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Crown Princess
Princess Cruises
Jan 29, 2027 - Feb 5, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,499pp
Jim's Onboard Credit
52% OFF
MSC World Europa
MSC Cruises
Nov 18, 2026 - Dec 5, 2026 (17 Nights)
Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Fort-De-France, Martinique
Average Starting Price
$759pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 26, 2027 - Dec 3, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,679pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 26, 2028 - Mar 11, 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
$9,608pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 6, 2028 - Mar 20, 2028 (14 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,220pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Mar 6, 2028 - Mar 20, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$1,522pp
Jim's Onboard Credit
MSC World Europa
MSC Cruises
Dec 2, 2026 - Dec 6, 2026 (4 Nights)
Bridgetown, Barbados • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$619pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 15, 2027 - Jan 22, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,489pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,969pp
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!

Seabourn Ovation
Seabourn
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$5,343pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 6, 2028 - Mar 27, 2028 (21 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$6,348pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 28, 2028 - Mar 6, 2028 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$769pp
Jim's Onboard Credit
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