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Silver Spirit
Silversea
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Fort-De-France, Martinique • Gustavia, St. Barts • Roseau, Dominica • Grenada • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$3,700pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Feb 25, 2028 - Mar 6, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,825pp
Jim's Onboard Credit
26% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Jan 15, 2028 - Jan 25, 2028 (10 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$8,449pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,219pp
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
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
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
$2,029pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 25, 2026 - Dec 5, 2026 (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
Viking Sky
Viking
Jan 3, 2029 - Jan 13, 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
$4,999pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Feb 28, 2028 - Mar 11, 2028 (12 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • St. Thomas • Fort Lauderdale
Average Starting Price
$1,685pp
Jim's Onboard Credit
Silver Shadow
Silversea
Feb 27, 2029 - Mar 10, 2029 (11 Nights)
San Juan del sur, Nicaragua • Gustavia, St. Barts • St John's, Antigua • Les Saintes, F.W.I. • Castries, St. Lucia • Canouan, Saint Vincent and the Grenadines • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan del sur, Nicaragua
Average Starting Price
$5,900pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Castries, St. Lucia • Willemstad, Curacao • Colon, Panama
Average Starting Price
$660pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 13, 2027 - Mar 27, 2027 (14 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 • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$11,618pp
Jim's Onboard Credit
Azamara Journey
Azamara
Dec 12, 2026 - Dec 18, 2026 (6 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$2,219pp
Jim's Onboard Credit
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