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47% OFF
MSC World America
MSC Cruises
Nov 27, 2027 - Dec 11, 2027 (14 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami
Average Starting Price
$1,631pp
Jim's Onboard Credit

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

Vision of the Seas
Royal Caribbean
Nov 29, 2026 - Dec 6, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$748pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 5, 2029 - Feb 19, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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 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
Sky Princess
Princess Cruises
Dec 27, 2028 - Jan 7, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Martinique • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,850pp
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!

Crown Princess
Princess Cruises
Jan 29, 2027 - Feb 5, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,499pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Dec 4, 2027 - Dec 18, 2027 (14 Nights)
Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,711pp
Jim's Onboard Credit

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

Norwegian Prima
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,229pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 28, 2029 - Feb 11, 2029 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,856pp
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!

Vision of the Seas
Royal Caribbean
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$866pp
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!

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
Sky Princess
Princess Cruises
Feb 11, 2029 - Feb 25, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale
Average Starting Price
$1,730pp
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!

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