British Virgin Islands

7-Day Classic Caribbean Yacht Harbors
Bridgetown, Barbados to Philipsburg, Sint Maarten

from $3,489.00 (USD)

Per Person

+ $165.00 taxes/fees

Feb 14, 2026
through Feb 21, 2026

More offers from Seabourn Cruise Line

Nights: 7

Ship: Seabourn Ovation

Price Per Night:$498.43 (USD)
(based on double occupancy, for comparison only)

Feb 14, 2026 through Feb 21, 2026

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

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

$3,489.00
Cat:V1
498.43 per night

More Details Contact Us

14-day Cruise to Caribbean: Cozumel Dominican Republic from Galveston, Texas on Norwegian Prima
Roundtrip from GALVESTON TEXAS, TX

from $1,348.75 (USD)

Per Person

+ $287.63 taxes/fees

Jan 17, 2025
through Jan 31, 2025

More offers from Norwegian Cruise Line

Nights: 14

Ship: Norwegian Prima

Price Per Night:$96.34 (USD)
(based on double occupancy, for comparison only)

Jan 17, 2025 through Jan 31, 2025

Itinerary: GALVESTON TEXAS, TX, Great Stirrup Cay, Bahamas, Tortola, British Virgin Islands, ST JOHNS ANTIGUA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, San Juan, Pr, PUERTO PLATA, DOMINICAN REPUBLIC, George Town, Cayman Islands, Cozumel, Mexico, GALVESTON TEXAS, TX

Explore breathtaking views on your 9-day cruise aboard Norwegian Prima. For stunning views, take a cable car ride to the peak of Mount Isabel de Torres in Puerto Plata. Take in the beautiful turquoise waters and the laidback Caribbean vibes on Long Bay Beach in Tortola. Day dreaming about your own private island? Continue your vacation in our very own Great Stirrup Cay, home to the new Silver Cove lagoon and upgraded oceanfront cabanas.

Other Categories Starting At:

Inside

$1,348.75
Cat:IF
96.34 per night

Outside

$1,849.25
Cat:OB
132.09 per night

Balcony

$2,399.15
Cat:BF
171.37 per night

Suite

$3,448.90
Cat:M4
246.35 per night

More Details Contact Us

Caribbean, 21 Nights

from $2,449.00 (USD)

Per Person

+ $286.20 taxes/fees

Mar 03, 2026
through Mar 24, 2026

More offers from Cunard Line

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$116.62 (USD)
(based on double occupancy, for comparison only)

Mar 03, 2026 through Mar 24, 2026

Itinerary: Miami, Florida, Grand Turk, Montego Bay, Jamaica, Belize City, Belize, Cozumel, Mexico, Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados...

The quaint and colorful architecture of Bridgetown and Castries await on this 21-night voyage on Queen Elizabeth, which also offers plenty of time on board to do as much or as little as you wish.

Other Categories Starting At:

Inside

$2,449.00
Cat:IF
116.62 per night

Outside

$3,149.00
Cat:FC
149.95 per night

Balcony

$3,949.00
Cat:CB
188.05 per night

Suite

$10,599.00
Cat:P2
504.71 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 10, 2026
through Jan 24, 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 10, 2026 through Jan 24, 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

Eastern Caribbean, 28 Nights

from $3,799.00 (USD)

Per Person

+ $149.99 taxes/fees

Feb 22, 2026
through Mar 22, 2026

More offers from Cunard Line

Nights: 28

Ship: Queen Victoria

Price Per Night:$135.68 (USD)
(based on double occupancy, for comparison only)

Feb 22, 2026 through Mar 22, 2026

Itinerary: London (Southampton), England, Madeira, Portugal, Tortola, B.V.I., St. Maarten, Netherlands Antilles, St. Kitts, ST Kitts/Nevis, Dominica, Dominica, St Lucia, Saint Lucia, Barbados, Barbados, Tenerife, Canary Islands, London (Southampton), England

Fulfill the ultimate holiday fantasy, sinking your toes into the white sands of Caribbean beaches on this 28-night voyage. On board, make use of Queen Victoria’s sun decks, as you sail between islands.

Other Categories Starting At:

Inside

$3,799.00
Cat:IF
135.68 per night

Outside

$5,699.00
Cat:FC
203.54 per night

Balcony

$6,299.00
Cat:CB
224.96 per night

Suite

$14,799.00
Cat:P2
528.54 per night

More Details Contact Us

Pre-Holiday Caribbean Refresh

from $1,473.00 (USD)

Per Person

+ $124.00 taxes/fees

Dec 06, 2024
through Dec 14, 2024

More offers from Virgin Voyages

Nights: 8

Ship: Resilient Lady

Price Per Night:$184.13 (USD)
(based on double occupancy, for comparison only)

Dec 06, 2024 through Dec 14, 2024

Itinerary: San Juan, Tortola, Philipsburg, Sailing, Bridgetown, Fort-de-France, Castries, Basseterre, San Juan

A breathtaking odyssey through some of the Caribbean's most scenic ports, this 8-night voyage starts in San Juan and visits Tortola, St. Maarten, Barbados, Martinique, and St. Lucia, making its final stop in St. Kitts and Nevis. Enjoy the famed South Friars Bay Beach and marvel at Basseterre's Victorian Berkeley Memorial Clock Tower before returning to Puerto Rico.

