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Region: Caribbean
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Washington, DC
Popularity | Flight Price

Founded in 1521 by Ponce de León, the capital of Puerto Rico, San Juan , is the oldest city in US territory. Home to 1.6 million (more than a third of the island's citizens), it is also the ... Read more...

AVG. FLIGHT
$210 IAD - SJU
Compare Flightsfrom Washington, DC to San Juan, Puerto Rico
AVG. 4-STAR HOTEL
$118+ nightly
Compare Hotelsin San Juan, Puerto Rico
HOTEL DEAL
$118 nightly, 46% drop
Caribe Hilton
All hotel deals

Most visitors to SANTO DOMINGO understandably make a beeline for the Zona Colonial , Santo Domingo's large, substantially intact colonial district, home to dozens of wonderful old buildings and a ... Read more...

AVG. FLIGHT
$356 DCA - SDQ
Compare Flightsfrom Washington, DC to Santo Domingo, Dominican Republic
AVG. 4-STAR HOTEL
$82+ nightly
Compare Hotelsin Santo Domingo, Dominican Republic

Originally a harbour base named Charles Town, NASSAU is the modern-day face of the Bahamas, visited by most everyone who comes down this way, not least for its service as a transport hub. Though ... Read more...

Best for: romantic, family, beach
AVG. 4-STAR HOTEL
$198+ nightly
Compare Hotelsin Nassau, Bahamas, the
HOTEL DEAL
$198 nightly, 37% drop
Atlantis, Paradise Island - Coral Towers
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The first town in Jamaica to be developed specifically as a resort, OCHO RIOS (usually just called "Ochi") abounds with neon-fronted duty-free stores, fast-food chains, bars, clubs and ... Read more...

AVG. 4-STAR HOTEL
$161+ nightly
Compare Hotelsin Ocho Rios, Jamaica
HOTEL DEAL
$161 nightly, 26% drop
Riu Ocho Rios All Inclusive
All hotel deals

Jamaica's second largest city, MONTEGO BAY nestles between the gently sloping Bogue, Kempshot and Salem hills, and extends some ten miles from the haunts of the suburban rich in Reading at its ... Read more...

AVG. FLIGHT
$371 IAD - MBJ
Compare Flightsfrom Washington, DC to Montego Bay, Jamaica
AVG. 4-STAR HOTEL
$152+ nightly
Compare Hotelsin Montego Bay, Jamaica

Cuba's answer to the Costa del Sol in Spain or Cancún in Mexico, VARADERO is dominated by tourism and almost nowhere are you out of sight of a hotel. However, anyone hoping for a polished, ... Read more...

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Grand Cayman Among the three Cayman Islands, Grand Cayman is overwhelmingly the largest, the most visited, and offers the most variety of activities. Where the two smaller islands mainly cater to ... Read more...

Best for: family, beach, romantic
AVG. 4-STAR HOTEL
$159+ nightly
Compare Hotelsin Grand Cayman Island, Cayman Islands
HOTEL DEAL
$159 nightly, 56% drop
The Westin Casuarina Resort
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Jamaica's shrine to permissive indulgence, NEGRIL has metamorphosed from deserted fishing beach to full-blown resort town in little over two decades. American hippies first started visiting what ... Read more...

AVG. 4-STAR HOTEL
$256+ nightly
Compare Hotelsin Negril, Jamaica

Founded on the western banks of a fabulous natural harbour, what was once the entire city of HAVANA now forms the most captivating part of Habana Vieja , the old city and the capital's tourist ... Read more...

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