Jibhop

Sea Cloud Spirit • Sea Cloud Cruises

8-night Southern Caribbean Arc via Terre-de-Haut & Soufriere

Dec 12, 2027 → Dec 20, 2027 • Philipsburg → Willemstad

From $5,298

$5,298 · $662/night · typical price · ↓10% below typical

$662/night

Typical price

↓10% below typical

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy

Nov 27, 2027 → Dec 4, 2027 • Saint John's → San Juan

$617 below typical

From $6,151

$6,151 · $879/night · typical price · ↓9% below typical

$879/night

Typical price

↓9% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Apr 8, 2028 → Apr 22, 2028 • Bridgetown → Philipsburg

$661 below typical

From $11,359

$11,359 · $811/night · typical price · ↓6% below typical

$811/night

Typical price

↓6% below typical

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Feb 28, 2027 → Mar 7, 2027 • Miami → San Juan

Lowest in 30 days

From $4,960

$4,960 · $709/night · typical price · ↓3% below typical

$709/night

Typical price

↓3% below typical

Explora III

14-night Eastern Caribbean Loop via Cruz Bay, Saint John & Terre-de-Haut

Dec 6, 2026 → Dec 20, 2026 • Miami ↔

$723 below typical

From $9,040

$9,040 · $646/night · typical price · ↓7% below typical

$646/night

Typical price

↓7% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

Mar 25, 2028 → Apr 8, 2028 • Philipsburg → Bridgetown

$738 below typical

From $11,525

$11,525 · $823/night · typical price · ↓6% below typical

$823/night

Typical price

↓6% below typical

Explora III

14-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Cruz Bay, Saint John

Nov 29, 2026 → Dec 13, 2026 • San Juan ↔

Lowest in 30 days ↘

From $9,600

$9,600 · $686/night · typical price · ↓2% below typical

$686/night

Typical price

↓2% below typical

Explora III

17-night Eastern Caribbean Arc via Sept-Iles, New York & Cruz Bay, Saint John

Oct 15, 2026 → Nov 1, 2026 • Quebec → San Juan

$1,117 below typical ↗

From $11,475

$11,475 · $675/night · typical price · ↓9% below typical

$675/night

Typical price

↓9% below typical

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Little Bay

Dec 10, 2026 → Dec 20, 2026 • Miami → San Juan

From $6,300

$6,300 · $630/night · good value · ↓13% below typical

$630/night

Good value

↓13% below typical

Emerald Sakara • Emerald Cruises

9-night Eastern Caribbean Loop via South Friars Bay, Deshaies & Little Bay

Dec 18, 2027 → Dec 27, 2027 • Philipsburg ↔

4% below typical

From $7,094

$7,094 · $788/night · typical price · ↓4% below typical

$788/night

Typical price

↓4% below typical

Explora III

14-night Eastern Caribbean Loop via Cruz Bay, Saint John, Terre-de-Haut & Philipsburg

Nov 22, 2026 → Dec 6, 2026 • Miami ↔

$600 below typical

From $9,160

$9,160 · $654/night · typical price · ↓6% below typical

$654/night

Typical price

↓6% below typical

Explora I • Explora Journeys

7-night Eastern Caribbean Arc via Puerto Plata & Philipsburg

Jan 29, 2027 → Feb 5, 2027 • Miami → San Juan

Lowest in 30 days $400 above typical

From $4,600

$4,600 · $657/night · typical price · ↑10% above typical

$657/night

Typical price

↑10% above typical

Explora III

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

Feb 12, 2027 → Feb 19, 2027 • San Juan → Miami

Lowest in 30 days

From $5,270

$5,270 · $753/night · typical price · ↑3% above typical

$753/night

Typical price

↑3% above typical

Explora IV

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Jan 29, 2028 → Feb 5, 2028 • Miami → San Juan

Lowest in 30 days

From $4,020

$4,020 · $574/night · typical price

$574/night

Typical price

Explora IV

7-night Eastern Caribbean Arc via Road Bay & Ocean Cay

Feb 19, 2028 → Feb 26, 2028 • San Juan → Miami

Lowest in 30 days

From $4,020

$4,020 · $574/night · typical price

$574/night

Typical price

Explora I • Explora Journeys

15-night Western Caribbean Arc via Cozumel, Puerto Santo Tomás de Castilla & Cruz Bay, Saint John

Dec 5, 2026 → Dec 20, 2026 • Miami → San Juan

$565 below typical

From $8,360

$8,360 · $557/night · typical price · ↓6% below typical

$557/night

Typical price

↓6% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

Mar 4, 2028 → Mar 18, 2028 • Philipsburg → Bridgetown

4% below typical

From $11,747

$11,747 · $839/night · typical price · ↓4% below typical

$839/night

Typical price

↓4% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Mar 18, 2028 → Apr 1, 2028 • Bridgetown → Philipsburg

4% below typical

From $11,747

$11,747 · $839/night · typical price · ↓4% below typical

$839/night

Typical price

↓4% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Jan 29, 2028 → Feb 12, 2028 • Bridgetown → Philipsburg

5% below typical

From $11,747

$11,747 · $839/night · typical price · ↓5% below typical

$839/night

Typical price

↓5% below typical

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy

Mar 11, 2028 → Mar 18, 2028 • Saint John's → San Juan

Great balance

From $6,484

$6,484 · $926/night · typical price · ↓4% below typical

$926/night

Typical price

↓4% below typical