Other Categories Starting At:

Inside

$1,473.00
Cat:IN
184.13 per night

Outside

$1,528.00
Cat:VW
191.00 per night

Balcony

$1,723.00
Cat:TL
215.38 per night

Suite

$3,963.00
Cat:SS
495.38 per night

More Details Contact Us

Antilles & Atlantic Gems
Roundtrip from Miami

from $9,499.00 (USD)

Per Person

Mar 09, 2026
through Apr 04, 2026

More offers from Oceania Cruises

Nights: 26

Ship: Allura

Price Per Night:$365.35 (USD)
(based on double occupancy, for comparison only)

Mar 09, 2026 through Apr 04, 2026

Itinerary: Miami, Oranjestad, Willemstad, St. George's, Kingstown, Fort-De-France, Tortola, Miami, Charleston, Norfolk...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$9,499.00
Cat:B5
365.35 per night

Suite

$15,399.00
Cat:PH3
592.27 per night

More Details Contact Us

10-Day Eastern Caribbean with Tortola

from $758.00 (USD)

Per Person

+ $224.39 taxes/fees

Mar 10, 2025
through Mar 20, 2025

More offers from Princess Cruises®

Nights: 10

Ship: Enchanted Princess

Price Per Night:$75.80 (USD)
(based on double occupancy, for comparison only)

Mar 10, 2025 through Mar 20, 2025

Itinerary: Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale

Other Categories Starting At:

Inside

$758.00
Cat:IF
75.80 per night

Outside

$1,428.00
Cat:O6
142.80 per night

Balcony

$1,355.00
Cat:BW
135.50 per night

Suite

$1,878.00
Cat:MF
187.80 per night

More Details Contact Us

Boston To San Juan Cruise
Boston, Massachusetts to San Juan, Puerto Rico

from $656.50 (USD)

Per Person

+ $189.98 taxes/fees

Nov 02, 2025
through Nov 09, 2025

More offers from Royal Caribbean International

Nights: 7

Ship: Brilliance of the Seas

Price Per Night:$93.79 (USD)
(based on double occupancy, for comparison only)

Nov 02, 2025 through Nov 09, 2025

Itinerary: Boston, Massachusetts, Cruising, Royal Naval Dockyard, Bermuda, Cruising, St. Johns, Antigua, Tortola, B.V.I., San Juan, Puerto Rico

Other Categories Starting At:

Inside

$656.50
Cat:ZI
93.79 per night

Outside

$839.00
Cat:YO
119.86 per night

Balcony

$1,148.50
Cat:XB
164.07 per night

Suite

$2,219.00
Cat:J3
317.00 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $696.50 (USD)

Per Person

+ $138.30 taxes/fees

Jan 11, 2026
through Jan 18, 2026

More offers from Royal Caribbean International

Nights: 7

Ship: Brilliance of the Seas

Price Per Night:$99.50 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2026 through Jan 18, 2026

Itinerary: San Juan, Puerto Rico, Cruising, Castries, St. Lucia, Basseterre, St Kitts & Nevis, St. Johns, Antigua, Tortola, B.V.I., Charlotte Amalie, St. Thomas, San Juan, Puerto Rico

Other Categories Starting At:

Inside

$696.50
Cat:ZI
99.50 per night

Outside

$776.00
Cat:YO
110.86 per night

Balcony

$1,217.00
Cat:XB
173.86 per night

Suite

$1,939.00
Cat:WS
277.00 per night

More Details Contact Us

STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $3,699.00 (USD)

Per Person

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, Roseau...

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

$3,699.00
Cat:B
264.21 per night

Balcony

N/A

Suite

$9,799.00
Cat:OS
699.93 per night

More Details Contact Us

Caribbean: Curacao, Aruba & Bonaire
Roundtrip from PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC

from $1,079.00 (USD)

Per Person

+ $146.83 taxes/fees

Dec 22, 2025
through Dec 29, 2025

More offers from Norwegian Cruise Line

Nights: 7

Ship: Norwegian Sky

Price Per Night:$154.14 (USD)
(based on double occupancy, for comparison only)

Dec 22, 2025 through Dec 29, 2025

Itinerary: PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, Kralendijk, Netherland Antilles, ST LUCIA, SAINT LUCIA, Basseterre, Saint Kitts - Nevis, Tortola, British Virgin Islands, PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC

Explore breathtaking views on your 7-day cruise aboard the newly refurbished Norwegian Sky. In Curaçao, splash around the warm sea with some friendly dolphins or journey inland to discover the enchanting Hato Caves and then visit a unique Ostrich farm and hang with one of the biggest birds on earth. Uncover the best of Aruba as you soak in fantastic vistas from the California Lighthouse, explore the Aloe Museum and visit the island’s popular Natural Bridge ruins.

