British Virgin Islands

Yucatan & Leeward Seafarer
Roundtrip from Miami

from $8,999.00 (USD)

Per Person

Jan 04, 2026
through Jan 28, 2026

More offers from Oceania Cruises

Jan 04, 2026 through Jan 28, 2026

Nights: 24

Ship: Allura

Price Per Night:$374.96 (USD)
(based on double occupancy, for comparison only)

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

$8,999.00
Cat: B5

Suite

$14,699.00
Cat: PH3

More Details Contact Us

Valiant Caribbean Holidays

from $1,528.00 (USD)

Per Person

+ N/A taxes/fees

Dec 20, 2025
through Dec 27, 2025

More offers from Virgin Voyages

Dec 20, 2025 through Dec 27, 2025

Nights: 7

Ship: Valiant Lady

Price Per Night:$218.29 (USD)
(based on double occupancy, for comparison only)

Itinerary: San Juan, Philipsburg, Basseterre, St. John's, Castries, Sailing, Tortola, San Juan

This 7-night idyllic journey departs from San Juan and docks the next day in St. Maarten. From there you'll head to St. Kitts followed by St. Johns in Antigua - the quintessential paradise lover's paradise - where you'll discover the epitome of a tropical haven. From there you'll dock in St. Lucia, then spend a day sailing to the British Virgin Islands before finally returning to San Juan.

Other Categories Starting At:

Inside

$1,528.00
Cat: IZ

Outside

$1,990.00
Cat: VZ

Balcony

$1,990.00
Cat: TZ

Suite

$4,588.00
Cat: SS

More Details Contact Us

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

from $5,389.00 (USD)

Per Person

+ $195.00 taxes/fees

Apr 01, 2026
through Apr 27, 2026

More offers from Holland America Line

Apr 01, 2026 through Apr 27, 2026

Nights: 26

Ship: Koningsdam

Price Per Night:$207.27 (USD)
(based on double occupancy, for comparison only)

Itinerary: Fort Lauderdale, St Thomas, Antigua, Tortola, San Juan, Half Moon Cay, Fort Lauderdale, Cartagena, Panama Canal (Cruising), Enter Panama Canal Cristobal...

Other Categories Starting At:

Inside

$5,389.00
Cat: N

Outside

$6,319.00
Cat: F

Balcony

$6,809.00
Cat: VH

Suite

$8,719.00
Cat: BC

More Details Contact Us

Resilient Valentine's Voyage

from $1,618.00 (USD)

Per Person

+ $137.00 taxes/fees

Feb 08, 2025
through Feb 15, 2025

More offers from Virgin Voyages

Feb 08, 2025 through Feb 15, 2025

Nights: 7

Ship: Resilient Lady

Price Per Night:$231.14 (USD)
(based on double occupancy, for comparison only)

Itinerary: San Juan, Tortola, Sailing, Bridgetown, Castries, St. John's, Philipsburg, San Juan

Set out from San Juan on this epic 7-night voyage to some of the Caribbean's most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then complete your whirlwind Caribbean tour by heading to Barbados, St. Lucia, Antigua, and St. Maarten.

Other Categories Starting At:

Inside

$1,618.00
Cat: IZ

Outside

$1,859.00
Cat: VZ

Balcony

$1,859.00
Cat: TZ

Suite

$4,427.00
Cat: SCP

More Details Contact Us

Caribbean: Dominican Republic & Antigua
Roundtrip from Miami, Fl

from $769.00 (USD)

Per Person

+ N/A taxes/fees

Mar 05, 2025
through Mar 14, 2025

More offers from Norwegian Cruise Line

Mar 05, 2025 through Mar 14, 2025

Nights: 9

Ship: Norwegian Pearl

Price Per Night:$85.44 (USD)
(based on double occupancy, for comparison only)

Itinerary: Miami, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, Tortola, British Virgin Islands, ST JOHNS ANTIGUA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, San Juan, Pr, Great Stirrup Cay, Bahamas, Miami, Fl

Explore breathtaking views on your 9-day cruise aboard Norwegian Pearl. 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

$769.00
Cat: IF

Outside

$989.00
Cat: OK

Balcony

$1,939.00
Cat: BF

Suite

$2,289.00
Cat: MA

More Details Contact Us

Caribbean, 21 Nights

from $2,519.00 (USD)

Per Person

+ $6,774.00 taxes/fees

Mar 03, 2026
through Mar 24, 2026

More offers from Cunard Line

Mar 03, 2026 through Mar 24, 2026

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$119.95 (USD)
(based on double occupancy, for comparison only)

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

$2,519.00
Cat: IF

Outside

$3,149.00
Cat: FC

Balcony

$3,809.00
Cat: BF

Suite

$10,139.00
Cat: P2

More Details Contact Us

Caribbean: Dominican Republic & Antigua
Roundtrip from JACKSONVILLE, FLORIDA, FL

from $1,019.00 (USD)

