US Virgin Islands

Caribbean & Central America Cruise
Philipsburg to Philipsburg

from $5,600.00 (USD)

Per Person

Feb 19, 2026
through Feb 26, 2026

More offers from Silversea Cruises

Nights: 7

Ship: Silver Shadow

Price Per Night:$800.00 (USD)
(based on double occupancy, for comparison only)

Feb 19, 2026 through Feb 26, 2026

Itinerary: Philipsburg, St. Maarten, St. John's, St. Thomas, Little Bay, Montserrat, Castries, Mayreau, Les Saintes, Philipsburg, St. Maarten

Other Categories Starting At:

Outside

N/A

Balcony

N/A

Suite

$5,600.00
Cat:VI
800.00 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $730.63 (USD)

Per Person

Jan 31, 2026
through Feb 07, 2026

More offers from Royal Caribbean International

Nights: 7

Ship: Jewel of the Seas

Price Per Night:$104.38 (USD)
(based on double occupancy, for comparison only)

Jan 31, 2026 through Feb 07, 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

Other Categories Starting At:

Inside

$730.63
Cat:ZI
104.38 per night

Outside

$907.63
Cat:3N
129.66 per night

Balcony

$1,059.63
Cat:XB
151.38 per night

Suite

N/A

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $798.54 (USD)

Per Person

Sep 05, 2026
through Sep 12, 2026

More offers from Royal Caribbean International

Nights: 7

Ship: Radiance of the Seas

Price Per Night:$114.08 (USD)
(based on double occupancy, for comparison only)

Sep 05, 2026 through Sep 12, 2026

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

Other Categories Starting At:

Inside

$798.54
Cat:ZI
114.08 per night

Outside

$836.54
Cat:YO
119.51 per night

Balcony

$1,205.04
Cat:XB
172.15 per night

Suite

N/A

More Details Contact Us

10-Day Southern Caribbean with Martinique
Roundtrip from Fort Lauderdale

from $1,013.00 (USD)

Per Person

Oct 28, 2025
through Nov 07, 2025

More offers from Princess Cruises®

Nights: 10

Ship: Caribbean Princess

Price Per Night:$101.30 (USD)
(based on double occupancy, for comparison only)

Oct 28, 2025 through Nov 07, 2025

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

Other Categories Starting At:

Inside

$1,013.00
Cat:ID
101.30 per night

Outside

$1,143.00
Cat:OW
114.30 per night

Balcony

N/A

Suite

N/A

More Details Contact Us

7-Day Eastern Caribbean with Puerto Rico
Roundtrip from Fort Lauderdale

from $689.00 (USD)

Per Person

Jan 11, 2026
through Jan 18, 2026

More offers from Princess Cruises®

Nights: 7

Ship: Sun Princess

Price Per Night:$98.43 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2026 through Jan 18, 2026

Itinerary: Fort Lauderdale, Princess Cays, San Juan, St Thomas, Fort Lauderdale

Other Categories Starting At:

Inside

$689.00
Cat:IF
98.43 per night

Outside

$839.00
Cat:O5
119.86 per night

Balcony

$1,039.00
Cat:DH
148.43 per night

Suite

N/A

More Details Contact Us

Southern Caribbean Holiday
Roundtrip from San Juan, Puerto Rico

from $1,261.10 (USD)

Per Person

Dec 26, 2026
through Jan 02, 2027

More offers from Royal Caribbean International

Nights: 7

Ship: Radiance of the Seas

Price Per Night:$180.16 (USD)
(based on double occupancy, for comparison only)

Dec 26, 2026 through Jan 02, 2027

Itinerary: San Juan, Puerto Rico, Tortola, B.V.I., Philipsburg, St. Maarten, St. Johns, Antigua, Basseterre, St Kitts & Nevis, St. Croix, U.S.V.I., Cruising, San Juan, Puerto Rico

Other Categories Starting At:

Inside

$1,261.10
Cat:ZI
180.16 per night

Outside

$1,354.60
Cat:YO
193.51 per night

Balcony

$1,901.10
Cat:XB
271.59 per night

Suite

N/A

More Details Contact Us

14-Day Eastern Caribbean: Bahamas & San Juan
Roundtrip from Fort Lauderdale

from $2,124.00 (USD)

