September Walking Holidays |

Why Visit in September

September is a rewarding time for a walking holiday in the United States Virgin Islands. The islands are quieter than during the peak winter months, so trails, beaches and waterfront villages often feel wonderfully unhurried. You can enjoy the scenery at your own pace, with plenty of opportunities to stop for a swim or a cold drink.

Expect warm Caribbean weather, high humidity and the possibility of short rain showers. These showers can freshen the landscape and leave the hills looking especially green, but it is sensible to plan walks for the cooler morning and carry water, sun protection and a light waterproof layer.

Caribbean Holidays, September Walking Holidays, Walkers exploring a forest trail in Virgin Islands National Park on St John, surrounded by tropical vegetation and glimpses of the sea

Best Island for Walking

St John is an excellent choice for a walking holiday, particularly if you enjoy nature and quieter surroundings. Much of the island is protected within Virgin Islands National Park, where trails lead through dry forest, tropical woodland and historic plantation ruins. The routes vary from gentle coastal strolls to more demanding uphill walks.

The Reef Bay Trail is one of the island’s best-known walks, passing through lush vegetation towards historic sugar estate remains and ancient petroglyphs. For an easier outing, the path around Annaberg Plantation combines history with impressive views over Leinster Bay. Always check local conditions before setting out, as rain can make some paths slippery.

Caribbean Holidays, September Walking Holidays, A peaceful Caribbean beach reached by a walking trail on St John, with white sand, clear shallow water and shady trees

Trails and Beaches

One of the great pleasures of walking in the US Virgin Islands is how easily a hike can be combined with time by the sea. Trails near Trunk Bay, Maho Bay and Cinnamon Bay offer memorable views, while nearby beaches provide ideal places to cool down after a morning on foot.

Snorkelling is often excellent in the clear water, so pack a mask if you have one or hire equipment locally. Keep an eye on the weather and sea conditions, particularly after heavy rain, and remember that exposed paths can become hot even when a breeze is blowing.

Caribbean Holidays, September Walking Holidays, A friendly local guide and travellers walking through a colourful Caribbean village street in St Thomas, with harbour views and island hills

Exploring Beyond St John

St Thomas adds a livelier contrast, with historic Charlotte Amalie, hillside viewpoints and walks around the island’s bays. You can browse local shops, visit historic landmarks and enjoy harbour views before returning to a waterfront restaurant for dinner.

Ferries make it possible to experience more than one island, although services can vary, so check timetables when planning your route. Whether you choose a guided walk or explore independently, the combination of warm hospitality, varied landscapes and uncrowded September days makes the United States Virgin Islands a memorable walking destination.