Per Person

+ N/A taxes/fees

Dec 01, 2025
through Dec 12, 2025

More offers from Norwegian Cruise Line

Dec 01, 2025 through Dec 12, 2025

Nights: 11

Ship: Norwegian Gem

Price Per Night:$92.64 (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

$1,019.00
Cat: IF

Outside

$1,249.00
Cat: OK

Balcony

$2,039.00
Cat: BF

Suite

$2,439.00
Cat: MB

More Details Contact Us

Transatlantic: Spain & Morocco
Barcelona, Spain to PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC

from $1,219.00 (USD)

Per Person

+ N/A taxes/fees

Dec 06, 2025
through Dec 22, 2025

More offers from Norwegian Cruise Line

Dec 06, 2025 through Dec 22, 2025

Nights: 16

Ship: Norwegian Sky

Price Per Night:$76.19 (USD)
(based on double occupancy, for comparison only)

Itinerary: Barcelona, Spain, CADIZ SEVILLE, SPAIN, Casablanca, Morocco, Agadir, Morocco, Arrecife, Spain, Santa Cruz De Tenerife, Spain, PORTO GRANDE, CAPE VERDE, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Tortola, British Virgin Islands, PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC

Explore breathtaking views on your transatlantic cruise aboard the newly refurbished Norwegian Sky. Savor a day touring Cádiz with a visit to the bustling Mercado Central de Abastos – a covered market boasting more than 150 stalls selling fresh seafood and delicious local cuisine – and recline on one of the town’s many beautiful beaches. Visit Casablanca’s central market, a massive kaleidoscope of colors, and see the modernist landmark of the Hassan II Mosque.

Other Categories Starting At:

Inside

$1,219.00
Cat: IF

Outside

$1,439.00
Cat: OF

Balcony

$2,619.00
Cat: BF

Suite

$5,799.00
Cat: SH

More Details Contact Us

Caribbean: Curacao, Aruba & Dominican Republic
Roundtrip from Tampa, Fl

from $1,039.00 (USD)

Per Person

+ N/A taxes/fees

Jan 04, 2026
through Jan 15, 2026

More offers from Norwegian Cruise Line

Jan 04, 2026 through Jan 15, 2026

Nights: 11

Ship: Norwegian Jewel

Price Per Night:$94.45 (USD)
(based on double occupancy, for comparison only)

Itinerary: Tampa, 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

Redefine January "chill" with an amazing cruise through paradise on Norwegian Jewel. Learn about Puerto Plata’s local history at the 16th century Fortaleza San Felipe or snorkel among colorful coral reefs near Dorado Beach. Then enjoy the scenic vistas along Tortola’s Sir Frances Drake’s Highway as you tour picturesque villages. In Oranjestad, discover the best of Aruba with visits to the Casibari Rock formation, the country’s famed Natural Bridge and more during your guided tour.

Other Categories Starting At:

Inside

$1,039.00
Cat: IF

Outside

$1,339.00
Cat: OK

Balcony

$2,039.00
Cat: BF

Suite

$2,439.00
Cat: MB

More Details Contact Us

Eastern Caribbean, 12 Nights (Q705)
Roundtrip from Miami, FL, USA

from $1,609.00 (USD)

Per Person

+ $8,887.00 taxes/fees

Feb 04, 2027
through Feb 16, 2027

More offers from Cunard Line

Feb 04, 2027 through Feb 16, 2027

Nights: 12

Ship: Queen Elizabeth

Price Per Night:$134.08 (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

A blend of sea days and time in port means you can have the best of both worlds. Treasure days on deck sunbathing when you’re not exploring the cultures, cuisines, and scenery across the Caribbean.

Other Categories Starting At:

Inside

$1,609.00
Cat: IF

Outside

$2,009.00
Cat: FC

Balcony

$2,559.00
Cat: CB

Suite

$7,159.00
Cat: P2

More Details Contact Us

SAN JUAN & THE VIRGIN ISLANDS

from $3,299.00 (USD)

Per Person

+ $69.00 taxes/fees

Nov 30, 2024
through Dec 07, 2024

More offers from Windstar Cruises

Nov 30, 2024 through Dec 07, 2024

Nights: 7

Ship: Star Pride

Price Per Night:$471.29 (USD)
(based on double occupancy, for comparison only)

Itinerary: San Juan, St. Thomas, Philipsburg, St. Maarten, Basseterre, Gustavia, 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

$3,299.00
Cat: S3

More Details Contact Us

10-Day Eastern Caribbean with Tortola
Roundtrip from Fort Lauderdale

from $919.00 (USD)