Per Person

+ $215.00 taxes/fees

Dec 07, 2025
through Dec 21, 2025

More offers from Holland America Line

Nights: 14

Ship: Eurodam

Price Per Night:$151.71 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2025 through Dec 21, 2025

Itinerary: Fort Lauderdale, Grand Turk, San Juan, St Thomas, Taino Bay (Puerta Plata), Fort Lauderdale, Half Moon Cay, Grand Turk, Amber Cove, Bimini, Fort Lauderdale

Other Categories Starting At:

Inside

$2,124.00
Cat:N
151.71 per night

Outside

$2,174.00
Cat:HH
155.29 per night

Balcony

$2,234.00
Cat:VH
159.57 per night

Suite

$3,684.00
Cat:SZ
263.14 per night

Category N - Flash Special: Book by Sunday 07/20/2025

More Details Contact Us

21-Day Eastern & Western Caribbean: Leeward Islands & Mexico
Roundtrip from Miami

from $4,199.00 (USD)

Per Person

+ $280.00 taxes/fees

Oct 31, 2026
through Nov 21, 2026

More offers from Holland America Line

Nights: 21

Ship: Zuiderdam

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

Oct 31, 2026 through Nov 21, 2026

Itinerary: Miami, St Maarten, Antigua, Martinique, Roseau, St Kitts, St Thomas, Relaxaway Half Moon Cay, Miami, Key West, Falmouth, Grand Cayman, Mahogany Bay, Cozumel, Relaxaway Half Moon Cay, Miami

Other Categories Starting At:

Inside

$4,199.00
Cat:N
199.95 per night

Outside

$5,049.00
Cat:HH
240.43 per night

Balcony

$5,799.00
Cat:VH
276.14 per night

Suite

$8,549.00
Cat:SZ
407.10 per night

Category N - Flash Special: Book by Sunday 07/20/2025

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $901.91 (USD)

Per Person

Oct 12, 2025
through Oct 19, 2025

More offers from Royal Caribbean International

Nights: 7

Ship: Rhapsody of The Seas

Price Per Night:$128.84 (USD)
(based on double occupancy, for comparison only)

Oct 12, 2025 through Oct 19, 2025

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

Other Categories Starting At:

Inside

$901.91
Cat:ZI
128.84 per night

Outside

$1,066.41
Cat:YO
152.34 per night

Balcony

$1,965.41
Cat:XB
280.77 per night

Suite

$2,572.91
Cat:WS
367.56 per night

More Details Contact Us

20-Day Caribbean Explorer
Roundtrip from Fort Lauderdale

from $1,809.00 (USD)

Per Person

Mar 29, 2026
through Apr 18, 2026

More offers from Princess Cruises®

Nights: 20

Ship: Caribbean Princess

Price Per Night:$90.45 (USD)
(based on double occupancy, for comparison only)

Mar 29, 2026 through Apr 18, 2026

Itinerary: Fort Lauderdale, Princess Cays, San Juan, St Kitts, St Lucia, Martinique, Antigua, Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale

Other Categories Starting At:

Inside

$1,809.00
Cat:IF
90.45 per night

Outside

$2,099.00
Cat:OZ
104.95 per night

Balcony

$3,059.00
Cat:BF
152.95 per night

Suite

$3,739.00
Cat:ME
186.95 per night

More Details Contact Us

Caribbean, 26 Nights (Q709A)
Roundtrip from Miami, FL, USA

from $2,969.00 (USD)

Per Person

+ $14,025.00 taxes/fees

Mar 18, 2027
through Apr 13, 2027

More offers from Cunard Line

Nights: 26

Ship: Queen Elizabeth

Price Per Night:$114.19 (USD)
(based on double occupancy, for comparison only)

Mar 18, 2027 through Apr 13, 2027

Itinerary: Miami, FL, USA, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, St. Thomas, Virgin Islands, U.S.A., St. Maarten, Netherlands Antilles, Barbados, Barbados, Curacao, Antilles, Bonaire, Aruba, Aruba, Aruba, Miami, FL, USA

This 26-night sailing takes you to charming port towns across the Caribbean. See colorful murals in Castries, flit between beaches and boutiques in Bridgetown, and walk on cobblestones in San Juan.

