Quiet, upscale Antigua is known for its numerous beaches (there’s over 300!), fantastic scuba diving and varied dining experiences. 

All-inclusive vacations with air starting at $799*

+ air credit offers up to an additional $425 off**.

*Departs NYC  **Select resorts


With average year-round temps in the 70s, it’s always a good time to visit Barbados’ white sand beaches, watch a cricket match or interact with sea turtles.

Vacations start at just $599*.

*departs FLL


Bring your golf clubs to Bermuda to try out the tiny island’s 7 championship golf courses–that is, when you’re not lying on the pink sand or showing off your knee-high socks and Bermuda shorts. It’s an easy, long weekend trip from the East Coast.

Packages starting at $899*.

*departs NYC

Cayman Islands

One of the Caribbean’s most favorite destinations for scuba, the Cayman Islands also boast the world-famous Seven Mile Beach, where you can try an array of water sports or even mingle with stingrays on the North Sound. 

All Cayman Islands vacations currently include a $200 air credit for 2019 travel.


Yes, it’s part of Mexico, but this island gem offers a Caribbean experience with a fun, Mexican vibe. Find out why divers LOVE Cozumel.

All-inclusive vacation packages with air start at just $699*.

*departs WAS


Sitting outside the hurricane zone, Curaçao enjoys fabulous year-round weather. When you’re done at the beach, visit the port of Willemstad for a bounty of shopping, nightlife and dining options.

Vacation packages with air start at $599*.

*departs MIA

Grand Bahama Island

The quieter, more laid-back sibling of Nassau, Grand Bahama Island is a favorite spot for fishing of all kinds, interacting with dolphins and rubbing elbows with the music-loving locals in Count Basie Square.

All Grand Bahama Island vacations include an $300 off with Summer Value Savings.

Puerto Rico

San Juan, Puerto Rico has never looked better, and you’ll love the abundance of dining options, nightlife and adventure-packed excursions.

Vacation packages with air start at $599*.

*departs FLL

St. Lucia

Lush, exotic St. Lucia is home to mountains, waterfalls and volcanos–all there for you to explore when you’re not lazing away the day on its pristine beaches.

Vacation packages with air start at $1,089*.

*departs FLL

St. Maarten/St. Martin

Island vibes with Dutch and French flair define St. Martin’s unique ambiance–whether you prefer a high-energy getaway or a laid-back atmosphere, you’ll find both on this island favorite.

Vacations with air start at just $599*.

*departs FLL

Turks & Caicos

Laid-back luxury is what defines family-friendly Turks & Caicos. You’ll never want to leave the jaw-dropping beauty of the beaches, but make time to check out the fun in Providenciales.

Vacation packages with air start at $699*.

*departs FLL


Limited time and availability. To be eligible for this promotion you must 1) be an approved ER&R Club member by 11:59 p.m. CST on November 4, 2019 2) be within the first 25 ER&R Club members to sign up for the promotion 3) make a double or single occupancy booking for 5 or more nights. Bookings must be made and payment must be collected through a designated CheapCaribbean agent between November 11-20, 2019. Travel must be completed between January,1 and June 30, 2020. Blackout dates include but are not limited to April 3-19 and May 20-27, 2020.


Flight accommodations will be booked in economy class or lower on United Airlines. Flight requests will be taken into account but are not guaranteed. In areas that are serviced by more than one airport (for example New York, Chicago, San Francisco), clients are expected to use the airport that provides the lowest fare available.


CheapCaribbean’s travel protection and cancellation policies for the hotel portion of the booking will apply. Travel protection will only be valid on the hotel-portion of the booking. Cancellation or a rebooking of your hotel stay outside of the allowed travel period will result in forfeiture of the free flight(s). Any changes to flights will be subject to the airline’s policies.


Offer not valid on previous bookings. Offer may not be combined with other special offers, discounts or promotions (including promotional codes). This promotion is not available to employees, or family members of employees, of CheapCaribbean or affiliated companies of the Apple Leisure Group.