Windswept Travel
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British Virgin Islands (19 offers included)

Caribbean, 21 Nights (Q705A)
Roundtrip from Miami, FL, USA
from $2,849.00 (USD)
Per Person
+ $20,768.00 taxes/fees
Queen Elizabeth
Cunard Line logo
More offers from Cunard Line
Nights: 21
Price Per Night:$135.67 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, FL, USA, San Juan, Puerto Rico, Antigua, Martinique, Faroe Islands, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica...
This 21-night roundtrip from Miami brings with it a chance to sample some of the finest rums and tequilas in port, as well as time spent enjoying the sunshine in streets, jungles, and on beaches.
Other Categories Starting At:
Inside
$2,849.00
Cat: IF
Outside
$3,549.00
Cat: FC
Balcony
$4,649.00
Cat: BF
Suite
$12,149.00
Cat: P2
More Details Contact Us
Caribbean & Central America Cruise
San Juan to San Juan
from $8,000.00 (USD)
Per Person
Offer Image
Silversea Cruises logo
More offers from Silversea Cruises
Nights: 12
Price Per Night:$666.67 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St John, Basseterre, St. Kitts, Day at sea, Mayreau, St George's, Day at sea, Oranjestad, Aruba, Willemstad, Curaçao, Kralendijk, Bonaire...
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$8,000.00
Cat: VI
More Details Contact Us
20-Day Caribbean Explorer
Roundtrip from Fort Lauderdale
from $1,593.00 (USD)
Per Person
Offer Image
Princess Cruises® logo
More offers from Princess Cruises®
Nights: 20
Price Per Night:$79.65 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Princess Cays, St Thomas, Dominica, St Lucia, Martinique, Antigua, Fort Lauderdale, Tortola, St Maarten...
Other Categories Starting At:
Inside
$1,593.00
Cat: IF
Outside
$1,733.00
Cat: OY
Balcony
$2,843.00
Cat: BF
Suite
$3,633.00
Cat: ME
More Details Contact Us
7-Day Southern Caribbean with Barbados
Roundtrip from San Juan
from $785.00 (USD)
Per Person
Offer Image
Princess Cruises® logo
More offers from Princess Cruises®
Nights: 7
Price Per Night:$112.14 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Barbados, Grenada, Dominica, St Kitts, Tortola, San Juan
Other Categories Starting At:
Inside
$785.00
Cat: IF
Outside
$903.00
Cat: OZ
Balcony
$1,185.00
Cat: BF
Suite
$1,485.00
Cat: ME
More Details Contact Us
14-Day Southern Caribbean Adventurer
Roundtrip from San Juan
from $1,341.00 (USD)
Per Person
Offer Image
Princess Cruises® logo
More offers from Princess Cruises®
Nights: 14
Price Per Night:$95.79 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Thomas, St Maarten, Antigua, Guadeloupe (Pointe-A-Pitre), Barbados, San Juan, Tortola, St Kitts, Antigua...
Other Categories Starting At:
Inside
$1,341.00
Cat: IF
Outside
$1,571.00
Cat: OZ
Balcony
$2,131.00
Cat: BF
Suite
N/A
More Details Contact Us
Caribbean: Dominican Republic & Antigua
Roundtrip from JACKSONVILLE, FLORIDA, FL
from $932.34 (USD)
Per Person
Offer Image
Norwegian Cruise Line logo
More offers from Norwegian Cruise Line
Nights: 11
Price Per Night:$84.76 (USD)
(based on double occupancy, for comparison only)
Itinerary: JACKSONVILLE, FLORIDA, FL, Grand Bahama Island, Bahamas, PUERTO PLATA, DOMINICAN REPUBLIC, Tortola, British Virgin Islands, ST JOHNS ANTIGUA, Basseterre, Saint Kitts - Nevis, San Juan, Pr, Great Stirrup Cay, Bahamas, JACKSONVILLE, FLORIDA, FL
Come experience a different winter wonderland in The Caribbean with Norwegian. In Puerto Plata, uncover the local history at the 16th century Fortaleza San Felipe or embark on an off-roading adventure through lush jungle to swim in cascading mountain pools. Take in the beautiful turquoise waters and the laidback island vibes on Long Bay Beach in Tortola. Then grab a frozen drink and lounge in your private beachfront cabana on Great Stirrup Cay, our tropical paradise just for you.
