May Island Hopping |

Plan a May Escape

A multi-country Caribbean holiday in May is a brilliant way to experience the United States Virgin Islands alongside nearby islands. Start in St Thomas, where lively Charlotte Amalie combines historic streets, waterfront restaurants and easy access to the sea. The weather is generally warm, with plenty of sunshine for exploring and relaxing.

May sits between the busier winter season and the quieter summer months, so you can often enjoy a more relaxed atmosphere. It is a good time to take island hopping at an easy pace, allowing enough days for swimming, sightseeing and long lunches by the water.

Caribbean Holidays, May Island Hopping, White sand beach on St Thomas in May with clear turquoise water, palm trees and snorkellers

Discover St Thomas

St Thomas makes a convenient starting point for a Caribbean multi-country trip. Spend a morning wandering through Charlotte Amalie, looking at colourful buildings and browsing local shops, then head towards Magens Bay for a classic beach afternoon. The calm, clear water is inviting, whether you fancy a gentle swim or simply want to cool off.

For a different view, take a boat trip around the coast or visit nearby Water Island. The sea is usually wonderfully clear in May, making it easy to spot bright fish close to shore. Evenings are made for fresh seafood, Caribbean flavours and watching the sky change colour over the harbour.

Caribbean Holidays, May Island Hopping, Ferry travelling between green Caribbean islands in May under a sunny blue sky

Add Nearby Islands

From the US Virgin Islands, it is simple to include another Caribbean destination in your itinerary. Ferries and short regional flights can connect you with islands such as the British Virgin Islands, where Tortola offers sheltered bays, scenic viewpoints and a distinctly laid-back character.

Alternatively, combine your stay with Puerto Rico for a broader holiday experience. Enjoy the historic architecture and restaurants of San Juan, then contrast city life with the beaches and small-island charm of the Virgin Islands. A travel expert can help match transport connections and hotel locations so the journey feels straightforward.

Caribbean Holidays, May Island Hopping, Relaxed Caribbean beach scene in May with sun loungers, gentle waves and a couple enjoying the view

Make the Most of May

Pack light clothing, swimwear, comfortable walking shoes and reliable sun protection. May can bring a brief tropical shower, but these often pass quickly and leave the air feeling fresh. Staying hydrated is important, especially when you are combining beach days with sightseeing.

Choose a flexible itinerary rather than trying to see everything. A few nights in St Thomas, time on a neighbouring island and a final stay in Puerto Rico can create a varied holiday without feeling rushed. With warm seas, welcoming island communities and plenty of choice, May is an excellent month for discovering the Caribbean one island at a time.