Other Categories Starting At:

Inside

$1,079.00
Cat:IF
154.14 per night

Outside

$1,279.20
Cat:OF
182.74 per night

Balcony

$1,729.00
Cat:BF
247.00 per night

Suite

$3,348.80
Cat:SH
478.40 per night

More Details Contact Us

11-day Cruise to Caribbean: Curacao, Aruba & Dominican Republic from Tampa, Florida on Norwegian Jewel
Roundtrip from Tampa, Fl

from $978.90 (USD)

Per Person

+ $201.49 taxes/fees

Dec 12, 2024
through Dec 23, 2024

More offers from Norwegian Cruise Line

Nights: 11

Ship: Norwegian Jewel

Price Per Night:$88.99 (USD)
(based on double occupancy, for comparison only)

Dec 12, 2024 through Dec 23, 2024

Itinerary: Tampa, Fl, Key West, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, Tortola, British Virgin Islands, CATALINA ISLAND D.R., DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, George Town, Cayman Islands, Tampa, Fl

Experience a new winter wonderland in paradise aboard Norwegian Jewel. Discover the best of Key West - America’s southernmost point - from picturesque beaches and historic sites to the colorful conch-style architecture. Then enjoy the scenic vistas along Tortola’s Sir Frances Drake’s Highway as you explore picturesque villages. Uncover the best of Aruba as you soak in fantastic vistas from the California Lighthouse, explore the Aloe Museum and visit the island’s popular Natural Bridge ruins.

Other Categories Starting At:

Inside

$978.90
Cat:I4
88.99 per night

Outside

$1,098.50
Cat:OK
99.86 per night

Balcony

$1,888.90
Cat:BF
171.72 per night

Suite

$2,299.05
Cat:MB
209.00 per night

More Details Contact Us

Star Flyer - Treasure Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Feb 28, 2026
through Mar 07, 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 28, 2026 through Mar 07, 2026

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

$1,730.00
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

Star Clipper - Antigua to Grenada 10 Nights

from $2,480.00 (USD)

Per Person

+ $340.00 taxes/fees

Jan 28, 2026
through Feb 07, 2026

More offers from Star Clippers

Nights: 10

Ship: Star Clipper

Price Per Night:$248.00 (USD)
(based on double occupancy, for comparison only)

Jan 28, 2026 through Feb 07, 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, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...

Other Categories Starting At:

Inside

$2,480.00
Cat:Category 6
248.00 per night

Outside

$2,900.00
Cat:Category 5
290.00 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

STAR COLLECTOR: CARIBBEAN EXPLORATIONS

from $4,499.00 (USD)

Per Person

Feb 15, 2025
through Mar 01, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$321.36 (USD)
(based on double occupancy, for comparison only)

Feb 15, 2025 through Mar 01, 2025

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

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

$4,499.00
Cat:B
321.36 per night

Balcony

N/A

Suite

$10,799.00
Cat:OS
771.36 per night

More Details Contact Us

14-Night Eastern Caribbean Voyage

from $1,551.20 (USD)

Per Person

+ $242.00 taxes/fees

Nov 08, 2025
through Nov 22, 2025

More offers from Azamara

Nights: 14

Ship: Azamara Quest

Price Per Night:$110.80 (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...

Other Categories Starting At:

Inside

$1,551.20
Cat:12
110.80 per night

Outside

$2,272.00
Cat:08
162.29 per night

Balcony

$2,992.00
Cat:V3
213.71 per night

Suite

$5,392.00
Cat:N2
385.14 per night

More Details Contact Us

Star Flyer - Treasure Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Jan 03, 2026
through Jan 10, 2026

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

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

Jan 03, 2026 through Jan 10, 2026

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

$1,730.00
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

Mar 01, 2025
through Mar 15, 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)

Mar 01, 2025 through Mar 15, 2025

Itinerary: Bridgetown, Barbados, Castries, Saint Lucia, Pointe-a-pitre, 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

More Details Contact Us

20-Day Caribbean Explorer

from $1,597.00 (USD)

Per Person

+ $349.20 taxes/fees

Nov 16, 2024
through Dec 06, 2024

More offers from Princess Cruises®

Nights: 20

Ship: Enchanted Princess

Price Per Night:$79.85 (USD)
(based on double occupancy, for comparison only)

Nov 16, 2024 through Dec 06, 2024

Itinerary: Fort Lauderdale, Tortola, St Kitts, Antigua, St Maarten, St Thomas, Grand Turk, Fort Lauderdale, Princess Cays, St Thomas...

Other Categories Starting At:

Inside

$1,597.00
Cat:IF
79.85 per night

Outside

N/A

Balcony

$1,927.00
Cat:BW
96.35 per night

Suite

N/A

More Details Contact Us

British Virgin Islands (20 offers included)