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Azamara Quest
Azamara
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$3,199pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 30, 2028 - Dec 10, 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
$3,799pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Dec 14, 2026 - Dec 24, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$2,179pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Charlestown, Nevis • Philipsburg, St. Maarten
Average Starting Price
$3,028pp
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!

Rhapsody of the Seas
Royal Caribbean
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$943pp
Jim's Onboard Credit
45% OFF
MSC Meraviglia
MSC Cruises
Jan 24, 2027 - Feb 7, 2027 (14 Nights)
Miami • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Miami • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Miami
Average Starting Price
$1,055pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$2,138pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$7,163pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Apr 4, 2028 - Apr 18, 2028 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$2,219pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 10, 2027 - Jan 17, 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
$679pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Fort-De-France, Martinique • Roseau, Dominica • 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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