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Viking Cruises

Viking Sea • Viking Cruises

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

Nov 5, 2026 → Nov 15, 2026 • San Juan ↔

From $5,399

$540/night

Viking Cruises

Viking Sea • Viking Cruises

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

Nov 15, 2026 → Nov 25, 2026 • San Juan ↔

From $4,899

$490/night

Viking Cruises

Viking Sea • Viking Cruises

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

Nov 25, 2026 → Dec 5, 2026 • San Juan ↔

From $4,899

$490/night

P&O Cruises

Arvia • P&O Cruises

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

Jan 1, 2028 → Jan 15, 2028 • Bridgetown ↔

0% below typical

From $2,499

$179/night

Typical price
P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Tortola, Philipsburg & Roseau

Jan 3, 2028 → Jan 17, 2028 • Basseterre, Saint Kitts ↔

0% below typical

From $2,499

$179/night

Typical price
Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

10-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Saint John's

Mar 30, 2027 → Apr 9, 2027 • San Juan → Miami

From $7,168

$717/night

Viking Cruises

Viking Sea • Viking Cruises

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

Dec 5, 2026 → Dec 15, 2026 • San Juan ↔

From $5,399

$540/night

Crystal Cruises

Crystal Serenity • Crystal Cruises

30-night Eastern Caribbean Arc via Kings Wharf, Antigua & Pointe-à-Pitre

Oct 12, 2027 → Nov 11, 2027 • New York → Buenos Aires

From $13,000

$433/night

Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

11-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Castries

Dec 7, 2027 → Dec 18, 2027 • Miami ↔

From $7,874

$716/night

Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

10-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Dec 18, 2027 → Dec 28, 2027 • Miami ↔

From $7,168

$717/night

Emerald Cruises

Emerald Sakara • Emerald Cruises

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

Jan 5, 2028 → Jan 12, 2028 • Philipsburg ↔

Great balance

From $6,318

$903/night

Typical price
Emerald Cruises

Emerald Sakara • Emerald Cruises

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

Feb 5, 2028 → Feb 12, 2028 • Philipsburg ↔

Great balance

From $6,318

$903/night

Typical price
Celebrity Cruises

Celebrity Beyond • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Tortola

Aug 16, 2026 → Aug 23, 2026 • Miami ↔

Great balance

From $896

$128/night

Typical price
Emerald Cruises

Emerald Kaia • Emerald Cruises

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

Jan 15, 2028 → Jan 22, 2028 • Saint John's → San Juan

Great balance

From $6,600

$943/night

Typical price
Emerald Cruises

Emerald Kaia • Emerald Cruises

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

Jan 29, 2028 → Feb 5, 2028 • Saint John's → San Juan

Great balance

From $6,600

$943/night

Typical price
MSC Cruises

MSC Seashore • MSC Cruises

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

Nov 5, 2027 → Nov 20, 2027 • Miami ↔

↗ Trending up

From $1,389

$93/night

Typical price
Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 17, 2028 → Mar 24, 2028 • Bridgetown ↔

$984 above typical

From $2,009

$287/night

Priced high

↑96% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Nov 26, 2027 → Dec 3, 2027 • Bridgetown ↔

$825 above typical

From $1,690

$241/night

Priced high

↑95% above typical

Norwegian Cruise Line

Norwegian Pearl • Norwegian Cruise Line

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

Dec 23, 2027 → Jan 3, 2028 • Philadelphia ↔

$930 above typical

From $1,979

$180/night

Priced high

↑89% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 3, 2028 → Mar 10, 2028 • Bridgetown ↔

$894 above typical

From $1,919

$274/night

Priced high

↑87% above typical

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