Valiant Lady · Voyage 07 / 09 · Planning guide
One more Caribbean week.
Dec 12 to 19 · 2026 · From San Juan
Five islands again. This time I’d change the rhythm: swap a big excursion for a town day, then choose the adventure you still want to try.
Illustrated inspiration, not a photograph of these ports.
Port names follow my published voyage record. They are not a day-by-day timetable. Confirm port order, berth, local time and all-aboard deadlines in the Sailor App.
These are ideas I’m considering, not claims that I’ve personally tried every outing. No date-specific availability, prices or events are promised.
Your ports, with a plan
Explore this voyage.
Tap a port on the map or choose one below. See my ideas, jump into the port guide and check the forecast for your planned day ashore.
Loading the route. The port guide links below work without the map.
Choose a port
Where shall we go?
The map connects directly to my plans in this guide.
Read the port guide →Weather for your visit
Forecasts appear when the planned visit is within range. Port dates must be confirmed before relying on a forecast.
Data from MET Norway · CC BY 4.0. Temperatures converted to °F; forecast sample selected by local time.Approximate port locations. Dashed lines connect the guide’s listed stops, not the ship’s navigation track. Port order and dates remain subject to confirmation in the Sailor App.
PORT IDEA 01 / 05
St. Maarten: one island, plenty of opinions
Make the day work
Check traffic with your driver before crossing the island. Maho plane watching is an optional separate outing, not a must-do detour. Confirm currency and card acceptance when ordering.
Bring back a story: one wide view, one little detail and one photo with you actually in it. Put the phone away for part of the day, too.
Dutch-side beach day or French-side wander?
Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.
Tell me on Instagram ↗PORT IDEA 02 / 05
Barbados: saltwater, then something delicious
Make the day work
Ask whether the quoted outing includes port transfers, admission and equipment. Conditions decide whether a swim happens. Wildlife sightings are a possibility, never a promise.
Bring back a story: one wide view, one little detail and one photo with you actually in it. Put the phone away for part of the day, too.
A swim first, or straight to lunch?
Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.
Tell me on Instagram ↗PORT IDEA 03 / 05
St. Lucia: pick a coast, enjoy the day
Make the day work
Confirm that pickup is from your actual cruise berth. Long transfers, road conditions and boat schedules matter here. Ask about steps and walking requirements before paying.
Bring back a story: one wide view, one little detail and one photo with you actually in it. Put the phone away for part of the day, too.
Pitons scenery or a northern beach day?
Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.
Tell me on Instagram ↗PORT IDEA 04 / 05
Martinique: bonjour is a good beginning
Make the day work
Bring some euros and check card acceptance. Do not assume a boat departure elsewhere on the island is near the cruise terminal. Give each transfer its own time allowance.
Bring back a story: one wide view, one little detail and one photo with you actually in it. Put the phone away for part of the day, too.
Garden greens or a pastry in town?
Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.
Tell me on Instagram ↗PORT IDEA 05 / 05
St. Kitts: good views, no pier sprint
Make the day work
Check your actual all-aboard time before booking. A Nevis outing introduces another crossing. For a short call, choose an excursion with a clear return plan or stay on St. Kitts.
Bring back a story: one wide view, one little detail and one photo with you actually in it. Put the phone away for part of the day, too.
Fortress views or feet in the sand?
Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.
Tell me on Instagram ↗Before you head down the gangway.
Screenshot the ship’s local contact details and confirm ship time. Bring the identification the ship requests, your key band, water and sun protection. Agree a return pickup and build in time for traffic and the walk back aboard.
Compare the whole cost: transport, admission, food, equipment and cancellation terms if the ship changes its call. For complicated transfers, compare a coordinated Shore Thing. Ask about accessibility and swimming requirements directly.
For documents and destination entry instructions, check Virgin’s current travel requirements for your nationality and sailing.
If you’d like a personal recommendation for planning help
My friends Samantha Robichaud and Kelly Roma at Fabulous Adventures Travel are people I’m happy to recommend if you’d like help arranging your own trip.
Same ship. More stories.
The ports are only part of it. I’m coming back for the people, the shows, the long dinners and the next story at Squid Ink. Follow along as these plans become memories.
Join The Logbook ↗ Follow @vv.sailor.mark ↗