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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!

Wind Star
Windstar Cruises
Nov 10, 2026 - Nov 24, 2026 (14 Nights)
Lisbon, Portugal • Bridgetown, Barbados
Average Starting Price
$3,596pp
Jim's Onboard Credit
66% OFF
Scenic Eclipse II
Scenic Ocean Cruises
Apr 14, 2027 - Apr 23, 2027 (9 Nights)
Bridgetown, Barbados • Funchal, Portugal
Average Starting Price
$4,516pp
Jim's Onboard Credit
Silver Ray
Silversea
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Grenada • Bequia Island, Saint Vincent • Fort-De-France, Martinique • St John's, Antigua • Charlestown, Nevis • San Juan, Puerto Rico
Average Starting Price
$4,500pp
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!

Celebrity Constellation
Celebrity Cruises
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$751pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 14, 2027 - Feb 24, 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
Norwegian Prima
Norwegian Cruise Line
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Roseau, Dominica • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,019pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Feb 15, 2027 - Feb 26, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,989pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Mar 2, 2027 - Mar 25, 2027 (23 Nights)
Bridgetown, Barbados • Funchal, Portugal • Porto Santo (Madeira), Portugal • Casablanca, Morocco • Lisbon, Portugal • Cadiz, Spain • Gibraltar • Malaga, Spain • Almeria, Spain • Cartagena, Spain • Palma de Mallorca, Spain • Barcelona, Spain
Average Starting Price
$6,146pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Feb 18, 2028 - Mar 10, 2028 (21 Nights)
Rio de Janeiro, Brazil • Maceio, Brazil • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Tortola • Miami
Average Starting Price
$7,799pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$910pp
Jim's Onboard Credit
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