Puerto Rico, an LGBTQ+ friendly destination, is the must visit island in the Caribbean while staying true to its rich culture and traditions.
Guests have unforgettable experiences that focus on the mind, body and soul with an immersive itinerary which includes culinary experiences, cultural activities, breathtaking beaches, outdoor adventures and drag that is serving tens across the board while supporting the LGBTQ+ community.
6 DAYS / 5 NIGHTS
$2,950 USD
Payment can be broken down into a deposit and monthly payments.
Trip itineraries are subject to change. For more information, check out our FAQs.
Welcome to the heart and soul of the Caribbean!
We are kicking off the trip with an Old San Juan Queer Walking Tour which dives into the colorful streets, rich history of the island and its meaningful connection to the LGBTQ+ community. The tour is serving herstory from the valuable perspective of a LGBTQ-owned tour operator.
While soaking up history and culture, we grab a tasty lunch at Coqui del Mar Gay Guesthouse.
For the welcome dinner, Cocina Abierta is turning up the heat with delicious food and chill vibes while serving traditional Puerto Rican favorites.
After dinner we are getting artsy with local queens who serve performances and join a paint and sip class at Pinser Pinta.
Start the day with some serious zen on the beach with Santosa Yoga which is serving poses along with a side of stunning views. After a refreshing yoga session, enjoy a laid-back breakfast with Planeta De Café, a local coffee brand, which is serving bold tastes and is owned by the hosts, Jarrell and Jose.
Next we are visiting Casa Bacardi, for a mixology class, guided tour of the world’s largest rum distillery and a Caribbean inspired lunch. After the Casa Bacardi experience, spend the afternoon exploring Old San Juan visiting art galleries, shops, eateries for dinner and sweet treats for dessert.
Before the night is over we are hitting the dance floor for a salsa class led by the fabulous choreographer Juan Carlos who runs an LGBTQ+ owned dance studio in Puerto Rico.
Ease into the day with a relaxed breakfast at the hotel before setting sail on a thrilling catamaran adventure with Boricua Charters for an afternoon of exploring Puerto Rico's gorgeous waters and stunning scenery.
After time on the crystal blue waters, relax by the pool at the hotel and enjoy a mojito before we leave for dinner to explore all the wonders of Puerto Rico and its rich local flavors.
Turn in the swim suit for an apron—it’s time to be a top chef. The cooking class and dinner with Traveling Spoon introduces how to make traditional Puerto Rican dishes.
After breakfast, we are taking the plunge with the Rain on Me adventure. We go on a journey through Puerto Rico's lush rainforests and stunning waterfalls.
After the rainforest we head to the Workroom Workshop which focuses on the art of drag with a designer from RuPaul’s Drag Race Mexico who shares the creative process along with a Drag Me session with local queens who share the process behind a drag transformation.
After the workshop guests attend Drag Me to Dinner which includes a multi-course culinary experience, curated cocktails as well as performances from queens from RuPaul’s Drag Race and a DJ spinning the athems.
After dinner we head to drag shows that serve charisma, uniqueness, nerve and talent.
Celebrate new best friends at an epic drag brunch at the Tryst Hotel. Let’s get loud for the beach side brunch which is serving delicious food, inspired cocktails, island breeze and over the top performances from Puerto Rican queens!
After the show, rest and relax with an afternoon at the beach. While enjoying fun in the sun guests often take time to reflect on the trip experience and the people they met during their time in beautiful Puerto Rico.
We are closing out with a farewell dinner at a Santaella which is a hot spot known for top-notch food and curated cocktails in a stylish atmosphere.
We savor a final breakfast together while cherishing the memories of an extraordinary trip. We celebrate the friendships formed and the experiences we shared during the trip.
It’s not goodbye, it’s until we see each other again which just might be on another Gaybor Trip or Gaybor Weekend!
WHAT'S INCLUDED
Trip Hosts
Trip Guides
Accommodations (4-star or higher)
Limited single room upgrades are available and can be added when booking (subject to availability)
5 breakfasts, 3 lunches, 4 dinners
Welcome Cocktail Party
Welcome Dinner at Cocina Abierta
Workroom Workshop in partnership with Drag in Demand
Drag Me to Dinner in partnership with Drag in Demand
Entry and drink(s) at LGBTQ+ venues
Old San Juan Queer Walking Tour
Sip and Paint Class
Planeta De Café Breakfast
Beach Yoga with Santosa Yoga
Casa Bacardi Mixology Class and Guided Tour
Salsa Class with Jan Latin Beat
Catamaran Sunset Cruise
Cooking Class and Dinner
Rain on Me Adventure
Drag Brunch at Tryst
Farewell Dinner at Santaella
Transportation
Donation to local LGBTQ+ nonprofit(s)
Donation to local nonprofit that supports and works with those with special needs
All activities are weather dependent and in the unlikely event that we are unable to run an activity, we will have a suitable alternative.
NOT INCLUDED
Airfare
Airport transfers
Meals not included in itinerary
Alcoholic beverages not included in itinerary
Mandatory trip insurance
Tips for local guides, hotel staff, etc
FLIGHT INFORMATION
FLY INTO SAN JUAN
You’ll need to fly into San Juan (SJU) in time for the start of the trip, which is 9:00am on day one. However, we recommend flying in earlier to have some time to relax or explore.
FLY OUT OF SAN JUAN
We recommend flying out of San Juan (SJU) or extending your trip to enjoy more time in San Juan. Feel free to fly out at any time.
Please check that your passport is valid for 3-months after your return date. For more information, visit our FAQs.
Looking to charter a Gaybor Trip to Puerto Rico for a special occasion, company retreat, getaway with the besties or group trip with your followers on social media?
When you charter a Gaybor Trip to Puerto Rico, with at least ten guests, as a Trip Leader you enjoy benefits during the trip.
As the Gaybor Trip hosts who are content creators and owners of a coffee brand, Planeta De Café, we’ve explored every corner of Puerto Rico which offers so much more than beautiful beaches. It’s a safe and welcoming destination for LGBTQ+ guests with a vibrant scene that is rooted in the art, history and people.
We are excited to share our love of Puerto Rico with an immersive itinerary packed with meaningful experiences that celebrate the island's rich culture and LGBTQ+ community while showing why one man's trash is all of our treasure and a must-visit destination for LGBTQ+ travelers and our allies.
Drag in Demand is proud to partner with Gaybor Trips to celebrate and support the art of drag with events that are included in the itinerary.
The Workroom Workshop goes behind the pink wall for an interactive experience focused on the art of drag with a designer from RuPaul’s Drag Race who shares the creative process behind some of the most iconic looks from the show along with a Drag Me session with local queens who share the process behind a drag transformation.
After the workshop guests attend Drag Me to Dinner which includes a multi-course culinary experience, curated cocktails as well as performances from queens from RuPaul’s Drag Race and a DJ spinning the athems.
After dinner we are heading to drag shows for dazzling performances that are serving charisma, uniqueness, nerve and talent.
