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Cunard Line

Queen Elizabeth • Cunard Line

21-night Eastern Caribbean Loop via San Juan, Cruz Bay, Saint John & Castries

Oct 15, 2026 → Nov 5, 2026 • Miami ↔

Lowest in 30 days $645 below typical

From $2,090

$100/night

Great deal

↓24% below typical

Royal Caribbean International

Vision of the Seas • Royal Caribbean International

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

Dec 13, 2026 → Dec 20, 2026 • San Juan ↔

Lowest in 180 days $134 below typical ↘ Trending down

From $550

$79/night

Good value

↓20% below typical

MSC Cruises

MSC Opera • MSC Cruises

25-night Itinerary ITLIV-ITGOA-FRMRS-ESBCN-MATNG-AGANU-SXPHI-KNBAS-DOLRM-DOCAI-BBBGI-MQFDF-GPPTP-VGRAD

Oct 29, 2026 → Nov 23, 2026 • Civitavecchia (Rome) → La Romana

$695 below typical ↗ Trending up

From $1,766

$71/night

Great deal

↓28% below 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

Oct 3, 2026 → Oct 10, 2026 • San Juan ↔

Lowest in 90 days $136 below typical ↘ Trending down

From $576

$82/night

Good value

↓19% below typical

Carnival Cruise Line

Carnival Firenze • Carnival Cruise Line

10-night Eastern Caribbean Loop via San Juan, Frederiksted, Saint Croix & Basseterre, Saint Kitts

Feb 26, 2027 → Mar 8, 2027 • Miami ↔

$239 below typical ↘ Trending down

From $579

$58/night

Great deal

↓29% below typical

Cunard Line

Queen Elizabeth • Cunard Line

21-night Eastern Caribbean Loop via Grand Turk Island, Willemstad & Cruz Bay, Saint John

Oct 27, 2026 → Nov 17, 2026 • Miami ↔

Lowest in 30 days $635 below typical

From $2,100

$100/night

Great deal

↓23% below typical

Royal Caribbean International

Harmony of the Seas • Royal Caribbean International

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

May 15, 2027 → May 22, 2027 • Port Canaveral ↔

Lowest in 180 days $312 below typical ↘ Trending down

From $1,098

$157/night

Great deal

↓22% below typical

Princess Cruises

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Jan 16, 2027 → Jan 26, 2027 • Fort Lauderdale ↔

Lowest in 30 days $219 below typical

From $973

$97/night

Good value

↓18% below typical

Princess Cruises

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Mar 27, 2027 → Apr 6, 2027 • Fort Lauderdale ↔

Lowest in 30 days $323 below typical

From $1,143

$114/night

Great deal

↓22% below typical

Silversea Cruises

Silver Nova • Silversea Cruises

15-night Eastern Caribbean Arc via Gibraltar & Philipsburg

Dec 3, 2027 → Dec 18, 2027 • Lisboa → Miami

$3,045 below typical

From $8,000

$533/night

Great deal

↓28% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Jan 8, 2027 → Jan 15, 2027 • Bridgetown ↔

$467 below typical

From $1,194

$171/night

Great deal

↓28% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Feb 19, 2027 → Feb 26, 2027 • Bridgetown ↔

$467 below typical

From $1,194

$171/night

Great deal

↓28% below typical

Celebrity Cruises

Celebrity Xcel • Celebrity Cruises

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

Mar 12, 2028 → Mar 19, 2028 • Fort Lauderdale ↔

Lowest in 90 days $212 below typical

From $962

$137/night

Good value

↓18% below typical

Princess Cruises

Coral Princess • Princess Cruises

10-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

Nov 18, 2026 → Nov 28, 2026 • Fort Lauderdale ↔

$378 below typical

From $1,044

$104/night

Great deal

↓27% below typical

Royal Caribbean International

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Jan 16, 2027 → Jan 23, 2027 • Miami ↔

Lowest in 180 days $273 below typical

From $1,344

$192/night

Good value

↓17% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

$284 below typical

From $788

$113/night

Great deal

↓26% below typical

MSC Cruises

MSC World Europa • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Jan 30, 2027 → Feb 6, 2027 • Fort-de-France ↔

Lowest in 180 days $307 below typical ↘ Trending down

From $643

$92/night

Great deal

↓32% below typical

Princess Cruises

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Apr 6, 2027 → Apr 16, 2027 • Fort Lauderdale ↔

Lowest in 30 days $313 below typical

From $1,153

$115/night

Great deal

↓21% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 10, 2027 → Jan 17, 2027 • San Juan ↔

Lowest in 180 days $174 below typical

From $738

$105/night

Good value

↓19% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Feb 21, 2027 → Feb 28, 2027 • San Juan ↔

Lowest in 180 days $174 below typical

From $738

$105/night

Good value

↓19% below typical

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