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29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Mar 20, 2027 - Mar 30, 2027 (10 Nights)
Miami • St. Thomas • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Tortola • San Juan, Puerto Rico
Average Starting Price
$7,299pp
Jim's Onboard Credit
Silver Dawn
Silversea
Dec 28, 2027 - Jan 4, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,300pp
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!

EXPLORA IV
Explora Journeys
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • St. Thomas • Cayo Levantado, Dominican Republic • Ocean Cay • Miami
Average Starting Price
$4,125pp
Jim's Onboard Credit
Eurodam
Holland America Line
Jan 2, 2028 - Jan 22, 2028 (20 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Montego Bay, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,714pp
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!

47% OFF
MSC World America
MSC Cruises
Jul 24, 2027 - Jul 31, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,184pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Grandeur of the Seas
Royal Caribbean
Aug 28, 2027 - Sep 4, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$648pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Dec 28, 2027 - Jan 8, 2028 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Bridgetown, Barbados • Martinique • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,179pp
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!

EXPLORA III
Explora Journeys
Mar 29, 2027 - Apr 5, 2027 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico
Average Starting Price
$6,125pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Mar 1, 2027 - Mar 8, 2027 (7 Nights)
San Juan, Puerto Rico • St John's, Antigua • Road Bay, Anguilla • Virgin Gorda, British Virgin Islands • Grand Turk • Miami
Average Starting Price
$4,550pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Viking Sea
Viking
Dec 17, 2027 - Dec 27, 2027 (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
$3,599pp
Jim's Onboard Credit
Silver Ray
Silversea
Feb 7, 2027 - Feb 19, 2027 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$7,200pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Apr 4, 2027 - Apr 21, 2027 (17 Nights)
San Juan, Puerto Rico • Ponta Delgada (Azores), Portugal • Funchal, Portugal • Melilla, Morocco • Motril, Spain • Ibiza, Spain • Palma (Majorca), Spain • Marseille (Provence), France • Nice, France • Livorno, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$2,619pp
Jim's Onboard Credit
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