Travel blog by Travels of Adam (Hipster Blog) – Travels of Adam (Hipster Blog) - Travel & Lifestyle Hipster Blog Puerto Rico is one of the top LGBTQ travel destinations thanks to a warm and friendly local population and a lot of great gay bars, clubs, and activities year-round. Use the gay travel guide to Puerto Rico below to help plan a trip to San Juan and other parts of the gay-friendly Caribbean island Of all the Caribbean islands, Puerto Rico is one of the most accepting and LGBTQ-friendly destinations. As an unincorporated territory of the United States, same-sex marriage has been legal since 2015.