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Your First Family Trip to the Caribbean

As I’m sitting on the plane, on the way home from our first trip to the Caribbean with the three kiddos, I wanted to share some tips and put your mind at ease when it comes to traveling internationally with your clan. We are all in agreement that this was the best vacation EVER!! Here’s some things to keep in mind as you start thinking about where you want to take your crew.

A Caribbean cruise is a great way to see more than one destination (including private islands) on a single trip., and only having to unpack once! Caribbean cruises can also be very cost-effective for big families since they include nearly unlimited food and entertainment options along with your lodging for one low price. Some cruise lines have family cabins that can sleep larger families with more than two kids. Most of the time, these family cabins consist of two connected rooms or a larger suite with separate living areas for up to 10 people. There are some pretty impressive suites out there, especially on Royal Caribbean’s Symphony of the Seas!

A great way to save some money (for souvenirs, of course!) is to drive to the cruise port vs. flying. Being based in PA, we are lucky to have ports in NY, NJ and MD super close. With the average cost of airfare in the $300 per person range, the savings are substantial if you can find a port close to home. If not, no worries! Several cruises leave from popular destination in Florida and for a really amazing cruise, San Juan is accessible from many gateways non-stop.

My family’s new favorite way to vacation is at an all-inclusive resort. These resorts are insanely convenient for families since they include all your food, all your drinks, your entertainment and more for a single price. The Caribbean is also full of all-inclusive resorts at all price points, so it’s an easy choice when you have kids in tow. We are on our way home from Beaches Turks & Caicos and to say we had an incredible time is an understatement. My 8 year old could not believe he could eat as much as he wanted and we didn’t have to pay after each meal!

Getting to the all-inclusive resorts in the Caribbean will require airfare. Many gateways offer exclusive charter flights which are a significant savings and a significant savings of time, since most are nonstop. Popular destinations for these flights are Mexico, Jamaica and the Dominican Republic. If you’re going to fly your big brood to the Caribbean, earning airline miles can also help. With at least some airline miles to work with, you may be able to cover a few to destinations in the Caribbean or to your cruise port. I have personally done this with Southwest Airlines. Since I tend to fly them the most domestically, racking up miles to use definitely helps. And, Southwest flies to many Caribbean destinations, and your bags fly for free too! Cha-ching!!!! Airline credit cards are also a great way to rack up miles and all of the major airlines offer them, usually bonusing a good chunk of points for joining.

The Caribbean can be considerably cheaper to visit outside of peak travel season, which is during winter months. Book a trip to the Caribbean from May to November and you’ll see big discounts on everything from hotels and condos to flights. Keep in mind that June-November is hurricane season, so always consider travel insurance- just in case.

I’d love to help take the stress out of planning your family’s trip to the Caribbean and there are no fees for my services. Email me at to find the perfect itinerary or resort to ensure a fun-filled trip for all!