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The Caribbean Under Sail
Clipper Tripper
This two-week journey pairs tall-ship travel with two beachfront beauties. The romance of sail is strong as you board Star Clipper for an adventure through the Caribbean’s off-track islands.
Star Clippers
Star Clippers is about the thrill of real sailing. A fleet of graceful tall ships built for those who find charm in classic nautical details. The atmosphere is informal, with sociable barbecues and anchorages chosen for beauty. It suits those who like things simple, spirited, and a touch on the adventurous side.
Star Clipper
Star Clipper is a true sailing ship, not a cruise liner in disguise. With space for just 166 guests, it feels intimate and sociable, and is more about shared experiences and conversation than Broadway-style shows and casinos. Cabins are compact but comfortable, with polished wood and portholes framing the view.
Itinerary overview
Days 1 to 3
Antigua
Show up in Antigua for a few nights at Galley Bay Resort & Spa, a mellow retreat tucked away on t...
Day 4
Antigua
Step on board the magnificent Star Clipper and set sail on your incredible island-hopping adventu...
Day 5
Saint Barthélemy
Anchor off Gustavia, where shuttered shops and cafés give the harbour a distinctly French feel. B...
Day 6
Norman Island, British Virgin Islands
Sail into the Sir Francis Drake Channel and drop anchor at Norman Island, long linked with pirate...
Day 7
White Bay and Tortola, British Virgin Islands
Start the day at White Bay on Jost Van Dyke, known for its sugar-soft beach. Later, head across t...
Day 8
Spanish Town and Captain’s Best Beach, British Virgin Islands
Climb through the maze of boulders at The Baths or wander into Spanish Town for a taste of local ...
Day 9
Philipsburg, St Maarten
Spend the day in Philipsburg, where Dutch and French influences jostle for attention. Stroll the ...
Day 10
Basseterre, Saint Kitts
Basseterre, where Georgian buildings and a buzzing square give the capital real character, is nex...
Days 11
Antigua to Barbados
Return to Antigua and disembark. A short flight whisks you over to Barbados for the final chapter...
Days 12 to 13
Barbados
Stay three nights at Little Good Harbour, a small beachfront hotel on Barbados’s quieter northwes...
Days 1 to 3
Antigua
Show up in Antigua for a few nights at Galley Bay Resort & Spa, a mellow retreat tucked away on the island’s west coast. With its thatched-roof suites, totally tropical gardens and long curve of sand, it’s the place to step into holiday mode.
Day 4
Antigua
Step on board the magnificent Star Clipper and set sail on your incredible island-hopping adventure.
Day 5
Saint Barthélemy
Anchor off Gustavia, where shuttered shops and cafés give the harbour a distinctly French feel. Browse the boutiques, settle into a waterside restaurant or head inland to find quieter sands tucked along the coast.
Day 6
Norman Island, British Virgin Islands
Sail into the Sir Francis Drake Channel and drop anchor at Norman Island, long linked with pirate legends. Swim into sea caves, snorkel among shoals of tropical fish, or stretch out on the sand.
Day 7
White Bay and Tortola, British Virgin Islands
Start the day at White Bay on Jost Van Dyke, known for its sugar-soft beach. Later, head across to Tortola to walk in the hills, snorkel from the shore, or watch the world go by from a shaded terrace.
Day 8
Spanish Town and Captain’s Best Beach, British Virgin Islands
Climb through the maze of boulders at The Baths or wander into Spanish Town for a taste of local island life. This afternoon it’s all up to the Captain where you dock. It’ll be a surprise but what’s pretty much guarenteed is a peaceful cove where you can swim straight from the ship.
Day 9
Philipsburg, St Maarten
Spend the day in Philipsburg, where Dutch and French influences jostle for attention. Stroll the colourful streets, order a fresh baguette at a French café, or explore further afield to discover hidden beaches and lively market towns.
Day 10
Basseterre, Saint Kitts
Basseterre, where Georgian buildings and a buzzing square give the capital real character, is next up. Later,head to South Friars Bay, a low-key stretch of coast backed by bars.
Days 11
Antigua to Barbados
Return to Antigua and disembark. A short flight whisks you over to Barbados for the final chapter of your journey.
Days 12 to 13
Barbados
Stay three nights at Little Good Harbour, a small beachfront hotel on Barbados’s quieter northwest coast. The white-washed cottages and palm-shaded paths give it a relaxed, homely feel. Dine on fresh seafood at the Fish Pot, wander into Speightstown, or spend your time listening to the soothing sound of the sea from a shaded lounger.
Day 14
Barbados
Hold those sun-kissed memories tight as you head back home.
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