Jibhop

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Saint George, Kingstown & Fort-de-France

Mar 23, 2027 → Apr 6, 2027 • Bridgetown ↔

From $2,243

$2,243 · $160/night · priced high · ↑59% above typical

$160/night

Priced high

↑59% above typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Tortola & Basseterre, Saint Kitts

Dec 10, 2027 → Dec 17, 2027 • Bridgetown ↔

From $1,538

$1,538 · $220/night · priced high · ↑57% above typical

$220/night

Priced high

↑57% above typical

MSC Seaview • MSC Cruises

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

Dec 19, 2026 → Dec 26, 2026 • Fort-de-France ↔

Great balance

From $1,459

$1,459 · $208/night · priced high · ↑54% above typical

$208/night

Priced high

↑54% above typical

Crown Princess • Princess Cruises

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

Jan 3, 2027 → Jan 8, 2027 • San Juan → Bridgetown

From $857

$857 · $171/night · priced high · ↑50% above typical

$171/night

Priced high

↑50% above typical

Crown Princess • Princess Cruises

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

Jan 3, 2027 → Jan 10, 2027 • San Juan ↔

From $1,189

$1,189 · $170/night · priced high · ↑48% above typical

$170/night

Priced high

↑48% above typical

Emerald Princess • Princess Cruises

8-night Eastern Caribbean Loop via Castries, San Juan & Saint Thomas

Jan 20, 2028 → Jan 28, 2028 • Bridgetown ↔

From $1,539

$1,539 · $192/night · priced high · ↑47% above typical

$192/night

Priced high

↑47% above typical

MSC Seaview • MSC Cruises

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

Mar 27, 2027 → Apr 3, 2027 • Fort-de-France ↔

Great balance

From $1,035

$1,035 · $148/night · priced high · ↑47% above typical

$148/night

Priced high

↑47% above typical

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Mar 9, 2027 → Mar 23, 2027 • Bridgetown ↔

From $1,981

$1,981 · $142/night · priced high · ↑40% above typical

$142/night

Priced high

↑40% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Feb 13, 2027 → Feb 20, 2027 • San Juan ↔

$301 above typical ↗

From $1,054

$1,054 · $151/night · priced high · ↑40% above typical

$151/night

Priced high

↑40% above typical

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Jan 12, 2027 → Jan 23, 2027 • Fort Lauderdale ↔

$464 above typical ↗

From $1,734

$1,734 · $158/night · priced high · ↑37% above typical

$158/night

Priced high

↑37% above typical

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Castries

Dec 29, 2026 → Jan 12, 2027 • Bridgetown ↔

From $2,621

$2,621 · $187/night · priced high · ↑34% above typical

$187/night

Priced high

↑34% above typical

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via Saint Thomas, Bridgetown & Castries

Nov 24, 2028 → Dec 15, 2028 • New York → Southampton

$1,118 above typical

From $4,402

$4,402 · $210/night · priced high · ↑34% above typical

$210/night

Priced high

↑34% above typical

MSC World Europa • MSC Cruises

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

Dec 19, 2026 → Dec 26, 2026 • Fort-de-France ↔

Great balance

From $1,251

$1,251 · $179/night · priced high · ↑32% above typical

$179/night

Priced high

↑32% above typical

Crown Princess • Princess Cruises

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

Feb 5, 2027 → Feb 12, 2027 • Bridgetown ↔

From $1,238

$1,238 · $177/night · priced high · ↑31% above typical

$177/night

Priced high

↑31% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau

Jan 16, 2027 → Jan 23, 2027 • San Juan ↔

$213 above typical ↗

From $916

$916 · $131/night · priced high · ↑30% above typical

$131/night

Priced high

↑30% above typical

Vision of the Seas • Royal Caribbean International

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

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

$183 above typical ↘

From $882

$882 · $126/night · priced high · ↑26% above typical

$126/night

Priced high

↑26% above typical

Crown Princess • Princess Cruises

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

Mar 12, 2027 → Mar 19, 2027 • Bridgetown ↔

Great balance

From $1,244

$1,244 · $178/night · priced high · ↑23% above typical

$178/night

Priced high

↑23% above typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Roseau & Antigua

Dec 19, 2026 → Dec 29, 2026 • Miami ↔

From $8,672

$8,672 · $867/night · priced high · ↑23% above typical

$867/night

Priced high

↑23% above typical

Seven Seas Prestige • Regent Seven Seas Cruises

12-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau

Mar 5, 2027 → Mar 17, 2027 • Miami ↔

From $10,484

$10,484 · $874/night · priced high · ↑23% above typical

$874/night

Priced high

↑23% above typical

MSC Seaview • MSC Cruises

7-night Eastern Caribbean Loop via Philipsburg, Saint John's & Basseterre, Saint Kitts

Mar 14, 2027 → Mar 21, 2027 • Pointe-à-Pitre ↔

Great balance

From $863

$863 · $123/night · priced high · ↑22% above typical

$123/night

Priced high

↑22% above typical