Valiant Lady · Voyage 05 / 09 · Planning guide
Familiar faces, fresh plans.
Nov 28 to Dec 5 · 2026 · From San Juan
We’re back among familiar islands. This is the week to try the option you skipped last time, or return to the place that made you smile.
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. Thomas: the beach can be the whole plan
Make the day work
Do not build your return around the last possible taxi. A separate St. John excursion adds ferry connections, so leave that for a day with a clearly workable schedule or a coordinated tour.
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.
Magens Bay or lunch 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 02 / 05
Tortola: a beach day with a return plan
Make the day work
Agree the total taxi fare, exact meeting point and return pickup before you leave. A trip to another island adds ferry or boat connections, so compare a coordinated Shore Thing if that is your priority.
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.
Beach afternoon or a town 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 03 / 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 ↗PORT IDEA 04 / 05
Antigua: history with a harbor view
Make the day work
The dockyard is an outing across the island. Confirm round-trip transport, admission and a return deadline. Check walking surfaces and shade if mobility or heat is a concern.
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.
Harbor history or beach-chair therapy?
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. 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 ↗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 ↗