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53% OFF
MSC Opera
MSC Cruises
Oct 25, 2027 - Nov 1, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic
Average Starting Price
$584pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Dec 28, 2028 - Jan 11, 2029 (14 Nights)
Miami • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Castries, St. Lucia • St John's, Antigua • Tortola • Miami
Average Starting Price
$7,599pp
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!

Emerald Princess
Princess Cruises
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$669pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 19, 2029 - Jan 29, 2029 (10 Nights)
Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Roseau, Dominica • St. Thomas • Miami
Average Starting Price
$7,499pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,040pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Feb 18, 2028 - Feb 25, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$859pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 20, 2027 - Apr 8, 2027 (19 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Funchal, Portugal • Portimão, Portugal • Lisbon, Portugal
Average Starting Price
$10,898pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Nov 6, 2027 - Nov 13, 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
$686pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Nov 6, 2027 - Nov 13, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Tortola • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,389pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Thomas • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,289pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Apr 4, 2027 - Apr 11, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$999pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Jan 15, 2027 - Jan 22, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$679pp
Jim's Onboard Credit
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