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Seabourn Quest
Seabourn
Dec 28, 2028 - Jan 7, 2029 (10 Nights)
Miami • San Juan, Puerto Rico • St. Kitts • Little Bay, Montserrat • Saint Barthelemy, Gustavia • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,113pp
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!

Resilient Lady
Virgin Voyages
Nov 8, 2026 - Nov 16, 2026 (8 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • Bimini • Miami
Average Starting Price
$872pp
Jim's Onboard Credit
48% OFF
Carnival Vista
Carnival Cruise Line
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$553pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Little Bay, Montserrat • Castries, St. Lucia • Fort-De-France, Martinique • Soper's Hole, Tortola • San Juan, Puerto Rico
Average Starting Price
$4,800pp
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!

Enchanted Princess
Princess Cruises
Jan 16, 2027 - Jan 26, 2027 (10 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,459pp
Jim's Onboard Credit
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
Valiant Lady
Virgin Voyages
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Vista
Oceania Cruises
Jan 19, 2029 - Jan 31, 2029 (12 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • George Town, Cayman Islands • Ocho Rios, Jamaica • La Romana, Dominican Republic • Tortola • San Juan, Puerto Rico • Miami
Average Starting Price
$4,999pp
Jim's Onboard Credit
30% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Nov 13, 2028 - Dec 3, 2028 (20 Nights)
Rome (Civitavecchia), Italy • Naples, Italy • Barcelona, Spain • Cruising the Mediterranean Sea • Malaga, Spain • Cadiz, Spain • Lisbon, Portugal • Cruising the Atlantic Ocean • Funchal, Portugal • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • San Juan, Puerto Rico • Cruising the Caribbean Sea • Cruising the Florida Straits • Miami
Average Starting Price
$13,099pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Road Bay, Anguilla • Ocean Cay • Miami
Average Starting Price
$4,020pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 24, 2028 - Feb 7, 2028 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
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