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11% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 10, 2027 - Jan 20, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$23,819pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Dec 11, 2027 - Dec 18, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Jan 3, 2028 - Jan 15, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Tortola • St. Thomas • Manhattan
Average Starting Price
$1,419pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Dec 27, 2028 - Jan 7, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Martinique • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,850pp
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!

Celebrity Xcel
Celebrity Cruises
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,085pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Nov 18, 2026 - Nov 28, 2026 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • Dominica • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$609pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 15, 2027 - Nov 29, 2027 (14 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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
$4,014pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$946pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Jan 27, 2028 - Feb 7, 2028 (11 Nights)
Philadelphia • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$1,029pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Apr 29, 2027 - May 13, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,908pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Jul 24, 2027 - Jul 31, 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
$956pp
Jim's Onboard Credit
Resilient Lady
Virgin Voyages
Jan 30, 2027 - Feb 7, 2027 (8 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Bimini • Miami
Average Starting Price
$1,032pp
Jim's Onboard Credit
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