British Virgin Islands

BAREFOOT BREAK IN THE BRITISH VIRGIN ISLANDS

from $1,999.00 (USD)

Per Person

+ $99.00 taxes/fees

Dec 02, 2025
through Dec 07, 2025

More offers from Windstar Cruises

Nights: 5

Ship: Wind Surf

Price Per Night:$399.80 (USD)
(based on double occupancy, for comparison only)

Dec 02, 2025 through Dec 07, 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

The British Virgin Islands is known as the yachting capital of the Caribbean and this five-day escape shows you why. Come with us to charming islands with a laid-back attitude, places where you can still find incredible natural beauty, and colonial towns that effortlessly blend Dutch, French, and Caribbean cultures. Explore 17th century forts and duty-free shopping on St. Maarten and St. Bart. Go snorkeling or take a Jeep off-roading on mountainous Tortola.

Other Categories Starting At:

Inside

N/A

Outside

$1,999.00
Cat:B
399.80 per night

Balcony

N/A

Suite

$4,899.00
Cat:OS
979.80 per night

More Details Contact Us

14-Day Antillean Treasure Holiday
Roundtrip from Bridgetown, Barbados

from $8,694.00 (USD)

Per Person

+ $230.00 taxes/fees

Dec 21, 2024
through Jan 04, 2025

More offers from Seabourn Cruise Line

Nights: 14

Ship: Seabourn Ovation

Price Per Night:$621.00 (USD)
(based on double occupancy, for comparison only)

Dec 21, 2024 through Jan 04, 2025

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Pointe-a-pitre, , Carambola Beach, Great Harbour, Jost Van Dyke, San Juan, Puerto Rico, Willemstad, Curacao, Kralendijk, Bonaire, Oranjestad, Aruba...

Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$8,694.00
Cat:V1
621.00 per night

Distinctive Voyages Special Offer!

More Details Contact Us

BEACH FUN & SUN: A REMOTE CARIBBEAN GETAWAY

from $2,399.00 (USD)

Per Person

+ $139.00 taxes/fees

Dec 14, 2025
through Dec 21, 2025

More offers from Windstar Cruises

Nights: 7

Ship: Wind Surf

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

Dec 14, 2025 through Dec 21, 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

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke.

Other Categories Starting At:

Inside

N/A

Outside

$2,399.00
Cat:B
342.71 per night

Balcony

N/A

Suite

$5,499.00
Cat:OS
785.57 per night

More Details Contact Us

14-Day Exotic Caribbean Isles
Roundtrip from Bridgetown, Barbados

from $6,344.00 (USD)

Per Person

+ $285.00 taxes/fees

Jan 24, 2026
through Feb 07, 2026

More offers from Seabourn Cruise Line

Nights: 14

Ship: Seabourn Ovation

Price Per Night:$453.14 (USD)
(based on double occupancy, for comparison only)

Jan 24, 2026 through Feb 07, 2026

Itinerary: Bridgetown, Barbados, Castries, Saint Lucia, Montserrat, St. Johns, Antigua and Barbuda, Carambola Beach, Great Harbour, Jost Van Dyke, Philipsburg, Sint Maarten, Frenchmans Cay, Carambola Beach, ...

Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$6,344.00
Cat:V1
453.14 per night

More Details Contact Us

13-Night Eastern Caribbean Voyage

from $1,411.20 (USD)

Per Person

+ $225.00 taxes/fees

Dec 06, 2025
through Dec 19, 2025

More offers from Azamara

Nights: 13

Ship: Azamara Quest

Price Per Night:$108.55 (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...

Other Categories Starting At:

Inside

$1,411.20
Cat:12
108.55 per night

Outside

$2,052.00
Cat:08
157.85 per night

Balcony

$2,692.00
Cat:V3
207.08 per night

Suite

$5,012.00
Cat:N2
385.54 per night

More Details Contact Us

Paradise Awaits
10 nights on board Seven Seas Grandeur

from $6,399.00 (USD)

Per Person

Nov 14, 2024
through Nov 24, 2024

More offers from Regent Seven Seas Cruises

Nights: 10

Ship: Seven Seas Grandeur

Price Per Night:$639.90 (USD)
(based on double occupancy, for comparison only)

Nov 14, 2024 through Nov 24, 2024

Itinerary: Miami, Cruising The Atlantic Ocean, Puerto Plata, San Juan, Gustavia, Roseau, St. John's, Tortola, Cruising The Atlantic Ocean, Cruising The Bahamian Waters...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$6,399.00
Cat:G2
639.90 per night

More Details Contact Us

20-Day Caribbean Explorer
Roundtrip from Fort Lauderdale

from $1,897.00 (USD)

Per Person

+ $410.96 taxes/fees

Mar 29, 2026
through Apr 18, 2026

More offers from Princess Cruises®

Nights: 20

Ship: Caribbean Princess

Price Per Night:$94.85 (USD)
(based on double occupancy, for comparison only)

Mar 29, 2026 through Apr 18, 2026

Itinerary: Fort Lauderdale, Princess Cays, St Thomas, Dominica, St Lucia, Martinique, Antigua, Fort Lauderdale, Princess Cays, St Thomas...

