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Norwegian Pearl
Norwegian Cruise Line
Feb 20, 2027 - Mar 2, 2027 (10 Nights)
Philadelphia • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$859pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Jan 22, 2028 - Feb 5, 2028 (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
$1,383pp
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!

Norwegian Luna
Norwegian Cruise Line
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$929pp
Jim's Onboard Credit
33% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Oct 28, 2028 - Nov 7, 2028 (10 Nights)
Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Gustavia, St. Barts • Miami
Average Starting Price
$6,099pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Jul 17, 2027 - Jul 24, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$3,112pp
Jim's Onboard Credit
49% OFF
MSC Seashore
MSC Cruises
Nov 20, 2027 - Dec 5, 2027 (15 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Miami • Ocean Cay • Puerto Plata, Dominican Republic • Grand Turk • Miami
Average Starting Price
$1,540pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Nieuw Amsterdam
Holland America Line
Feb 28, 2027 - Mar 21, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,169pp
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!

Icon of the Seas
Royal Caribbean
Jul 17, 2027 - Jul 24, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,941pp
Jim's Onboard Credit
58% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$699pp
Jim's Onboard Credit
35% OFF
Carnival Firenze
Carnival Cruise Line
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • St. Lucia • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,135pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 29, 2028 - Feb 5, 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
$833pp
Jim's Onboard Credit
Celebrity Beyond
Celebrity Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
Fort Lauderdale • St. Thomas • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,344pp
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!

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