Puerto Rico Holidays |

Start in San Juan

San Juan is an excellent place to begin a multi-country Caribbean holiday in May. The Puerto Rican capital combines an easy-going beach atmosphere with lively streets, historic buildings and some of the best food in the region. Spend your first morning wandering through Old San Juan, where bright blue, yellow and pink façades line cobbled lanes leading towards the sea.

Make time for Castillo San Felipe del Morro, the impressive fort standing above the Atlantic. Its broad lawns and sea views give you a real sense of Puerto Rico’s history, while nearby cafés are ideal for a cold drink and a plate of local specialities. In the evening, enjoy music, seafood and the friendly buzz of La Placita de Santurce.

Caribbean Holidays, Puerto Rico Holidays, Lush El Yunque rainforest with waterfalls, tropical foliage and a walking trail in May

Rainforest Adventures

After a few days in San Juan, head east to El Yunque National Forest for a change of pace. The rainforest is filled with enormous trees, palms and bright tropical plants, and the sound of birds and running water follows you along the trails. Short walks lead to viewpoints and waterfalls, making it possible to enjoy the scenery without planning a demanding expedition.

May is a particularly pleasant time to explore, with warm temperatures and a fresh, green landscape. Showers can arrive quickly, so pack light waterproof clothing and comfortable shoes. A guided visit is a good option if you would like to learn about the forest’s wildlife and indigenous Taíno connections.

Caribbean Holidays, Puerto Rico Holidays, Relaxed Caribbean beach with turquoise water, palm trees and colourful island boats in May sunshine

Add Another Island

A multi-country trip lets you pair Puerto Rico with another Caribbean destination, creating a holiday with plenty of variety. You might continue to the Dominican Republic for long sandy beaches and vibrant local culture, or choose the US Virgin Islands for clear water, sailing and relaxed island days. Each stop adds a different flavour to the journey.

When planning a May itinerary, allow enough time for travel between islands and check flight or ferry connections carefully. A well-paced route could include city sightseeing in San Juan, rainforest walks in Puerto Rico and several quiet beach days elsewhere. This balance means you can explore without feeling that you are constantly packing and unpacking.

Caribbean Holidays, Puerto Rico Holidays, Outdoor Caribbean restaurant with local dishes, colourful drinks and friendly evening atmosphere in Puerto Rico

Food, Music And Culture

Food is one of the pleasures of travelling around Puerto Rico. Try mofongo, made with mashed plantain, or sample roast pork, fresh seafood and creamy rice dishes at a family-run restaurant. Street snacks and strong coffee are perfect for keeping you going during a day of sightseeing.

Puerto Rican culture is also best experienced through its music and everyday life. Listen for salsa and bomba in local bars, browse independent shops and chat to residents when you can. May offers warm evenings that are made for outdoor dining, gentle walks and discovering a new neighbourhood after sunset.

Caribbean Holidays, Puerto Rico Holidays, Couple enjoying a scenic Caribbean multi-country holiday, looking over turquoise sea from a Puerto Rican viewpoint

Plan Your Escape

Puerto Rico works brilliantly as part of a Caribbean multi-country holiday because it offers history, nature, beaches and excellent transport links in one destination. May is a smart time to travel, with hot weather, attractive sea temperatures and a lively atmosphere before the busiest summer period.

Whether you prefer a few nights in the capital followed by island relaxation, or an active itinerary that includes rainforest and coastal excursions, your trip can be tailored around you. Start with the places you most want to see, then build in time to slow down and enjoy the warm Caribbean welcome.