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Home > Travel > Deals
Featured image for Southern Caribbean Cruise aboard Valiant Lady
Cruise
Southern Caribbean Cruise aboard Valiant Lady
Board in Port of San Juan, Puerto Rico, USA on Friday, November 20, 2026 for a Southern Caribbean itinerary visiting San Juan, Puerto Rico, USA, Charlotte Amalie, St. Thomas, U.S. Virgin Islands, Willemstad, Curaçao, Oranjestad, Aruba, Basseterre, St. Kitts and Nevis, and Philipsburg, St. Maarten, with recent cabin pricing captured as low as $2,602 per cabin for two sailors.
As low as $2,602 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 Valiant Lady.

ShipValiant Lady
Sailing datesFriday, November 20, 2026 – Saturday, November 28, 2026
RouteRound trip from Port of San Juan, Puerto Rico, USA
Featured stopsCharlotte Amalie, St. Thomas, U.S. Virgin Islands · Willemstad, Curaçao · Oranjestad, Aruba · Basseterre, St. Kitts and Nevis · Philipsburg, St. Maarten
Recently found from$2,602 per cabin for two sailors

This 8-night Thanksgiving sailing departs from San Juan, first docking at the stunning St. Thomas, U.S. Virgin Islands. After a day at sea, arrive in Willemstad, Curaçao's capital that combines European influences with Caribbean cultures (and vibrant architecture). Next, wake up in Aruba, followed by sailing to St. Kitts and Nevis, then on to St. Maarten, before returning to San Juan.

Board Valiant Lady in Port of San Juan, Puerto Rico, USA on Friday, November 20, 2026 and debark in Port of San Juan, Puerto Rico, USA on Saturday, November 28, 2026. Recent pricing was captured as low as $2,602 per cabin for two sailors.

Itinerary Overview

Day 1 – Friday, November 20, 2026 · San Juan, Puerto Rico, USA

Departure from San Juan, Puerto Rico, USA

Departs 8:00 PM

Board in San Juan, Puerto Rico, USA, settle into the ship, and get ready for sailaway around 8:00 PM.

  • Boarding
  • Dining
  • Entertainment
Day 2 – Saturday · Charlotte Amalie, St. Thomas, U.S. Virgin Islands

Port day: Charlotte Amalie, St. Thomas, U.S. Virgin Islands

8:00 AM – 6:00 PM

Arrive in Charlotte Amalie, St. Thomas, U.S. Virgin Islands around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. Charlotte Amalie is a dynamic Caribbean city nestled into the lush landscapes of the renowned island of St. Thomas.

  • Excursions
  • Food
  • Shopping
Day 3 – Sunday · 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 – Monday · Willemstad, Curaçao

Port day: Willemstad, Curaçao

9:00 AM – 7:00 PM

Arrive in Willemstad, Curaçao around 9:00 AM and enjoy the port before the scheduled 7:00 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 5 – Tuesday · Oranjestad, Aruba

Port day: Oranjestad, Aruba

9:00 AM – 10:00 PM

Arrive in Oranjestad, Aruba around 9:00 AM and enjoy the port before the scheduled 10:00 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 6 – 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 7 – Thursday · Basseterre, St. Kitts and Nevis

Port day: Basseterre, St. Kitts and Nevis

8:00 AM – 6:00 PM

Arrive in Basseterre, St. Kitts and Nevis around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. From rum tastings and beach hangs to rainforest explorations and catamarans to Nevis, the capital of St. Kitts' social scene revolves around good living and chat.

  • Excursions
  • Beach Day
  • Food
  • Shopping
Day 8 – 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 9 – Saturday, November 28, 2026 · 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 Valiant Lady in Port of San Juan, Puerto Rico, USA for an exciting 8-night Southern Caribbean cruise visiting San Juan, Puerto Rico, USA, Charlotte Amalie, St. Thomas, U.S. Virgin Islands, Willemstad, Curaçao, Oranjestad, Aruba, Basseterre, St. Kitts and Nevis, 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 $2,602 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 $2,602 per cabin
    Limited-time savings shown at last check: 31% off
  • Sea ViewRecently found from $3,024 per cabin
    Limited-time savings shown at last check: 35% off
  • Sea TerraceRecently found from $3,344 per cabin
    Limited-time savings shown at last check: 41% off
  • Rockstar QuartersRecently found from $9,104 per cabin
  • Mega Rockstar QuartersRecently found from $16,304 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-caribbeanvaliant-ladynov2026

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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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