Our multi-sport gay tour begins with a night in South Beach, then winds southwest through the Everglades and Key Largo and dozens of smaller tropical islands on our way to the historic town of Key West. Enjoy handpicked restaurants showcasing the excellent local seafood and cuisine of this Cuban- and Caribbean-influenced region. In Gay Key West we will enjoy watersports, a drag show, and much more. Key West is home to colorful and fun gay locals; a city whose official motto is “One Human Family.”


  • Gay South Beach!
    Gay South Beach!
    Our lovely hotel is in chic, trendy South Beach (the southern portion of Miami Beach). 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. Dinner is at a local gay-friendly restaurant before discovering the dazzling gay nightlife that South Beach has to offer!
  • Florida Everglades and Local Tropical Flavor
    Florida Everglades and Local Tropical Flavor
    Tour the Everglades by airboat and attend a kitschy, informative presentation on alligators, crocodiles, and snakes native to this unique habitat. After lunch visit a winery that uses only tropical fruits (such as lychee, guava, and starfruit). We may also swing into a fruit stand where shoppers can find strange and exotic fruits grown nearby, some of which are never found in mainstream grocery stores. Perhaps order a sapodilla or dragonfruit smoothie and grab a stick of alligator jerky for the road. Leave the mainland this afternoon and check into our lovely Key Largo hotel.
  • Diving or Snorkeling in Turquoise Water
    Diving or Snorkeling in Turquoise Water
    Spend a portion of our day scuba diving (for those who are already certified) or snorkeling (for those without scuba experience). 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. We’ll eat lunch together today and later enjoy happy hour at the Tiki Bar. Dinner tonight is at an intimate Thai and sushi restaurant.
  • Kayaking Through Mangroves; Experience Native Keys Flora and Fauna
    Kayaking Through Mangroves; Experience Native Keys Flora and Fauna
    The dappled turquoise and aqua waters of the Atlantic Ocean and the Gulf of Mexico can be as gentle as any lake, perfect for kayaking. Take a short bike ride ato 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. After lunch the afternoon is 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!
  • Surrounded by Sparkling Water
    Surrounded by Sparkling Water
    We have a long and beautiful bike ride today, with various scenic spots, beaches, cafes, and restaurants to stop at along the way. Atop a bridge, a cyclist can stop and peer into the pristine water, where there may be sea turtles and schools of fish feeding near the pylons. We regroup for dinner together at an excellent local restaurant, and share our stories from the day.
  • The Highest Vista on the Overseas Highway
    The Highest Vista on the Overseas Highway
    Today, cross one of the prettiest (and certainly the most famous) stretches in the Keys, the Seven Mile Bridge. Perhaps detour to Big Pine Key, home to the tiny, endangered (and adorable) Key Deer. For a bit of casual, southern Florida fun at the half-way point, stop at the local "putt-putt" course. This themed mini-golf course is landscaped in lush sub-tropical foliage and flamboyant winter-flowering plants. Ride into Key West this evening and be surprised at how gay the town really is, with many couples holding hands about town, sunning together at the beach, or sharing a cozy dinner at any restaurant in town. Dine together at one of Key West’s best restaurants (it’s so hard to choose!), and take in a famous drag show!
  • Gay Key West and Clothing-Optional Paddling!
    Gay Key West and Clothing-Optional Paddling!
    We’ll enjoy getting out on the water today with a gay, clothing-optional, back-country paddleboarding tour. This is a workout, and we’ll be sure to pack plenty of snacks and fresh water. We’ll have lunch together, then have an 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.
  • Watersports!
    Play in the warm Florida water! Our all-day watersport adventure takes us jetskiing, parasailing, snorkeling, and sunbathing on the deck of the catamaran. Bring your sunscreen, towel, and waterproof camera! Our farewell dinner will take place tonight at a local gay friendly restaurant.
  • Departure or Begin Optional Extension
    Departure or Begin Optional Extension
    Guests leaving today will be transferred to the Key West Airport. Others may choose to stay for the Optional Extension to to visit Dry Tortugas National Park and to enjoy casual fun in Key West.
  • Dry Tortugas
    Dry Tortugas
    Stay a bit longer for a glorious flight and day visit to Dry Tortugas National Park.
  • Pricing
  • Testimonials
  • Important Notes
  • Included


Title Description Pricing Notes Price
Standard reservation

based on a shared room (2014)

4698 pp
Single Supplement

for solo travelers who wish to enjoy a private bedroom and bathroom

1300 pp


“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 a 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

Important Notes

Note: Details File
Activity Level

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 jetski rides, serene and marvelous views while parasailing, and playful fun in the sparkling turquoise water.

What’s Included

Airport/hotel transfers; 8 Breakfasts, 4 lunches, and 6 dinners, with alcoholic beverages at the welcome and farewell dinners; Accommodations: 8 nights of comfortable lodging; All activities and transportation as described; Sports equipment rental for activities described . All HE Travel tours include complimentary Medical & Evacuation Insurance.

What’s NOT Included

A few meals (4 lunches and 2 dinners); Airfare to and from destinations; Personal items including: alcoholic beverages, snacks, laundry, telephone calls, gratuities for guide(s) and HE Travel host.

  • Highlights

* 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 private, clothing-optional, gay paddleboarding tour. * Experience one of Key West’s famous drag shows and dive into the gay club scene with a local guide who can introduce you to everybody! * Live it up aboard a catamaran which sets sail for an all-day adventure full of jetskiing, 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.

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