Section I · The Ranked Twelve
From best to twelfth.
Sorted by what each pocket does well at its price point. The number-one pick is the one we would book first given a free pick from all twelve.
No. I
The Christophe Harbour and southeast peninsula villa, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: Christophe Harbour, the southeast peninsula. Peak rate: $28,000 to $44,000 / week. Usually included: housekeeping, pool maintenance, resort and marina access, security. Usually not: chef as standard, total seclusion.
Why it ranks here: Christophe Harbour is the master-planned estate on the southeast peninsula around the Park Hyatt, with the superyacht marina, the beach clubs, and the best estate villas on the island looking across The Narrows to Nevis. It clears the rest because no other pocket pairs the beaches, the marina, the resort service, and the villa quality at this scale.
What we would change: Christophe Harbour is a managed development still filling in, so the setting is estate-and-resort rather than wild, and rates are the island's highest. Take a finished estate villa with the marina and beach clubs, accepting the resort context for the service and the beaches.
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No. II
The Frigate Bay villa, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: Frigate Bay, the resort strip. Peak rate: $22,000 to $38,000 / week. Usually included: housekeeping, pool maintenance, golf access where present. Usually not: chef, seclusion.
Why it ranks here: Frigate Bay is the resort strip on the neck of the peninsula, with a calm Caribbean beach on one side and the Atlantic on the other, the golf course, the beach bars of the Strip, and the most services close at hand, the pick for a group that wants the liveliest, most convenient base. A five-bedroom here is the pick for the resort strip and the two-beach neck.
What we would change: Frigate Bay is the busiest, most built-up part of the island, with the beach bars running late on the Strip. Book it for the convenience and the action, taking a villa above the bay rather than on the bar strip if you want quiet.
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No. III
The Sand Bank Bay and quiet peninsula coves villa, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: Sand Bank Bay, the peninsula coves. Peak rate: $24,000 to $40,000 / week. Usually included: housekeeping, pool maintenance, security. Usually not: chef, services near, nightlife.
Why it ranks here: Sand Bank Bay and the quieter coves along the southeast peninsula hold private estate villas on their own stretches of sand, the pocket for a group that wants the peninsula's beaches and seclusion away from the marina and the strip. A five-bedroom here is the pick for a private cove on the best coast.
What we would change: the quiet coves are away from the restaurants and shops, so this is a self-catering, car-based stay with the marina and the strip a short drive. Book it for the private beach and the calm, arranging a chef and supplies for the seclusion.
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No. IV
The Belle Mont and northwest slopes villa, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: the northwest slopes, around Belle Mont. Peak rate: $22,000 to $38,000 / week. Usually included: housekeeping, pool maintenance, golf and farm access where present. Usually not: a beach at the door, chef.
Why it ranks here: the northwest slopes of Mount Liamuiga hold the Belle Mont estate, the organic-farm-and-golf development above the sea with cottages and villas in the hills, the pocket for a group that wants the green volcanic interior, the farm-to-table cooking, and the long views over the sea to Sint Eustatius. A five-bedroom here is the pick for the highland-and-farm side of the island.
What we would change: the slopes sit above the coast, so the beaches are a drive down and the setting is mountain-and-farm rather than waterfront. Book it for the views, the golf, and the farm, with the peninsula beaches a 30 to 40-minute drive.
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No. V
The Ottley's and plantation-estate great house, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: the old sugar estates in the hills. Peak rate: $20,000 to $36,000 / week. Usually included: housekeeping, pool, gardens, often a cook. Usually not: a beach at the door.
Why it ranks here: the old sugar estates such as Ottley's and the great houses in the foothills offer the historic, plantation-house version of a St. Kitts stay, stone houses in tropical gardens with pools and the rainforest behind, the pick for a group that wants the island's history and the cooler hills over the beach. A five-bedroom great house here is the pick for the plantation setting.
What we would change: the estates sit inland in the hills, so the beaches are a 15 to 25-minute drive and the appeal is the gardens and the history. Book it for the great-house setting and the cool, with the peninsula beaches a short drive.
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No. VI
The Cockleshell Bay and southern tip villa, five-bedroom.
Typical: 5 BR, sleeps 10. Pocket: Cockleshell Bay, the southern tip. Peak rate: $22,000 to $38,000 / week. Usually included: housekeeping, pool maintenance, security. Usually not: chef, services near.
Why it ranks here: Cockleshell Bay at the southern tip of the peninsula is the long calm beach looking straight across The Narrows to Nevis, with the water taxi to Nevis and the beach bars nearby, the pick for a group that wants the best swimming beach and the Nevis view. A five-bedroom here is the pick for the southern-tip beaches.
