82 deals from our U.S. site*
* Taxes and fees may be additional.
Deals through December
Cayman Islands
 
Deals through December
Featured Destination: U.S. Virgin Islands
 
 
Saturdays & Sundays October 2015 - May 2016
LAN Airlines
 
Travel through March 2016
Fairmont Southampton
 
Select departures August-October
CheapCaribbean.com
 
 
Depart April 10, 17; +$50-$200 other dates
CruCon Cruise Outlet
 
Select August -November departures
CheapCaribbean.com
 
Select September-December departures; more availab
CheapCaribbean.com
 
Deals through December
Featured Destination: Cayman Islands
 
Select dates Aug. 25 - Dec. 3, 2015
BookIt.com
 
Travel options through December
Starwood Hotels and Resorts
 
Select August-November departures
CheapCaribbean.com
 
Priced for October; more departures available
Delta Vacations
 
 
Select departures September-October
Featured Destination: U.S. Virgin Islands
 
Depart Nov. 28; +$50 Nov. 21
Priceline Cruises
 
 
Travel options through December
Starwood Hotels and Resorts
 
Cheap Roundtrip Fares to Hamilton from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More