Jibhop

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Jost Van Dyke, Saint-Barthélemy & Little Bay

Feb 6, 2027 → Feb 16, 2027 • San Juan → Bridgetown

From $7,100

$7,100 · $710/night · typical price · ↓1% below typical

$710/night

Typical price

↓1% below typical

Crown Princess • Princess Cruises

7-night Southern Caribbean Loop via Saint Thomas, Pointe-à-Pitre & Roseau

Jan 31, 2027 → Feb 7, 2027 • San Juan ↔

From $793

$793 · $113/night · typical price · ↓1% below typical

$113/night

Typical price

↓1% below typical

Celebrity Constellation • Celebrity Cruises

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

Mar 6, 2027 → Mar 13, 2027 • San Juan ↔

↗

From $758

$758 · $108/night · typical price · ↓2% below typical

$108/night

Typical price

↓2% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Nov 21, 2026 → Nov 28, 2026 • San Juan ↔

↗

From $659

$659 · $94/night · typical price · ↓2% below typical

$94/night

Typical price

↓2% below typical

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Terre-de-Haut

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

From $7,100

$7,100 · $1,014/night · priced high · ↑41% above typical

$1,014/night

Priced high

↑41% above typical

Silver Dawn • Silversea Cruises

7-night Eastern Caribbean Loop via Philipsburg & Roseau

Dec 28, 2027 → Jan 4, 2028 • San Juan ↔

From $5,900

$5,900 · $843/night · priced high · ↑34% above typical

$843/night

Priced high

↑34% above typical

Silver Ray • Silversea Cruises

8-night Eastern Caribbean Arc via Cruz Bay, Saint John & Fort-de-France

Dec 26, 2027 → Jan 3, 2028 • San Juan → Miami

From $7,400

$7,400 · $925/night · priced high · ↑29% above typical

$925/night

Priced high

↑29% above typical

Silver Nova • Silversea Cruises

8-night Eastern Caribbean Arc via Charlestown & Roseau

Dec 29, 2026 → Jan 6, 2027 • San Juan → Miami

From $7,100

$7,100 · $888/night · priced high · ↑24% above typical

$888/night

Priced high

↑24% above typical

Valiant Lady • Virgin Voyages

7-night ABC Islands Loop via Willemstad & Cruz Bay, Saint John

Mar 27, 2027 → Apr 3, 2027 • San Juan ↔

From $1,708

$1,708 · $244/night · priced high · ↑23% above typical

$244/night

Priced high

↑23% above typical

Silver Dawn • Silversea Cruises

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

Dec 21, 2027 → Dec 28, 2027 • San Juan ↔

From $5,400

$5,400 · $771/night · priced high · ↑22% above typical

$771/night

Priced high

↑22% above typical

Silver Dawn • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Fort-de-France

Feb 5, 2028 → Feb 12, 2028 • San Juan ↔

From $5,400

$5,400 · $771/night · priced high · ↑22% above typical

$771/night

Priced high

↑22% above typical

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Basseterre, Saint Kitts & Little Bay

Feb 26, 2027 → Mar 5, 2027 • San Juan ↔

From $5,900

$5,900 · $843/night · priced high · ↑17% above typical

$843/night

Priced high

↑17% above typical

Crown Princess • Princess Cruises

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

Jan 3, 2027 → Jan 17, 2027 • San Juan ↔

From $1,859

$1,859 · $133/night · priced high · ↑16% above typical

$133/night

Priced high

↑16% above typical

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Little Bay

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

From $5,700

$5,700 · $814/night · priced high · ↑13% above typical

$814/night

Priced high

↑13% above typical

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Jost Van Dyke & Little Bay

Dec 20, 2026 → Dec 27, 2026 • San Juan ↔

From $5,500

$5,500 · $786/night · typical price · ↑9% above typical

$786/night

Typical price

↑9% above typical

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Little Bay, Saint John's & Saint-Barthélemy

Jan 30, 2027 → Feb 6, 2027 • San Juan ↔

From $5,400

$5,400 · $771/night · typical price · ↑7% above typical

$771/night

Typical price

↑7% above typical

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Jan 15, 2028 → Jan 25, 2028 • San Juan ↔

From $6,400

$6,400 · $640/night · typical price · ↑2% above typical

$640/night

Typical price

↑2% above typical

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Feb 12, 2028 → Feb 22, 2028 • San Juan ↔

From $6,300

$6,300 · $630/night · typical price

$630/night

Typical price

Emerald Kaia • Emerald Cruises

9-night Eastern Caribbean Arc: Saint-John, Ponce & Grand Turk Island

Feb 20, 2029 → Mar 1, 2029 • San Juan → Miami

1% below typical

From $8,536

$8,536 · $948/night · typical price · ↓1% below typical

$948/night

Typical price

↓1% below typical

SeaDream I • SeaDream Yacht Club

7-night Eastern Caribbean Arc: Salinas & Jost Van Dyke

Mar 10, 2029 → Mar 17, 2029 • San Juan ↔

2% below typical

From $4,892

$4,892 · $699/night · typical price · ↓2% below typical

$699/night

Typical price

↓2% below typical