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Norwegian Aura
Norwegian Cruise Line
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,349pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 29, 2028 - Feb 12, 2028 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$10,808pp
Jim's Onboard Credit
29% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 7, 2029 - Feb 17, 2029 (10 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$7,299pp
Jim's Onboard Credit
Azamara Quest
Azamara
Feb 16, 2028 - Mar 22, 2028 (35 Nights)
Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$14,819pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
May 28, 2028 - Jun 4, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,219pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,239pp
Jim's Onboard Credit
42% OFF
MSC Opera
MSC Cruises
Jun 25, 2027 - Jul 2, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique
Average Starting Price
$1,060pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Tortola • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$3,079pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,149pp
Jim's Onboard Credit
Norwegian Luna
Norwegian Cruise Line
Mar 19, 2028 - Mar 26, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,279pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 27, 2027 - Jan 9, 2028 (13 Nights)
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 • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • Philipsburg, St. Maarten
Average Starting Price
$3,760pp
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
Mar 5, 2028 - Mar 19, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,908pp
Jim's Onboard Credit
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