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Departures Itineraries
Virgin Voyages

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Basseterre, Saint Kitts

Nov 15, 2026 → Nov 25, 2026 • Miami ↔

Lowest in 90 days $101 below typical
$1,290 · $129/night · typical price · ↓7% below typical
Virgin Voyages

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Basseterre, Saint Kitts

Feb 22, 2027 → Mar 4, 2027 • Miami ↔

Lowest in 90 days $99 below typical
$1,191 · $119/night · typical price · ↓8% below typical
Phoenix Reisen

MS Aurelia • Phoenix Reisen

71-night Itinerary VICHA-VGTOV-SXPHI-BLSBH-KNBAS-AGSJO-DMRSU-MQFDF-LCCAS-BBBGI-VCKTN-GDSTG-BRFOR-BRREC-BRMCZ-BRSSA-BRRIO-BRBZC-BRPAT-BRPBO-BRRIG-UYPDP-UYMVD-ARBUE-FKPSY-P222471-ARUSH-CLPUQ-CLPCH-CLPMC-CLSAI-PECLL-ECMEC-CRGLF-GTPRQ-MXCSL

Oct 27, 2028 → Jan 6, 2029 • Miami → Los Angeles

Lowest in 180 days $2,704 below typical
$33,499 · $472/night · typical price · ↓7% below typical
MSC Cruises

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop via Samana, Spanish Town & Basseterre, Saint Kitts

Jan 4, 2027 → Jan 11, 2027 • La Romana ↔

Great balance
$590 · $84/night · great deal · ↓26% below typical
P&O Cruises

Arvia • P&O Cruises

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

Dec 4, 2026 → Dec 18, 2026 • Bridgetown ↔

$1,890 · $135/night · great deal · ↓26% below typical
P&O Cruises

Arvia • P&O Cruises

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

Dec 3, 2027 → Dec 17, 2027 • Bridgetown ↔

$1,890 · $135/night · great deal · ↓26% below typical
P&O Cruises

Arvia • P&O Cruises

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

Dec 4, 2027 → Dec 18, 2027 • Bridgetown ↔

$1,890 · $135/night · great deal · ↓26% below typical
MSC Cruises

MSC World Europa • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Mar 13, 2027 → Mar 20, 2027 • Fort-de-France ↔

Great balance
$869 · $124/night · great deal · ↓21% below typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Sep 26, 2026 → Oct 3, 2026 • San Juan ↔

$99 below typical
$599 · $86/night · good value · ↓14% below typical
P&O Cruises

Iona • P&O Cruises

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

Jan 22, 2028 → Feb 5, 2028 • Bridgetown ↔

13% below typical
$2,228 · $159/night · good value · ↓13% below typical
Oceania Cruises

Oceania Marina • Oceania Cruises

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

Feb 7, 2028 → Feb 17, 2028 • Miami ↔

Lowest in 180 days
$3,099 · $310/night · typical price · ↓5% below typical
Oceania Cruises

Oceania Marina • Oceania Cruises

10-night Eastern Caribbean Loop via Puerto Plata, San Juan & Frederiksted, Saint Croix

Feb 17, 2028 → Feb 27, 2028 • Miami ↔

Lowest in 180 days
$3,099 · $310/night · typical price · ↓5% below typical
Celebrity Cruises

Celebrity Beyond • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Apr 25, 2027 → May 2, 2027 • Fort Lauderdale ↔

$128 below typical
$871 · $124/night · good value · ↓13% below typical
Princess Cruises

Sky Princess • Princess Cruises

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

Dec 5, 2027 → Dec 12, 2027 • Fort Lauderdale ↔

Great balance
$636 · $91/night · great deal · ↓33% below typical
P&O Cruises

Arvia • P&O Cruises

14-night Eastern Caribbean Arc via Santa Cruz de Tenerife & Philipsburg

Oct 22, 2027 → Nov 5, 2027 • Southampton → Bridgetown

Lowest in 180 days $107 below typical
$1,593 · $114/night · typical price · ↓6% below typical
Celebrity Cruises

Celebrity Eclipse • Celebrity Cruises

12-night Eastern Caribbean Loop via Kralendijk, Oranjestad & Willemstad

Mar 20, 2028 → Apr 1, 2028 • Fort Lauderdale ↔

$236 below typical ↗
$1,480 · $123/night · good value · ↓14% below typical
Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

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

Nov 9, 2026 → Nov 21, 2026 • New York ↔

Lowest in 30 days $104 below typical
$1,369 · $114/night · typical price · ↓7% below typical
Silversea Cruises

Silver Shadow • Silversea Cruises

12-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Little Bay

Nov 18, 2026 → Nov 30, 2026 • Miami ↔

$7,400 · $617/night · great deal · ↓26% below typical
Regent Seven Seas Cruises

Seven Seas Grandeur • Regent Seven Seas Cruises

27-night Itinerary DOPOP-DOCAL-PRSJU-BLSBH-DMRSU-GPPTP-KNBAS-VGTOV-USMIA-BSNAS-PTPDL-ESSPC-MATNG-ESAGP-ESALC

Mar 20, 2028 → Apr 16, 2028 • Miami → Barcelona

$2,358 below typical
$14,563 · $539/night · good value · ↓14% below typical
Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Jun 19, 2027 → Jun 26, 2027 • San Juan ↔

Lowest in 180 days $62 below typical ↘
$906 · $129/night · typical price · ↓6% below typical