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Emerald Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Vision of the Seas
Royal Caribbean
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Grenada • Bridgetown, Barbados • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,241pp
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!

EXPLORA I
Explora Journeys
Jan 4, 2027 - Jan 11, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami
Average Starting Price
$6,635pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 12, 2027 - Feb 19, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,660pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico
Average Starting Price
$3,560pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Apr 23, 2028 - Apr 29, 2028 (6 Nights)
Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,649pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • San Juan, Puerto Rico • Samana, Dominican Republic • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,015pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Caribbean Princess
Princess Cruises
Jan 7, 2029 - Jan 14, 2029 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$875pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$669pp
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!

Seabourn Pursuit
Seabourn
Aug 23, 2028 - Oct 18, 2028 (56 Nights)
Reykjavik, Iceland • Grundarfjordur, Iceland • Dynjandi, Iceland • Patreksfjordur, Iceland • Ittoqqortoormiit (Scoresbysund), Greenland • Exploring Scoresbysund • Northeast Greenland National Park • Northeast Greenland National Park • Northeast Greenland National Park • Northeast Greenland National Park • Siglufjordur, Iceland • Flatey Island, Iceland • Exploring The Outer Islands of Heimaey • Heimaey (Vestmannaeyjar), Iceland • Reykjavik, Iceland • Exploring The Outer Islands of Heimaey • Heimaey (Vestmannaeyjar), Iceland • Prince Christian Sound, Greenland • Prince Christian Sound, Greenland • Kangikitsok, Greenland • Qaqortoq (Julianehåb), Greenland • Hvalsey, Greenland • Brattahlid (Qassiarsuk), Greenland • Nain, Canada • Nachvak Fiord, Torngat Mts, Canada • Eclipse Channel, Labrador, Canada • Saglek Fjord, Labrador, Canada • Hopedale, Labrador • Indian Harbour, Newfoundland • L'Anse aux Meadows, Newfoundland • Red Bay, Canada • Norris Point, Newfoundland • Halifax, Nova Scotia • Hamilton, Bermuda • San Juan, Puerto Rico • Oranjestad, Aruba • Panama Canal Cruising • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Guayaquil, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • Valparaíso, Chile
Average Starting Price
$49,813pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$559pp
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!

58% OFF
Carnival Magic
Carnival Cruise Line
Mar 6, 2027 - Mar 14, 2027 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$464pp
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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