Destination Page: Dominica2

Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 22, 2025
through Mar 29, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Mar 22, 2025 through Mar 29, 2025

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

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Inside

$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

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14-Night Eastern Caribbean Voyage

from $3,539.00 (USD)

Per Person

Nov 08, 2025
through Nov 22, 2025

More offers from Azamara

Nights: 14

Ship: Azamara Quest

Price Per Night:$252.79 (USD)
(based on double occupancy, for comparison only)

Nov 08, 2025 through Nov 22, 2025

Itinerary: San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...

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Inside

$3,539.00
Cat:10
252.79 per night

Outside

$3,719.00
Cat:08
265.64 per night

Balcony

$3,979.00
Cat:V3
284.21 per night

Suite

$6,239.00
Cat:N2
445.64 per night

More Details Contact Us

Southern Caribbean Holiday
Roundtrip from San Juan, Puerto Rico

from $1,094.81 (USD)

Per Person

Dec 20, 2025
through Dec 27, 2025

More offers from Royal Caribbean International

Nights: 7

Ship: Jewel of the Seas

Price Per Night:$156.40 (USD)
(based on double occupancy, for comparison only)

Dec 20, 2025 through Dec 27, 2025

Itinerary: San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, St. Croix, U.S.V.I., Roseau, Dominica, Bridgetown, Barbados, Cruising, San Juan, Puerto Rico

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Inside

$1,094.81
Cat:ZI
156.40 per night

Outside

$1,214.81
Cat:YO
173.54 per night

Balcony

$1,464.81
Cat:XB
209.26 per night

Suite

N/A

More Details Contact Us

Caribbean & Amazon Icons
Boston to Miami

from $9,599.00 (USD)

Per Person

Oct 27, 2025
through Dec 07, 2025

More offers from Oceania Cruises

Nights: 41

Ship: Insignia

Price Per Night:$234.12 (USD)
(based on double occupancy, for comparison only)

Oct 27, 2025 through Dec 07, 2025

Itinerary: Boston, Newport, Hamilton, St. George, Gustavia, St. John's, Castries, Bridgetown, St. George's, Kralendijk...

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Inside

N/A

Outside

$9,599.00
Cat:D
234.12 per night

Balcony

$14,099.00
Cat:B2
343.88 per night

Suite

$20,499.00
Cat:PH2
499.98 per night

More Details Contact Us

Caribbean & Central America Cruise
Bridgetown to Bridgetown

from $9,900.00 (USD)

Per Person

Dec 22, 2025
through Jan 05, 2026

More offers from Silversea Cruises

Nights: 14

Ship: Silver Spirit

Price Per Night:$707.14 (USD)
(based on double occupancy, for comparison only)

Dec 22, 2025 through Jan 05, 2026

Itinerary: Bridgetown, Castries, St George's, Day at sea, Philipsburg, St. Maarten, St. Thomas, Basseterre, St. Kitts, St. John's, Roseau, Bequia...

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Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$9,900.00
Cat:VI
707.14 per night

More Details Contact Us

Southern Caribbean Holiday
Roundtrip from San Juan, Puerto Rico

from $1,197.27 (USD)

Per Person

Dec 27, 2025
through Jan 03, 2026

More offers from Royal Caribbean International

Nights: 7

Ship: Jewel of the Seas

Price Per Night:$171.04 (USD)
(based on double occupancy, for comparison only)

Dec 27, 2025 through Jan 03, 2026

Itinerary: San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, St. Croix, U.S.V.I., Roseau, Dominica, Bridgetown, Barbados, Cruising, San Juan, Puerto Rico

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Inside

$1,197.27
Cat:ZI
171.04 per night

Outside

$1,242.77
Cat:YO
177.54 per night

Balcony

$1,823.77
Cat:XB
260.54 per night

Suite

N/A

More Details Contact Us

Royal Clipper - Windward Islands 7 Nights

from $1,790.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 07, 2026
through Mar 14, 2026

