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Valiant Lady · Voyage 04 / 09 · Planning guide

Eight nights of island time.

Nov 20 to 28 · 2026 · From San Juan

Eight nights gives this week a little breathing room. Let’s use it for a few proper adventures and a few very unhurried lunches.

Illustrated Caribbean voyage inspiration

Illustrated inspiration, not a photograph of these ports.

Plans now. Memories after we sail.

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.

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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

My plan to consider

Choose Magens Bay for a straightforward beach outing. Arrange transport both ways and ask what admission, chairs and facilities will cost before committing.

A different kind of day

Stay with Charlotte Amalie for a town stroll and lunch. Confirm the actual berth first, then choose a taxi or walking route that suits the day.

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 ↗

Official destination or attraction information ↗

PORT IDEA 02 / 05

Curaçao: color first, camera second

My plan to consider

Explore Willemstad at an unhurried pace, making space for the waterfront, street details and a local lunch. Pick a direction rather than collecting every neighborhood.

A different kind of day

On another call, consider a beach day at Blue Bay or a west-coast outing. Choose a single beach or a defined tour route and check access arrangements.

Make the day work

Confirm transfers, beach admission and chair charges separately. If you see turtles, let them approach and leave freely. No chasing, feeding or touching for a photograph.

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.

Colorful streets or turquoise water?

Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.

Tell me on Instagram ↗

Official destination or attraction information ↗

PORT IDEA 03 / 05

Aruba: the hammock has competition

My plan to consider

Make Eagle Beach your main outing. A simple beach day leaves room to enjoy the island rather than watching the clock between activities.

A different kind of day

Keep it local with Oranjestad and a relaxed lunch, or choose a prebooked boat trip with confirmed port-compatible timings.

Make the day work

Beach operators may meet away from the cruise terminal. Include check-in and transfers in the day. A sunset outing only works if its return fits the confirmed all-aboard deadline.

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 chair or a boat with a view?

Which would you choose? Tag @vv.sailor.mark in your port-day Story so I can see your version.

Tell me on Instagram ↗

Official destination or attraction information ↗

PORT IDEA 04 / 05

St. Kitts: good views, no pier sprint

My plan to consider

Choose a scenic island outing around Brimstone Hill, with transport and current visitor access confirmed. Ask about slopes and steps before deciding it is your kind of day.

A different kind of day

For a slower visit, consider Cockleshell Bay with a taxi pickup arranged in advance. Beach, lunch and the view can be enough.

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 ↗

Official destination or attraction information ↗

PORT IDEA 05 / 05

St. Maarten: one island, plenty of opinions

My plan to consider

Keep the first visit simple: Philipsburg, the Great Bay waterfront and a long lunch. Pick a beach chair only after asking exactly what the package includes.

A different kind of day

On a repeat call, consider Marigot on the French side with a driver and a confirmed pickup. Choose that as the main outing rather than adding an island circuit.

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 ↗

Official destination or attraction information ↗

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.

Meet Fabulous Adventures Travel ↗ · Samantha on Instagram ↗

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.

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