British Virgin Islands

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $797.82 (USD)

Per Person

Jan 31, 2027
through Feb 07, 2027

More offers from Royal Caribbean International

Nights: 7

Ship: Brilliance of the Seas

Price Per Night:$113.97 (USD)
(based on double occupancy, for comparison only)

Jan 31, 2027 through Feb 07, 2027

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
113.97 per night

Outside

$897.82
Cat:YO
128.26 per night

Balcony

$1,266.82
Cat:XB
180.97 per night

Suite

N/A

More Details Contact Us

16-Day Eastern Caribbean Holiday: Amber Cove & Bahamas
Roundtrip from Fort Lauderdale

from $3,264.00 (USD)

Per Person

+ $200.00 taxes/fees

Dec 11, 2026
through Dec 27, 2026

More offers from Holland America Line

Nights: 16

Ship: Nieuw Amsterdam

Price Per Night:$204.00 (USD)
(based on double occupancy, for comparison only)

Dec 11, 2026 through Dec 27, 2026

Itinerary: Fort Lauderdale, St Maarten, Antigua, Tortola, San Juan, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Grand Turk, Amber Cove, Key West, Fort Lauderdale

Other Categories Starting At:

Inside

$3,264.00
Cat:N
204.00 per night

Outside

$3,764.00
Cat:HH
235.25 per night

Balcony

$4,364.00
Cat:VH
272.75 per night

Suite

$6,864.00
Cat:SZ
429.00 per night

Category N - Flash Special: Book by Sunday 07/13/2025

More Details Contact Us

10-Day Eastern Caribbean with Tortola
Roundtrip from Fort Lauderdale

from $1,039.00 (USD)

Per Person

Mar 07, 2026
through Mar 17, 2026

More offers from Princess Cruises®

Nights: 10

Ship: Enchanted Princess

Price Per Night:$103.90 (USD)
(based on double occupancy, for comparison only)

Mar 07, 2026 through Mar 17, 2026

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

Other Categories Starting At:

Inside

$1,039.00
Cat:IF
103.90 per night

Outside

N/A

Balcony

$1,470.00
Cat:BW
147.00 per night

Suite

$1,739.00
Cat:MF
173.90 per night

More Details Contact Us

Eastern Caribbean Voyage

from $4,669.00 (USD)

Per Person

Dec 19, 2025
through Jan 06, 2026

More offers from Azamara

Nights: 18

Ship: Azamara Quest

Price Per Night:$259.39 (USD)
(based on double occupancy, for comparison only)

Dec 19, 2025 through Jan 06, 2026

Itinerary: San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Bridgetown, Mayreau, Grenadines, Castries, Roseau, Basseterre, St.Kitts, Philipsburg, Road Town, Tortola, Miami, Florida

Other Categories Starting At:

Inside

$4,669.00
Cat:10
259.39 per night

Outside

$4,819.00
Cat:08
267.72 per night

Balcony

$5,319.00
Cat:V3
295.50 per night

Suite

N/A

More Details Contact Us

28-Day Ultimate Caribbean: Amber Cove & Bahamas
Roundtrip from Miami

from $4,894.00 (USD)

Per Person

+ $310.00 taxes/fees

Jan 03, 2026
through Jan 31, 2026

More offers from Holland America Line

Nights: 28

Ship: Zuiderdam

Price Per Night:$174.79 (USD)
(based on double occupancy, for comparison only)

Jan 03, 2026 through Jan 31, 2026

Itinerary: Miami, Half Moon Cay, Amber Cove, San Juan, St Kitts, Tortola, St Maarten, Antigua, Martinique, Barbados, Grenada, Scarborough, Aruba, Curacao, Ocho Rios, Grand Cayman, Cozumel, Miami, Half Moon Cay, Grand Turk, Amber Cove, Key West, Miami

Other Categories Starting At:

Inside

$4,894.00
Cat:N
174.79 per night

Outside

$5,704.00
Cat:HH
203.71 per night

Balcony

$6,284.00
Cat:VH
224.43 per night

Suite

$10,114.00
Cat:SZ
361.21 per night

Category N - Flash Special: Book by Sunday 07/13/2025

More Details Contact Us

Caribbean: Dominican Republic & St. Thomas
Roundtrip from New York City, Ny

from $1,477.50 (USD)