Other Categories Starting At:
Inside
$932.34
Cat: I4
Outside
$1,062.34
Cat: OK
Balcony
$1,882.34
Cat: BF
Suite
$1,982.34
Cat: MA
More Details Contact Us
Caribbean Christmas Cruise: Barbados, St. Lucia & St. Thomas
from $2,859.00 (USD)
Per Person
Azamara Journey Exterior
Azamara logo
More offers from Azamara
Nights: 16
Price Per Night:$178.69 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua...
Other Categories Starting At:
Inside
$2,859.00
Cat: 12
Outside
$3,519.00
Cat: 08
Balcony
$4,719.00
Cat: V3
Suite
$7,759.00
Cat: N2
More Details Contact Us
Caribbean Enchantment
New York to Miami
from $5,399.00 (USD)
Per Person
Offer Image
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 14
Ship: Vista
Price Per Night:$385.64 (USD)
(based on double occupancy, for comparison only)
Itinerary: New York, Charlotte Amalie, Tortola, St. John's, Basseterre, Castries, St. George's, Willemstad, Oranjestad, Miami
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$5,399.00
Cat: B5
Suite
$8,449.00
Cat: PH3
More Details Contact Us
Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico
from $797.82 (USD)
Per Person
Brilliance of the Seas Exterior Side
Royal Caribbean International logo
More offers from Royal Caribbean International
Nights: 7
Price Per Night:$113.97 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, Roseau, Dominica, St. Croix, U.S.V.I., Basseterre, St Kitts & Nevis, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
$797.82
Cat: ZI
Outside
$897.82
Cat: YO
Balcony
$1,266.82
Cat: XB
Suite
N/A
More Details Contact Us
BAREFOOT BREAK IN THE BRITISH VIRGIN ISLANDS
from $2,099.00 (USD)
Per Person
+ $51.00 taxes/fees
Wind Surf Capri
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 5
Ship: Wind Surf
Price Per Night:$419.80 (USD)
(based on double occupancy, for comparison only)
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
$2,099.00
Cat: B
Balcony
N/A
Suite
N/A
More Details Contact Us
STAR COLLECTOR: A LESSER ANTILLES ODYSSEY
from $6,199.00 (USD)
Per Person
+ $99.00 taxes/fees
Wind Spirit Tahiti
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 22
Ship: Wind Spirit
Price Per Night:$281.77 (USD)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
N/A
Outside
$6,199.00
Cat: B
Balcony
N/A
Suite
N/A
More Details Contact Us
Caribbean Compass
14 nights on board Seven Seas Mariner
from $8,999.00 (USD)
Per Person
Offer Image
Regent Seven Seas Cruises logo
More offers from Regent Seven Seas Cruises
Nights: 14
Price Per Night:$642.79 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Cruising The Old Bahama Channel, Cruising The Caribbean Sea, Oranjestad, Willemstad, Bonaire (Kralendijk), Cruising The Caribbean Sea, Basseterre, Gustavia, St. John's...
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$8,999.00
Cat: H
More Details Contact Us
Caribbean, 21 Nights (Q707A)
Roundtrip from Miami, FL, USA
from $2,939.00 (USD)
Per Person
+ $20,768.00 taxes/fees
Queen Elizabeth
Cunard Line logo
More offers from Cunard Line
Nights: 21
Price Per Night:$139.95 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica...
Soak up the atmosphere in bustling harbors in Antigua and Barbados, before exploring Miami’s fusion food scene and Maya ruins in Cozumel, on this 21-night Caribbean adventure on Queen Elizabeth.
