Jibhop

Silver Spirit • Silversea Cruises

7-night Eastern Caribbean Loop via Castries, Terre-de-Haut & Philipsburg

Mar 11, 2028 → Mar 18, 2028 • Bridgetown ↔

From $5,400

$5,400 · $771/night · great deal · ↓25% below typical

$771/night

Great deal

↓25% below typical

Coral Princess • Princess Cruises

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

Nov 18, 2026 → Nov 28, 2026 • Fort Lauderdale ↔

From $1,044

$1,044 · $104/night · great deal · ↓29% below typical

$104/night

Great deal

↓29% below typical

Explora I • Explora Journeys

16-night Eastern Caribbean Arc via Ocho Rios, Puerto Santo Tomás de Castilla & Roatán

Jan 20, 2027 → Feb 5, 2027 • Miami → San Juan

Lowest in 30 days

From $9,240

$9,240 · $578/night · typical price · ↓4% below typical

$578/night

Typical price

↓4% below typical

Emerald Sakara • Emerald Cruises

7-night Eastern Caribbean Loop: Basseterre, Saint Kitts & Road Bay

Nov 20, 2027 → Nov 27, 2027 • Philipsburg ↔

$443 below typical

From $5,763

$5,763 · $823/night · typical price · ↓7% below typical

$823/night

Typical price

↓7% below typical

MS Aurelia • Phoenix Reisen

12-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Tortola & Philipsburg

Oct 27, 2028 → Nov 8, 2028 • Miami → Bridgetown

Lowest in 180 days $370 below typical

From $5,749

$5,749 · $479/night · typical price · ↓6% below typical

$479/night

Typical price

↓6% below typical

Queen Elizabeth • Cunard Line

14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 9, 2027 → Dec 23, 2027 • Miami ↔

Lowest in 180 days $107 below typical

From $1,587

$1,587 · $113/night · typical price · ↓6% below typical

$113/night

Typical price

↓6% below typical

Oceania Sonata • Oceania Cruises

10-night Eastern Caribbean Loop via San Juan, Charlotte Amalie, Saint Thomas & Basseterre, Saint Kitts

Feb 2, 2028 → Feb 12, 2028 • Miami ↔

Lowest in 180 days

From $4,799

$4,799 · $480/night · typical price · ↓3% below typical

$480/night

Typical price

↓3% below typical

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Philipsburg

Nov 1, 2026 → Nov 8, 2026 • San Juan ↔

$76 below typical

From $617

$617 · $88/night · good value · ↓11% below typical

$88/night

Good value

↓11% below typical

Oceania Sirena • Oceania Cruises

31-night Eastern Caribbean Arc via Cozumel, Roatán & Harvest Caye

Nov 21, 2027 → Dec 22, 2027 • Miami ↔

Lowest in 180 days

From $8,299

$8,299 · $268/night · typical price · ↓3% below typical

$268/night

Typical price

↓3% below typical

Silver Shadow • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Little Bay

Nov 7, 2026 → Nov 18, 2026 • Miami ↔

From $7,000

$7,000 · $636/night · great deal · ↓24% below typical

$636/night

Great deal

↓24% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jul 31, 2027 → Aug 7, 2027 • San Juan ↔

Lowest in 30 days $53 below typical

From $916

$916 · $131/night · typical price · ↓5% below typical

$131/night

Typical price

↓5% below typical

Emerald Princess • Princess Cruises

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

Dec 12, 2027 → Dec 26, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓23% below typical

$108/night

Great deal

↓23% below typical

Silver Ray • Silversea Cruises

12-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Castries & Fort-de-France

Mar 20, 2028 → Apr 1, 2028 • Bridgetown → Miami

From $8,200

$8,200 · $683/night · great deal · ↓25% below typical

$683/night

Great deal

↓25% below typical

Vista

12-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Saint John's

Nov 13, 2028 → Nov 25, 2028 • Miami ↔

Lowest in 180 days $270 below typical

From $4,899

$4,899 · $408/night · typical price · ↓5% below typical

$408/night

Typical price

↓5% below typical

Celebrity Eclipse • Celebrity Cruises

12-night Eastern Caribbean Loop via Kralendijk, Oranjestad & Willemstad

Mar 20, 2028 → Apr 1, 2028 • Fort Lauderdale ↔

$211 below typical ↗

From $1,505

$1,505 · $125/night · good value · ↓12% below typical

$125/night

Good value

↓12% below typical

Iona • P&O Cruises

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

Jan 21, 2028 → Feb 4, 2028 • Bridgetown ↔

11% below typical

From $2,296

$2,296 · $164/night · good value · ↓11% below typical

$164/night

Good value

↓11% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Oct 24, 2026 → Oct 31, 2026 • San Juan ↔

$84 below typical

From $615

$615 · $88/night · good value · ↓12% below typical

$88/night

Good value

↓12% below typical

Oceania Sonata • Oceania Cruises

11-night Eastern Caribbean Loop via Puerto Plata, San Juan & Charlotte Amalie, Saint Thomas

Feb 19, 2028 → Mar 1, 2028 • Miami ↔

Lowest in 180 days

From $5,299

$5,299 · $482/night · typical price · ↓2% below typical

$482/night

Typical price

↓2% below typical

Enchanted Princess • Princess Cruises

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

Dec 17, 2026 → Dec 27, 2026 • Fort Lauderdale ↔

20% below typical

From $953

$953 · $95/night · great deal · ↓20% below typical

$95/night

Great deal

↓20% below typical

Grandeur of the Seas • Royal Caribbean International

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

Oct 23, 2027 → Oct 30, 2027 • San Juan ↔

Lowest in 180 days

From $663

$663 · $95/night · typical price · ↓5% below typical

$95/night

Typical price

↓5% below typical