Our first place we stayed on our trip was at Siboney Beach Club on Dickenson Bay. Its right on the beach with a pool, nice balcony rooms, and well manicured private beach. Their restaurant SaltPlage is right on the beach. The food was good, but service and the kitchen hours weren't the best. Dickenson seems to still be recovering from Covid because a lot of the places were closed or run down. The ginormous Sandals resort just down the beach takes up half the bay. We explored off the bay and walked to a really nice French restaurant called Casa Roots, highly recommend. We also walked to BeachLimerz which was pretty far, but worth it. It was quiet despite being a highly recommended place, but the people were super friendly. We stumbled upon Fort James while there too. You can walk all over the Fort and the view is amazing. Glad we got to see this part of the island, but I wouldn't stay here for more than a couple nights, which is what we did.
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