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$255.71 (USD)
(based on double occupancy, for comparison only)

Mar 07, 2026 through Mar 14, 2026

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,790.00
Cat:Category 6
255.71 per night

Outside

$2,040.00
Cat:Category 5
291.43 per night

Balcony

N/A

Suite

$3,880.00
Cat:Deluxe Suite with Veranda
554.29 per night

More Details Contact Us

Southern Caribbean Cruise

from $1,208.81 (USD)

Per Person

Oct 18, 2025
through Oct 29, 2025

More offers from Celebrity Cruises

Nights: 11

Ship: Celebrity Reflection

Price Per Night:$109.89 (USD)
(based on double occupancy, for comparison only)

Oct 18, 2025 through Oct 29, 2025

Itinerary: Fort Lauderdale, Florida, Philipsburg, St. Maarten, Fort- De- France, Martinique, Castries, St. Lucia, Bridgetown, Barbados, Roseau, Dominica, St. Johns, Antigua, Fort Lauderdale, Florida

Other Categories Starting At:

Inside

$1,208.81
Cat:I2
109.89 per night

Outside

$1,438.81
Cat:O2
130.80 per night

Balcony

$1,856.31
Cat:V3
168.76 per night

Suite

$3,740.31
Cat:S1
340.03 per night

More Details Contact Us

STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $5,399.00 (USD)

Per Person

+ $120.00 taxes/fees

Jan 18, 2025
through Feb 01, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$385.64 (USD)
(based on double occupancy, for comparison only)

Jan 18, 2025 through Feb 01, 2025

Itinerary: Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Philipsburg, St. Maarten, Falmouth Harbour, Road Bay...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $3,699.00 (USD)

Per Person

+ $120.00 taxes/fees

Dec 07, 2025
through Dec 21, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$264.21 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2025 through Dec 21, 2025

Itinerary: Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Road Bay...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Inside

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STAR COLLECTOR: WINDWARD TREASURES: AN ANTILLES ODYSSEY

from $5,429.00 (USD)

Per Person

+ $69.00 taxes/fees

Jan 18, 2025
through Feb 01, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Spirit

Price Per Night:$387.79 (USD)
(based on double occupancy, for comparison only)

Jan 18, 2025 through Feb 01, 2025

Itinerary: Bridgetown, Pigeon Island, The Pitons, Castries, Kingstown, Mayreau, St. George's, Bequia, Bridgetown, St. John's...

Indulge in exquisite white-sand delights and delicious regional cuisine during this voyage to the Lesser Antilles’ Windward Islands, a journey rich in exclusive excursions seldom experienced by others. Trek through a private nature reserve inhabited by lyrical thrushes, curious macaws, and radiant tropical birds to Mount Pimard’s summit views above Pigeon Island. Sample local St. Lucian bites and Trinidadian culinary delights during a walking food tour at Rodney Bay.

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Windward Islands 7 Nights

from $1,700.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 08, 2025
through Mar 15, 2025

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$242.86 (USD)
(based on double occupancy, for comparison only)

Mar 08, 2025 through Mar 15, 2025

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friar's Bay (beach), St. Kitts (PM), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,700.00
Cat:Category 6
242.86 per night

Outside

$1,940.00
Cat:Category 5
277.14 per night

Balcony

N/A

Suite

$3,520.00
Cat:Deluxe Suite with Veranda
502.86 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from Fort Lauderdale, Florida

from $1,063.84 (USD)

Per Person

Jan 24, 2025
through Feb 02, 2025

More offers from Royal Caribbean International

Nights: 9

Ship: Grandeur of the Seas

Price Per Night:$118.20 (USD)
(based on double occupancy, for comparison only)

