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
$580/night
View by
235 total
Emerald Sakara • Emerald Cruises
7-night Eastern Caribbean Loop: Basseterre, Saint Kitts & Road Bay
Nov 20, 2027 → Nov 27, 2027 • Philipsburg ↔
From $5,866
$838/night
Typical price
↓4% below typical
Silver Ray • Silversea Cruises
11-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Saint-Barthélemy
Dec 11, 2026 → Dec 22, 2026 • Miami ↔
From $7,900
$718/night
Seven Seas Mariner • Regent Seven Seas Cruises
10-night Eastern Caribbean Loop via Nassau, San Juan & Cruz Bay, Saint John
Apr 5, 2027 → Apr 15, 2027 • Miami ↔
From $6,404
$640/night
Seven Seas Mariner • Regent Seven Seas Cruises
14-night Eastern Caribbean Arc via Oranjestad, Willemstad & Kralendijk
Apr 15, 2027 → Apr 29, 2027 • Miami → New York
From $9,003
$643/night
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
From $6,261
$894/night
Typical price
↓4% below typical
Oceania Allura • Oceania Cruises
7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas & Philipsburg
Feb 5, 2027 → Feb 12, 2027 • Miami → San Juan
From $3,749
$536/night
Priced high
↑34% above typical
Seven Seas Grandeur • Regent Seven Seas Cruises
10-night Eastern Caribbean Arc via Tortola, Saint-Barthélemy & Philipsburg
Jan 5, 2028 → Jan 15, 2028 • Miami → Bridgetown
From $6,461
$646/night
Silver Ray • Silversea Cruises
12-night Eastern Caribbean Arc via San Juan, Basseterre, Saint Kitts & Saint-Barthélemy
Feb 7, 2027 → Feb 19, 2027 • Miami → Bridgetown
From $8,900
$742/night
Silver Ray • Silversea Cruises
12-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Saint George's & Road Bay
Feb 26, 2027 → Mar 10, 2027 • Bridgetown → Miami
From $8,900
$742/night
Emerald Sakara • Emerald Cruises
6-night Eastern Caribbean Arc via Cruz Bay, Saint John & Nevis
Jan 3, 2027 → Jan 9, 2027 • Saint Thomas → San Juan
From $5,956
$993/night
Typical price
↓4% below typical
Explora IV
7-night Eastern Caribbean Arc via Saint-Barthélemy, Spanish Town & Ocean Cay
Nov 27, 2027 → Dec 4, 2027 • San Juan → Miami
From $4,020
$574/night
Typical price
↓4% below typical
Explora IV
7-night Eastern Caribbean Arc via Providenciales & Road Bay
Mar 11, 2028 → Mar 18, 2028 • Miami → San Juan
From $4,020
$574/night
Typical price
↓4% below typical
Explora IV
7-night Eastern Caribbean Arc via Providenciales & Saint-Barthélemy
Mar 25, 2028 → Apr 1, 2028 • Miami → San Juan
From $4,020
$574/night
Typical price
↓4% below typical
Explora IV
7-night Eastern Caribbean Arc via Providenciales & Road Bay
Apr 8, 2028 → Apr 15, 2028 • Miami → San Juan
From $4,020
$574/night
Typical price
↓4% below typical
Explora IV
7-night Eastern Caribbean Arc via Providenciales & Road Bay
Apr 22, 2028 → Apr 29, 2028 • Miami → San Juan
From $4,020
$574/night
Typical price
↓4% below typical
Le Ponant • Ponant Cruises
7-night Eastern Caribbean Arc via Charlestown & Falmouth
Apr 3, 2028 → Apr 10, 2028 • Saint-Barthélemy → Pointe-à-Pitre
From $7,910
$1,130/night
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
$609/night
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
$609/night
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
$610/night