We know your time is valuable, and unless you have the resources, money and time to visit all 7,000 Caribbean Islands (don’t worry they’re not all inhabited!), then you might easily miss some of the most unbelievable locations, excursions, activities, culinary explorations and adventures on offer throughout this beautiful collection of countries.

Which is why we have compiled our ultimate Caribbean Bucket List, created through personal experience (I know, we’re VERY lucky!) and tales told from friends and family who have experienced something unforgettable. During your Luxury Villa Rental in the Caribbean, we strongly recommend you tick off as many as you can, and make your visit as memorable as can be!

The Baths, Virgin Gorda


  1. Ride through the surf on the East Coast of Barbados with Ocean Echo Stables.
  2. Taste the best breadfruit chips at the Hummingbird Beach Resort in St Lucia, framed by an amazing view of the Pitons.
  3. Island hop in the BVI with a local ferry and a sense of adventure.
  4. Drink nutmeg-sprinkled painkiller cocktails at the legendary Soggy Dollar Bar on Jost Van Dyke, and perfect your ring game technique.
  5. Venture to The Baths in Virgin Gorda and climb amongst the huge boulders that dot the picturesque shoreline. Look out for a formation known as the cathedral which is just spectacular.
  6. Listen to the gentle surf on Crane Beach in Barbados, and feel the unique coral-pink sand between your toes.
  7. Board a Schooner for a traditional whirlwind sail around The Grenadines, and make sure you practise your diving straight into the azure waters.
  8. Eat a proper Roti, packed with Curry Goat at the Roti Den in Speightstown, Barbados.
  9. For the rockstar feel, hire a helicopter and explore the Caribbean landscapes by sky.
  10. Kick back with a movie at the unique Globe Drive-In in Christchurch, Barbados – you’ll feel like you’ve stepped back in time and the hot dogs are delicious!
  11. Hike the Blue Mountains of Jamaica and experience each emotional sunrise from the peak.
  12. Drink a real rum punch. From a plastic cup. With plenty of ice.
  13. Swim with turtles and unpack your snorkel for a rare glimpse of the most incredible ocean wildlife.
  14. Sail into Calivigny Island and be welcomed by the ultra luxurious feel and first-class service.
  15. Catch the speedboat from Tortola to Scrub Island at sunset and be blown away by the natural beauty of the British Virgin Islands.
  16. Fine dine at The Cliff in Barbados for the culinary journey of a lifetime
  17. Fill up and party at the Shirley Heights Lookout BBQ every Sunday. A true  Antiguan institution.
  18. Get jumpin’ at Barbados’ legendary Carnival. Also known as Cropover/Kadooment this annual celebration involves a lot of rum, a lot of soca music and a LOT of fun.
  19. Taste REAL chocolate at The Grenada Chocolate Company and support local trade.
  20. Oistins Fish Fry on a Friday Night in Southern Barbados blends charm, music, incredible rustic food and the ultimate in Caribbean authenticity.
  21. Dance your cares away in an extraordinary location at the Fireball Full Moon Party on Trellis Bay, Tortola.
  22. Let go on the ‘Island of All-Right’ and swing down to the annual music festival – Reggae Sumfest, in Jamaica.
  23. Dip your toes amongst multi-coloured starfish on Jumby Bay Beach; the world’s Best Caribbean Resort.
  24. Watch a cricket game at the Kensington Oval in the home of West-Indies Sport: Barbados.
  25. The St Lucia Jazz Festival is essential for music lovers, looking for something new and exciting.
  26. Grab a bite to eat at Basil’s Bar on Mustique. The ultimate in exclusivity and a famous celebrity haunt.
  27. Take a twilight submarine tour to see the extensive reefs and ocean wildlife from a new perspective in Barbados.
  28. Treat yourself to Canouans Signature Relaxation Massage in a haven of relaxation. Their glass-bottomed, ocean huts let you examine the corals while your stresses float away.
  29. Delve into the depths of Barbados’ limestone core and unearth adventures at Harrisons Caves, where motorised trains take you into the heart of the island with fascinating geology.
  30. Buy fresh produce from local markets and let your in-house Private Cooks teach you their traditional Caribbean cuisine – good for the soul (and the stomach).
  31. Climb aboard a concorde in Barbados, and take-off to fun!
  32. The Drive-in Volcano in St Lucia, is bursting with naturally created Sulphur Springs and give guests an insight into the history of the island.
  33. Experience 360-degree views of the Ocean and first-class luxury playing golf on Canouan Island.
  34. Those with a need-for-speed will get a thrill from River Tubing In Grenada.
  35. Conservation and the cute-factor go hand-in-hand at the Old Hegg Turtle Sanctuary in Bequia, where these gentle giants are protected and nurtured.
  36. The Underwater sculpture park in Grenada is a fascinating stop-off for those with Scuba/Snorkelling abilities.
  37. Lose yourself in almost pre-historic flower forests in Barbados.
  38. For those who belong on the seas, Deep Sea Fishing in the BVI is a treat for all those with sea-legs.
  39. Take to the forest heights and conquer a Zip Wire in St Lucia.
  40. Experience the unforgettable in Tortola and swim amongst the gentle dolphins.
  41. Grab your irons and play golf amongst green monkeys at Apes Hill in Barbados.
  42. Lie back and gaze at the stars on Jumby Bay with the resident astronomer, Mr David Stubbs.
  43. Get back to nature and swim under a waterfall in Grenada at the Seven Sisters Falls.
  44. Tour a rum distillery e.g. Mount Gay in Barbados (with plenty of free samples!)
  45. Sit down, take 5 and sip on the best coffee in the world in Jamaica.
  46. Watch the famous and truly mesmerising Bajan sunset via a sunset cruise in Barbados.
  47. Swim amongst nature’s ocean gliders at Stingray City in Antigua.
  48. Find your own adrenaline rush white-water rafting in Jamaica’s Montego Bay.
  49. Grab your board and tackle the best surfing spot Barbados has to offer on the East Coast at Soup Bowl.
  50. Slice off a piece of the action at Paulo’s Churrasco do Brasil in St Lawrence’s Gap, Barbados with its authentic gaucho style flame-grilled meats.
  51. Sip a Martini (Shaken, not stirred) at the Bizot Bar based in the Goldeneye Hotel in Jamaica. Only for the most glamorous of travellers dahhhhhling.
  52. Celebrity-spot in the playground of the glitterati: St Barts.
  53. Slide your toes into the unusual black sands on the coasts of St Lucia, combined with a stay at a Luxury Villa.
  54. Eat Coconut and Banana French Toast for breakfast at the beautiful Caravela Restaurant on Scrub Island, then take your personalised golf buggy down to the private beach.
  55. Sign up to the ‘Turtle Call List’ at Jumby Bay and be collected day or night, when the female Hawksbill Turtles swim to shore to lay eggs. A truly magical experience.

If our unforgettable moments have inspired you to travel the Caribbean, contact our Luxury Villa Specialists for expert travel advice and more information. Alternatively, if you’d like to contribute your own special adventures and memories, please comment below!

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