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Featured image for Bermuda & Caribbean: NYC to San Juan aboard Valiant Lady
Cruise
Bermuda & Caribbean: NYC to San Juan aboard Valiant Lady
Board in Port of New York City, New York , USA on Monday, October 19, 2026 for a Bermuda itinerary visiting New York City, New York , USA, Royal Naval Dockyard, Bermuda, The Beach Club at Bimini, Bahamas, St. Croix, U.S. Virgin Islands, Philipsburg, St. Maarten, Tortola, British Virgin Islands, and San Juan, Puerto Rico, USA, with recent cabin pricing captured as low as $2,136 per cabin for two sailors.
As low as $2,136 per cabin
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Rachael Roberts
SOLD AND SERVICED BY
Rachael Roberts
LAST UPDATED ON
June 12, 2026

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Departure

  • Port of New York City, New York , USA

Destination

  • Port of San Juan, Puerto Rico, USA

Voyage at a glance

12-night Bermuda & Caribbean sailing aboard Valiant Lady.

ShipValiant Lady
Sailing datesMonday, October 19, 2026 – Saturday, October 31, 2026
RoutePort of New York City, New York, USA → Port of San Juan, Puerto Rico, USA
Featured stopsRoyal Naval Dockyard, Bermuda · The Beach Club at Bimini, Bahamas · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · Tortola, British Virgin Islands
Recently found from$2,136 per cabin for two sailors

This 12-night one-way escape departs from New York, sailing to Bermuda for two full days before heading to our exclusive Beach Club at Bimini. Then, explore St. Croix's verdant rainforests, the stunning beaches of St. Maarten, and the wondrous beauty overlooking the peaks of Tortola, before ending your journey in the vibrant streets of San Juan.

Itinerary Overview

Day 1 – Monday, October 19, 2026 · New York City, New York , USA

Departure from New York City, New York , USA

Departs 5:00 PM

Board in New York City, New York , USA, settle into the ship, and get ready for sailaway around 5:00 PM.

  • Boarding
  • Dining
  • Entertainment
Day 2 – Tuesday · Sailing

Sailing

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

  • Sailing
  • Dining
  • Entertainment
  • Spa & Fitness
Day 3 – Wednesday · Royal Naval Dockyard, Bermuda

Port day: Royal Naval Dockyard, Bermuda

Arrives 4:00 PM

Arrive in Royal Naval Dockyard, Bermuda around 4:00 PM with time to explore the destination. If there's one thing you must do in this quaint tropical paradise, dip your toes in the pink sand before you leave.

  • Excursions
  • Food
  • Shopping
Day 4 – Thursday · Royal Naval Dockyard, Bermuda

Port day: Royal Naval Dockyard, Bermuda

Departs 4:00 PM

Enjoy Royal Naval Dockyard, Bermuda before the scheduled 4:00 PM departure. If there's one thing you must do in this quaint tropical paradise, dip your toes in the pink sand before you leave.

  • Excursions
  • Food
  • Shopping
Day 5 – Friday · 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 – 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 7 – Sunday · The Beach Club at Bimini, Bahamas

Port day: The Beach Club at Bimini, Bahamas

8:00 AM – 6:00 PM

Arrive in The Beach Club at Bimini, Bahamas around 8:00 AM and enjoy the port before the scheduled 6:00 PM departure. Besides exploring the islands' incredible biodiversity, relax at our private beach club experience, Virgin Voyages Beach Club at Bimini.

  • Excursions
  • Beach Day
  • Food
  • Shopping
Day 8 – 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 9 – Tuesday · Sailing

Sailing

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

  • Sailing
  • Dining
  • Entertainment
  • Spa & Fitness
Day 10 – Wednesday · St. Croix, U.S. Virgin Islands

Port day: St. Croix, U.S. Virgin Islands

9:00 AM – 6:00 PM

Arrive in St. Croix, U.S. Virgin Islands around 9:00 AM and enjoy the port before the scheduled 6:00 PM departure. St. Croix — whose charm is characterised by lush mountains, lively waters, and a rich history where piracy, art, and a mixture of cultures intertwine.

  • Excursions
  • Food
  • Shopping
Day 11 – Thursday · Philipsburg, St. Maarten

Port day: Philipsburg, St. Maarten

8:00 AM – 6:00 PM

Arrive in Philipsburg, St. Maarten around 8:00 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 12 – Friday · 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 13 – Saturday, October 31, 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 New York City, New York , USA for an exciting 12-night Bermuda cruise visiting New York City, New York , USA, Royal Naval Dockyard, Bermuda, The Beach Club at Bimini, Bahamas, St. Croix, U.S. Virgin Islands, Philipsburg, St. Maarten, Tortola, British Virgin Islands, and San Juan, Puerto Rico, USA.
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 $2,136 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 $2,136 per cabin
    Limited-time savings shown at last check: 32% off
  • Sea ViewRecently found from $2,376 per cabin
    Limited-time savings shown at last check: 30% off
  • Sea TerraceRecently found from $2,616 per cabin
    Limited-time savings shown at last check: 40% off
  • Rockstar QuartersRecently found from $10,056 per cabin
  • Mega Rockstar QuartersRecently found from $16,800 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

allcruisesbermudavaliant-ladyoct2026