Scarlet Lady Winter 2027–2028 Now On Sale: Southern Caribbean Sailings
Scarlet Lady’s Winter 2027 to 2028 voyages from San Juan, including Southern Caribbean itineraries and a Halloween Transatlantic crossing, are now available to book.
Scarlet Lady’s Winter 2027–2028 season from San Juan includes Southern Caribbean sailings and a Halloween Transatlantic, on sale now.
Virgin Voyages has released the Scarlet Lady San Juan sailings for Winter 2027–2028, offering a full season of Southern Caribbean itineraries.
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. To book with VV Insider use the links below. Booking with us includes additional perks including up to $200 Sail Forward Loot (where applicable) and Red Diamond Club access.
| 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
If you are considering one of these sailings, especially the Halloween Transatlantic or holiday departures, we recommend booking early and utilize pay-in-full for a 10% discount on most cabin types.
When booking with VV Insider, we can offer our up to $200 “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, send us an enquiry.
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.