Other Categories Starting At:

Inside

$2,969.00
Cat:IE
114.19 per night

Outside

$3,519.00
Cat:FC
135.35 per night

Balcony

$4,429.00
Cat:CB
170.35 per night

Suite

$12,609.00
Cat:P2
484.96 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $803.18 (USD)

Per Person

Oct 31, 2026
through Nov 07, 2026

More offers from Royal Caribbean International

Nights: 7

Ship: Radiance of the Seas

Price Per Night:$114.74 (USD)
(based on double occupancy, for comparison only)

Oct 31, 2026 through Nov 07, 2026

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

Other Categories Starting At:

Inside

$803.18
Cat:ZI
114.74 per night

Outside

$924.18
Cat:YO
132.03 per night

Balcony

$1,186.68
Cat:XB
169.53 per night

Suite

N/A

More Details Contact Us

West Indies Explorer
Roundtrip from San Juan

from $3,799.00 (USD)

Per Person

Jan 05, 2027
through Jan 15, 2027

More offers from Viking Ocean Cruises

Nights: 10

Ship: Viking Sea

Price Per Night:$379.90 (USD)
(based on double occupancy, for comparison only)

Jan 05, 2027 through Jan 15, 2027

Itinerary: San Juan, Tortola (Road Town), St. Kitts (Basseterre), Castries, Bridgetown, Roseau, Antigua (St. John’s), Philipsburg, St. Thomas (Charlotte Amalie), San Juan

Set sail on a roundtrip voyage from San Juan to explore the colorful Caribbean. Start deep in the heart of this tropical paradise and avoid the long sea days associated with most Caribbean cruises—allowing you to visit more ports and spend more time discovering rich island cultures. Immerse yourself in the British, French and Dutch cultures of the Lesser Antilles as you cruise azure waters from Tortola and St. Lucia to Dominica, St. Martin and St. Thomas.

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$13,999.00
Cat:OS
1,399.90 per night

More Details Contact Us

St Thomas Padi Discover Scuba Course

from $165.00 (USD)

Per Person

Mar 07, 2025
through Jul 15, 2027

More offers from Shore Excursions Group

Mar 07, 2025 through Jul 15, 2027

Location(s): St. Thomas

For guests who have never gone diving, here is the chance to experience the thrill of being underwater and visiting a live reef.

More Details Contact Us

Discover the Vibes of the Caribbean
Miami to St Thomas

from $14,580.00 (USD)

Per Person

Nov 30, 2026
through Dec 13, 2026

More offers from Emerald Cruises

Nights: 13

Ship: Emerald Sakara

Price Per Night:$1,121.54 (USD)
(based on double occupancy, for comparison only)

Nov 30, 2026 through Dec 13, 2026

Itinerary: Miami, Florida, USA, Nassau, Bahamas, Emerald Bay, Exuma's, Bahamas, San Salvador Island, Bahamas, Gordon's Beach, Long Island, Bahamas, Grand Turk, Turks & Caicos Islands, 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:

Outside

$14,580.00
Cat:D
1,121.54 per night

Balcony

$20,680.00
Cat:B
1,590.77 per night

Suite

$32,580.00
Cat:T
2,506.15 per night

More Details Contact Us

West Indies Island Hopping
San Juan to San Juan

from $6,495.00 (USD)

Per Person

Dec 20, 2027
through Dec 27, 2027

More offers from Emerald Cruises

Nights: 7

Ship: Emerald Kaia

Price Per Night:$927.86 (USD)
(based on double occupancy, for comparison only)

Dec 20, 2027 through Dec 27, 2027

Itinerary: San Juan, Puerto Rico, St. John – St. Thomas, U.S. Virgin Islands, St. Thomas, U.S. Virgin Islands, Gustavia, Saint Barthélemy, Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico

Uncover remote beaches, vibrant towns, and crystal-clear waters from San Juan to Saint Barthélemy and explore the diverse cultures and natural wonders of Puerto Rico, the U.S. and British Virgin Islands.

