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Azamara Quest
Azamara
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$3,529pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 29, 2027 - Jan 8, 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

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 Xcel
Celebrity Cruises
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
Fort Lauderdale • Samana, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,011pp
Jim's Onboard Credit
26% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 27, 2028 - Feb 6, 2028 (10 Nights)
Miami • Gustavia, St. Barts • St. Kitts • St. Lucia • Dominica • Pointe-à-Pitre, Guadeloupe • Miami
Average Starting Price
$7,099pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 14, 2027 - Jan 25, 2027 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Cape Liberty
Average Starting Price
$1,841pp
Jim's Onboard Credit
FREE Specialty Dining Meal
EXPLORA III
Explora Journeys
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • St. Thomas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami
Average Starting Price
$10,725pp
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!

Celebrity Beyond
Celebrity Cruises
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,272pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 3, 2028 - Jan 10, 2028 (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
$2,443pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
Miami • San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$4,368pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Jan 3, 2028 - Jan 11, 2028 (8 Nights)
San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$3,840pp
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!

Valiant Lady
Virgin Voyages
Jan 23, 2027 - Jan 29, 2027 (6 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • San Juan, Puerto Rico
Average Starting Price
$834pp
Jim's Onboard Credit
Azamara Journey
Azamara
Dec 5, 2026 - Dec 18, 2026 (13 Nights)
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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$7,469pp
Jim's Onboard Credit
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