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Star Legend
Windstar Cruises
Jan 24, 2028 - Jan 31, 2028 (7 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$2,411pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,618pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Vision of the Seas
Royal Caribbean
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$850pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Viking Sky
Viking
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,499pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Jan 2, 2028 - Jan 6, 2028 (4 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$481pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$768pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Sep 18, 2027 - Sep 25, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$650pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 13, 2027 - Jan 21, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,920pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 22, 2027 - Dec 13, 2027 (21 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Catalina Island, Dominican Republic • Santa Domingo, Dominican Republic • Cartagena, Colombia • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Isla Parida, Panama • Puerto Jimenez (Golfo Dulce), Costa Rica • Quepos, Costa Rica • Puerto Caldera, Costa Rica
Average Starting Price
$7,565pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Pointe-à-Pitre, Guadeloupe • Marigot Bay, St. Lucia • Ocean Cay • Miami
Average Starting Price
$3,755pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 21, 2027 - Feb 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$749pp
Jim's Onboard Credit
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