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Cruise Dates

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November 2026

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Wind Surf

Windstar Cruises

Dec 19, 2027 - Jan 3, 2028 (15 Nights)

Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • 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 • Charlestown, Nevis • 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

$4,620pp

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!

Sun Princess

Princess Cruises

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale

Average Starting Price

$619pp

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!

Viking Hnoss

Viking

Sep 16, 2028 - Sep 23, 2028 (7 Nights)

Amsterdam, Netherlands • Kinderdijk, Netherlands • Cologne, Germany • Koblenz, Germany • Middle Rhine • Rudesheim, Germany • Speyer, Germany • Strasbourg, France • Breisach, Germany • Basel, Switzerland

Average Starting Price

Jun 25, 2027 - Jun 28, 2027 (3 Nights)

Port Canaveral (Orlando), Florida • Nassau • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

49% OFF

Nov 20, 2027 - Nov 27, 2027 (7 Nights)

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique

Average Starting Price

$999pp

Jim's Onboard Credit

Norwegian Breakaway

Norwegian Cruise Line

May 2, 2027 - May 9, 2027 (7 Nights)

Boston • Halifax, Nova Scotia • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • Boston

Average Starting Price

Mar 4, 2028 - Mar 11, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Sep 16, 2027 - Oct 9, 2027 (23 Nights)

Kangerlussuaq, Greenland • Nuuk (Godthaab), Greenland • Pangnirtung, Nunavut • Kekerten Island, Nunavut • Lady Franklin Island, Canada • Monumental Island (Nunavut), Canada • Lower Savage Islands, Canada • Resolution Island, Nunavut, Canada • Nachvak Fiord, Torngat Mts, Canada • Ramah Bay, Torngat Mts, Canada • Rose Island, Bahamas • Hebron, Canada • Nain, Canada • Indian Harbour, Newfoundland • Battle Harbour, Labrador • L'Anse aux Meadows, Newfoundland • Halifax, Nova Scotia • Carambola Beach, Saint Kitts and Nevis • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados

Average Starting Price

$25,218pp

Jim's Onboard Credit

52% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Jul 3, 2027 - Jul 8, 2027 (5 Nights)

Tampa • Key West, Florida • Cozumel • Tampa

Average Starting Price

64% OFF

Feb 21, 2027 - Feb 27, 2027 (6 Nights)

Miami • Nassau • Ocean Cay • Grand Turk • Miami

Average Starting Price

$348pp

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!