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Island Hopping Caribbean Travel

Multi-island Caribbean trips that hold together: entry rules checked island by island, regional flights and ferries mapped, a budget that counts every leg, and festivals and small islands timed right.

Free · Mac (Apple silicon) and Windows · v1.0.0 · Other platforms

Then open the Marketplace in the app, search for Island Hopping Caribbean Travel, and click Install. It goes into your own files, and works offline from then on.

What it installs.

1

Pillar

1

Area

50

Projects

202

Starter tasks

🌴 Caribbean Life & Diaspora

Island Hopping Caribbean Travel

Travelling around the Caribbean: regional airlines and ferries, entry rules, festivals by island, budgets and building a multi-island trip.

  1. Island wish list and rough route map
  2. Entry rules checked for every island on the route
  3. Regional airline and ferry network map
  4. Full-cost budget for a multi-island trip
  5. Health entry rules and a travel clinic visit
  6. Insurance that covers missed inter-island connections
  7. Currency plan for EC dollars, guilders, euros and more
  8. Travel document pack, on paper and offline
  9. Phone and data across several islands
  10. Island-hopping fund with a monthly transfer
  11. Inter-island fare watch and price log
  12. Schedule change checks on booked regional flights
  13. Yearly festival calendar by island
  14. Passport, visa and permit expiry tracker
  15. Hurricane season plan for trips June to November
  16. Island-by-island travel notes
  17. Multi-leg reconfirmation checklist before departure
  18. Entry rules in the French, Dutch, US and British territories
  19. Departure taxes and airport fees by island
  20. Getting around each island without a hire car
  21. Driving permits and car hire across the islands
  22. Local laws and customs that catch visitors out
  23. Survival phrases in Kweyol, Papiamento, French and Spanish
  24. Ferry crossings, sea conditions and seasickness
  25. Heritage sites visited with care and context
  26. Signature dishes to eat on each island
  27. Choosing hub islands for the route
  28. Flights, ferries or a sailing charter for each leg
  29. One base island or moving every few days
  30. Separate tickets versus one through booking
  31. Packing light for small planes and ferries
  32. Choosing where to stay on each island
  33. Choosing the season for the trip
  34. Festival-timed route through the Windward and Leeward Islands
  35. Music festival weekend on a neighbouring island
  36. Regatta week as a spectator
  37. Island-hopping honeymoon or anniversary trip
  38. Island hopping with young children
  39. Solo island hopping safety plan
  40. Travelling the islands with limited mobility
  41. Travel rights as a CARICOM national
  42. Adding a second island to a trip home
  43. Backpacking the islands on a student budget
  44. Checking local laws as an LGBTQ+ traveller
  45. Diving across islands with no-fly intervals planned
  46. Sailing the Grenadines with customs clearance
  47. Reaching Saba, Montserrat, Barbuda and Carriacou
  48. Guyana and Suriname interior by light aircraft
  49. Cuba leg with its own entry and money rules
  50. Visiting every CARICOM member state

Where it starts.

Each project arrives with its purpose, milestones and first tasks written out. Here is how the first three read.

Island wish list and rough route map

Most multi-island trips start as a vague wish to see a few islands and end with a route that zigzags across the map and burns two days on connections.

First tasks

  • Write down every Caribbean island you would like to see and why
  • Group the islands by sub-region on a printed or online map
  • Draw one route through three to five islands that does not double back
  • Allocate nights to each island and total them against your leave
  • Move the islands that do not fit onto a list for a later trip

Entry rules checked for every island on the route

Each country and territory in the region sets its own entry rules, so the passport that gets you into Barbados without a question may still need a visa, an online arrival card or a US travel authorisation further along the route. Checking every stop against your actual nationality before booking avoids being refused boarding at a small airport with no way to fix it.

First tasks

  • List every island on the route with the country or territory it belongs to
  • Check each one on its official immigration page for your nationality
  • Note passport validity, onward ticket and arrival card rules for each stop
  • Apply for any visa or travel authorisation the route needs

Regional airline and ferry network map

Getting between islands is the hard part of island hopping: some pairs have several flights a day, others one flight a week or a ferry that sails only when the sea allows.

First tasks

  • Search each island's airport website for the airlines that serve it
  • List the ferry operators for island pairs separated by a short crossing
  • Mark each island pair with who connects it and how often
  • Find a hub for every pair with no direct link

Make it yours.

Install Island Hopping Caribbean Travel, then tell Aurum the date you're aiming for. It checks whether the plan fits the weeks you actually have.

Free · Mac (Apple silicon) and Windows · v1.0.0 · Other platforms

Blueprints are general information to help you organise your own work. They are not medical, financial, legal or other professional advice. See the Terms.