Departure months
Trip length
Search
P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Feb 26, 2028 → Mar 11, 2028 • Bridgetown ↔

From $2,607

$186/night

Typical price

↑2% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Castries, Saint George's & Bridgetown

Dec 12, 2026 → Dec 26, 2026 • Antigua ↔

From $2,566

$183/night

Typical price

↑1% above typical

P&O Cruises

Arvia • P&O Cruises

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

Dec 31, 2027 → Jan 14, 2028 • Bridgetown ↔

From $2,566

$183/night

Typical price

↑1% above typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

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

Dec 23, 2028 → Jan 6, 2029 • Philipsburg → Bridgetown

From $11,619

$830/night

Typical price

↑1% above typical

MSC Cruises

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Jan 26, 2027 → Feb 9, 2027 • Bridgetown ↔

From $1,846

$132/night

Royal Caribbean International

Star of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas

Sep 6, 2026 → Sep 13, 2026 • Port Canaveral ↔

Great balance

From $1,457

$208/night

Typical price

↑1% above typical

Royal Caribbean International

Allure of the Seas • Royal Caribbean International

8-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Coco Cay

Jun 27, 2026 → Jul 5, 2026 • Fort Lauderdale ↔

Great balance

From $1,465

$183/night

Typical price

↑1% above typical

Princess Cruises

Emerald Princess • Princess Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Fort-de-France

Feb 20, 2028 → Feb 27, 2028 • San Juan ↔

From $986

$141/night

Typical price

↑1% above typical

Princess Cruises

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 $940

$134/night

Typical price

↑1% above typical

P&O Cruises

Iona • P&O Cruises

26-night Transatlantic Crossing via Philipsburg, Fort-de-France & Roseau

Mar 6, 2028 → Apr 1, 2028 • Basseterre, Saint Kitts → Southampton

From $3,850

$148/night

Typical price

↑1% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Nov 21, 2027 → Dec 5, 2027 • San Juan ↔

From $1,746

$125/night

Typical price

↑1% above typical

MSC Cruises

MSC Seashore • MSC Cruises

14-night Eastern Caribbean Loop via Ocean Cay, Grand Turk Island & Philipsburg

Jan 9, 2028 → Jan 23, 2028 • Miami ↔

From $1,268

$91/night

Explora IV

8-night Eastern Caribbean Arc via Providenciales, Saint-Barthélemy & Cruz Bay, Saint John

Nov 5, 2027 → Nov 13, 2027 • Miami → San Juan

From $4,835

$604/night

Typical price

↑1% above typical

Emerald Cruises

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 $6,600

$943/night

Typical price

↑1% above typical

Emerald Cruises

Emerald Kaia • Emerald Cruises

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

Mar 25, 2028 → Apr 1, 2028 • Saint John's → San Juan

Great balance

From $6,600

$943/night

Typical price

↑1% above typical

Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Dec 1, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

From $1,234

$112/night

Typical price

↑1% above typical

Celebrity Cruises

Celebrity Eclipse • Celebrity Cruises

9-night Eastern Caribbean Loop via Saint John's & Castries

Apr 2, 2027 → Apr 11, 2027 • Fort Lauderdale ↔

From $1,170

$130/night

Typical price

↑1% above typical

Emerald Cruises

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

From $11,957

$854/night

Typical price
Emerald Cruises

Emerald Sakara • Emerald Cruises

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

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

From $11,957

$854/night

Typical price
Emerald Cruises

Emerald Sakara • Emerald Cruises

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

Apr 15, 2028 → Apr 22, 2028 • Philipsburg ↔

Great balance

From $6,092

$870/night

Typical price

Filters

Filters

Reset
Deal Signals
Trip Style
Cabin Type
Ports Visited
Cruise Line & Ship
Price

Per person