Other Categories Starting At:

Inside

$1,897.00
Cat:IF
94.85 per night

Outside

$2,061.00
Cat:OZ
103.05 per night

Balcony

$3,517.00
Cat:BF
175.85 per night

Suite

$4,697.00
Cat:ME
234.85 per night

More Details Contact Us

STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $4,699.00 (USD)

Per Person

+ $265.00 taxes/fees

Feb 08, 2025
through Feb 22, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$335.64 (USD)
(based on double occupancy, for comparison only)

Feb 08, 2025 through Feb 22, 2025

Itinerary: Philipsburg, St. Maarten, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands...

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.

Other Categories Starting At:

Inside

N/A

Outside

$4,699.00
Cat:B
335.64 per night

Balcony

N/A

Suite

$10,999.00
Cat:OS
785.64 per night

More Details Contact Us

Star Clipper - Antigua to Antigua 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 21, 2026
through Mar 28, 2026

More offers from Star Clippers

Nights: 7

Ship: Star Clipper

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

Mar 21, 2026 through Mar 28, 2026

Itinerary: St. John's, Antigua, Gustavia, St. Barts, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands , White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Philipsburg, St. Maarten, Basseterre, St. Kitts (morning)...

Other Categories Starting At:

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

More Details Contact Us

14-Day Exotic Caribbean In Depth
Roundtrip from Bridgetown, Barbados

from $7,824.00 (USD)

Per Person

+ $335.00 taxes/fees

Feb 15, 2025
through Mar 01, 2025

More offers from Seabourn Cruise Line

Nights: 14

Ship: Seabourn Ovation

Price Per Night:$558.86 (USD)
(based on double occupancy, for comparison only)

Feb 15, 2025 through Mar 01, 2025

Itinerary: Bridgetown, Barbados, Castries, Saint Lucia, Terre-de-Haut, Iles des Saintes, Guadeloupe, St. Johns, Antigua and Barbuda, Great Harbour, Jost Van Dyke, Carambola Beach, Philipsburg, Sint Maarten, Frenchmans Cay, Carambola Beach, Fort-De-France, Martinique...

Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$7,824.00
Cat:V1
558.86 per night

Distinctive Voyages Special Offer!

More Details Contact Us

Caribbean, 21 Nights

from $2,149.00 (USD)

Per Person

+ $294.23 taxes/fees

Oct 16, 2025
through Nov 06, 2025

More offers from Cunard Line

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$102.33 (USD)
(based on double occupancy, for comparison only)

Oct 16, 2025 through Nov 06, 2025

Itinerary: Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida, Amber Cove,Dominican Republic, Montego Bay, Jamaica...

The shores of Central America and the Caribbean await on this voyage. From tree-lined beaches in Montego Bay to Mayan ruins in Belize, you’ll find a little slice of paradise in every port you visit.

Other Categories Starting At:

Inside

$2,149.00
Cat:IF
102.33 per night

Outside

$2,699.00
Cat:FC
128.52 per night

Balcony

$3,529.00
Cat:BF
168.05 per night

Suite

$9,519.00
Cat:P2
453.29 per night

More Details Contact Us

St. Kitts And Tortola

from $773.50 (USD)

Per Person

+ $131.86 taxes/fees

Dec 14, 2024
through Dec 21, 2024

More offers from Celebrity Cruises

Nights: 7

Ship: Celebrity Apex

Price Per Night:$110.50 (USD)
(based on double occupancy, for comparison only)

Dec 14, 2024 through Dec 21, 2024

Itinerary: Fort Lauderdale, Florida, Basseterre, St Kitts & Nevis, Tortola, B.V.I., Puerto Plata, Dominican Rep, Fort Lauderdale, Florida

Other Categories Starting At:

Inside

$773.50
Cat:DI
110.50 per night

Outside

$800.50
Cat:O2
114.36 per night

Balcony

$1,002.50
Cat:E3
143.21 per night

Suite

$2,700.00
Cat:MS
385.71 per night

Amenity Departure Dates Special Offer!

More Details Contact Us

Eclectic Caribbean
Roundtrip from Miami

from $3,499.00 (USD)

Per Person

Dec 10, 2025
through Dec 21, 2025

More offers from Oceania Cruises

Nights: 11

Ship: Allura

Price Per Night:$318.09 (USD)
(based on double occupancy, for comparison only)

Dec 10, 2025 through Dec 21, 2025

Itinerary: Miami, Nassau, San Juan, Basseterre, Bridgetown, Castries, St. John's, Tortola, Miami

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$3,499.00
Cat:B5
318.09 per night

Suite

$5,499.00
Cat:PH3
499.91 per night

Amenity Departure Dates Special Offer!

More Details Contact Us

STAR COLLECTOR: A LESSER ANTILLES ODYSSEY

from $5,999.00 (USD)

Per Person

+ $497.00 taxes/fees

Jan 04, 2026
through Jan 25, 2026

More offers from Windstar Cruises

Nights: 21

Ship: Wind Surf

Price Per Night:$285.67 (USD)
(based on double occupancy, for comparison only)

Jan 04, 2026 through Jan 25, 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, 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.

