Jibhop

Celebrity Ascent • Celebrity Cruises

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

Dec 4, 2026 → Dec 14, 2026 • Fort Lauderdale ↔

$132 below typical ↘

From $1,347

$1,347 · $135/night · typical price · ↓9% below typical

$135/night

Typical price

↓9% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

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

Feb 14, 2028 → Feb 24, 2028 • Bridgetown ↔

20% below typical

From $5,743

$5,743 · $574/night · good value · ↓20% below typical

$574/night

Good value

↓20% below typical

MSC Seashore • MSC Cruises

13-night Eastern Caribbean Loop via Saint John's, Charlotte Amalie, Saint Thomas & Ocean Cay

Dec 5, 2027 → Dec 18, 2027 • Miami ↔

Lowest in 30 days $74 below typical

From $1,152

$1,152 · $89/night · typical price · ↓6% below typical

$89/night

Typical price

↓6% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Dec 20, 2027 → Jan 3, 2028 • La Romana ↔

17% below typical

From $1,379

$1,379 · $99/night · good value · ↓17% below typical

$99/night

Good value

↓17% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Oct 10, 2026 → Oct 17, 2026 • San Juan ↔

$62 below typical ↗

From $664

$664 · $95/night · typical price · ↓8% below typical

$95/night

Typical price

↓8% below typical

MSC Seaview • MSC Cruises

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

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

Great balance

From $770

$770 · $110/night · good value · ↓19% below typical

$110/night

Good value

↓19% below typical

Celebrity Xcel • Celebrity Cruises

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

Mar 21, 2027 → Mar 28, 2027 • Miami ↔

$82 below typical

From $1,091

$1,091 · $156/night · typical price · ↓7% below typical

$156/night

Typical price

↓7% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Aug 15, 2026 → Aug 22, 2026 • San Juan ↔

$75 below typical ↗

From $914

$914 · $131/night · typical price · ↓8% below typical

$131/night

Typical price

↓8% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Oranjestad & Willemstad

Feb 4, 2028 → Feb 14, 2028 • Bridgetown ↔

From $5,960

$5,960 · $596/night · good value · ↓17% below typical

$596/night

Good value

↓17% below typical

Scarlet Lady • Virgin Voyages

8-night ABC Islands Loop via Philipsburg, Saint John's & Roseau

Dec 18, 2027 → Dec 26, 2027 • San Juan ↔

Lowest in 180 days

From $1,112

$1,112 · $139/night · typical price · ↓1% below typical

$139/night

Typical price

↓1% below typical

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Saint-Barthélemy & Ocean Cay

Feb 27, 2028 → Mar 5, 2028 • San Juan → Miami

Lowest in 30 days

From $4,020

$4,020 · $574/night · typical price · ↓1% below typical

$574/night

Typical price

↓1% below typical

MSC World Europa • MSC Cruises

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

Dec 15, 2026 → Dec 29, 2026 • Bridgetown ↔

Lowest in 180 days

From $2,291

$2,291 · $164/night · typical price · ↓4% below typical

$164/night

Typical price

↓4% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Eastern Caribbean Loop via Kingstown, Castries & Fort-de-France

Jan 25, 2028 → Feb 4, 2028 • Bridgetown ↔

From $6,040

$6,040 · $604/night · good value · ↓16% below typical

$604/night

Good value

↓16% below typical

Oceania Marina • Oceania Cruises

12-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Saint John's

Dec 10, 2026 → Dec 22, 2026 • Miami ↔

From $3,442

$3,442 · $287/night · typical price · ↓4% below typical

$287/night

Typical price

↓4% 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 ↔

Lowest in 90 days ↘

From $1,473

$1,473 · $147/night · typical price

$147/night

Typical price

Oceania Vista • Oceania Cruises

12-night Miami → Charlotte Amalie, Saint Thomas → Philipsburg → Saint-Barthélemy + 5 more

Nov 25, 2026 → Dec 7, 2026 • Miami ↔

14% below typical

From $4,749

$4,749 · $396/night · good value · ↓14% below typical

$396/night

Good value

↓14% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg

Dec 13, 2027 → Dec 20, 2027 • La Romana ↔

Great balance

From $729

$729 · $104/night · good value · ↓12% below typical

$104/night

Good value

↓12% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Mar 25, 2028 → Apr 1, 2028 • San Juan ↔

Lowest in 180 days

From $817

$817 · $117/night · typical price

$117/night

Typical price

Valiant Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Saint Thomas, Road Town, Tortola & Basseterre, Saint Kitts

Nov 28, 2026 → Dec 5, 2026 • San Juan ↔

Lowest in 30 days $210 above typical

From $1,113

$1,113 · $159/night · priced high · ↑23% above typical

$159/night

Priced high

↑23% above typical

Rhapsody of the Seas • Royal Caribbean International

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

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

Lowest in 30 days $200 above typical

From $1,079

$1,079 · $154/night · priced high · ↑23% above typical

$154/night

Priced high

↑23% above typical