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Scarlet Lady
Virgin Voyages
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 9, 2027 - Feb 22, 2027 (13 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 • Oranjestad, Aruba
Average Starting Price
$8,163pp
Jim's Onboard Credit
Norwegian Breakaway
Norwegian Cruise Line
Jan 19, 2028 - Jan 24, 2028 (5 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$619pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,565pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Nov 29, 2026 - Dec 13, 2026 (14 Nights)
Fort Lauderdale • Celebration Key • Cozumel • Roatan, Honduras • Fort Lauderdale • Celebration Key • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,132pp
Jim's Onboard Credit
Viking Idi
Viking
Dec 8, 2027 - Dec 19, 2027 (11 Nights)
Prague, Czech Republic • Nuremberg, Germany • Bamberg, Germany • Wurzburg, Germany • Heidelberg, Germany • Mainz, Germany • Rudesheim, Germany • Middle Rhine • Cochem, Germany • Bernkastel - Kues, Germany • Trier, Germany • Reims, France • Le Havre, France • Le Havre, France • Le Havre, France
Average Starting Price
$4,799pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 2027 (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
$670pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Seabourn Venture
Seabourn
Oct 2, 2028 - Oct 10, 2028 (8 Nights)
Halifax, Nova Scotia • St. Kitts • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$4,653pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$823pp
Jim's Onboard Credit
FREE Specialty Dining Meal
49% OFF
MSC Opera
MSC Cruises
Jun 24, 2027 - Jul 8, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,658pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 12, 2026 - Dec 26, 2026 (14 Nights)
Fort Lauderdale • Nassau • Grand Turk • Amber Cove, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,184pp
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!

Disney Dream
Disney Cruise Line
Jun 7, 2027 - Jun 11, 2027 (4 Nights)
Port Canaveral (Orlando), Florida • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,085pp
Jim's Onboard Credit
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