Jan 24, 2025 through Feb 02, 2025

Itinerary: Fort Lauderdale, Florida, Cruising, Philipsburg, St. Maarten, Roseau, Dominica, Basseterre, St Kitts & Nevis, San Juan, Puerto Rico, Puerto Plata, Dominican Rep, Cruising, Fort Lauderdale, Florida

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Inside

$1,063.84
Cat:4V
118.20 per night

Outside

$1,509.84
Cat:1N
167.76 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

11-Day Eastern Caribbean Wayfarer
Roundtrip from Fort Lauderdale, Florida, US

from $1,659.00 (USD)

Per Person

+ $150.00 taxes/fees

Nov 27, 2024
through Dec 08, 2024

More offers from Holland America Line

Nights: 11

Ship: Eurodam

Price Per Night:$150.82 (USD)
(based on double occupancy, for comparison only)

Nov 27, 2024 through Dec 08, 2024

Itinerary: Fort Lauderdale, Florida, US, Days At Sea, St. Thomas, U.S.V.I., Basseterre, St Kitts and Nevis, Roseau, Dominica, Castries, Saint Lucia, St. Johns, Antigua and Barbuda, Philipsburg, Sint Maarten, Days At Sea, Half Moon Cay, Bahamas...

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Inside

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Royal Clipper - Windward Islands 7 Nights

from $1,790.00 (USD)

Per Person

+ $235.00 taxes/fees

Dec 13, 2025
through Dec 20, 2025

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$255.71 (USD)
(based on double occupancy, for comparison only)

Dec 13, 2025 through Dec 20, 2025

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,790.00
Cat:Category 6
255.71 per night

Outside

$2,040.00
Cat:Category 5
291.43 per night

Balcony

N/A

Suite

$3,880.00
Cat:Deluxe Suite with Veranda
554.29 per night

More Details Contact Us

11-Day Eastern Caribbean: Windward & Leeward Islands
Roundtrip from Fort Lauderdale, Florida, US

from $2,089.00 (USD)

Per Person

+ $155.00 taxes/fees

Dec 09, 2025
through Dec 20, 2025

More offers from Holland America Line

Nights: 11

Ship: Koningsdam

Price Per Night:$189.91 (USD)
(based on double occupancy, for comparison only)

Dec 09, 2025 through Dec 20, 2025

Itinerary: Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...

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Inside

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Outside

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Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Dec 14, 2024
through Dec 21, 2024

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Dec 14, 2024 through Dec 21, 2024

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

Other Categories Starting At:

Inside

$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

13-Night Eastern Caribbean Voyage

from $2,609.00 (USD)

Per Person

Dec 06, 2025
through Dec 19, 2025

More offers from Azamara

Nights: 13

Ship: Azamara Quest

Price Per Night:$200.69 (USD)
(based on double occupancy, for comparison only)

Dec 06, 2025 through Dec 19, 2025

Itinerary: San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...

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Inside

$2,609.00
Cat:12
200.69 per night

Outside

$3,219.00
Cat:08
247.62 per night

Balcony

$3,489.00
Cat:V3
268.38 per night

Suite

$5,409.00
Cat:N2
416.08 per night

More Details Contact Us

An Extended Journey to Tropical Splendor

from $7,365.00 (USD)

Per Person

Nov 29, 2024
through Dec 13, 2024

More offers from Explora Journeys

Nights: 14

Ship: Explora II

Price Per Night:$526.07 (USD)
(based on double occupancy, for comparison only)

Nov 29, 2024 through Dec 13, 2024

Itinerary: San Juan, Gustavia, St. John's (Antigua), Basseterre, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Road Bay, Roseau, Saint-Pierre...