Other Categories Starting At:

Outside

$6,495.00
Cat:D
927.86 per night

Balcony

N/A

Suite

$8,320.00
Cat:B
1,188.57 per night

More Details Contact Us

7-Day Eastern Caribbean: San Juan & St. Thomas
Roundtrip from Miami, Florida, US

from $1,404.00 (USD)

Per Person

+ $140.00 taxes/fees

Apr 11, 2026
through Apr 18, 2026

More offers from Holland America Line

Nights: 7

Ship: Zuiderdam

Price Per Night:$200.57 (USD)
(based on double occupancy, for comparison only)

Apr 11, 2026 through Apr 18, 2026

Itinerary: Miami, Florida, US, Days At Sea, Grand Turk, Turks and Caicos, San Juan, Puerto Rico, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas, Miami, Florida, US

Other Categories Starting At:

Inside

$1,404.00
Cat:N
200.57 per night

Outside

$1,504.00
Cat:HH
214.86 per night

Balcony

$1,804.00
Cat:VH
257.71 per night

Suite

$2,654.00
Cat:SZ
379.14 per night

Category N - Flash Special: Book by Sunday 07/20/2025

More Details Contact Us

24-Day Panama Canal & Eastern Caribbean
San Diego to Fort Lauderdale

from $4,159.00 (USD)

Per Person

Oct 09, 2025
through Nov 02, 2025

More offers from Holland America Line

Nights: 24

Ship: Eurodam

Price Per Night:$173.29 (USD)
(based on double occupancy, for comparison only)

Oct 09, 2025 through Nov 02, 2025

Itinerary: San Diego, Puerto Vallarta, Huatulco, Puerto Chiapas, Puerto Quetzal, Acajutla, Puntarenas, Panama Canal (Cruising), Enter Panama Canal Balboa, Exit Panama Canal Cristobal, Aruba, Fort Lauderdale, Grand Turk, San Juan, St Thomas, Half Moon Cay, Fort Lauderdale

Other Categories Starting At:

Inside

$4,159.00
Cat:N
173.29 per night

Outside

$4,309.00
Cat:HH
179.54 per night

Balcony

$5,389.00
Cat:VH
224.54 per night

Suite

$10,279.00
Cat:SS
428.29 per night

More Details Contact Us

Southern Caribbean Cruise
Roundtrip from San Juan, Puerto Rico

from $808.46 (USD)

Per Person

Feb 06, 2027
through Feb 13, 2027

More offers from Royal Caribbean International

Nights: 7

Ship: Radiance of the Seas

Price Per Night:$115.49 (USD)
(based on double occupancy, for comparison only)

Feb 06, 2027 through Feb 13, 2027

Itinerary: San Juan, Puerto Rico, Tortola, B.V.I., Philipsburg, St. Maarten, St. Johns, Antigua, Basseterre, St Kitts & Nevis, St. Croix, U.S.V.I., Cruising, San Juan, Puerto Rico

Other Categories Starting At:

Inside

$808.46
Cat:ZI
115.49 per night

Outside

$908.46
Cat:YO
129.78 per night

Balcony

$1,294.96
Cat:XB
184.99 per night

Suite

N/A

More Details Contact Us

21-Day Western & Eastern Caribbean: Mexico & Leeward Islands
Roundtrip from Fort Lauderdale

from $4,024.00 (USD)

Per Person

+ $265.00 taxes/fees

Jan 14, 2026
through Feb 04, 2026

More offers from Holland America Line

Nights: 21

Ship: Koningsdam

Price Per Night:$191.62 (USD)
(based on double occupancy, for comparison only)

Jan 14, 2026 through Feb 04, 2026

Itinerary: Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Mahogany Bay, Cozumel, Fort Lauderdale, St Maarten, Antigua, Martinique, Roseau, St Kitts, St Thomas, Half Moon Cay, Fort Lauderdale

Other Categories Starting At:

Inside

$4,024.00
Cat:N
191.62 per night

Outside

$4,514.00
Cat:F
214.95 per night

Balcony

$5,234.00
Cat:VH
249.24 per night

Suite

$6,764.00
Cat:BC
322.10 per night

Category N - Flash Special: Book by Sunday 07/20/2025

More Details Contact Us

US Virgin Islands (20 offers included)