Per Person

Nov 09, 2026
through Nov 21, 2026

More offers from Norwegian Cruise Line

Nights: 12

Ship: Norwegian Bliss

Price Per Night:$123.13 (USD)
(based on double occupancy, for comparison only)

Nov 09, 2026 through Nov 21, 2026

Itinerary: New York City, Ny, PUERTO PLATA, DOMINICAN REPUBLIC, San Juan, Pr, Basseterre, Saint Kitts - Nevis, Tortola, British Virgin Islands, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, New York City, Ny

Set sail on a spectacular 12-day round-trip sailing from New York to the Caribbean with Norwegian. In Puerto Plata, visit Fortaleza San Felipe, which was built in the 16th century or head to the Amber Museum, which is filled with a unique collection of valuable Dominican amber. Wander San Juan's picturesque cobblestone streets, plazas and chapels, all reflecting its rich Spanish heritage. And on the island of St.

Other Categories Starting At:

Inside

$1,477.50
Cat:IF
123.13 per night

Outside

$1,877.50
Cat:OB
156.46 per night

Balcony

$2,127.50
Cat:BF
177.29 per night

Suite

$2,427.50
Cat:MC
202.29 per night

More Details Contact Us

An Extended Journey of Idyllic Coves and Captivating Cultures

from $8,360.00 (USD)

Per Person

Feb 24, 2026
through Mar 11, 2026

More offers from Explora Journeys

Nights: 15

Ship: Explora II

Price Per Night:$557.33 (USD)
(based on double occupancy, for comparison only)

Feb 24, 2026 through Mar 11, 2026

Itinerary: Miami, Charlotte Amalie (Saint Thomas), Jost van Dyke, St. John's (Antigua), Gustavia, San Juan, St. George's (Grenada), Bequia, Bridgetown, Martinique/Fort de France, Gustavia, Basseterre, San Juan

Beneath the brilliant sun, over the sparkling sea, we travel the tropics from Miami to Basseterre. En route, uncover the spectacular beaches of Jost van Dyke and the lively spirit of San Juan.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$8,360.00
Cat:OT2
557.33 per night

More Details Contact Us

Ultimate Southern Caribbean

from $1,167.57 (USD)

Per Person

Jan 02, 2026
through Jan 12, 2026

More offers from Celebrity Cruises

Nights: 10

Ship: Celebrity Ascent

Price Per Night:$116.76 (USD)
(based on double occupancy, for comparison only)

Jan 02, 2026 through Jan 12, 2026

Itinerary: Fort Lauderdale, Florida, Tortola, B.V.I., St. Johns, Antigua, Bridgetown, Barbados, Castries, St. Lucia, Basseterre, St Kitts & Nevis, Fort Lauderdale, Florida

Other Categories Starting At:

Inside

$1,357.57
Cat:DI
135.76 per night

Outside

$1,757.57
Cat:O2
175.76 per night

Balcony

$2,437.57
Cat:E3
243.76 per night

Suite

$7,197.57
Cat:MS
719.76 per night

More Details Contact Us

A Journey to Antillian Isles and Sublime Sunsets

from $3,690.00 (USD)

Per Person

Mar 11, 2026
through Mar 18, 2026

More offers from Explora Journeys

Nights: 7

Ship: Explora II

Price Per Night:$527.14 (USD)
(based on double occupancy, for comparison only)

Mar 11, 2026 through Mar 18, 2026

Itinerary: San Juan, Road Bay, St. John's (Antigua), St. Maarten/Philipsburg, Spanish Town (Virgin Gorda), Miami

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$3,690.00
Cat:OT1
527.14 per night

More Details Contact Us

Caribbean, 21 Nights

from $2,964.00 (USD)

Per Person

+ $21,422.00 taxes/fees

Nov 26, 2026
through Dec 17, 2026

More offers from Cunard Line

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$141.14 (USD)
(based on double occupancy, for comparison only)

Nov 26, 2026 through Dec 17, 2026

Itinerary: Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, Florida

Discover the vibrance of the Lesser Antilles on this 21-night voyage. Experience bright-hued towns, jungle-cloaked ruins, and volcanic peaks as you sail to a diverse array of tropical destinations.

