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Azamara Quest
Azamara
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,769pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Dec 4, 2026 - Dec 14, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$6,724pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 30, 2028 - Jan 9, 2029 (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
$4,499pp
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!

Wind Surf
Windstar Cruises
Mar 27, 2027 - Apr 11, 2027 (15 Nights)
Philipsburg, St. Maarten • Funchal, Portugal • Porto Santo (Madeira), Portugal • Lisbon, Portugal
Average Starting Price
$2,805pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$2,160pp
Jim's Onboard Credit
52% OFF
MSC Meraviglia
MSC Cruises
Jan 30, 2027 - Feb 7, 2027 (8 Nights)
Miami • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Miami
Average Starting Price
$528pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St. Croix • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$553pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Seabourn Ovation
Seabourn
Dec 28, 2027 - Jan 8, 2028 (11 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • Road Bay, Anguilla • Falmouth (English Harbour), Antigua & Barbuda • St. Kitts • Terre de Haut, Guadeloupe • Kralendijk, Bonaire • Willemstad, Curacao • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$7,788pp
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 Pride
Windstar Cruises
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,368pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 10, 2027 - Jan 24, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,676pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 23, 2028 - Jan 2, 2029 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,650pp
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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