Jibhop

Silver Dawn • Silversea Cruises

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

Dec 11, 2027 → Dec 21, 2027 • San Juan ↔

From $5,800

$5,800 · $580/night · typical price · ↓8% below typical

$580/night

Typical price

↓8% below typical

Vision of the Seas • Royal Caribbean International

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

Nov 8, 2026 → Nov 15, 2026 • San Juan ↔

↗

From $639

$639 · $91/night · typical price · ↓5% below typical

$91/night

Typical price

↓5% below typical

Vision of the Seas • Royal Caribbean International

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

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

↗

From $639

$639 · $91/night · typical price · ↓5% below typical

$91/night

Typical price

↓5% below typical

Explora I • Explora Journeys

23-night Transatlantic Crossing via Cruz Bay, Saint John, Road Bay & Spanish Town

Mar 1, 2027 → Mar 24, 2027 • San Juan → Barcelona

From $12,825

$12,825 · $558/night · typical price · ↓4% below typical

$558/night

Typical price

↓4% below typical

Emerald Princess • Princess Cruises

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

Feb 13, 2028 → Feb 27, 2028 • San Juan ↔

From $1,828

$1,828 · $131/night · typical price · ↓6% below typical

$131/night

Typical price

↓6% below typical

SeaDream II • SeaDream Yacht Club

7-night Eastern Caribbean Arc via Samana & Grand Turk Island

Mar 25, 2028 → Apr 1, 2028 • San Juan → Freeport, Grand Bahama

$284 below typical

From $5,273

$5,273 · $753/night · typical price · ↓5% below typical

$753/night

Typical price

↓5% below typical

Emerald Kaia • Emerald Cruises

9-night Bahamas One-Way via Ponce & Grand Turk Island

Feb 10, 2028 → Feb 19, 2028 • San Juan → Miami

From $8,369

$8,369 · $930/night · typical price · ↓3% below typical

$930/night

Typical price

↓3% below typical

Emerald Princess • Princess Cruises

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

Jan 9, 2028 → Jan 23, 2028 • San Juan ↔

4% below typical

From $1,771

$1,771 · $127/night · typical price · ↓4% below typical

$127/night

Typical price

↓4% below typical

Emerald Princess • Princess Cruises

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

Nov 28, 2027 → Dec 5, 2027 • San Juan ↔

Great balance

From $840

$840 · $120/night · typical price · ↓3% below typical

$120/night

Typical price

↓3% below typical

Crown Princess • Princess Cruises

14-night Eastern Caribbean Arc via Saint Thomas, Pointe-à-Pitre & Roseau

Jan 31, 2027 → Feb 14, 2027 • San Juan ↔

5% below typical

From $1,523

$1,523 · $109/night · typical price · ↓5% below typical

$109/night

Typical price

↓5% below typical

Emerald Princess • Princess Cruises

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

Jan 23, 2028 → Feb 6, 2028 • San Juan ↔

3% below typical

From $1,786

$1,786 · $128/night · typical price · ↓3% below typical

$128/night

Typical price

↓3% below typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 16, 2028 → Jan 23, 2028 • San Juan ↔

Great balance

From $897

$897 · $128/night · typical price · ↓2% below typical

$128/night

Typical price

↓2% below typical

Norwegian Viva • Norwegian Cruise Line

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

Dec 5, 2027 → Dec 12, 2027 • San Juan ↔

From $1,099

$1,099 · $157/night · typical price · ↓9% below typical

$157/night

Typical price

↓9% below typical

Silver Dawn • Silversea Cruises

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

Jan 4, 2028 → Jan 15, 2028 • San Juan ↔

From $6,700

$6,700 · $609/night · typical price · ↓3% below typical

$609/night

Typical price

↓3% below typical

Silver Dawn • Silversea Cruises

11-night Southern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Roseau

Jan 25, 2028 → Feb 5, 2028 • San Juan ↔

From $6,700

$6,700 · $609/night · typical price · ↓3% below typical

$609/night

Typical price

↓3% below typical

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Arc via Saint-Barthélemy, Roseau & Fort-de-France

Feb 22, 2028 → Mar 3, 2028 • San Juan → Miami

From $6,100

$6,100 · $610/night · typical price · ↓3% below typical

$610/night

Typical price

↓3% below typical

Emerald Princess • Princess Cruises

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

Jan 9, 2028 → Jan 16, 2028 • San Juan ↔

Great balance

From $915

$915 · $131/night · typical price

$131/night

Typical price

Oceania Allura • Oceania Cruises

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

Feb 19, 2027 → Feb 27, 2027 • San Juan → Miami

From $3,299

$3,299 · $412/night · priced high · ↑20% above typical

$412/night

Priced high

↑20% above typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 30, 2028 → Feb 6, 2028 • San Juan ↔

Great balance

From $1,017

$1,017 · $145/night · priced high · ↑10% above typical

$145/night

Priced high

↑10% above typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

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

Great balance

From $1,017

$1,017 · $145/night · priced high · ↑10% above typical

$145/night

Priced high

↑10% above typical