Other Categories Starting At:
Inside
$2,939.00
Cat: IE
Outside
$3,439.00
Cat: FC
Balcony
$4,239.00
Cat: CB
Suite
$11,639.00
Cat: P2
More Details Contact Us
Southern Caribbean Cruise: St.Barts, Antigua & Tortola
from $1,869.00 (USD)
Per Person
Azamara Journey Exterior
Azamara logo
More offers from Azamara
Nights: 9
Price Per Night:$207.67 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Virgin Gorda, Gustavia, Philipsburg, St. John's, Antigua, Basseterre, St.Kitts, Road Town, Tortola, Miami, Florida
Other Categories Starting At:
Inside
$1,869.00
Cat: 12
Outside
$2,269.00
Cat: 08
Balcony
$3,059.00
Cat: V3
Suite
$4,389.00
Cat: N2
More Details Contact Us
Caribbean Essence
San Juan to Miami
from $3,499.00 (USD)
Per Person
Oceania Allura
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 8
Ship: Allura
Price Per Night:$437.38 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Gustavia, Philipsburg, Basseterre, St. John's, Tortola, Miami
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$3,499.00
Cat: B5
Suite
$5,149.00
Cat: PH3
More Details Contact Us
Tortola, St. Kitts & Puerto Plata
from $921.98 (USD)
Per Person
Non-Refundable
Celebrity Beyond
Celebrity Cruises logo
More offers from Celebrity Cruises
Nights: 7
Price Per Night:$131.71 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, Puerto Plata, Dominican Rep, Tortola, B.V.I., Basseterre, St Kitts & Nevis, Miami, Florida
Other Categories Starting At:
Inside
$936.98
Cat: Z
Outside
$921.98
Cat: Y
Balcony
$958.48
Cat: EX
Suite
$3,285.48
Cat: MS
More Details Contact Us
November Nights in the Eastern Caribbean
from $1,272.00 (USD)
Per Person
+ $238.00 taxes/fees
Tortola
Virgin Voyages logo
More offers from Virgin Voyages
Nights: 8
Price Per Night:$159.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, Sailing, Puerto Plata, San Juan, Tortola, Sailing, Beach Club at Bimini, Miami, Florida
This stunning sojourn leaves Miami and sails a day to the picturesque silvers coasts, crystalline cenotes and lush jungles of Puerto Plata, Dominican Republic. Next, awake to the blissful sound of crashing waves in San Juan before arriving the next day in magical Tortola, nestled into the British Virgin Islands. Then sail two days to our private Beach Club at Bimini before returning to Miami.
Other Categories Starting At:
Inside
$1,272.00
Cat: IZ
Outside
$1,512.00
Cat: VZ
Balcony
$1,752.00
Cat: TZ
Suite
$4,160.00
Cat: SS
More Details Contact Us
Caribbean & Central America Cruise
Miami to San Juan
from $5,800.00 (USD)
Per Person
Offer Image
Silversea Cruises logo
More offers from Silversea Cruises
Nights: 12
Price Per Night:$483.33 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Fl, Day at sea, St John, Philipsburg, St. Maarten, Basseterre, St. Kitts, Les Saintes, Castries, Fort-De-France, Little Bay, Montserrat, St. John's...
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$5,800.00
Cat: VI
More Details Contact Us
Caribbean, 28 Nights (Q703B)
Roundtrip from Miami, FL, USA
from $3,739.00 (USD)
Per Person
+ $30,086.00 taxes/fees
Queen Elizabeth
Cunard Line logo
More offers from Cunard Line
Nights: 28
Price Per Night:$133.54 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, FL, USA, Freeport, Bahamas, Curacao, Antilles, Bonaire, Aruba, Aruba, Aruba, Miami, FL, USA, Nassau, Bahamas, Amber Cove,Dominican Republic, Grand Turk, Half Moon Cay...
Get to know friendly locals while exploring the incredible landscapes of the Caribbean. Find yourself among pristine beaches, verdant jungles, and warm natural pools under the sun.
Other Categories Starting At:
Inside
$3,739.00
Cat: IF
Outside
$4,889.00
Cat: EF
Balcony
$6,039.00
Cat: BF
Suite
$15,739.00
Cat: P2
More Details Contact Us