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Valiant Lady
Virgin Voyages
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Cabo Rojo, Dominican Republic • San Juan, Puerto Rico
Average Starting Price
$1,393pp
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!

EXPLORA II
Explora Journeys
Mar 12, 2028 - Mar 19, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • Gustavia, St. Barts • Fredrikstad (for Oslo), Norway • Ocean Cay • Miami
Average Starting Price
$3,915pp
Jim's Onboard Credit
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!

Azamara Quest
Azamara
Dec 19, 2027 - Jan 5, 2028 (17 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • Portsmouth, Dominica • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$4,929pp
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!

Viking Sea
Viking
Feb 24, 2027 - Mar 6, 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
$6,799pp
Jim's Onboard Credit
Silver Dawn
Silversea
Feb 24, 2028 - Mar 3, 2028 (8 Nights)
San Juan, Puerto Rico • St. Kitts • Gustavia, St. Barts • Deshaies, Guadeloupe • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$4,000pp
Jim's Onboard Credit
Viking Sky
Viking
Feb 7, 2028 - Feb 17, 2028 (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
Silver Shadow
Silversea
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Little Bay, Montserrat • Castries, St. Lucia • Fort-De-France, Martinique • Soper's Hole, Tortola • San Juan, Puerto Rico
Average Starting Price
$4,800pp
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!

Star Legend
Windstar Cruises
Jan 10, 2028 - Jan 24, 2028 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$714pp
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 12, 2027 - Dec 19, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$722pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,159pp
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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