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Cruise Dates

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November 2026

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49% OFF

MSC Opera

MSC Cruises

Dec 27, 2027 - Jan 10, 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

$2,482pp

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!

Wind Surf

Windstar Cruises

Jan 30, 2027 - Feb 13, 2027 (14 Nights)

Philipsburg, St. Maarten • 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 • Falmouth (English Harbour), Antigua & Barbuda • 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

Dec 19, 2026 - Dec 26, 2026 (7 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

Average Starting Price

50% OFF

Dec 20, 2027 - Jan 3, 2028 (14 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • 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

Average Starting Price

Jan 23, 2027 - Jan 30, 2027 (7 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

Average Starting Price

Mar 17, 2029 - Mar 24, 2029 (7 Nights)

Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados

Average Starting Price

54% OFF

Mar 29, 2027 - Apr 5, 2027 (7 Nights)

Average Starting Price

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

Average Starting Price

Dec 9, 2028 - Dec 23, 2028 (14 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados

Average Starting Price

49% OFF

Jan 10, 2028 - Jan 17, 2028 (7 Nights)

Average Starting Price

Jan 9, 2027 - Jan 16, 2027 (7 Nights)

Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

Mar 10, 2029 - Mar 17, 2029 (7 Nights)

Average Starting Price

$5,168pp

Jim's Onboard Credit

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