Stories by CheapCaribbean

Best Times to Book Your Beach Vacay

August 11, 2019 0 Comments

While it seems as though there really can’t be a bad time to book a beach vacation, there are definitely times that are better than others! It will all depend on what’s driving your decision. Are you looking for the best time to experience the Caribbean weather? Or maybe you just want to find the cheapest getaway possible. It all revolve around what’s of the utmost importance to the traveler- aka YOU!

Trade out white snow for white sand

As winter approaches in your hometown, it’s easy to crave the beach. Apparently though, everyone else is thinking the same thing you are because the peak season for travel to most places in the Caribbean is November to April. But, can you really think of anything better than escaping the bitter cold to enjoy endless sunshine? We think not! If you don’t mind rates being slightly higher in the midst of peak season, then this is definitely the best time to escape to warmer weather. Maybe even get to celebrate a holiday with a piña colada in hand? Pro tip: peak travel season doesn’t mean you still can’t score a good deal!

Parasailing off the coast of Grace Bay Beach

Views from Grace Bay Beach (Photo by: @j_passiglia)

Sweet Summertime = Sweet Deals

If you’re searching for the greatest bang for your buck, then winter time might not be the best choice for you. Consider taking your summer vacay down to Mexico or the Caribbean! The summer and early fall months offer some of the more cost-effective deals in light of hurricane season. But the small risk is worth the low prices–and you still get the same warm weather, silky sands and clear waters. If hurricane season worries you but you still want to have your summer vacay on white sandy beaches, then consider one of the ABC islands: Aruba, Bonaire and Curaçao. These islands lie outside of the hurricane belt and offer the same beautiful views and amenities you’re used to. Planning your getaway in the early months of fall not only scores you lower prices, but resorts are also less crowded due to school being in session!

Last minute plans lead to the best trips

There might be times that are better than others to book your dream getaway, but sometimes you want to book it now! Spontaneity makes for some of the best trips, therefore, you have to check out some of our last-minute deals. With new resorts and locations always being added, you are sure to find the perfect beach vacay with a few days to spare before departure.

Abandoned tiki hut on the Curaçao beach

Curaçao doesn’t seem too bad after seeing this view! (Photo by: @marjoleinzinkhann)

While booking your dream beach vacation depends on your own personal preferences, there really isn’t a bad time to fly down to paradise! What are you waiting for? Check out some of our favorite Caribbean spots for your next trip of a lifetime! And while you’re planning your next vacay, check out ways to add transfers at your booking to make your trip as seamless as possible!

Haley Hogan

All I really need in this life is the beach and a little bit of ice cream.




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.