Jibhop

Celebrity Ascent • Celebrity Cruises

10-night Eastern Caribbean Loop via Philipsburg, Castries & Bridgetown

Apr 7, 2028 → Apr 17, 2028 • Fort Lauderdale ↔

$396 below typical

From $1,465

$1,465 · $147/night · great deal · ↓21% below typical

$147/night

Great deal

↓21% below typical

MSC Opera • MSC Cruises

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

Feb 15, 2027 → Feb 22, 2027 • La Romana ↔

Great balance

From $579

$579 · $83/night · great deal · ↓34% below typical

$83/night

Great deal

↓34% below typical

MSC Opera • MSC Cruises

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

Dec 6, 2027 → Dec 20, 2027 • La Romana ↔

56% below typical

From $729

$729 · $52/night · great deal · ↓56% below typical

$52/night

Great deal

↓56% below typical

Silver Dawn • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Saint John's

Mar 3, 2028 → Mar 14, 2028 • Miami ↔

From $6,300

$6,300 · $573/night · great deal · ↓37% below typical

$573/night

Great deal

↓37% below typical

Silver Dawn • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Saint John's

Mar 14, 2028 → Mar 25, 2028 • Miami ↔

From $6,300

$6,300 · $573/night · great deal · ↓37% below typical

$573/night

Great deal

↓37% below typical

Queen Mary 2 • Cunard Line

30-night Eastern Caribbean Arc via New York, Road Town, Tortola & Philipsburg

Dec 12, 2026 → Jan 11, 2027 • Southampton ↔

$993 below typical

From $4,169

$4,169 · $139/night · good value · ↓19% below typical

$139/night

Good value

↓19% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Grand Turk Island, Ocean Cay & Philipsburg

Nov 15, 2026 → Nov 29, 2026 • Miami ↔

68% below typical

From $398

$398 · $28/night · great deal · ↓68% below typical

$28/night

Great deal

↓68% below typical

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 ↔

$161 below typical ↗

From $652

$652 · $65/night · good value · ↓20% below typical

$65/night

Good value

↓20% below typical

MSC Meraviglia • MSC Cruises

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

Jan 2, 2027 → Jan 10, 2027 • Miami ↔

Great balance

From $599

$599 · $75/night · great deal · ↓41% below typical

$75/night

Great deal

↓41% below typical

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Tortola

Dec 10, 2027 → Dec 22, 2027 • New York ↔

Lowest in 180 days $170 below typical ↘

From $1,249

$1,249 · $104/night · good value · ↓12% below typical

$104/night

Good value

↓12% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Ocean Cay

Dec 19, 2026 → Jan 2, 2027 • Miami ↔

50% below typical

From $958

$958 · $68/night · great deal · ↓50% below typical

$68/night

Great deal

↓50% below typical

Enchanted Princess • Princess Cruises

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

Mar 7, 2027 → Mar 17, 2027 • Fort Lauderdale ↔

40% below typical

From $998

$998 · $100/night · great deal · ↓40% below typical

$100/night

Great deal

↓40% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Grand Turk Island, Ocean Cay & Philipsburg

Feb 7, 2027 → Feb 21, 2027 • Miami ↔

48% below typical

From $1,196

$1,196 · $85/night · great deal · ↓48% below typical

$85/night

Great deal

↓48% below typical

Oceania Sonata • Oceania Cruises

44-night Eastern Caribbean Arc via Puerto Quetzal, Panama Canal & Cozumel

Jan 6, 2028 → Feb 19, 2028 • Los Angeles → Miami

Lowest in 180 days $1,173 below typical

From $20,549

$20,549 · $467/night · typical price · ↓5% below typical

$467/night

Typical price

↓5% below typical

Oceania Sirena • Oceania Cruises

12-night Eastern Caribbean Loop via Nassau, Puerto Plata & San Juan

Dec 10, 2027 → Dec 22, 2027 • Miami ↔

Lowest in 180 days $357 below typical

From $3,499

$3,499 · $292/night · typical price · ↓9% below typical

$292/night

Typical price

↓9% below typical

Explora IV

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Pointe-à-Pitre

Nov 20, 2027 → Nov 27, 2027 • Miami → San Juan

Lowest in 30 days $505 below typical

From $4,020

$4,020 · $574/night · good value · ↓11% below typical

$574/night

Good value

↓11% below typical

Explora IV

7-night Eastern Caribbean Arc via Providenciales & Saint-Barthélemy

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

Lowest in 30 days $505 below typical

From $4,020

$4,020 · $574/night · good value · ↓11% below typical

$574/night

Good value

↓11% below typical

Explora IV

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Pointe-à-Pitre

Apr 29, 2028 → May 6, 2028 • San Juan → Miami

Lowest in 30 days $505 below typical

From $4,020

$4,020 · $574/night · good value · ↓11% below typical

$574/night

Good value

↓11% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Ocean Cay

Jan 2, 2027 → Jan 16, 2027 • Miami ↔

43% below typical

From $1,016

$1,016 · $73/night · great deal · ↓43% below typical

$73/night

Great deal

↓43% below typical

MSC Meraviglia • MSC Cruises

8-night Eastern Caribbean Arc via San Juan & Basseterre, Saint Kitts

Dec 5, 2026 → Dec 13, 2026 • Miami ↔

From $559

$559 · $70/night · great deal · ↓49% below typical

$70/night

Great deal

↓49% below typical