Logo
Woodspring Travel, LLC
Sign In
All Deals
Cruises
Last Minute
January
February
March
April
May
June
July
August
September
October
November
December
Beach Vacations
USA
Caribbean
Mexico
Mediterranean
East Mediterranean
South Florida Metropolitan Area
Europe
Fall
Spring
Summer
Winter
Canada
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 Saturday, November 28, 2026 for a Southern Caribbean itinerary visiting San Juan, Puerto Rico, USA, Charlotte Amalie, St. Thomas, U.S. Virgin Islands, Tortola, British Virgin Islands, Basseterre, St. Kitts and Nevis, St. John's, Antigua, and Philipsburg, St. Maarten, with recent cabin pricing captured as low as $2,086 per cabin for two sailors.
As low as $2,086 per cabin
Check Availability & Book →
♡ SAVE
⇢ SHARE
Rachael Roberts
SOLD AND SERVICED BY
Rachael Roberts
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

7-night Caribbean sailing aboard Valiant Lady.

ShipValiant Lady
Sailing datesSaturday, November 28, 2026 – Saturday, December 5, 2026
RouteRound trip from Port of San Juan, Puerto Rico, USA
Featured stopsCharlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, British Virgin Islands · Basseterre, St. Kitts and Nevis · St. John's, Antigua · Philipsburg, St. Maarten
Recently found from$2,086 per cabin for two sailors

This 7-night pre-holiday sailing departs San Juan, docking the next day on the colorful shores with picturesque waters of St. Thomas, US Virgin Islands. Next sail over to Tortola, followed by the bustling beach town of Basseterre, St. Kitts and Nevis. Next arrive in the epicenter of paradise, St. John's, Antigua, then over to St. Maarten, before returning to San Juan.

Itinerary Overview

Day 1 – Saturday, November 28, 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 – Sunday · 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 – 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 · Tortola, British Virgin Islands

Port day: Tortola, British Virgin Islands

9:00 AM – 6:00 PM

Arrive in Tortola, British Virgin Islands around 9:00 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 5 – Wednesday · 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 6 – Thursday · St. John's, Antigua

Port day: St. John's, Antigua

8:00 AM – 8:00 PM

Arrive in St. John's, Antigua around 8:00 AM and enjoy the port before the scheduled 8:00 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 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, December 5, 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 7-night Southern Caribbean cruise visiting San Juan, Puerto Rico, USA, Charlotte Amalie, St. Thomas, U.S. Virgin Islands, Tortola, British Virgin Islands, Basseterre, St. Kitts and Nevis, St. John's, Antigua, 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 $2,086 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 $2,086 per cabin
    Limited-time savings shown at last check: 34% off
  • Sea ViewRecently found from $2,478 per cabin
    Limited-time savings shown at last check: 32% off
  • Sea TerraceRecently found from $2,226 per cabin
    Limited-time savings shown at last check: 40% off
  • Rockstar QuartersRecently found from $5,726 per cabin
  • Mega Rockstar QuartersRecently found from $8,526 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.

Tags

allcruisessouthern-caribbeanvaliant-ladynov2026