Jibhop

Iona • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Dec 10, 2027 → Dec 24, 2027 • Bridgetown ↔

From $1,796

$1,796 · $128/night · great deal · ↓20% below typical

$128/night

Great deal

↓20% below typical

Vista

14-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas, Tortola & Cruz Bay, Saint John

Oct 28, 2026 → Nov 11, 2026 • New York → Miami

$681 below typical

From $5,349

$5,349 · $382/night · good value · ↓11% below typical

$382/night

Good value

↓11% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jun 12, 2027 → Jun 19, 2027 • San Juan ↔

Lowest in 30 days

From $956

$956 · $137/night · typical price · ↓5% below typical

$137/night

Typical price

↓5% below typical

Crown Princess • Princess Cruises

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

Feb 21, 2027 → Mar 7, 2027 • San Juan ↔

From $1,426

$1,426 · $102/night · great deal · ↓25% below typical

$102/night

Great deal

↓25% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Fort-de-France & Saint-Barthélemy

Feb 5, 2028 → Feb 17, 2028 • Bridgetown ↔

From $7,100

$7,100 · $592/night · great deal · ↓21% below typical

$592/night

Great deal

↓21% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Oranjestad

Feb 17, 2028 → Feb 29, 2028 • Bridgetown ↔

From $7,100

$7,100 · $592/night · great deal · ↓21% below typical

$592/night

Great deal

↓21% below typical

Star Princess • Princess Cruises

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

Dec 12, 2027 → Dec 22, 2027 • Port Canaveral ↔

25% below typical

From $937

$937 · $94/night · great deal · ↓25% below typical

$94/night

Great deal

↓25% below typical

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Bridgetown

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

Lowest in 30 days

From $1,419

$1,419 · $203/night · typical price · ↓5% below typical

$203/night

Typical price

↓5% below typical

Emerald Princess • Princess Cruises

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

Dec 5, 2027 → Dec 19, 2027 • San Juan ↔

20% below typical

From $1,566

$1,566 · $112/night · great deal · ↓20% below typical

$112/night

Great deal

↓20% below typical

Seabourn Ovation • Seabourn

19-night Southern Caribbean Crossing via Tortola, South Friars Bay & Les Trois-Îlets

Mar 18, 2028 → Apr 6, 2028 • Philipsburg → Lisboa

$1,228 below typical ↗

From $9,898

$9,898 · $521/night · good value · ↓11% below typical

$521/night

Good value

↓11% below typical

Crown Princess • Princess Cruises

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

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

20% below typical

From $738

$738 · $105/night · good value · ↓20% below typical

$105/night

Good value

↓20% below typical

Crown Princess • Princess Cruises

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

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

20% below typical

From $738

$738 · $105/night · good value · ↓20% below typical

$105/night

Good value

↓20% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days

From $1,036

$1,036 · $148/night · typical price · ↓4% below typical

$148/night

Typical price

↓4% below typical

Vista

14-night Southern Caribbean Loop via Georgetown, South Carolina, Falmouth & Oranjestad

Nov 11, 2026 → Nov 25, 2026 • Miami ↔

$631 below typical ↗

From $5,399

$5,399 · $386/night · good value · ↓10% below typical

$386/night

Good value

↓10% below typical

Silver Spirit • Silversea Cruises

11-night Southern Caribbean Loop via Port Elizabeth, Bequia, Saint George's & Willemstad

Feb 29, 2028 → Mar 11, 2028 • Bridgetown ↔

From $6,600

$6,600 · $600/night · great deal · ↓20% below typical

$600/night

Great deal

↓20% below typical

Oceania Vista • Oceania Cruises

14-night New York → Charlotte Amalie, Saint Thomas → Tortola → Saint John's + 6 more

Oct 28, 2026 → Nov 11, 2026 • New York → Miami

22% below typical

From $4,999

$4,999 · $357/night · great deal · ↓22% below typical

$357/night

Great deal

↓22% below typical

Celebrity Ascent • Celebrity Cruises

10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's

Jan 15, 2027 → Jan 25, 2027 • Fort Lauderdale ↔

$151 below typical ↘

From $1,325

$1,325 · $132/night · good value · ↓10% below typical

$132/night

Good value

↓10% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Philipsburg

Dec 5, 2026 → Dec 19, 2026 • Bridgetown ↔

From $1,931

$1,931 · $138/night · great deal · ↓25% below typical

$138/night

Great deal

↓25% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Tortola

Nov 21, 2026 → Dec 5, 2026 • Bridgetown ↔

16% below typical

From $1,823

$1,823 · $130/night · good value · ↓16% below typical

$130/night

Good value

↓16% below typical

Celebrity Eclipse • Celebrity Cruises

9-night Eastern Caribbean Loop via Saint John's & Castries

Nov 24, 2026 → Dec 3, 2026 • Fort Lauderdale ↔

$138 below typical ↗

From $1,149

$1,149 · $128/night · good value · ↓11% below typical

$128/night

Good value

↓11% below typical