Sailing Search

38 Cruises

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,236

as little as

$462/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$3,236

as little as

$462/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Bonus Details

$3,236 USD

$4,136 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,324

as little as

$475/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

Avg. per person

From

$3,324

as little as

$475/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Bonus Details

$3,324 USD

$4,224 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

8 Nights Western Mediterranean Cruise

Departing From

Venice

Duration

8 Nights

Ship

Star Legend

Port of Call

Venice - Venice - Zadar - Dubrovnik - Dubrovnik - Messina (taormina) - Naples - RomeItinerary Details

Itinerary Details

8 Nights Western Mediterranean Cruise

Departing From

Venice

Avg. per person

From

$3,458

as little as

$432/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

8 Nights

Ship

Star Legend

Port of Call

Venice - Venice - Zadar - Dubrovnik - Dubrovnik - Messina (taormina) - Naples - RomeItinerary Details

Itinerary Details

Avg. per person

From

$3,458

as little as

$432/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Jan 4, 2026 - Jan 12, 2026 Sun - Mon

Interior

Oceanview

Balcony

Suite

Jan 4, 2026 - Jan 12, 2026 Sun - Mon

Bonus Details

$3,458 USD

$4,898 USD

$6,418 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,522

as little as

$503/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$3,522

as little as

$503/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Jan 18, 2026 - Jan 25, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 18, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$3,522 USD

$4,222 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

10 Nights Caribbean Cruise

Duration

10 Nights

Ship

Wind Spirit

Port of Call

Bridgetown - Mayreau - Roseau - Anse Mitan - Charlestown - Basseterre - St Johns - Falmouth Harbour - Gustavia - Road Bay - Philipsburg, St MaartenItinerary Details

Itinerary Details

10 Nights Caribbean Cruise

Avg. per person

From

$3,720

as little as

$372/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

10 Nights

Ship

Wind Spirit

Port of Call

Bridgetown - Mayreau - Roseau - Anse Mitan - Charlestown - Basseterre - St Johns - Falmouth Harbour - Gustavia - Road Bay - Philipsburg, St MaartenItinerary Details

Itinerary Details

Avg. per person

From

$3,720

as little as

$372/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Jan 4, 2026 - Jan 14, 2026 Sun - Wed

Interior

Oceanview

Balcony

Suite

Jan 4, 2026 - Jan 14, 2026 Sun - Wed

Bonus Details

$3,720 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

Filter Cruises

38 Cruises

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

DO YOU HAVE A FUTURE CRUISE CREDIT? Redeem your future cruise credit with CruiseDirector. Call us today 1-888-409-2784.

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

JOIN THE VOYAGER CLUB! Members receive Airport Club Access, Concierge Support, Price Assurance & More.

8 Nights Western Mediterranean Cruise

8 Nights Western Mediterranean Cruise

MAKE THE WORLD GREENER CruiseDirector and One Tree Planted are planting a tree for every passenger who sails with us.

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

BEST PRICE GUARANTEE! If you find a lower price online, we’ll match it!

10 Nights Caribbean Cruise

10 Nights Caribbean Cruise

FREE HOLDS Lock in a great price, finalize plans & pay later. Free Holds available on the final step

DO YOU HAVE A FUTURE CRUISE CREDIT?

Redeem your future cruise credit with CruiseDirector. Call us today 1-888-409-2784.

JOIN THE VOYAGER CLUB!

Members receive Airport Club Access, Concierge Support, Price Assurance & More.

MAKE THE WORLD GREENER

CruiseDirector and One Tree Planted are planting a tree for every passenger who sails with us.

BEST PRICE GUARANTEE!

If you find a lower price online, we’ll match it!

FREE HOLDS

Lock in a great price, finalize plans & pay later. Free Holds available on the final step