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Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$7,365.00
Cat:OT1
526.07 per night

More Details Contact Us

Ultimate Snowbird Paradise
Roundtrip from Miami

from $37,099.00 (USD)

Per Person

Jan 08, 2025
through Apr 08, 2025

More offers from Oceania Cruises

Nights: 90

Ship: Vista

Price Per Night:$412.21 (USD)
(based on double occupancy, for comparison only)

Jan 08, 2025 through Apr 08, 2025

Itinerary: Miami, Cruising The Straits Of Florida, George Town, Cruising The Caribbean Sea, Cartagena, Panama Canal Daylight Transit, Cruising The Pacific Ocean, Puntarenas, Corinto, Puerto Quetzal...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$40,099.00
Cat:A3
445.54 per night

Suite

N/A

More Details Contact Us

9-Night Caribbean Journey Voyage

from $1,959.00 (USD)

Per Person

Mar 22, 2025
through Mar 31, 2025

More offers from Azamara

Nights: 9

Ship: Azamara Journey

Price Per Night:$217.67 (USD)
(based on double occupancy, for comparison only)

Mar 22, 2025 through Mar 31, 2025

Itinerary: Bridgetown, Castries, Roseau, Charlestown, Philipsburg, Virgin Gorda, San Juan, Puerto Rico, Miami, Florida

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Inside

$1,959.00
Cat:Z
217.67 per night

Outside

$2,049.00
Cat:Y
227.67 per night

Balcony

$2,829.00
Cat:X
314.33 per night

Suite

$5,459.00
Cat:N2
606.56 per night

More Details Contact Us

STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $5,099.00 (USD)

Per Person

+ $120.00 taxes/fees

Jan 11, 2025
through Jan 25, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$364.21 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2025 through Jan 25, 2025

Itinerary: Philipsburg, St. Maarten, Falmouth Harbour, Gustavia, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Road Bay, Philipsburg, St. Maarten, Charlestown...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Transatlantic Crossing And Eastern Caribbean, 22 Nights (M506D)
New York, New York to London (Southampton), England

from $3,469.00 (USD)

Per Person

+ $7,229.00 taxes/fees

Mar 15, 2025
through Apr 06, 2025

More offers from Cunard Line

Nights: 22

Ship: Queen Mary 2

Price Per Night:$157.68 (USD)
(based on double occupancy, for comparison only)

Mar 15, 2025 through Apr 06, 2025

Itinerary: New York, New York, St. Maarten, Netherlands Antilles, St Lucia, Saint Lucia, Grenada, Grenada, Barbados, Barbados, Dominica, Dominica, St. Kitts, ST Kitts/Nevis, Tortola, B.V.I., New York, New York, London (Southampton), England

Start this 22-night voyage in New York before sailing to the warm and inviting shores of the Caribbean, and back to New York. Next a Transatlantic Crossing brings ample time to relish life on board.

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Inside

$3,469.00
Cat:IF
157.68 per night

Outside

$4,649.00
Cat:EF
211.32 per night

Balcony

$4,789.00
Cat:DF
217.68 per night

Suite

N/A

More Details Contact Us

STAR COLLECTOR: HIDDEN GEMS OF THE CARIBBEAN

from $4,899.00 (USD)

Per Person

+ $95.00 taxes/fees

Jan 14, 2026
through Jan 31, 2026

More offers from Windstar Cruises

Nights: 17

Ship: Wind Spirit

Price Per Night:$288.18 (USD)
(based on double occupancy, for comparison only)

Jan 14, 2026 through Jan 31, 2026

Itinerary: Philipsburg, St. Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia...

Dive, dine, and delight in iconic Caribbean island destinations during a far-ranging Caribbean loop that conveniently begins and ends in Philipsburg on St. Maarten. Cruise a kayak through sapphire waters near Little Bay, Monserrat, and peer at shadowy fruit bats suspended throughout coastal caves. Drift and spin in a floating tube on a rainforest stream outside Roseau on Dominica prior to sipping rum cocktails mixed with tangy tropical juices.