Other Categories Starting At:

Inside

$2,964.00
Cat:IF
141.14 per night

Outside

$3,712.00
Cat:FC
176.76 per night

Balcony

$4,617.00
Cat:CB
219.86 per night

Suite

$12,824.00
Cat:P2
610.67 per night

More Details Contact Us

Treasure Islands

from $2,010.00 (USD)

Per Person

Mar 20, 2027
through Mar 27, 2027

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$287.14 (USD)
(based on double occupancy, for comparison only)

Mar 20, 2027 through Mar 27, 2027

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), Gustavia, St. Barts, Philipsburg, St. Maarten

Other Categories Starting At:

Inside

$2,010.00
Cat:Category 6
287.14 per night

Outside

$2,320.00
Cat:Category 5
331.43 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

Caribbean & Central America Cruise
San Juan to Bridgetown

from $6,100.00 (USD)

Per Person

Feb 06, 2027
through Feb 16, 2027

More offers from Silversea Cruises

Nights: 10

Ship: Silver Shadow

Price Per Night:$610.00 (USD)
(based on double occupancy, for comparison only)

Feb 06, 2027 through Feb 16, 2027

Itinerary: San Juan, Jost Van Dyke (British Virgin Islands), Gustavia, St Barthelemy, Basseterre, St. Kitts, Little Bay, Montserrat, Les Saintes, Roseau, Trois Ilets, Castries, St George's, Bridgetown

Other Categories Starting At:

Outside

N/A

Balcony

N/A

Suite

$6,100.00
Cat:VI
610.00 per night

More Details Contact Us

BEACH FUN & SUN: A REMOTE CARIBBEAN GETAWAY

from $2,599.00 (USD)

Per Person

+ $68.00 taxes/fees

Mar 28, 2026
through Apr 04, 2026

More offers from Windstar Cruises

Nights: 7

Ship: Wind Surf

Price Per Night:$371.29 (USD)
(based on double occupancy, for comparison only)

Mar 28, 2026 through Apr 04, 2026

Itinerary: Philipsburg, St. Maarten, St. John's, Road Bay, 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

$2,599.00
Cat:B
371.29 per night

Balcony

N/A

Suite

$5,699.00
Cat:OS
814.14 per night

More Details Contact Us

Eastern Caribbean Voyage

from $3,929.00 (USD)

Per Person

Oct 31, 2025
through Nov 15, 2025

More offers from Azamara

Nights: 15

Ship: Azamara Quest

Price Per Night:$261.93 (USD)
(based on double occupancy, for comparison only)

Oct 31, 2025 through Nov 15, 2025

Itinerary: Miami, Florida, Charlotte Amalie, St. Thomas, Road Town, Tortola, Basseterre, St.Kitts, Philipsburg, Gustavia, San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown

Other Categories Starting At:

Inside

$3,929.00
Cat:11
261.93 per night

Outside

$4,099.00
Cat:08
273.27 per night

Balcony

$5,319.00
Cat:V3
354.60 per night

Suite

$7,139.00
Cat:N2
475.93 per night

More Details Contact Us

Splendours of the Caribbean
San Juan to St Thomas

from $5,860.00 (USD)

Per Person

Dec 07, 2026
through Dec 13, 2026

More offers from Emerald Cruises

Nights: 6

Ship: Emerald Sakara

Price Per Night:$976.67 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2026 through Dec 13, 2026

Itinerary: San Juan, Puerto Rico, Cruz Bay, Saint John, US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthélemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands

Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$5,860.00
Cat:B
976.67 per night

Suite

$8,810.00
Cat:Y
1,468.33 per night

More Details Contact Us

SAN JUAN & THE VIRGIN ISLANDS

from $2,499.00 (USD)

