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26% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • St John's, Antigua • Tortola • Miami
Average Starting Price
$8,349pp
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!

Celebrity Ascent
Celebrity Cruises
Mar 29, 2027 - Apr 9, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,837pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Oct 29, 2027 - Nov 7, 2027 (9 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$884pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Nov 7, 2027 - Nov 14, 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
$759pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Dec 3, 2027 - Dec 10, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$2,094pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Roseau, Dominica • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,019pp
Jim's Onboard Credit
Eurodam
Holland America Line
Nov 21, 2027 - Dec 12, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$5,094pp
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!

31% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Jan 5, 2028 - Jan 15, 2028 (10 Nights)
Miami • Tortola • Gustavia, St. Barts • Philipsburg, St. Maarten • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$6,749pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Nov 12, 2027 - Nov 20, 2027 (8 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,112pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$706pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Mar 22, 2027 - Apr 2, 2027 (11 Nights)
Fort Lauderdale • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,715pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Mar 16, 2027 - Mar 27, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,219pp
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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