Per Person

Nov 07, 2025
through Nov 17, 2025

More offers from Princess Cruises®

Nov 07, 2025 through Nov 17, 2025

Nights: 10

Ship: Caribbean Princess

Price Per Night:$91.90 (USD)
(based on double occupancy, for comparison only)

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

Other Categories Starting At:

Inside

$919.00
Cat: IF

Outside

$982.00
Cat: OZ

Balcony

$1,554.00
Cat: BF

Suite

$2,014.00
Cat: ME

More Details Contact Us

Caribbean: San Juan, Tortola & Dominican Republic
Roundtrip from New York City, Ny

from $1,789.00 (USD)

Per Person

+ N/A taxes/fees

Feb 23, 2025
through Mar 07, 2025

More offers from Norwegian Cruise Line

Feb 23, 2025 through Mar 07, 2025

Nights: 12

Ship: Norwegian Escape

Price Per Night:$149.08 (USD)
(based on double occupancy, for comparison only)

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

Get ready to experience your own slice of paradise on this roundtrip cruise to The Caribbean aboard Norwegian Escape. In Puerto Plata, uncover the local history at the 16th century Fortaleza San Felipe or embark on a jungle adventure to see Damajagua’s Waterfalls. In San Juan, the second oldest city in the Americas, you’ll find a little bit of everything: beaches, city life and lush rainforests to explore.

Other Categories Starting At:

Inside

$1,789.00
Cat: IX

Outside

$2,089.00
Cat: OX

Balcony

$2,389.00
Cat: BF

Suite

$2,819.00
Cat: MX

More Details Contact Us

Cultural Currents
20 nights on board Seven Seas Mariner

from $10,999.00 (USD)

Per Person

Mar 26, 2027
through Apr 15, 2027

More offers from Regent Seven Seas Cruises

Mar 26, 2027 through Apr 15, 2027

Nights: 20

Ship: Seven Seas Mariner

Price Per Night:$549.95 (USD)
(based on double occupancy, for comparison only)

Itinerary: Miami, Great Stirrup Cay, Cruising The Straits Of Florida, Costa Maya, Harvest Caye, Roatan, Cruising The Caribbean Sea, Montego Bay, George Town, Cruising The Straits Of Florida...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$10,999.00
Cat: H

More Details Contact Us

Seattle To Miami, 40 Nights

from $4,899.00 (USD)

Per Person

+ $16,469.00 taxes/fees

Sep 18, 2025
through Oct 28, 2025

More offers from Cunard Line

Sep 18, 2025 through Oct 28, 2025

Nights: 40

Ship: Queen Elizabeth

Price Per Night:$122.48 (USD)
(based on double occupancy, for comparison only)

Itinerary: Seattle, Washington, Ketchikan, Alaska, Tracy Arm, Alaska, Juneau, Alaska, Sitka, AK, USA, Victoria, BC, Canada, Seattle, Washington, San Francisco, California, Los Angeles, California, Cabo San Lucas, Mexico...

From the far reaches of icy Alaska to the sunny shores of the Caribbean, you’ll find yourself packing for all seasons on this voyage that offers time ashore in multiple regions of the Americas.

Other Categories Starting At:

Inside

$4,899.00
Cat: IE

Outside

$5,869.00
Cat: FC

Balcony

$6,949.00
Cat: CA

Suite

$19,269.00
Cat: P1

More Details Contact Us

Caribbean Quest
14 nights on board Seven Seas Mariner

from $8,399.00 (USD)

Per Person

Dec 20, 2025
through Jan 03, 2026

More offers from Regent Seven Seas Cruises

Dec 20, 2025 through Jan 03, 2026

Nights: 14

Ship: Seven Seas Mariner

Price Per Night:$599.93 (USD)
(based on double occupancy, for comparison only)

Itinerary: Miami, Cruising The Bahamian Waters, Cruising The Caribbean Sea, Oranjestad, Bonaire (Kralendijk), Willemstad, Cruising The Caribbean Sea, St. George's, Castries, Pointe A Pitre...

Other Categories Starting At:

Inside

N/A

Outside

N/A

Balcony

N/A

Suite

$8,399.00
Cat: G

More Details Contact Us

20-Day Caribbean Explorer
Roundtrip from Fort Lauderdale

from $1,832.00 (USD)

Per Person

Oct 28, 2025
through Nov 17, 2025

More offers from Princess Cruises®

Oct 28, 2025 through Nov 17, 2025

Nights: 20

Ship: Caribbean Princess

Price Per Night:$91.60 (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

$1,832.00
Cat: IF

Outside

$1,956.00
Cat: OZ

Balcony

$3,047.00
Cat: BF

Suite

$3,952.00
Cat: ME

More Details Contact Us

21719 Harper Ave, St. Clair Shores, MI

British Virgin Islands (17 offers included)