We Visited 4 Caribbean Islands Without Changing Hotels
Capturing the magic of Virgin Gorda, British Virgin Islands. A beautiful beach memory from our December 2023 trip, preserved in our personal travel archive. Photo from our personal travel collection.
One hotel, several islands, and an international border in the middle. Our December trip combined St. Thomas and St. John in the U.S. Virgin Islands with day trips to Jost Van Dyke and Virgin Gorda in the British Virgin Islands.
We stayed seven nights at the Westin on St. John. That gave us one place to return to after our island outings. For families traveling with older parents, the useful question is how much moving around everyone will enjoy.
Goldie’s Quick Answer: Choose one home base, leave space between boat days, and check entry requirements before booking a British Virgin Islands excursion. A nearby island can still mean an international trip.
Our December 2023 island itinerary. Flight, road, and ferry connections are illustrated schematically. BVI departure ports and any connections should be confirmed with the operator.
Arrival route shown on the map: Fly to St. Thomas (STT), drive to Red Hook, ferry to Cruz Bay on St. John, then drive to the Westin at Great Cruz Bay. Official St. John transfer guide
These are the outings recorded in our trip notes. The open days below are suggestions for families adapting the week to their own pace.
Saturday December 9. Arrive in St. Thomas and transfer to St. John. Our notes listed a 5 p.m. ferry transfer. Settle into the Westin.
Sunday December 10. Suggested easy day: enjoy the resort and keep the schedule light.
Monday December 11. Ferry day trip to Jost Van Dyke in the British Virgin Islands.
Tuesday and Wednesday December 12 and 13. Suggested flexible days: choose a beach outing or resort time, with a rest break whenever the family needs one.
Thursday December 14. Ferry day trip to Virgin Gorda in the British Virgin Islands. Our expenses included a separate car rental there.
Friday December 15. Blacksheep Charter, 9 a.m. to 4 p.m., as recorded in our itinerary.
Saturday December 16. Return home. Our notes listed a noon ferry transfer.
The ferry times above belong to our 2023 itinerary. Confirm current sailings and allow time for loading, road travel, and airport check-in.
What families should check before booking
The border crossing. Virgin Gorda and Jost Van Dyke are in the British Virgin Islands. BVI tourism guidance requires a passport for entry and departure by sea or air. Check current requirements for every traveler and confirm the return arrangements. BVI entry requirements
The transfers. A passenger ferry and a car barge serve different needs. Ask the rental company whether the car may travel on your chosen route. Confirm boarding steps, assistance, and restroom access with the operator. St. Thomas to St. John car barge information
The walking. Ask the hotel about the exact room, steps, bathroom setup, and route to dining. For each outing, ask about sand, uneven ground, and places to sit. Build the day around the person who needs the most breaks.
Goldie’s Extended Packing Table
Choose by age, destination, and planned activities. These are packing options, not a claim that we used every product. Product links open searches or provider pages; check the exact model and instructions.
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Use and what to check |
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For luggage, keys, or a stroller. AirTags are for belongings, not tracking children or grandparents. |
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UPPAbaby G-LUXE single stroller; UPPAbaby side-by-side double stroller |
Choose one that fits your children and car. Check age limits, folded size, and site restrictions. |
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An option where strollers are restricted. Check fit and size limits; keep the baby’s airway clear. |
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Optional pool clothing. Check the garment’s UPF label; exposed skin still needs sun protection. |
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Optional outdoor clothing. Confirm both insect-treatment instructions and the individual garment’s UPF rating. |
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Hawaiian Tropic SPF 70 sunscreen; Babyganics SPF 50 sunscreen |
Check formula and age guidance. Follow the label and use shade and clothing too. |
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For the baby’s travel kit; choose and use a model according to your pediatrician’s guidance. |
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Pack only if used for your child; follow cleaning instructions and match filters to the device. |
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Useful during toilet training. Check stability on the toilet and clean before repacking. |
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Huggies diapers; Pull-Ups training pants; Huggies baby wipes |
Bring the usual size and extras for delays. Wipes do not disinfect surfaces. |
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For planned pool time. Change frequently; swim diapers are not leakproof. |
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A training aid is not automatically a life jacket. Choose an approved, correctly fitted life jacket when needed and supervise closely. |
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Optional feeding privacy. Keep the baby’s face visible and avoid overheating. |
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Optional only if the model permits travel use. Follow mounting instructions; do not alter hotel alarms. |
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Leave U.S. plug covers home for this route; ask hotels about childproofing compatible with their outlets. |
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Useful for temporary labels. It does not make cords, outlets, or sharp edges child-safe. |
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Small additions to the family’s first-aid kit for minor scrapes; keep dressings clean and dry. |
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Optional for suitable outdoor use. Keep netting secured away from infants; check fit and sleep guidance. |
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Optional if needed. Follow age and application instructions for the exact product. |
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Optional for rain or pool days. Check fit and closure; test before putting your phone inside. |
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For bright outings. Check fit and the product’s UV protection specification. |
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Usually optional for a short hotel trip. Confirm model support, setup, and network requirements. |
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Check European plug compatibility and every device’s voltage rating. A plug adapter is not a voltage converter. |
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Useful when the rental car has a USB-A port; confirm the port and your phone connector. |
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For a compatible USB-C device. Standard airplane headphone sockets need a different connection. |
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Verizon international plans; AT&T international plans; T-Mobile international plans |
Confirm Portugal and Spain coverage, data limits, call charges, and activation with your carrier. |
Make room for the time together
A family trip does not need a different island every day. Keep the outings everyone wants most, then protect the time to rest together. The shared memories are the reason to go.
Travel links provide current planning information; confirm details before booking.
GoldieCircle Disclaimer
GoldieCircle may recommend third-party products and services based on internal evaluation. Such recommendations do not constitute a warranty or guarantee of performance, suitability, or lifespan. All products and services are subject to their respective providers’ terms and conditions. GoldieCircle assumes no liability for any claims or damages arising from the use of any recommended product or service.
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