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Allura
Oceania Cruises
Mar 11, 2027 - Mar 21, 2027 (10 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$4,799pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Feb 5, 2027 - Mar 1, 2027 (24 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • St. Pierre • Bridgetown, Barbados • Port of Spain, Trinidad • Port of Spain, Trinidad • Macapa, , Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Devil's Island, France • Bequia Island, Saint Vincent • Bridgetown, Barbados • Castries, St. Lucia • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$17,100pp
Jim's Onboard Credit
Azamara Onward
Azamara
Dec 22, 2027 - Jan 5, 2028 (14 Nights)
Miami • Nassau • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St. Pierre • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Miami
Average Starting Price
$4,099pp
Jim's Onboard Credit

Jim's Ship Pick
One of my absolute favorite ships! Small, simple, and luxurious without feeling stuffy - and perfect for immersive, port-intensive cruises!

Sonata
Oceania Cruises
Feb 2, 2028 - Feb 12, 2028 (10 Nights)
Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Pointe-à-Pitre, Guadeloupe • Tortola • Miami
Average Starting Price
$4,799pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Dec 27, 2027 - Jan 10, 2028 (14 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 • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,504pp
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!

Brilliant Lady
Virgin Voyages
Feb 22, 2027 - Mar 4, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami
Average Starting Price
$1,191pp
Jim's Onboard Credit
Island Princess
Princess Cruises
Nov 15, 2027 - Nov 29, 2027 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,354pp
Jim's Onboard Credit
28% OFF
Carnival Pride
Carnival Cruise Line
Nov 28, 2027 - Dec 10, 2027 (12 Nights)
Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • Martinique • Bridgetown, Barbados • St. Lucia • St. Kitts • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore
Average Starting Price
$1,530pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Nov 28, 2027 - Dec 10, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,269pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,213pp
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
Nov 23, 2027 - Dec 4, 2027 (11 Nights)
Fort Lauderdale • George Town, Cayman Islands • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,336pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$804pp
Jim's Onboard Credit
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