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Sonata
Oceania Cruises
Mar 1, 2028 - Mar 11, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami
Average Starting Price
$4,799pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 12, 2027 - Feb 28, 2027 (16 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Miami
Average Starting Price
$12,560pp
Jim's Onboard Credit
30% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Dec 3, 2028 - Dec 13, 2028 (10 Nights)
Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$6,849pp
Jim's Onboard Credit
Vista
Oceania Cruises
Jan 7, 2029 - Jan 31, 2029 (24 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • George Town, Cayman Islands • Ocho Rios, Jamaica • La Romana, Dominican Republic • Tortola • San Juan, Puerto Rico • Miami
Average Starting Price
$9,699pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami
Average Starting Price
$1,098pp
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!

Allura
Oceania Cruises
Feb 19, 2027 - Mar 11, 2027 (20 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Nassau • Miami
Average Starting Price
$11,349pp
Jim's Onboard Credit
Marina
Oceania Cruises
Feb 7, 2028 - Feb 17, 2028 (10 Nights)
Miami • Nassau • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St John's, Antigua • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$3,549pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 3, 2027 - Jan 14, 2027 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty
Average Starting Price
$1,393pp
Jim's Onboard Credit
FREE Specialty Dining Meal
47% OFF
Carnival Celebration
Carnival Cruise Line
Sep 26, 2027 - Oct 3, 2027 (7 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami
Average Starting Price
$566pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 1, 2027 - Dec 12, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,754pp
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!

EXPLORA I
Explora Journeys
Jan 4, 2027 - Jan 20, 2027 (16 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami
Average Starting Price
$12,785pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Dec 22, 2027 - Jan 3, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$2,269pp
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!

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