Caribbean Blog

Fresh cocktails prepared by your own bartender!
Fresh cocktails prepared by your own bartender!

Best Staffed Villas in the Caribbean



The only thing better than staying in a Caribbean villa is staying in a staffed Caribbean villa. After all, who really wants to cook on vacation? Some travelers like the idea of grilling their own fresh-caught fish, but being wined and dined while watching a tropical sunset is…

Party all night along the picturesque coastline
Party all night along the picturesque coastline

SXM Festival: The Hottest Music Festival in the Caribbean

St. Martin’s annual music festival is back and better than ever! The Caribbean is home to rich culture and history, and the SXM Festival is a great way to enjoy all the vibrance the islands have to offer.

Tipping in the Caribbean: An Island by Island Guide

Tipping can be one of the trickiest parts of travel— some regions won’t accept tips at all, whereas others will tack on additional fees until you’re bone-dry. The Caribbean is made up of several different cultures and islands, and our team at WhereToStay wants to clear up any misconceptions or…

Best Things to Do in the Cayman Islands

My husband, Steve, and I just got back from a trip to Grand Cayman, and we couldn’t resist sharing our favorite places with you. This list has some trusted treasures and some brand-new spots, with something for everyone. Enjoy!

Necker Island is Back!

We’re excited to announce that the ultimate private getaway, Necker Island, is reopening for rental October 2018. Necker is a gem in the British Virgin Islands that’s hosted rock stars, royalty, and every other celebrity in between. It’s also home to protected wildlife, like lemurs, flamingos, and giant tortoises.…

Celebrate Rum Day With These 7 Caribbean Cocktails

Happy Rum Day from WhereToStay.com!

In honor of the day, we’ve round up our favorite seven cocktail recipes. What do they have in common? You guessed it: rum.

Top 10 St. Barts Villas

St. Barts is known as a luxurious getaway for rockstars, supermodels, actors, and professional athletes. The island offers fine cuisine, designer boutiques, hot nightclubs, and art galleries; but, it’s also a family-friendly spot with water sports, casual dining, and historical villages. Regardless of age or preferences, everyone loves the island’s…

Best Turks and Caicos Beachfront Villas of 2018

Turks and Caicos is home to the Caribbean’s most beautiful beaches and most luxurious villa rentals. At WhereToStay, we want to help you find the perfect vacation rental for your Caribbean getaway. To make your planning process easier, here’s a list of Turks and Caicos villas that are perfect…

Vacation Hacks: Travel Insurance Edition

If you’ve recently booked a vacation to the Caribbean, you’re likely in the midst of planning and preparing. Whether you’re shopping for the perfect swimsuit, scouting out the most exciting attractions, or setting up a romantic evening under the stars, you’re probably counting the days until you step off the…

Why You Need to Visit the Cayman Islands

The Cayman Islands are the sapphires of the Caribbean. Turks and Caicos and St. Barts may be the best-known and most glittery, but Cayman shines in its own way. The Cayman Islands are a trio of lovely, unspoiled islands with enviably high standards of living and the best scuba…

Grocery Stores on Providenciales, Turks and Caicos

There’s something so luxurious about having access to a kitchen, and your own food, while on vacation. Tracking down the best grocery stores to meet your needs, however, can be tricky when you’re in an unfamiliar country. To help guide Turks and Caicos visitors, we’ve rounded up the best grocery…

Where To Stay

Home Page
My Trip
My Favorites
Blog