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STAR COLLECTOR: A LESSER ANTILLES ODYSSEY

from $6,199.00 (USD)

Per Person

+ $99.00 taxes/fees

Feb 21, 2026
through Mar 14, 2026

More offers from Windstar Cruises

Nights: 21

Ship: Wind Spirit

Price Per Night:$295.19 (USD)
(based on double occupancy, for comparison only)

Feb 21, 2026 through Mar 14, 2026

Itinerary: Philipsburg, St. Maarten, St. John's, Road Bay, Soper's Hole, Virgin Gorda / Prickly Pear, British Virgin Islands, Soper's Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St. Maarten, Basseterre...

Embrace extraordinary experiences exclusive to small ship cruising during this three-week exploration of the Caribbean’s Lesser Antilles island chain. Swim with dolphins during an extended overnight stay in Jost Van Dyke in the British Virgin Islands. Savor African, European, and Indian ingredients and influences in popular Caribbean dishes as you sample spicy regional cuisine in the Fairview Great House on St. Kitts.

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Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Jan 25, 2025
through Feb 01, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Jan 25, 2025 through Feb 01, 2025

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

Other Categories Starting At:

Inside

$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Jan 11, 2025
through Jan 18, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2025 through Jan 18, 2025

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

Other Categories Starting At:

Inside

$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

STAR COLLECTOR: IVORY BEACHES & SAPPHIRE SEAS OF THE CARIBBEAN

from $3,399.00 (USD)

Per Person

+ $103.00 taxes/fees

Dec 02, 2025
through Dec 14, 2025

More offers from Windstar Cruises

Nights: 12

Ship: Wind Surf

Price Per Night:$283.25 (USD)
(based on double occupancy, for comparison only)

Dec 02, 2025 through Dec 14, 2025

Itinerary: Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau...

Escape on an extraordinary tropical vacation on this twelve-day cruise to hidden harbors and secluded beaches throughout the Lesser Antilles in the Caribbean. Board a catamaran bound for Norman Island off Tortola and listen to pirate legends and treasure tales prior to your secluded snorkeling excursion among pristine reefs and tropical fish.

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Windward Island Escape
Roundtrip from Bridgetown

from $2,699.00 (USD)

Per Person

Jan 22, 2025
through Jan 29, 2025

More offers from Oceania Cruises

Nights: 7

Ship: Sirena

Price Per Night:$385.57 (USD)
(based on double occupancy, for comparison only)

Jan 22, 2025 through Jan 29, 2025

Itinerary: Bridgetown, Fort-De-France, Gustavia, Roseau, Castries, Kingstown, St. George's, Bridgetown

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Inside

$2,699.00
Cat:G
385.57 per night

Outside

$2,899.00
Cat:D
414.14 per night

Balcony

N/A

Suite

N/A

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An Extended Journey of Central American Jungles and Caribbean Isles

from $8,660.00 (USD)

Per Person

Feb 04, 2025
through Feb 21, 2025

More offers from Explora Journeys

Nights: 17

Ship: Explora II

Price Per Night:$509.41 (USD)
(based on double occupancy, for comparison only)

Feb 04, 2025 through Feb 21, 2025

Itinerary: Miami, Key West, Cayman Brac, Cozumel, Costa Maya, Merida (Progreso), Miami, Road Bay, Roseau, Basse-Terre...

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$8,660.00
Cat:OT1
509.41 per night

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21-Day Eastern Caribbean Wayfarer / Western Explorer
Roundtrip from Fort Lauderdale, Florida, US

from $3,589.00 (USD)

Per Person

+ $265.00 taxes/fees

Mar 01, 2025
through Mar 22, 2025

More offers from Holland America Line

Nights: 21

Ship: Eurodam

Price Per Night:$170.90 (USD)
(based on double occupancy, for comparison only)

Mar 01, 2025 through Mar 22, 2025

Itinerary: Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...

