Includes: Airport/hotel transfers; 9 Breakfasts, 4 lunches, and 7 dinners, with alcoholic beverages at the welcome and farewell dinners; Accommodations: 9 nights of comfortable lodging; All activities and transportation as described; Sports equipment rental for activities described. HE Travel provides complimentary Medical & Evacuation Insurance for every US Resident on our group tours who do not have other coverage.

Not Included: A few meals (4 lunches and 2 dinners); Airfare to Miami; Airfare from Key West; Personal items including alcoholic beverages, snacks, laundry, telephone calls, gratuities for guide(s) and HE Travel tour director.

$5098 per person in a shared room (we’re happy to pair you with a roommate, if available)

$1700 Optional Single Supplement (for solo travelers who wish to enjoy a private bedroom and bathroom)

Excursion to the Dry Tortugas

Price Includes: All meals (1 sack lunch, 1 dinner, 1 breakfast before departure); Accommodations for 1 night in Key West; a Half-Day excursion by seaplane to/from Dry Tortugas National Park; entry cost at National Park.

Not Included: Alcoholic drinks with meals or personal expenses, gratuities for guide(s) and HE Travel tour director.

$800 per person in a shared room (we’re happy to pair you with a roommate, if available)
$990 for a single person in a private room with private bathroom

“The reason I take HE trips is that someone organizes everything. My home/work schedule is always busy so I would never have time to think about all the things needed to put together a trip….. I can do a “beach vacation” or a “Disney World” trip on my own but never travel around exploring somewhere. This is the most important thing for me. I don’t know why it was such a long time since my last trip with you…I need to not wait so long for the next trip” – Matthew D., Ontario, Canada

“A fascinating tour that allowed for great enjoyment and visits to different habitats.” – K.A. Kristoffersen, Norway

“The inaugural Florida Keys and Gay Key West Adventure Tour in December 2013 was a great trip, and I’m eager to provide this experience for our customers again in 2014! I loved sharing the gorgeous natural beauty of the Florida Keys, as well as the quirky, fun, friendly, sunny, gay place that is my hometown.” – Zachary Moses, HE Travel Marketing Director, Key West, FL

Most of our trips draw more single travelers than couples. When couples do join us, it’s usually because they’re looking forward to interacting with a gay group; if they wanted a holiday by themselves, they wouldn’t have signed up to travel with us. Furthermore, the activities included with our trips serve as natural ice-breakers. Within a day, you’ll be traveling with friends. You don’t need to pay the single supplement if you’re traveling alone. We’ll be happy to match you with a roommate. Pay the single supplement only if you want a bedroom to yourself.

For selected trips, including cruises, we will charge half the single supplement if you request a roommate but we can’t match you with someone.

This tour starts in Miami Beach (also called South Beach) and ends in Key West, Florida.

Miami International Airport is the closest airport to our starting point in South Beach, with Fort Lauderdale being about 20 miles farther away.

Key West International Airport now has a wide variety of flights on most major carriers.

Physical Challenge Level 3

The Florida Keys are home to rich and diverse wildlife, exciting watersports, gorgeous ocean vistas, and one of the friendliest gay cities in America: Key West. Our adventure offers snorkeling in shallow waters, two days of bicycling (30-50 miles,  flat terrain, racing bikes with dropped handlebars), two-person kayaking in gentle ocean conditions, thrilling jet ski rides, serene and marvelous views while parasailing, and playful fun in the sparkling turquoise water.

For answers to your additional questions, please email or call 305-294-8174

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