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Celebrity Eclipse
Celebrity Cruises
Dec 23, 2027 - Jan 5, 2028 (13 Nights)
Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$2,283pp
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!

Silver Nova
Silversea
Dec 21, 2028 - Jan 3, 2029 (13 Nights)
Fort Lauderdale • San Juan del sur, Nicaragua • Gustavia, St. Barts • St. Kitts • Roseau, Dominica • Willemstad, Curacao • Oranjestad, Aruba • Oranjestad, Aruba • Fort Lauderdale
Average Starting Price
$8,700pp
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!

Explorer of the Seas
Royal Caribbean
Nov 18, 2026 - Nov 27, 2026 (9 Nights)
Port Canaveral (Orlando), Florida • St John's, Antigua • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$692pp
Jim's Onboard Credit
Oosterdam
Holland America Line
Dec 11, 2027 - Dec 22, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,739pp
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 Shadow
Silversea
Feb 6, 2027 - Feb 16, 2027 (10 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Little Bay, Montserrat • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados
Average Starting Price
$4,450pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Mar 6, 2027 - Mar 27, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, 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
$3,949pp
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!

Rhapsody of the Seas
Royal Caribbean
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$568pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Sonata
Oceania Cruises
Jan 11, 2029 - Jan 23, 2029 (12 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$6,199pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 7, 2027 - Dec 17, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$4,319pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 9, 2027 - Dec 19, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
Jim's Onboard Credit
20% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Mar 5, 2027 - Mar 17, 2027 (12 Nights)
Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Tortola • Miami
Average Starting Price
$12,149pp
Jim's Onboard Credit
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