Sir Timothy’s Hill & South Friar’s Bay

The taxi ride that brought us to our resort on the first day came with a brief geography lesson from the driver free of charge. The island of St. Kitts is shaped like a baseball bat (with its sister island Nevis rounding out the “bat and ball” description), and is formed by an insular area and a stretch of land known as the Southeast Peninsula that snakes outwards towards Nevis.

This peninsula stretches long and thin between the Caribbean Sea and the Atlantic Ocean, and as we pulled up towards Frigate Bay, our driver informed us that the best place from which to enjoy stunning views of both water masses was atop Sir Timothy’s Hill, a hill popular with visitors and locals for its strenuous but rewarding hike.

Never ones to back down from a challenge, Jessica and I set off on our third day at the resort hoping to climb the hill, take in the views, and come down the other side to grab some seafood and cocktails at the beach on South Friar’s Bay.

A word of caution: St. Kitts is a challenging place to discover on foot. You’ll seldom find any sidewalks to walk on; instead, depending on where you are, you’ll have to either walk on the grass or forge your path through the drainage ditches on either side of the road. Most people get around by car, but there’s really not many people on the island, so as a pedestrian you shouldn’t feel too endangered by the passing cars.

We walked for a while along the side of the main road leading up Sir Timothy’s Hill before coming to an off-road trail leading directly up to the summit. It was about a 20-minute hike in total. Along the way, we were treated to some fantastic views of our resort.

Sir Timothy's Hill – View of the Marriott Resort St. Kitts

Sir Timothy’s Hill – View of the Marriott Resort St. Kitts

Once atop the hill, the scenery was even more captivating. We had full view of the mountainous Southeast Peninsula sprawling outwards in front of us, flanked by the Atlantic on its left and the Caribbean on its right, the volcanic peak of Nevis rising solemnly in the distance.

Sir Timothy's Hill – View from halfway up

Sir Timothy’s Hill – View from halfway up

Sir Timothy's Hill – View from peak

Sir Timothy’s Hill – View from peak

After cooling off from our hike in the hilltop breeze, we came down the other side and walked along the road again, this time for about 30 minutes, until we arrived at the beach on South Friar’s Bay. Located on the Caribbean coast, this beach was home to quite a few bars and restaurants that served food and drinks until the early evening.

South Friar's Bay – Beach

South Friar’s Bay – Beach

We grabbed a seat at the Shipwreck Beach Bar, a lively spot at the southern end of the beach. Jessica ordered the nachos and I had the conch fritter meal (a popular Caribbean food made from the tough meat of sea-dwelling molluscs, served with rice, fries, and salad on the side). We also got some piña coladas to unwind a bit after our exertions in the sun.

South Friar's Bay – Shipwreck Beach Bar welcome sign

South Friar’s Bay – Shipwreck Beach Bar welcome sign

South Friar's Bay – Shipwreck Beach Bar interior

South Friar’s Bay – Shipwreck Beach Bar interior

South Friar's Bay – Lunch at Shipwreck Beach Bar

South Friar’s Bay – Lunch at Shipwreck Beach Bar

The food was great – I doused my conch fritter with extra-spicy Caribbean hot sauce – and it was amazing to cast our gaze over the endless water as we ate.

The Shipwreck Beach Bar also lays out a few beach chairs for its guests, so we lounged in the sun for a bit after lunch. According to our taxi driver friend, the waters of the Caribbean Sea are meant to be calmer than the Atlantic, but on this particular day the waves were crashing loud and strong.

There were also more hammocks tied up among the trees outside Shipwreck’s upper level, where we relaxed for a bit as well. It seemed as though just when we thought we had run out of things to make us go, “This is the life!“, another was waiting around the corner.

South Friar's Bay – Shipwreck Beach Bar hammock

South Friar’s Bay – Shipwreck Beach Bar hammock

That’s when the monkeys came down the hill to hang out!

South Friar's Bay – Mischievous monkeys

South Friar’s Bay – Mischievous monkeys

I had earlier asked the Shipwreck staff where the monkeys were, since a few reviews I had read claimed that the monkeys around here weren’t shy to come and mingle the people. She had told me that they’re a “moody” bunch.

Well, I was so glad to see them out and about, roaming freely, dashing around in search of the tiniest morsel of food. Of course, there were signs saying “do not feed the monkeys” (apparently they aren’t native to the island and have been causing all sorts of problems, including raiding the beach bars for their cocktails), but even just watching them fight among themselves for some fruit scraps was terrific.

On our walk back to the resort, we took a slightly different path and caught some sunset views of the two Friar’s Bay beaches (North Friar’s Bay was a smaller stretch on the Atlantic side) and the Southeast Peninsula.

View of North Friar's Bay

View of North Friar’s Bay


The Shipwreck Beach Bar is a great place to spend an afternoon if you’re looking to check out a new beach further away from the resort. I highly recommend paying it a visit for its authentic and affordable food selection, the tremendous views of the Caribbean Sea, and the friendly pack of monkeys who’ll do anything they can to goad you into discreetly sneaking them a bite (just don’t let them near your margaritas!)

You can take a cab from the Marriott to South Friar’s Bay for US$12, though I would of course recommend making the trek via Sir Timothy’s Hill and witnessing one of the signature views of the island. There’s something about a grueling hike in the sun that makes the ice-cold cocktails at the end so much more rewarding.

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