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Cruise Dates

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October 2026

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45% OFF

MSC Meraviglia

MSC Cruises

Feb 13, 2027 - Feb 27, 2027 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Nassau • Ocean Cay • Grand Turk • Miami

Average Starting Price

$1,155pp

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!

9% OFF

Crystal Serenity

Crystal Cruises

Dec 22, 2027 - Jan 8, 2028 (17 Nights)

Fort Lauderdale • Grand Turk • Pointe-à-Pitre, Guadeloupe • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Cap Cana (Punta Cana), Dominican Republic • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$8,850pp

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!

Celebrity Ascent

Celebrity Cruises

Jan 14, 2028 - Jan 24, 2028 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Castries, St. Lucia • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Jan 10, 2027 - Jan 20, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • Les Saintes, F.W.I. • St. Kitts • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados

Average Starting Price

Jan 8, 2028 - Jan 18, 2028 (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

$4,299pp

Jim's Onboard Credit

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 27, 2028 - Feb 5, 2028 (9 Nights)

Miami • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Philipsburg, St. Maarten • Miami

Average Starting Price

Dec 28, 2027 - Jan 7, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • St. Kitts • Little Bay, Montserrat • Saint Barthelemy, Gustavia • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

$6,753pp

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!

Celebrity Constellation

Celebrity Cruises

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Mar 7, 2027 - Mar 21, 2027 (14 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami • Providenciales, Turks and Caicos Islands • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

$10,395pp

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!

Star Legend

Windstar Cruises

Jan 3, 2028 - Jan 17, 2028 (14 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

Feb 24, 2027 - Mar 6, 2027 (10 Nights)

Average Starting Price

49% OFF

Dec 18, 2027 - Jan 2, 2028 (15 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami • Grand Turk • Puerto Plata, Dominican Republic • Ocean Cay • Nassau • Miami

Average Starting Price

$2,180pp

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!

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