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Norwegian Pearl
Norwegian Cruise Line
Nov 27, 2027 - Dec 8, 2027 (11 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Philadelphia
Average Starting Price
$1,203pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Feb 19, 2028 - Mar 1, 2028 (11 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$5,299pp
Jim's Onboard Credit
20% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Apr 29, 2027 - May 15, 2027 (16 Nights)
New York, New York • Atlantic Ocean cruising • Halifax, Nova Scotia • Atlantic Ocean cruising • St John's, Newfoundland • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • Ponta Delgada (Azores), Portugal • Atlantic Ocean cruising • Funchal, Portugal • Santa Cruz de Tenerife, Spain • Arrecife (Lanzarote), Spain • Agadir, Morocco • Casablanca, Morocco • Atlantic Ocean cruising • Lisbon, Portugal
Average Starting Price
$13,899pp
Jim's Onboard Credit
Silver Ray
Silversea
Dec 26, 2027 - Jan 3, 2028 (8 Nights)
San Juan, Puerto Rico • St. John • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$5,500pp
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
Dec 4, 2027 - Dec 12, 2027 (8 Nights)
Fort Lauderdale • Samana, Dominican Republic • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,154pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Oct 30, 2027 - Nov 27, 2027 (28 Nights)
Miami • Nassau • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • Santa Domingo, Dominican Republic • San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Castries, St. Lucia • Port of Spain, Trinidad • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Belize City • Cozumel • Progreso, Mexico • Miami
Average Starting Price
$6,584pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Celebrity Eclipse
Celebrity Cruises
Apr 2, 2027 - Apr 11, 2027 (9 Nights)
Fort Lauderdale • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • St. Thomas • Fort Lauderdale
Average Starting Price
$1,661pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$699pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 5, 2027 - Dec 12, 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
$754pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Dec 10, 2027 - Dec 19, 2027 (9 Nights)
Miami • St John's, Antigua • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami
Average Starting Price
$986pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 2, 2028 - Jan 13, 2028 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty
Average Starting Price
$1,472pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Oct 12, 2027 - Oct 21, 2027 (9 Nights)
New York, New York • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$3,930pp
Jim's Onboard Credit
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