Whether you choose to spend your time lazing on the beach in glitzy Barbados, cruising through gin-clear waters of the British Virgin Islands, exploring old spice estates in Grenada or hiking through the Saint Lucian jungle, a trip to the Caribbean is every bit as impressive as its reputation suggests.
Our best advice is to visit several islands to get a sense of the region’s diversity and our sample itineraries intend to show you how. Devised by our Caribbean specialists and based on routes that work particularly well, they aim to offer some inspiration before our specialists set to work tailoring your itinerary to your personal interests and ensuring you make the most out of your time in the region.
Start planning your tailor-made trip by contacting one of our Caribbean specialists
These itineraries are designed to give you some suggestions for what is possible when you travel in the Caribbean, and they showcase some of the routes that we've found work particularly well. Treat them simply as inspiration, because your trip will be created uniquely for you by one of our specialists based on your particular tastes and interests.
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Stay at an historic cocoa plantation set among Saint Lucia's rainforest and discover the famous pitons before heading to Grenada for a week of relaxation and exploration.
Discover Grenada's nutmeg and cocoa plantations and beautiful countryside before heading to St Lucia for a week on the beach at the charming Ti Kaye Resort.
Spend a few days exploring Antigua's beautiful coastline and discovering its colonial history before flying to Barbados to relax at a peaceful west coast beach resort.
Experience Bridgetown on foot with a guided walking tour.
Join the locals on a Friday evening for Oistins Fish Fry.
Visit Bequia's small, quaint capital town, Port Elizabeth.
Navigate your way along the Belmont coastal walkway.
Discover the very different characters and landscapes of 3 different islands with a few days in Barbados and Grenada before heading to sleepy Bequia's beautiful beaches.
Discover the small, friendly island of Nevis, staying at a charming resort set in the ruins of an historic sugar plantation before heading to the golden sands of beautiful Antigua.
Enjoy the Art Deco architecture and exciting atmosphere of Miami Beach before flying to Antigua’s stunning coastline and colonial history for a relaxing week at a luxurious beach resort.
Embark on a seafaring adventure navigating the Windward Isles onboard the Royal Clipper Sailing vessel.
Take some time to visit the historical highlights on Barbados, including St. Nicholas Abbey, Bathsheba and Holetown.
Sample some of the island's best food in Speightstown or Oistins.
Sail out to a secluded sandbank in the turquoise ocean.
Watch the setting sun over Pink Sands Beach.
Snorkel in the world’s third-largest barrier reef.
Taste local rum and traditional dishes like cracked conch.
Visit the historic streets of Dunmore town on Harbour Island.
Enjoy incredible views of Saint Lucia's pitons from a beautiful resort set among the rainforest before heading to the north coast of the island for a relaxing week at an elegant beach resort.
Stay at Antigua's picturesque English Harbour, discovering the island's cultural heritage and beautiful coastline before flying over to Grenada to explore the lush, volcanic landscape and spend time at a luxurious beach resort.
Visit the island of Antigua, exploring its landscape and historic sites before heading to the soft white sands of Barbados’ west coast for a week of relaxation.
Explore the quiet, undeveloped east coast of Barbados before spending a week on a beautiful private island in the Grenadines.
Learn about the vibrant spice history of Grenada.
Explore Grenada's quiet northern territory.
Hike the rainforest surrounding the prestigious Piton Mountains.
Enjoy the bars and restaurants in Rodney Bay Marina.
Discover the dramatic scenery of southwest Saint Lucia with the volcanic spires of the pitons rising majestically from the sea and the lush rainforest of the interior, then head over to relax on the beautiful island paradise of Petit St Vincent.
