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Celebrity Constellation
Celebrity Cruises
Feb 6, 2027 - Feb 13, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$768pp
Jim's Onboard Credit
35% OFF
Carnival Firenze
Carnival Cruise Line
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • St. Lucia • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,135pp
Jim's Onboard Credit
21% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Feb 16, 2028 - Mar 2, 2028 (15 Nights)
Miami • Tortola • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • George Town, Cayman Islands • Miami
Average Starting Price
$13,049pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Feb 14, 2027 - Mar 6, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami
Average Starting Price
$4,444pp
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!

Silver Spirit
Silversea
Mar 19, 2027 - Mar 31, 2027 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$5,000pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$804pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$678pp
Jim's Onboard Credit
Island Princess
Princess Cruises
Nov 29, 2027 - Dec 13, 2027 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • Bridgetown, Barbados • St. Lucia • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,024pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$636pp
Jim's Onboard Credit
25% OFF
Vista
Oceania Cruises
Nov 11, 2026 - Nov 25, 2026 (14 Nights)
Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Miami
Average Starting Price
$4,875pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,364pp
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!

9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Mar 10, 2028 (27 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Santo Tomas de Castilla, Guatemala • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$12,610pp
Jim's Onboard Credit
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