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Star Pride
Windstar Cruises
Feb 28, 2028 - Mar 13, 2028 (14 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Bocas Del Toro, Panama • Panama Canal, Panama • Cartagena, Colombia • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$6,235pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Feb 2, 2029 - Feb 9, 2029 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$945pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Mar 21, 2027 - Apr 5, 2027 (15 Nights)
Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico
Average Starting Price
$14,105pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 19, 2027 - Feb 26, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,669pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$959pp
Jim's Onboard Credit
55% OFF
MSC World America
MSC Cruises
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$558pp
Jim's Onboard Credit

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

Regal Princess
Princess Cruises
Jan 22, 2029 - Feb 5, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,874pp
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!

Sky Princess
Princess Cruises
Feb 4, 2029 - Feb 18, 2029 (14 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,634pp
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!

Star Pride
Windstar Cruises
Feb 21, 2028 - Mar 13, 2028 (21 Nights)
Caldera, Costa Rica • Playa Flamingo, Costa Rica • Punta Leona, Costa Rica • Quepos, Costa Rica • Puerto Jimenez (Golfo Dulce), Costa Rica • Isla Parida, Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Bocas Del Toro, Panama • Panama Canal, Panama • Cartagena, Colombia • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$9,307pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Mar 21, 2027 - Mar 29, 2027 (8 Nights)
Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico
Average Starting Price
$5,850pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 12, 2027 - Feb 19, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,479pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Apr 22, 2028 - Apr 29, 2028 (7 Nights)
San Juan, Puerto Rico • Cabo Rojo, Dominican Republic • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Galveston
Average Starting Price
$899pp
Jim's Onboard Credit
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