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Cruise Dates

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November 2026

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Wind Surf

Windstar Cruises

Dec 26, 2026 - Jan 9, 2027 (14 Nights)

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

Average Starting Price

$7,099pp

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!

Norwegian Viva

Norwegian Cruise Line

Nov 1, 2027 - Nov 15, 2027 (14 Nights)

Lisbon, Portugal • Las Palmas (Gran Canaria), Spain • Mindelo, Cape Verde • Tortola • Great Stirrup Cay • Miami

Average Starting Price

$1,589pp

Jim's Onboard Credit

Norwegian Escape

Norwegian Cruise Line

Feb 5, 2027 - Feb 12, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

48% OFF

Apr 23, 2028 - May 5, 2028 (12 Nights)

Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain

Average Starting Price

$768pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

Sep 15, 2028 - Sep 20, 2028 (5 Nights)

Manhattan • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • Manhattan

Average Starting Price

$799pp

Jim's Onboard Credit

Adventure of the Seas

Royal Caribbean

Jan 30, 2027 - Feb 7, 2027 (8 Nights)

Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

$994pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

48% OFF

MSC World Atlantic

MSC Cruises

Sep 16, 2028 - Sep 30, 2028 (14 Nights)

Port Canaveral (Orlando), Florida • Ocean Cay • Costa Maya • Cozumel • Nassau • Port Canaveral (Orlando), Florida • Ocean Cay • Grand Turk • Puerto Plata, Dominican Republic • Nassau • Port Canaveral (Orlando), Florida

Average Starting Price

$1,562pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

46% OFF