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Home > Travel > Deals
Featured image for Southern Caribbean & Aruban Holidays aboard Scarlet Lady
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
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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

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.

  • Excursions
  • Food
  • Shopping
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% off
  • Sea ViewRecently found from $2,544 per cabin
    Limited-time savings shown at last check: 38% off
  • Sea TerraceRecently found from $3,184 per cabin
    Limited-time savings shown at last check: 40% off
  • Rockstar 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.

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allcruisessouthern-caribbeanscarlet-ladydec2027

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Woodspring Travel, LLC is independently owned and operated. Travel services are arranged by Woodspring Travel, LLC, an independent agency affiliated with Nexion, LLC. CST #2071045-50. Fla. Seller of Travel Reg. No. ST38545. Washington UBI #603 046 768. Registration as a seller of travel does not constitute approval by the State of California. For customer service, booking questions, or complaints, please contact Woodspring Travel, LLC directly at contact@woodspringtravel.com.


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