Jibhop

Seven Seas Prestige • Regent Seven Seas Cruises

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

Dec 18, 2027 → Dec 28, 2027 • Miami ↔

From $7,168

$7,168 · $717/night · typical price

$717/night

Typical price

Rotterdam • Holland America

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

Dec 1, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

↗

From $1,234

$1,234 · $112/night · typical price

$112/night

Typical price

Emerald Princess • Princess Cruises

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

Nov 26, 2027 → Dec 3, 2027 • Bridgetown ↔

$854 above typical

From $1,724

$1,724 · $246/night · priced high · ↑98% above typical

$246/night

Priced high

↑98% above typical

Emerald Princess • Princess Cruises

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

Mar 17, 2028 → Mar 24, 2028 • Bridgetown ↔

$981 above typical

From $2,034

$2,034 · $291/night · priced high · ↑93% above typical

$291/night

Priced high

↑93% above typical

Emerald Princess • Princess Cruises

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

Mar 3, 2028 → Mar 10, 2028 • Bridgetown ↔

$891 above typical

From $1,944

$1,944 · $278/night · priced high · ↑85% above typical

$278/night

Priced high

↑85% above typical

Emerald Princess • Princess Cruises

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

Jan 7, 2028 → Jan 14, 2028 • Bridgetown ↔

$783 above typical

From $1,714

$1,714 · $245/night · priced high · ↑84% above typical

$245/night

Priced high

↑84% above typical

Emerald Princess • Princess Cruises

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

Feb 4, 2028 → Feb 11, 2028 • Bridgetown ↔

$718 above typical

From $1,694

$1,694 · $242/night · priced high · ↑74% above typical

$242/night

Priced high

↑74% above typical

Emerald Princess • Princess Cruises

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

Dec 24, 2027 → Dec 31, 2027 • Bridgetown ↔

$716 above typical ↘

From $1,734

$1,734 · $248/night · priced high · ↑70% above typical

$248/night

Priced high

↑70% above typical

Rotterdam • Holland America

11-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Roseau

Dec 22, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

$798 above typical ↗

From $2,034

$2,034 · $185/night · priced high · ↑65% above typical

$185/night

Priced high

↑65% above typical

Crown Princess • Princess Cruises

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

Dec 27, 2026 → Jan 10, 2027 • San Juan ↔

$1,177 above typical

From $3,084

$3,084 · $220/night · priced high · ↑62% above typical

$220/night

Priced high

↑62% above typical

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

Crown Princess • Princess Cruises

7-night Itinerary PRSJU-VISTT-GPPTP-DMRSU-GDSTG

Jan 29, 2027 → Feb 5, 2027 • Bridgetown ↔

$479 above typical

From $1,294

$1,294 · $185/night · priced high · ↑59% above typical

$185/night

Priced high

↑59% 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

Emerald Princess • Princess Cruises

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

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

$545 above typical ↗

From $1,563

$1,563 · $223/night · priced high · ↑54% above typical

$223/night

Priced high

↑54% above typical

Celebrity Ascent • Celebrity Cruises

11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries

Dec 24, 2026 → Jan 4, 2027 • Fort Lauderdale ↔

$847 above typical

From $2,473

$2,473 · $225/night · priced high · ↑52% above typical

$225/night

Priced high

↑52% 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

$275 above typical

From $857

$857 · $171/night · priced high · ↑47% above typical

$171/night

Priced high

↑47% 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 ↔

$374 above typical

From $1,189

$1,189 · $170/night · priced high · ↑46% above typical

$170/night

Priced high

↑46% above typical

Emerald Princess • Princess Cruises

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

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

$476 above typical

From $1,539

$1,539 · $192/night · priced high · ↑45% above typical

$192/night

Priced high

↑45% 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

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 ↔

$261 above typical ↘

From $934

$934 · $133/night · priced high · ↑39% above typical

$133/night

Priced high

↑39% above typical