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Seabourn Quest
Seabourn
Dec 4, 2027 - Dec 18, 2027 (14 Nights)
Miami • St. John • Saint Barthelemy, Gustavia • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • Little Bay, Montserrat • St John's, Antigua • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,653pp
Jim's Onboard Credit
Celebrity Xcel
Celebrity Cruises
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
Fort Lauderdale • Samana, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,001pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami
Average Starting Price
$6,785pp
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!

22% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Mar 20, 2028 - Apr 16, 2028 (27 Nights)
Miami • Cruising the Atlantic Ocean • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Atlantic Ocean cruising • Atlantic Ocean cruising • Miami • Nassau • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • Ponta Delgada (Azores), Portugal • Atlantic Ocean cruising • Santa Cruz de la Palma, Spain • Atlantic Ocean cruising • Tangier, Morocco • Malaga, Spain • Alicante, Spain • Barcelona, Spain
Average Starting Price
$16,049pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 29, 2027 - Feb 5, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$5,025pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
Miami • St. John • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Dec 20, 2027 - Dec 27, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • 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

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 Journey
Azamara
Nov 21, 2026 - Dec 5, 2026 (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 • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$5,089pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Dec 28, 2027 - Jan 11, 2028 (14 Nights)
Fort Lauderdale • George Town, Cayman Islands • Montego Bay, Jamaica • La Romana, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$7,030pp
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!

Seabourn Ovation
Seabourn
Nov 21, 2026 - Dec 5, 2026 (14 Nights)
San Juan, Puerto Rico • St. Barthelemy, F.W.I • St. Kitts • Les Trois-Îlets • Port Elizabeth, South Africa • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Rodney Bay, Saint Lucia • Dominica • Terre de Haut, Guadeloupe • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$6,684pp
Jim's Onboard Credit
15% OFF
Marina
Oceania Cruises
Feb 23, 2027 - Mar 5, 2027 (10 Nights)
Miami • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$3,527pp
Jim's Onboard Credit
Silver Spirit
Silversea
Feb 20, 2029 - Mar 4, 2029 (12 Nights)
Miami • San Juan del sur, Nicaragua • Gustavia, St. Barts • St John's, Antigua • Roseau, Dominica • St. Kitts • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$5,300pp
Jim's Onboard Credit
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