Virgin Voyages

Valiant Lady • Virgin Voyages

8-night ABC Islands Loop via Oranjestad, Willemstad & Kralendijk

Jan 29, 2027 → Feb 6, 2027 • San Juan ↔

Lowest in 30 days $160 above typical
$1,272 · $159/night · priced high · ↑14% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

8-night Southern Caribbean Loop via Saint Thomas, Bridgetown & Kingstown

Mar 19, 2027 → Mar 27, 2027 • San Juan ↔

Lowest in 30 days $160 above typical
$1,272 · $159/night · priced high · ↑14% above typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night ABC Islands Loop via Charlotte Amalie, Saint Thomas & Kralendijk

Feb 20, 2028 → Feb 27, 2028 • San Juan ↔

Lowest in 180 days $103 above typical
$834 · $119/night · priced high · ↑14% above typical
Royal Caribbean International

Star of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas

Jun 13, 2027 → Jun 20, 2027 • Port Canaveral ↔

Lowest in 30 days $267 above typical
$2,226 · $318/night · priced high · ↑14% above typical
Virgin Voyages

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Puerto Plata & San Juan

Dec 19, 2026 → Dec 27, 2026 • Miami ↔

Lowest in 90 days $160 above typical
$1,352 · $169/night · priced high · ↑13% above typical
P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Feb 6, 2027 → Feb 20, 2027 • Bridgetown ↔

Lowest in 30 days $308 above typical
$2,607 · $186/night · priced high · ↑13% above typical
Cunard Line

Queen Elizabeth • Cunard Line

26-night Transatlantic Crossing via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 23, 2027 → Jan 18, 2028 • Miami → Southampton

Lowest in 180 days $437 above typical
$3,737 · $144/night · priced high · ↑13% above typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jan 15, 2028 → Jan 22, 2028 • San Juan ↔

Lowest in 180 days $84 above typical
$756 · $108/night · priced high · ↑13% above typical
P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔

Lowest in 30 days $270 above typical
$2,539 · $181/night · priced high · ↑12% above typical
P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Nov 26, 2027 → Dec 10, 2027 • Bridgetown ↔

Lowest in 30 days $212 above typical
$2,026 · $145/night · priced high · ↑12% above typical
P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Nov 27, 2027 → Dec 11, 2027 • Bridgetown ↔

Lowest in 30 days $212 above typical
$2,026 · $145/night · priced high · ↑12% above typical

Vista

9-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas & Saint-Barthélemy

Feb 7, 2029 → Feb 16, 2029 • Miami ↔

Lowest in 180 days $443 above typical
$4,299 · $478/night · priced high · ↑11% above typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Apr 15, 2028 → Apr 22, 2028 • San Juan ↔

Lowest in 180 days $93 above typical
$910 · $130/night · priced high · ↑11% above typical
Carnival Cruise Line

Carnival Magic • Carnival Cruise Line

8-night Eastern Caribbean Loop via Half Moon Cay & San Juan

Mar 11, 2028 → Mar 19, 2028 • Miami ↔

Lowest in 180 days $72 above typical
$746 · $93/night · priced high · ↑11% above typical
Disney Cruise Line

Disney Dream • Disney Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Disney Castaway Cay

Feb 19, 2027 → Feb 26, 2027 • Fort Lauderdale ↔

Lowest in 30 days $223 above typical
$2,363 · $338/night · priced high · ↑10% above typical
Disney Cruise Line

Disney Destiny • Disney Cruise Line

7-night Eastern Caribbean Loop via Lighthouse Point, Florida & San Juan

Dec 12, 2026 → Dec 19, 2026 • Fort Lauderdale ↔

Lowest in 90 days $224 above typical
$2,481 · $354/night · typical price · ↑10% above typical
Oceania Cruises

Oceania Allura • Oceania Cruises

10-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Philipsburg

Dec 2, 2026 → Dec 12, 2026 • Miami ↔

Lowest in 90 days $395 above typical
$4,449 · $445/night · typical price · ↑10% above typical
Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

May 29, 2027 → Jun 5, 2027 • San Juan ↔

Lowest in 180 days $78 above typical
$896 · $128/night · typical price · ↑10% above typical
P&O Cruises

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Roseau

Dec 17, 2027 → Dec 31, 2027 • Bridgetown ↔

Lowest in 30 days $243 above typical
$2,809 · $201/night · typical price · ↑9% above typical
Seabourn

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Arc via Castries, Little Bay & South Friars Bay

Feb 13, 2027 → Feb 27, 2027 • Bridgetown ↔

Lowest in 30 days $899 above typical
$10,398 · $743/night · typical price · ↑9% above typical