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Wind Surf
Windstar Cruises
Nov 20, 2027 - Dec 5, 2027 (15 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • 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 • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$4,845pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Jan 21, 2028 - Jan 28, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$849pp
Jim's Onboard Credit
5% OFF
Nieuw Amsterdam
Holland America Line
Dec 11, 2026 - Dec 20, 2026 (9 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$829pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Brilliant Lady
Virgin Voyages
Dec 28, 2026 - Jan 7, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • St John's, Antigua • Bimini • Miami
Average Starting Price
$1,690pp
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
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$4,543pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Nov 29, 2026 - Dec 6, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Grand Turk • Miami
Average Starting Price
$4,575pp
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!

20% OFF
Allura
Oceania Cruises
Dec 2, 2026 - Dec 12, 2026 (10 Nights)
Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • St. Croix • Tortola • Miami
Average Starting Price
$4,680pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Feb 1, 2027 - Feb 13, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,119pp
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
$749pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 25, 2027 - Jan 1, 2028 (7 Nights)
San Juan, Puerto Rico • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Tortola • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,959pp
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!

Sirena
Oceania Cruises
Oct 25, 2027 - Nov 21, 2027 (27 Nights)
Montreal, Quebec • Quebec City, Quebec • Saguenay, Quebec • Baie-Comeau, Quebec • Havre-Saint-Pierre, Quebec • Corner Brook, Newfoundland • Sydney, Nova Scotia • Halifax, Nova Scotia • Saint John, New Brunswick • Portland, Maine • New York, New York • Tortola • St John's, Antigua • Basseterre, St. Kitts and Nevis • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$8,899pp
Jim's Onboard Credit
Norwegian Luna
Norwegian Cruise Line
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,019pp
Jim's Onboard Credit
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