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Grandeur of the Seas
Royal Caribbean
Aug 28, 2027 - Sep 4, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$648pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 7, 2027 - Dec 17, 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
$4,299pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Jan 26, 2028 - Feb 4, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • St John's, Antigua • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,005pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • 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
$4,319pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 13, 2027 - Nov 20, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Lucia • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,359pp
Jim's Onboard Credit
28% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 7, 2028 - Jan 17, 2028 (10 Nights)
Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,749pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 9, 2027 - Dec 19, 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
$3,799pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Nov 23, 2027 - Dec 4, 2027 (11 Nights)
Miami • San Juan, Puerto Rico • Saint Barthelemy, Gustavia • Little Bay, Montserrat • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,153pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Nov 29, 2026 - Dec 20, 2026 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,164pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

EXPLORA IV
Explora Journeys
Dec 23, 2027 - Dec 30, 2027 (7 Nights)
Miami • St. Thomas • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$4,685pp
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!

Marina
Oceania Cruises
Dec 27, 2027 - Jan 6, 2028 (10 Nights)
Miami • Nassau • San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$3,499pp
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!

31% OFF
Carnival Breeze
Carnival Cruise Line
Jan 29, 2028 - Feb 12, 2028 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • St John's, Antigua • St. Lucia • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,326pp
Jim's Onboard Credit
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