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Vista
Oceania Cruises
Dec 16, 2028 - Jan 7, 2029 (22 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Nassau • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$10,149pp
Jim's Onboard Credit
48% OFF
MSC Seashore
MSC Cruises
Jan 15, 2028 - Jan 23, 2028 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,358pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 5, 2027 - Feb 12, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico
Average Starting Price
$7,240pp
Jim's Onboard Credit
Silver Ray
Silversea
Dec 22, 2026 - Jan 5, 2027 (14 Nights)
Miami • Grand Turk • St. Kitts • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • St. John • San Juan, Puerto Rico • Miami
Average Starting Price
$10,100pp
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!

Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 8, 2027 (5 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$680pp
Jim's Onboard Credit
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
Marina
Oceania Cruises
Feb 1, 2027 - Feb 13, 2027 (12 Nights)
Miami • Oranjestad, Aruba • Willemstad, Curacao • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$3,949pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 2, 2027 - Jan 9, 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
$811pp
Jim's Onboard Credit
Silver Nova
Silversea
Jan 6, 2027 - Jan 18, 2027 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St. Kitts • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Bridgetown, Barbados
Average Starting Price
$7,200pp
Jim's Onboard Credit
71% OFF
MSC Meraviglia
MSC Cruises
Nov 21, 2026 - Nov 29, 2026 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$538pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 7, 2026 - Nov 14, 2026 (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
$1,043pp
Jim's Onboard Credit
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