Scarlet Lady Winter 2027–2028 Preview: Southern Caribbean Sailings
Preview Scarlet Lady’s Winter 2027 to 2028 season from San Juan with Southern Caribbean voyages and a Halloween Transatlantic, on sale February 19.
Scarlet Lady’s Winter 2027–2028 season from San Juan includes Southern Caribbean sailings and a Halloween Transatlantic, on sale February 19.
Virgin Voyages has confirmed that Scarlet Lady will return to San Juan for Winter 2027–2028, offering a full season of Southern Caribbean itineraries.
These voyages go on sale on February 19, 2026. As expected, the deployment includes a mix of 6, 7, 8 and 12 night sailings, plus a Halloween Transatlantic crossing from Barcelona to Puerto Rico.
San Juan Homeport for Winter 2027–2028
Scarlet Lady will once again homeport in San Juan, Puerto Rico, giving access to longer Southern Caribbean routes that are not typically possible from Miami.
This allows for deeper Caribbean itineraries including Aruba, Curaçao, Barbados, Dominica, St. Lucia, Antigua, St. Maarten, Tortola and more. The season begins with a 12 night repositioning voyage.
Full Scarlet Lady Winter 2027–2028 Schedule
Below is the full deployment based on the official preview document. Register for interest using the links below, we’ll be in touch with more details soon!
| Start Date | Nights | Itinerary | Ports of Call |
|---|---|---|---|
| Oct 31, 2027 | 12 | Halloween Transatlantic from Spain | Barcelona | At Sea | Tangier | At Sea | Lanzarote | At Sea | At Sea | At Sea | At Sea | At Sea | At Sea | At Sea | San Juan |
| Nov 12, 2027 | 8 | Southern Caribbean Cruise | San Juan | Tortola | Basseterre | At Sea | Bridgetown | Castries | Roseau | Philipsburg | San Juan |
| Nov 20, 2027 | 7 | Southern Caribbean & Aruban Nights | San Juan | At Sea | Oranjestad | Willemstad | At Sea | St. John’s | Philipsburg | San Juan |
| Nov 27, 2027 | 7 | Southern Caribbean Cruise | San Juan | Tortola | At Sea | Bridgetown | Castries | Roseau | Philipsburg | San Juan |
| Dec 11, 2027 | 7 | Southern Caribbean & Aruban Nights | San Juan | Philipsburg | St. John’s | Castries | At Sea | Oranjestad | At Sea | San Juan |
| Dec 18, 2027 | 8 | Southern Caribbean & Aruban Holidays | San Juan | Philipsburg | St. John’s | Roseau | At Sea | Oranjestad | Willemstad | At Sea | San Juan |
| Dec 26, 2027 | 7 | Southern Caribbean Cruise New Year’s | San Juan | Philipsburg | At Sea | Bridgetown | Fort-de-France | St. John’s | St. Thomas | San Juan |
| Jan 2, 2028 | 6 | Southern Caribbean Cruise | San Juan | At Sea | Kingstown | Bridgetown | Roseau | Philipsburg | San Juan |
| Jan 15, 2028 | 7 | Southern Caribbean Cruise | San Juan | St. Thomas | At Sea | Bridgetown | Kingstown | St. John’s | Philipsburg | San Juan |
| Jan 22, 2028 | 7 | Southern Caribbean & Aruban Nights | San Juan | At Sea | Oranjestad | At Sea | Castries | St. John’s | Philipsburg | San Juan |
| Jan 29, 2028 | 7 | Southern Caribbean Cruise | San Juan | Philipsburg | At Sea | Bridgetown | Fort-de-France | Basseterre | St. Thomas | San Juan |
| Feb 12, 2028 | 7 | Southern Caribbean Cruise | San Juan | St. Thomas | At Sea | Bridgetown | Castries | St. John’s | Philipsburg | San Juan |
| Mar 11, 2028 | 7 | Southern Caribbean Cruise | San Juan | St. Thomas | At Sea | Bridgetown | Fort-de-France | Roseau | Philipsburg | San Juan |
Release Overview
San Juan departures allow for more varied and port intensive Caribbean itineraries compared to traditional Florida sailings. Aruba and Curaçao feature heavily, and there are multiple Barbados and Dominica calls across the season.
The 6 night option in January provides a slightly shorter alternative, while holiday sailings cover both Christmas and New Year’s.
Booking with VV Insider
These voyages go on sale February 19, 2026.
If you are considering one of these sailings, especially the Halloween Transatlantic or holiday departures, we recommend registering early interest.
When booking with VV Insider, we can offer our “Sail Forward” Sailor Loot on eligible sailings, plus your booking also includes access to the Red Diamond Club, a VV Insider Program offering perks like ad-free content, our loyalty system and personalized planning.
We can also help coordinate groups and Circles if you are traveling with friends or family.
Register your Interest for each itinerary visa the links above.
Overview
Scarlet Lady’s Winter 2027–2028 season continues Virgin Voyages’ focus on Southern Caribbean itineraries from San Juan. With a Transatlantic crossing, holiday sailings and multiple Aruba and Barbados routes, this is one of the most diverse winter deployments in the fleet.
Look out for further deployment releases throughout March, for more details click here.
