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Vision of the Seas
Royal Caribbean
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$907pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Dec 22, 2026 - Jan 12, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale
Average Starting Price
$3,689pp
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!

Seabourn Ovation
Seabourn
Oct 30, 2027 - Nov 27, 2027 (28 Nights)
Athens (Piraeus), Greece • Valletta, Malta • Trapani, Italy • Cagliari, Italy • Alghero, Italy • Mahon, Spain • Barcelona, Spain • Valencia, Spain • Cartagena, Spain • Motril, Spain • Melilla, Morocco • Cadiz, Spain • Porto, Portugal • Lisbon, Portugal • Funchal, Portugal • St John's, Antigua • St. Kitts • Trois Ilets, Martinique • Bridgetown, Barbados
Average Starting Price
$18,013pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,835pp
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!

48% OFF
MSC Meraviglia
MSC Cruises
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,915pp
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!

Valiant Lady
Virgin Voyages
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$763pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$1,318pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 15, 2027 - Jan 25, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$6,799pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 14, 2027 - Nov 28, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$4,019pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 5, 2027 - Jan 21, 2027 (16 Nights)
Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$12,960pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Jan 4, 2027 - Jan 15, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$3,517pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$1,049pp
Jim's Onboard Credit
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