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Zuiderdam
Holland America Line
Feb 14, 2027 - Mar 6, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami
Average Starting Price
$4,444pp
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!

Silver Spirit
Silversea
Nov 3, 2028 - Nov 12, 2028 (9 Nights)
Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Grand Turk • Miami
Average Starting Price
$3,700pp
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!

Celebrity Summit
Celebrity Cruises
Nov 21, 2027 - Nov 28, 2027 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$619pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jan 23, 2027 - Jan 29, 2027 (6 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • San Juan, Puerto Rico
Average Starting Price
$834pp
Jim's Onboard Credit
48% OFF
MSC Seashore
MSC Cruises
Dec 5, 2027 - Dec 18, 2027 (13 Nights)
Miami • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$1,181pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Jan 29, 2027 - Feb 7, 2027 (9 Nights)
Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,834pp
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!

EXPLORA IV
Explora Journeys
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
Miami • St. John • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Mar 26, 2028 - Apr 2, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St John's, Antigua • Fort Lauderdale
Average Starting Price
$2,299pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$636pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 3, 2027 - Jan 14, 2027 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty
Average Starting Price
$1,463pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Prima
Norwegian Cruise Line
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,219pp
Jim's Onboard Credit
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
$1,618pp
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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