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14-Day Eastern Caribbean: Antilles & Private Island Holiday
Roundtrip from Fort Lauderdale, Florida, US

from $3,044.00 (USD)

Per Person

+ $180.00 taxes/fees

Dec 21, 2025
through Jan 04, 2026

More offers from Holland America Line

Nights: 14

Ship: Volendam

Price Per Night:$217.43 (USD)
(based on double occupancy, for comparison only)

Dec 21, 2025 through Jan 04, 2026

Itinerary: Fort Lauderdale, Florida, US, Days At Sea, Cruz Bay, St. John, U.S. Virgin Islands, Days At Sea, Port-of-Spain, Trinidad and Tobago, Saint Georges, Grenada, Roseau, Dominica, Castries, Saint Lucia, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda...

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11-Day Eastern Caribbean: Windward & Leeward Islands
Roundtrip from Fort Lauderdale, Florida, US

from $2,194.00 (USD)

Per Person

+ $150.00 taxes/fees

Jan 24, 2026
through Feb 04, 2026

More offers from Holland America Line

Nights: 11

Ship: Koningsdam

Price Per Night:$199.45 (USD)
(based on double occupancy, for comparison only)

Jan 24, 2026 through Feb 04, 2026

Itinerary: Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...

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Iberian Explorer
Barcelona to London (Tilbury)

from $2,399.00 (USD)

Per Person

Jan 10, 2026
through Jan 17, 2026

More offers from Viking Ocean Cruises

Nights: 7

Ship: Viking Vela

Price Per Night:$342.71 (USD)
(based on double occupancy, for comparison only)

Jan 10, 2026 through Jan 17, 2026

Itinerary: Barcelona, Murcia (Cartagena), Granada (Málaga), Sail the Strait of Gibraltar, Vigo, Sail the Atlantic Ocean, Portsmouth, London (Tilbury)

Circumnavigate the Iberian Peninsula and uncover the historic treasures of Spain. Explore the Roman past and tranquil beauty of Cartagena and its Murcia province. Visit Málaga, the city of Picasso’s birth, and Granada’s Alhambra palace. Cruise through the Strait of Gibraltar and into the scenic bay of Vigo, gateway to Santiago de Compostela. This enlightening itinerary is complemented by a call on England’s maritime city of Portsmouth.

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Outside

N/A

Balcony

$2,399.00
Cat:V1
342.71 per night

Suite

$3,799.00
Cat:PS3
542.71 per night

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27-Day Amazon Explorer
Roundtrip from Miami

from $6,864.00 (USD)

Per Person

+ $120.00 taxes/fees

Feb 08, 2025
through Mar 07, 2025

More offers from Holland America Line

Nights: 27

Ship: Zaandam

Price Per Night:$254.22 (USD)
(based on double occupancy, for comparison only)

Feb 08, 2025 through Mar 07, 2025

Itinerary: Miami, St Maarten, St Lucia, Scarborough, Cruising The Amazon River, Crossing The Amazon River Bar, Barra Norte Sea, Barra Norte River, Cruising The Amazon River, Cross Equator...

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Transoceanic Special Voyage: Lisbon to Bridgetown

from $13,500.00 (USD)

Per Person

Nov 25, 2025
through Dec 15, 2025

More offers from Silversea Cruises

Nights: 20

Ship: Silver Spirit

Price Per Night:$675.00 (USD)
(based on double occupancy, for comparison only)

Nov 25, 2025 through Dec 15, 2025

Itinerary: Lisbon, Day at sea, Funchal, Madeira, Santa Cruz De La Palma (Canary Islands), Day at sea, Mindelo, Day at sea, Bridgetown, Castries, Fort-De-France...

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N/A

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$13,500.00
Cat:PA
675.00 per night

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East to Ancient Worlds
Miami to Athens (Piraeus)

from $11,499.00 (USD)

Per Person

Apr 04, 2026
through May 07, 2026

More offers from Oceania Cruises

Nights: 33

Ship: Allura

Price Per Night:$348.45 (USD)
(based on double occupancy, for comparison only)

Apr 04, 2026 through May 07, 2026

Itinerary: Miami, San Juan, Basseterre, Castries, Roseau, Charlotte Amalie, Miami, Great Stirrup Cay, Royal Naval Dockyard, Ponta Delgada (Azores)...

