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Star Pride
Windstar Cruises
Nov 15, 2027 - Nov 22, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Jul 17, 2027 - Jul 24, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$868pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Dec 28, 2026 - Jan 7, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • St John's, Antigua • Bimini • Miami
Average Starting Price
$1,690pp
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!

Regal Princess
Princess Cruises
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$539pp
Jim's Onboard Credit
Seabourn Venture
Seabourn
Oct 1, 2027 - Oct 9, 2027 (8 Nights)
Halifax, Nova Scotia • St. Kitts • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$4,853pp
Jim's Onboard Credit
9% OFF
Crystal Grace
Crystal Cruises
Jan 19, 2029 - Feb 19, 2029 (31 Nights)
Fort Lauderdale • Grand Turk • Samana, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • St. Kitts • Gustavia, St. Barts • San Juan, Puerto Rico • Gustavia, St. Barts • Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Scarborough (Tobago), Trinidad and Tobago • Devil's Island, France • Fortaleza, Brazil • Recife, Brazil • Maceio, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Santos (Sao Paulo), Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina
Average Starting Price
$18,210pp
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!

Crown Princess
Princess Cruises
Feb 7, 2027 - Feb 21, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,428pp
Jim's Onboard Credit
Silver Nova
Silversea
Feb 22, 2028 - Mar 4, 2028 (11 Nights)
Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St John's, Antigua • St. Kitts • St. John • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Feb 7, 2027 - Feb 21, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,275pp
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!

Rotterdam
Holland America Line
Feb 2, 2027 - Feb 13, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,419pp
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!

9% OFF
Crystal Serenity
Crystal Cruises
Dec 29, 2027 - Jan 8, 2028 (10 Nights)
San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Cap Cana (Punta Cana), Dominican Republic • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$5,380pp
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!

Norwegian Prima
Norwegian Cruise Line
Dec 18, 2027 - Dec 25, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,809pp
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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