What we would change: the southern tip is the furthest point of the peninsula, so it is a drive from Frigate Bay and Basseterre and the services are limited. Book it for the calm beach and the Nevis crossing, with the strip a 15-minute drive back up the peninsula.
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No. VII
The South Friars Bay villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: South Friars Bay, the central peninsula. Peak rate: $18,000 to $32,000 / week. Usually included: housekeeping, pool maintenance. Usually not: chef, seclusion.
Why it ranks here: South Friars Bay sits midway along the peninsula, a popular Caribbean-side beach with the liveliest beach bars on the island and good swimming, a central, sociable pocket with the strip and the marina both close, the pick for a group that wants the beach-bar scene at a lower number. A four-bedroom here is the value pick for the central peninsula.
What we would change: South Friars is the beach-bar beach, busy and lively, so a villa near it hears the music and shares the sand. Book it for the bars and the central position, taking a house above the bay for any quiet.
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No. VIII
The Basseterre heights villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: the hills above Basseterre, the capital. Peak rate: $18,000 to $30,000 / week. Usually included: housekeeping, pool maintenance, parking. Usually not: a beach at the door, seclusion.
Why it ranks here: the hills above Basseterre hold villas with views over the capital, the harbor, and the cruise port, the pocket closest to the town, the markets, and the airport, the pick for a group that wants the town and the easiest access over a beach setting. A four-bedroom here is the pick for the capital and the harbor view.
What we would change: Basseterre is a working port and cruise town, so the setting is city-and-harbor rather than beach, and the cruise days fill the center. Book it for the town and the access, with the peninsula beaches a 15 to 20-minute drive south.
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No. IX
The Dieppe Bay and far north villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: Dieppe Bay, the far north. Peak rate: $18,000 to $30,000 / week. Usually included: housekeeping, pool maintenance, garden. Usually not: white sand, services near, the peninsula close.
Why it ranks here: Dieppe Bay and the north coast below Mount Liamuiga are the quietest, most traditional part of the island, with black-sand beaches, fishing villages, and the rainforest behind, the pick for a group that wants the old, local St. Kitts away from the resorts. A four-bedroom here is the pick for the quiet north.
What we would change: the north has black sand and is a real drive from the peninsula and the airport, so this is a quiet, rural base rather than a beach-resort one. Book it for the local life and the rainforest, accepting the dark sand and the distance from the south.
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No. X
The Sandy Point and Brimstone Hill villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: Sandy Point, the northwest coast. Peak rate: $18,000 to $28,000 / week. Usually included: housekeeping, pool maintenance, garden. Usually not: white sand, services near.
Why it ranks here: Sandy Point on the northwest coast sits below the Brimstone Hill Fortress, the UNESCO World Heritage site that crowns the island, a historic town pocket of villas with the fortress, the dive sites, and the sunset coast close at hand, the pick for a group that wants the history and the west-coast diving. A four-bedroom here is the pick for the Brimstone Hill side.
What we would change: Sandy Point is a west-coast town a drive from the peninsula beaches, so the appeal is the fortress, the diving, and the sunsets rather than a marquee beach. Book it for Brimstone Hill and the west coast, with the peninsula a 30-minute drive.
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No. XI
The Cayon and windward coast villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: Cayon, the windward east. Peak rate: $18,000 to $28,000 / week. Usually included: housekeeping, pool maintenance, garden. Usually not: calm swimming beaches, services near.
Why it ranks here: Cayon and the windward east coast catch the trade winds and the Atlantic surf, a green, rural pocket of villas above the sea with the breeze, the views, and the cane country, the pick for a group that wants the cooler, windward side and the open ocean. A four-bedroom here is the pick for the windward coast.
What we would change: the windward coast is windy with Atlantic swell rather than calm Caribbean swimming, so the bathing is at the peninsula a drive south. Book it for the breeze, the views, and the quiet, with the swimming beaches on the leeward side.
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No. XII
The Conaree and central east villa, four-bedroom.
Typical: 4 BR, sleeps 8. Pocket: Conaree, the central east coast. Peak rate: $18,000 to $26,000 / week. Usually included: housekeeping, pool maintenance, garden, parking. Usually not: a calm beach at the door, seclusion.
Why it ranks here: Conaree on the central east coast near the airport holds villas above the Atlantic shore close to Basseterre and the peninsula, the most central and convenient pocket at the lowest rates, the contrarian pick for a group that wants a practical base near the airport and the town. A four-bedroom here is the lowest-number pick for the central island.
What we would change: Conaree is near the airport and the road rather than a marquee beach, with Atlantic surf rather than calm swimming, so the appeal is the central position and the price. Book it for the access and the value, with the peninsula beaches a 15-minute drive south.
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