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Seabourn Ovation
Seabourn
Feb 5, 2028 - Feb 19, 2028 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
Average Starting Price
$10,008pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,509pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 7, 2028 - Feb 21, 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
$1,632pp
Jim's Onboard Credit
30% OFF
MSC World Europa
MSC Cruises
Dec 15, 2026 - Dec 29, 2026 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Bridgetown, Barbados
Average Starting Price
$1,808pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Dec 4, 2026 - Dec 12, 2026 (8 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Scenic Cruising the Pitons • Scarborough (Tobago), Trinidad and Tobago • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Grenada • Willemstad, Curacao • Oranjestad, Aruba
Average Starting Price
$3,060pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 19, 2028 - Mar 4, 2028 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
Average Starting Price
$9,708pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 14, 2028 - Feb 21, 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
$829pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 12, 2027 - Feb 19, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,479pp
Jim's Onboard Credit
20% OFF
MSC World Europa
MSC Cruises
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,632pp
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!

Star Legend
Windstar Cruises
Nov 12, 2026 - Dec 4, 2026 (22 Nights)
Malaga, Spain • Tangier, Morocco • Casablanca, Morocco • Funchal, Portugal • Bridgetown, Barbados • Anse Mitan, Martinique • Rodney Bay, Saint Lucia • Rodney Bay, Saint Lucia • Castries, St. Lucia • Scenic Cruising the Pitons • Mayreau Island, Saint Vincent and the Grenadines • Grenada • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$9,174pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 13, 2027 - Feb 27, 2027 (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
$10,518pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Feb 21, 2028 - Mar 6, 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
$1,602pp
Jim's Onboard Credit
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