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N/A

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N/A

Balcony

$11,499.00
Cat:B4
348.45 per night

Suite

$16,999.00
Cat:PH2
515.12 per night

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STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $4,999.00 (USD)

Per Person

+ $120.00 taxes/fees

Mar 08, 2025
through Mar 22, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$357.07 (USD)
(based on double occupancy, for comparison only)

Mar 08, 2025 through Mar 22, 2025

Itinerary: Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Charlestown...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Caribbean, 21 Nights (Q706A)
Roundtrip from Miami, FL, USA

from $2,739.00 (USD)

Per Person

+ $16,568.00 taxes/fees

Feb 16, 2027
through Mar 09, 2027

More offers from Cunard Line

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$130.43 (USD)
(based on double occupancy, for comparison only)

Feb 16, 2027 through Mar 09, 2027

Itinerary: Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica...

Take each day as slowly as you like on this 21-night sailing in the Caribbean that includes captivating ports like Montego Bay in Jamaica, San Juan in Puerto Rico, and Philipsburg in St. Maarten.

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Inside

$2,739.00
Cat:IF
130.43 per night

Outside

$3,389.00
Cat:FC
161.38 per night

Balcony

$4,239.00
Cat:CA
201.86 per night

Suite

$11,589.00
Cat:P2
551.86 per night

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STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $5,099.00 (USD)

Per Person

+ $120.00 taxes/fees

Feb 08, 2025
through Feb 22, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$364.21 (USD)
(based on double occupancy, for comparison only)

Feb 08, 2025 through Feb 22, 2025

Itinerary: Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Jost Van Dyke, Great Harbour...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Royal Clipper - Windward Islands 7 Nights

from $1,790.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 21, 2026
through Mar 28, 2026

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$255.71 (USD)
(based on double occupancy, for comparison only)

Mar 21, 2026 through Mar 28, 2026

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,790.00
Cat:Category 6
255.71 per night

Outside

$2,040.00
Cat:Category 5
291.43 per night

Balcony

N/A

Suite

$3,880.00
Cat:Deluxe Suite with Veranda
554.29 per night

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A Journey of Wild Isles and Charmed Creole Harbours

from $4,315.00 (USD)

Per Person

Dec 06, 2024
through Dec 13, 2024

More offers from Explora Journeys

Nights: 7

Ship: Explora II

Price Per Night:$616.43 (USD)
(based on double occupancy, for comparison only)

Dec 06, 2024 through Dec 13, 2024

Itinerary: Miami, Charlotte Amalie (Saint Thomas), Road Bay, Roseau, Saint-Pierre, Bridgetown

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N/A

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$4,315.00
Cat:OT1
616.43 per night

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STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $4,099.00 (USD)

Per Person

+ $79.00 taxes/fees

Jan 31, 2026
through Feb 14, 2026

More offers from Windstar Cruises

Nights: 14

Ship: Wind Spirit

Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)

Jan 31, 2026 through Feb 14, 2026

Itinerary: Philipsburg, St. Maarten, St. John's, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Charlestown...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Star Flyer - Leeward Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Feb 21, 2026
through Feb 28, 2026

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$247.14 (USD)
(based on double occupancy, for comparison only)

Feb 21, 2026 through Feb 28, 2026

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

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Inside

$1,730.00
Cat:Category 6
247.14 per night

Outside

$2,030.00
Cat:Category 5
290.00 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $3,699.00 (USD)

Per Person

+ $120.00 taxes/fees

Mar 14, 2026
through Mar 28, 2026

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$264.21 (USD)
(based on double occupancy, for comparison only)

Mar 14, 2026 through Mar 28, 2026

Itinerary: Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Charlestown...

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

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Destination Page: Dominica2 (45 offers included)