Other Categories Starting At:

Inside

N/A

Outside

$5,999.00
Cat:B
285.67 per night

Balcony

N/A

Suite

$15,199.00
Cat:OS
723.76 per night

More Details Contact Us

Eastern Caribbean, 14 Nights

from $1,249.00 (USD)

Per Person

+ $222.62 taxes/fees

Mar 15, 2025
through Mar 29, 2025

More offers from Cunard Line

Nights: 14

Ship: Queen Mary 2

Price Per Night:$89.21 (USD)
(based on double occupancy, for comparison only)

Mar 15, 2025 through Mar 29, 2025

Itinerary: New York, New York, St. Thomas, Virgin Islands, U.S.A., St. Maarten, Netherlands Antilles, St Lucia, Saint Lucia, Barbados, Barbados, Dominica, Dominica, St. Kitts, ST Kitts/Nevis, Tortola, B.V.I., New York, New York

Sail round trip from New York to the palm-fringed beaches of the Caribbean on this 14-night voyage on Queen Mary 2. On board, fill your days with various activities, or perhaps do nothing at all.

Other Categories Starting At:

Inside

$1,249.00
Cat:IE
89.21 per night

Outside

$1,799.00
Cat:EF
128.50 per night

Balcony

$1,899.00
Cat:DF
135.64 per night

Suite

$6,449.00
Cat:P2
460.64 per night

Distinctive Voyages Special Offer!

More Details Contact Us

Yucatan & Leeward Seafarer
Roundtrip from Miami

from $8,899.00 (USD)

Per Person

Jan 04, 2026
through Jan 28, 2026

More offers from Oceania Cruises

Nights: 24

Ship: Allura

Price Per Night:$370.79 (USD)
(based on double occupancy, for comparison only)

Jan 04, 2026 through Jan 28, 2026

Itinerary: Miami, Costa Maya, Cozumel, Belize City, Santo Tomas, Roatan, Montego Bay, George Town, Key West, Miami...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$8,899.00
Cat:B5
370.79 per night

Suite

$14,499.00
Cat:PH3
604.13 per night

More Details Contact Us

Transatlantic Crossing And Caribbean Celebration, 21 Nights

from $4,199.00 (USD)

Per Person

+ $265.33 taxes/fees

Dec 13, 2026
through Jan 03, 2027

More offers from Cunard Line

Nights: 21

Ship: Queen Mary 2

Price Per Night:$199.95 (USD)
(based on double occupancy, for comparison only)

Dec 13, 2026 through Jan 03, 2027

Itinerary: London (Southampton), England, New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York

What could be better than Christmas spent in the Caribbean sunshine? This festive voyage offers days ashore to explore the likes of Dominica and Barbados, with plenty of festive cheer on board.

Other Categories Starting At:

Inside

$4,199.00
Cat:IF
199.95 per night

Outside

$5,799.00
Cat:EF
276.14 per night

Balcony

$5,999.00
Cat:DF
285.67 per night

Suite

$13,699.00
Cat:P2
652.33 per night

More Details Contact Us

Transatlantic Crossing and Caribbean Celebration, 22 Nights

from $4,599.00 (USD)

Per Person

+ $242.36 taxes/fees

Dec 20, 2026
through Jan 11, 2027

More offers from Cunard Line

Nights: 22

Ship: Queen Mary 2

Price Per Night:$209.05 (USD)
(based on double occupancy, for comparison only)

Dec 20, 2026 through Jan 11, 2027

Itinerary: New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York, London (Southampton), England

Join in the festive fun and games on board as you celebrate Christmas in the Caribbean sunshine. Then, enjoy a New Year’s Eve to remember, counting down to midnight as you sail toward New York.

Other Categories Starting At:

Inside

$4,599.00
Cat:IF
209.05 per night

Outside

$6,199.00
Cat:EF
281.77 per night

Balcony

$6,399.00
Cat:DF
290.86 per night

Suite

$14,299.00
Cat:P2
649.95 per night

More Details Contact Us

Tortola, Antigua & Bahamas

from $659.00 (USD)

Per Person

+ $194.06 taxes/fees

Nov 30, 2025
through Dec 07, 2025

More offers from Celebrity Cruises

Nights: 7

Ship: Celebrity Beyond

Price Per Night:$94.14 (USD)
(based on double occupancy, for comparison only)

Nov 30, 2025 through Dec 07, 2025

Itinerary: Miami, Florida, Nassau, Bahamas, Tortola, B.V.I., St. Johns, Antigua, Miami, Florida

Other Categories Starting At:

Inside

$659.00
Cat:I2
94.14 per night

Outside

$691.00
Cat:O2
98.71 per night

Balcony

$855.00
Cat:P2
122.14 per night

Suite

$3,830.00
Cat:MS
547.14 per night

Amenity Departure Dates Special Offer!

More Details Contact Us

Treasure Islands Christmas Cruise 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Dec 21, 2024
through Dec 28, 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 21, 2024 through Dec 28, 2024

Itinerary: Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands , Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...

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