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A Tropical Island Hop
An Caribbean Island combo of St Kitts & Nevis


One country, two islands two miles apart, a duo of island vibes. We can’t think of a smarter way to explore St Kitts & Nevis than completing the pair. This is a holiday for the history buffs, the nature lovers and the Caribbean completists looking for something a little different.
From £2,049 - £2,499 per person
Itinerary overview
Highlights of trip
St Kitts
Begin on the slightly more buzzing of the two islands. The one that wears its past on its sleeve, but embraces the 21st Century in the bars, restaurants and resorts of Frigate Bay, Basseterre and beyond. Volcanic backdrops are pretty much a constant, whether you’re wandering through UNESCO-listed forts, sprawling plantations with a dark past, or trawling the coast for beaches and bays.
Pools, palm trees and Frigate Bay at your feet. Restaurants at the hotel but also suites with kitchens for sunset soirées, midnight snacks and stretching that budget further.
Every day can come with a little something extra - star gazing, sound healing and rum tasting - plus free daily fun for the kids.
Nevis
Be in the room where it happened on Nevis, a smaller island that’s probably best known as the birthplace of Broadway and the West End’s most famous Founding Father, Alexander Hamilton. The landscapes are a carbon copy of St Kitts but in miniature – think forested slopes of a dormant volcano, and some beautiful beaches – but the scene is far quieter, meaning there’s little else to focus on than vegging out.
A boutique Caribbean retreat where timeless charm and modern luxury blend seamlessly.
If you want to spark a little romance, chase some rainforest adventure or get a nature fix (hello tree frogs and Talipo palms) this is the place to do it.
New York
Start off your holiday in style with an optional stop in the Big Apple en route to the Caribbean. Whether it's your first time in New York City or your 15th, there's always something new to discover. Divide you time between the shops of Fifth Avenue, brightly-lit Midtown, the sprawling Central Park, and the cool neighbourhoods of lower and upper Manhattan.
This is urban New York and a perfect location for first-time visitors to easily reach all the must-see attractions.
Fun-loving Staypineapple goes to prove that a hotel doesn’t need to be high-end luxury to have oodles of personality.
Guide price information
Based on 3rd November 2026 departure
Based on 2nd March 2027 departure
Guide price information is based on economy class international flights, accommodation, transport and experiences as detailed in the itinerary above. Guide prices do not include optional things to do. Prices can change both up and down and these prices represent only a guide, call us for up-to-date prices. The cost of your holiday depends upon the time of year you travel, duration of your holiday, preferred departure airport, airlines, hotels and things to do. Prices are per person based on 2 adults sharing a room.
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