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Viking Sea
Viking
Dec 5, 2026 - Dec 15, 2026 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$5,299pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 20, 2028 - Mar 5, 2028 (14 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Celebration Key • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,709pp
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 20, 2028 - Mar 5, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • Cozumel • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,168pp
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!

Rhapsody of the Seas
Royal Caribbean
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St. Croix • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$553pp
Jim's Onboard Credit
FREE Specialty Dining Meal
41% OFF
Carnival Vista
Carnival Cruise Line
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$689pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 10, 2027 - Jan 24, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,676pp
Jim's Onboard Credit
8% OFF
Crystal Serenity
Crystal Cruises
Aug 20, 2027 - Sep 3, 2027 (14 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Cartagena, Colombia • Cartagena, Colombia • Port Antonio, Jamaica • Cabo Rojo, Dominican Republic • La Romana, Dominican Republic • San Juan, Puerto Rico • Charleston • Charleston • New York, New York
Average Starting Price
$6,090pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,239pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Feb 10, 2029 - Feb 24, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,214pp
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!

Sun Princess
Princess Cruises
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
Fort Lauderdale • Celebration Key • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$829pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 13, 2029 - Jan 23, 2029 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,150pp
Jim's Onboard Credit
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