Per Person

+ $63.00 taxes/fees

Nov 15, 2026
through Nov 22, 2026

More offers from Windstar Cruises

Nights: 7

Ship: Star Pride

Price Per Night:$357.00 (USD)
(based on double occupancy, for comparison only)

Nov 15, 2026 through Nov 22, 2026

Itinerary: San Juan, CRUZ BAY, ST. JOHN, Virgin Islands (U.S.), Basseterre, Gustavia, Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$2,499.00
Cat:SP
357.00 per night

More Details Contact Us

Discover the yachting islands of the Caribbean
San Juan to San Juan

from $14,710.00 (USD)

Per Person

Jan 03, 2026
through Jan 17, 2026

More offers from Emerald Cruises

Nights: 14

Ship: Emerald Azzurra

Price Per Night:$1,050.71 (USD)
(based on double occupancy, for comparison only)

Jan 03, 2026 through Jan 17, 2026

Itinerary: San Juan, Puerto Rico, Culebra Island & Vieques Island, Puerto Rico, St. John, U.S. Virgin Islands, Jost Van Dyke, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthélemy, Little Bay, Montserrat, St John's, Antigua, Barbuda, Antigua and Barbuda, Îles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthélemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico

Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

$14,710.00
Cat:B
1,050.71 per night

Suite

$22,960.00
Cat:Y
1,640.00 per night

More Details Contact Us

STAR COLLECTOR: BEACHES & BASTIONS OF THE BVI AND SPANISH CARIBBEAN

from $4,099.00 (USD)

Per Person

+ $99.00 taxes/fees

Nov 30, 2025
through Dec 13, 2025

More offers from Windstar Cruises

Nights: 13

Ship: Star Pride

Price Per Night:$315.31 (USD)
(based on double occupancy, for comparison only)

Nov 30, 2025 through Dec 13, 2025

Itinerary: San Juan, CRUZ BAY, ST. JOHN, Virgin Islands (U.S.), Gustavia, Basseterre, Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, Santo Domingo, Cartagena, San Blas, Panama, Colón

This is the kind of voyage where each day is postcard-perfect and no two are exactly alike. Get a champagne facial at BVI’s Jost Van Dyke’s Bubbly Pool with its effervescent fizz powered by the ocean, and trek through huge round granite boulders on Virgin Gorda, BVI to find The Baths, its eerie grottoes dancing with light from the turquoise water. Kayak through a bioluminescent bay near San Juan, your paddle drawing glowing patterns in the dark waters.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$4,099.00
Cat:SP
315.31 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $908.89 (USD)

Per Person

Dec 07, 2025
through Dec 14, 2025

More offers from Royal Caribbean International

Nights: 7

Ship: Brilliance of the Seas

Price Per Night:$129.84 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2025 through Dec 14, 2025

Itinerary: San Juan, Puerto Rico, Cruising, Kralendijk, Bonaire, Willemstad, Curacao, Oranjestad, Aruba, Cruising, Tortola, B.V.I., San Juan, Puerto Rico

Other Categories Starting At:

Inside

$908.89
Cat:ZI
129.84 per night

Outside

$938.89
Cat:YO
134.13 per night

Balcony

$1,034.89
Cat:XB
147.84 per night

Suite

N/A

More Details Contact Us

Caribbean New Year Cruise: Barbados, Aruba & St. Barts

from $3,879.00 (USD)

Per Person

Dec 28, 2026
through Jan 14, 2027

More offers from Azamara

Nights: 17

Ship: Azamara Journey

Price Per Night:$228.18 (USD)
(based on double occupancy, for comparison only)

Dec 28, 2026 through Jan 14, 2027

Itinerary: Bridgetown, Willemstad, Oranjestad, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan, Virgin Gorda, Gustavia, Philipsburg, St. John's, Antigua, Basseterre, St.Kitts, Road Town, Tortola, Miami, Florida

Other Categories Starting At:

Inside

$3,879.00
Cat:11
228.18 per night

Outside

$4,389.00
Cat:08
258.18 per night

Balcony

$4,799.00
Cat:V3
282.29 per night

Suite

$8,589.00
Cat:N2
505.24 per night

More Details Contact Us

British Virgin Islands (20 offers included)