Cruise
Southern Caribbean & Aruban Holidays aboard Scarlet Lady
Board in Port of San Juan, Puerto Rico, USA on Saturday, December 18, 2027 for a Southern Caribbean itinerary visiting San Juan, Puerto Rico, USA, Philipsburg, St. Maarten, St. John's, Antigua, Roseau, Dominica, Oranjestad, Aruba, and Willemstad, Curaçao, with recent cabin pricing captured as low as $2,224 per cabin for two sailors.
As low as $2,224 per cabin
Check Availability & Book →
SOLD AND SERVICED BY
Rachael Roberts
Woodspring Travel, LLC
LAST UPDATED ON
June 12, 2026
Share this webpage with others
Share buttons open the selected service with a tracked Woodspring Travel deal link. Some services may require you to sign in before posting.
Voyage at a glance
8-night Caribbean sailing aboard Scarlet Lady.
ShipScarlet Lady
Sailing datesSaturday, December 18, 2027 – Sunday, December 26, 2027
RouteRound trip from Port of San Juan, Puerto Rico, USA
Featured stopsPhilipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Oranjestad, Aruba · Willemstad, Curaçao
Recently found from$2,224 per cabin for two sailors
This 8-night Southern Caribbean holiday voyage departs San Juan, stopping in Philipsburg, St. Maarten and St. Johns, Antigua before exploring the lush landscapes of Roseau, Dominica. After a day at sea, you'll soak up the vibrant vibes of Oranjestad, wander colorful Willemstad, then enjoy one final sea day before returning to San Juan.
Itinerary Overview
🛳️
Day 1 – Saturday, December 18, 2027 · 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 · Philipsburg, St. Maarten
Port day: Philipsburg, St. Maarten
9:00 AM – 6:00 PM
Arrive in Philipsburg, St. Maarten around 9:00 AM and enjoy the port before the scheduled 6:00 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 3 – Monday · St. John's, Antigua
Port day: St. John's, Antigua
9:00 AM – 6:00 PM
Arrive in St. John's, Antigua around 9:00 AM and enjoy the port before the scheduled 6:00 PM departure. Home to 365 white sandy beaches, this Antiguan city is perfect for beachside lounging, snorkeling, or hiking up to Fort Barrington for panoramic views of the island.
- Excursions
- Beach Day
- Food
- Shopping
📍
Day 4 – Tuesday · Roseau, Dominica
Port day: Roseau, Dominica
8:00 AM – 6:00 PM
Arrive in Roseau, Dominica around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. Surrounded by jungles, spend your time immersing yourself in the 350+ rivers, impressive waterfalls and verdant landscapes.
🚢
Day 5 – Wednesday · Sailing
Sailing
Enjoy a full day of sailing with time for dining, entertainment, ocean views, and relaxing onboard.
- Sailing
- Dining
- Entertainment
- Spa & Fitness
📍
Day 6 – Thursday · Oranjestad, Aruba
Port day: Oranjestad, Aruba
8:00 AM – 8:00 PM
Arrive in Oranjestad, Aruba around 8:00 AM and enjoy the port before the scheduled 8:00 PM departure. Known as "One Happy Island", Aruba is home to electric-colored architecture uncrowded beaches, and crystal-clear water perfect for a diving glimpse of the marine life.
- Excursions
- Beach Day
- Food
- Shopping
📍
Day 7 – Friday · Willemstad, Curaçao
Port day: Willemstad, Curaçao
8:00 AM – 6:00 PM
Arrive in Willemstad, Curaçao around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. A little piece of Europe at the edge of the Caribbean, Curaçao delivers a delightful Dutch vibe with picturesque weather, pristine beaches, and relaxing essence.
- Excursions
- Beach Day
- Food
- Shopping
🚢
Day 8 – Saturday · Sailing
Sailing
Enjoy a full day of sailing with time for dining, entertainment, ocean views, and relaxing onboard.
- Sailing
- Dining
- Entertainment
- Spa & Fitness
🛳️
Day 9 – Sunday, December 26, 2027 · 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 8-night Southern Caribbean cruise visiting San Juan, Puerto Rico, USA, Philipsburg, St. Maarten, St. John's, Antigua, Roseau, Dominica, Oranjestad, Aruba, and Willemstad, Curaçao.
✨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 $2,224 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 $2,224 per cabin
Limited-time savings shown at last check: 35% offSea ViewRecently found from $2,544 per cabin
Limited-time savings shown at last check: 38% offSea TerraceRecently found from $3,184 per cabin
Limited-time savings shown at last check: 40% offRockstar QuartersRecently found from $9,920 per cabin
Mega Rockstar QuartersRecently found from $13,600 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.
Gallery
View of Vigin Voyages ship
❮
❯
Tags
allcruisessouthern-caribbeanscarlet-ladydec2027
Report a legal concern about this deal
