Stories by CheapCaribbean

Caribbean Island Bucket List

June 3, 2019 0 Comments

There’s no doubt the Caribbean is one of the most desirable travel destinations in the world. It has hundreds of white sand beaches, picturesque views, spectacular hiking, endless snorkel and scuba diving sites and the list could go on! With so much to do, planning a trip to the Caribbean can often be overwhelming when you’re not sure where to start, but here’s a pretty good way to kick-off your Caribbean island bucket list!

Explore the Crystal Caves of Bermuda

When you discover this breathtaking natural wonder in Bermuda, you’ll wonder why you didn’t go sooner. Swim through the Crystal Caves in its crystal-clear water that looks no deeper than two or three feet–but it’s actually 50! While you wander through the caves, don’t forget to look up and witness thousands of crystalized stalactites just above you… it’s quite the sight to see.

Caribbean Island Bucket List

Exploring Bermuda’s Crystal Caves (Photo by: @kristenkanoelani)

Stroll the cobblestone streets of Old San Juan, Puerto Rico

Strolling down the cobblestone streets of Old San Juan may actually feel like you’re taking a stroll through the island’s cultural past–it’s like a dream! The Puerto Rican city is an official National Historic Site and UNESCO World Heritage Site for its historic buildings, landmarks and cultural events throughout its history. You’ll find the most colorful buildings, quaint cafés and shops, Castillo San Felipe and much more! Explore the city via guided tours or at your own pace… either way, it will be an incredible experience to cross off your Caribbean island bucket list! The best part? No passports are even needed to visit Puerto Rico (score!).

Caribbean Island Bucket List

Ocean views through the colorful streets of Old San Juan (Photo by: @bontraveler)

Take in the views at Shirley Heights Lookout in Antigua

You’ll never find a more perfect view than on this stunning Caribbean island. From the top of Antigua’s Shirley Heights Lookout, you can see for miles and miles out into the English and Falmouth Harbors. And on clear days, you’ll even catch sight of the island of Guadeloupe and the Montserrat Volcano. This view brings travelers from all over the world just to experience its natural beauty, and is a true Caribbean gem that you don’t want to miss!

Caribbean Islands Bucket List

This view couldn’t get any more perfect. (Photo by: @charzevans)

Swim with the stingrays at Stingray City, Grand Cayman

Take a swim with these gentle sea creatures in about 13-feet of crystal-clear, aquamarine water. The water of Grand Cayman is mostly calm, which makes for stress-free interactions with the little (but, kinda big) guys. It’s not one of the best places to snorkel in the Caribbean for no reason!

Caribbean Island Bucket List

Making friends in Stingray City (Photo by: @kvn_roberts)

Experience the unique Dutch-Caribbean culture of Curaçao

From the colorful, Dutch Colonial-style buildings lining Curaçao’s iconic pier to the charming Floating Market, you’ll instantly fall in love with the island’s culture and vibrant atmosphere. Grab a cocktail, or two, at the Iguana Cafe and witness the famous Queen Emma Bridge, a.k.a the Swinging Old Lady, open for boats passing through the capital. Pro tip: See the bridge at night when it’s all lit up with all the vibrant colors of Curaçao!

Caribbean Island Bucket List

Views of the colorful buildings in Curacao’s capital, Willemstad. (Photo by: @dalereodriguez)

Lounge on the sugary-soft sands of Sugar Beach, St. Lucia or Grace Bay, Turks & Caicos

Sugar Beach, St. Lucia and Grace Bay, Turks and Caicos are both equally what dreams are made of. Both consisting of stellar views of the Caribbean Sea, miles and miles of white sand beaches and gorgeous surrounding landscapes, there’s no doubt that these destinations would be on a True Beach Lover’s Caribbean island bucket list!

How dreamy is this view from Grace Bay, Turks and Caicos? (Photo by: @beeboxes)

If these dreamy, bucket list-worthy destinations haven’t convinced you to start packing your bags yet, then you have to check out these fantastic, limited-time-only deals that you don’t want to pass up!

Rachel Tellez

Storyteller and grammar nerd by day, traveler and adventure seeker by long weekend.




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.