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Featured image for Southern Caribbean Cruise aboard Scarlet Lady
Cruise
Southern Caribbean Cruise aboard Scarlet Lady
Board in Port of San Juan, Puerto Rico, USA on Saturday, April 8, 2028 for a Southern Caribbean itinerary visiting San Juan, Puerto Rico, USA, Tortola, British Virgin Islands, Bridgetown, Barbados, Castries, St. Lucia, Roseau, Dominica, and Philipsburg, St. Maarten, with recent cabin pricing captured as low as $1,806 per cabin for two sailors.
As low as $1,806 per cabin
Check Availability & Book →
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Rachael Roberts
SOLD AND SERVICED BY
Rachael Roberts
LAST UPDATED ON
June 12, 2026

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Voyage at a glance

7-night Caribbean sailing aboard Scarlet Lady.

ShipScarlet Lady
Sailing datesSaturday, April 8, 2028 – Saturday, April 15, 2028
RouteRound trip from Port of San Juan, Puerto Rico, USA
Featured stopsTortola, British Virgin Islands · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · Philipsburg, St. Maarten
Recently found from$1,806 per cabin for two sailors

This 7-night Southern Caribbean sailing departs San Juan for a sun-soaked escape to Road Town, Tortola, followed by a relaxing day at sea before exploring Bridgetown, soaking up the beauty of Castries, discovering the lush charm of Roseau, and strolling through Philipsburg, St. Maarten before returning to San Juan.

Itinerary Overview

Day 1 – Saturday, April 8, 2028 · San Juan, Puerto Rico, USA

Departure from San Juan, Puerto Rico, USA

Departs 6:00 PM

Board in San Juan, Puerto Rico, USA, settle into the ship, and get ready for sailaway around 6:00 PM.

  • Boarding
  • Dining
  • Entertainment
Day 2 – Sunday · Tortola, British Virgin Islands

Port day: Tortola, British Virgin Islands

8:00 AM – 6:00 PM

Arrive in Tortola, British Virgin Islands around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. The largest of the British Virgin Islands boasts famed natural wonders like The Baths of Tortola giving way to vibrant reefs and snow-white beaches.

  • Excursions
  • Beach Day
  • Food
  • Shopping
Day 3 – Monday · Sailing

Sailing

Enjoy a full day of sailing with time for dining, entertainment, ocean views, and relaxing onboard.

  • Sailing
  • Dining
  • Entertainment
  • Spa & Fitness
Day 4 – Tuesday · Bridgetown, Barbados

Port day: Bridgetown, Barbados

8:00 AM – 6:00 PM

Arrive in Bridgetown, Barbados around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. Miles of sandy beaches and teal waters meet rhythmic local culture and unbelievably mouth-watering classic dishes in this electric Barbadian city.

  • Excursions
  • Beach Day
  • Food
  • Shopping
Day 5 – Wednesday · Castries, St. Lucia

Port day: Castries, St. Lucia

8:00 AM – 6:00 PM

Arrive in Castries, St. Lucia around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. Visit the sulfur hot springs, hike through the Piton mountains, or soak in the volcanic mud baths — the capital of St Lucia is a sanctuary for outdoor enthusiasts.

  • Excursions
  • Food
  • Shopping
Day 6 – Thursday · Roseau, Dominica

Port day: Roseau, Dominica

8:00 AM – 5:00 PM

Arrive in Roseau, Dominica around 8:00 AM and enjoy the port before the scheduled 5:00 PM departure. Surrounded by jungles, spend your time immersing yourself in the 350+ rivers, impressive waterfalls and verdant landscapes.

  • Excursions
  • Food
  • Shopping
Day 7 – Friday · Philipsburg, St. Maarten

Port day: Philipsburg, St. Maarten

8:00 AM – 5:00 PM

Arrive in Philipsburg, St. Maarten around 8:00 AM and enjoy the port before the scheduled 5:00 PM departure. This vibrant, eclectic city is the ideal place for beach bums, shopaholics, foodies, and outdoor adventure enthusiasts alike.

  • Excursions
  • Beach Day
  • Food
  • Shopping
Day 8 – Saturday, April 15, 2028 · San Juan, Puerto Rico, USA

Arrival in San Juan, Puerto Rico, USA

Arrives 6:30 AM

Arrive back in San Juan, Puerto Rico, USA around 6:30 AM for debarkation. Please allow up to an hour for the Gangway to open to disembark

  • Boarding
  • Dining
  • Entertainment

Highlights

Step aboard Scarlet Lady in Port of San Juan, Puerto Rico, USA for an exciting 7-night Southern Caribbean cruise visiting San Juan, Puerto Rico, USA, Tortola, British Virgin Islands, Bridgetown, Barbados, Castries, St. Lucia, Roseau, Dominica, and Philipsburg, St. Maarten.
This itinerary blends the easy anticipation of sailaway with destination days made for photos, great meals, and unhurried exploring. Expect polished shipboard style, coastal energy, and the kind of pacing that makes the trip feel effortless.
Recent cabin pricing was captured as low as $1,806 per cabin for two sailors, subject to live availability.
Recently found pricing

Cabin pricing snapshot

Recent cabin prices we found for this sailing. Pricing is shown per cabin for two sailors and may change at any time.

Cabin Types
  • InsiderRecently found from $1,806 per cabin
    Limited-time savings shown at last check: 33% off
  • Sea ViewRecently found from $2,086 per cabin
    Limited-time savings shown at last check: 38% off
  • Sea TerraceRecently found from $2,506 per cabin
    Limited-time savings shown at last check: 41% off
  • Rockstar QuartersRecently found from $7,700 per cabin
  • Mega Rockstar QuartersRecently found from $11,060 per cabin

Final taxes, fees, promotions, or availability can change.

Additional Information

This offer availability and pricing is constantly subject to change. We suggest to book this now.

Other sailings to consider:

Tags

allcruisessouthern-caribbeanscarlet-ladyapr2028