Cumberland Bay
A deep leeward anchorage below steep green slopes, used by yachts crossing the chain.
Updated 3 September 2026
Cumberland Bay cuts into the leeward coast below slopes that rise steeply and are covered in coconut and banana, and the water in it drops away so quickly that yachts moor bow-to with a line ashore rather than swinging at anchor. Boat boys meet arriving vessels and take lines. A few restaurants operate on the beach. It is one of the standard stops on the passage down the island chain.
The landscape
- The deep anchorage - water dropping away so fast that boats moor with lines ashore.
- The steep slopes - coconut and banana running down to the bay on all sides.
- The beach restaurants - the small places along the shore.
- The sailing route - a standard stop on the passage through the islands.
When to go
December to May is the dry and sailing season. Hurricane season runs June to November. The bay is quiet outside the yachting months.
What to expect
Boat boys can be persistent and arrangements are best settled clearly on arrival. Facilities ashore are basic. The road down from the highway is steep and rough.
Nearby
Wallilabou is south, and Chateaubelair is north.
What to pack for Cumberland Bay
Chosen from what this place is for. Tap a kit for the full checklist.
- Broken-in walking shoes or boots - Grip and ankle support matter more than looks; never hike in brand-new boots. Find on Amazon
- Layers + a waterproof shell - Mountain weather turns fast; a packable rain jacket saves the day. Find on Amazon
- Daypack with rain cover - 20-30 litres holds water, snacks, layers and a first-aid kit. Find on Amazon
- Offline maps + a power bank - Download the trail before you lose signal; carry backup charge. Find on Amazon
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