10 Tips for Island Hopping in the Caribbean

Our expert has visited more than 100 Caribbean islands. Here are his travel tips for planning your Caribbean vacation.


Over the years, my kids and I have visited more than 100 islands in the Caribbean, either by plane, ship or sailboat. Just like each U.S. state, each Caribbean island is unique and has its own flavor. Some are more accessible than others, some are more resistant to the weather and some are even relatively mosquito-free year-round. A lot of factors come into play when you plan to go island hopping. Read these 10 travel tips, and your trip ought to go off without a hitch.

1. Pick Your Island

With thousands of islands to choose from, making a decision can be difficult. If you’re looking for nightlife and a crowd, consider Jamaica, the Bahamas and Puerto Rico. The search for fabulous beaches should steer you toward the Dominican Republic, the pink sands of Bermuda, or the fabulous Seven Mile Beach on Grand Cayman. Peace and solitude (and no beaches) would be Saba—one of my favorites and a great island for hikers; be prepared for the airport, the most dramatic, white-knuckle approach I have ever experienced.

2. Cruising In

If you’re looking for a taste of each island, a cruise is the way to go. You typically are in port during the day and can get a good snapshot of island life with a cruise-sponsored tour. I prefer to get a “real” taste of the island and take a half-day tour with a local taxi driver. He will be your personal chauffer for the day, and you’re guaranteed to find some interesting people and usually some great food. Remember: Negotiate your taxi fare before getting in the car. If a driver says he will be back to pick you up—he will. I have yet to have one leave me stranded.

3. When to Go

The good part about the Caribbean is that there is no real “bad” time to go. Peak season is December to April, when the weather is best, so rates will be higher. Summers will be hot, and there will be rain each day, but that’s when the best deals are offered. It’s also hurricane season from June 1 to Nov. 30. The sun will rise and hurricanes will come—you can count on it. If you’re on a cruise—no worries. Today’s ships are fast enough and technologically savvy enough to outrun almost any storm. But you may miss an island or two. For island-based vacations, keep up on the news and make sure you have adequate insurance if you need to cancel [For more information about travel insurance, read our insurance tips series: Types of Travel Insurance, Do You Need Travel Insurance? and Where to Buy Travel Insurance. Even riding out a storm is an option. Most countries depend on tourism and have the infrastructure to ensure your safety.

4. Why Go

The Caribbean lends itself to many purposes. Of course honeymoons and romantic trips top the list, but the Caribbean is also the perfect spot for families, destination weddings, business meetings (they’re tax free in Jamaica and a few other islands), or, as I have done, for a solo trip to just forget your worries and get away from it all!

5. Travel Documents

There are no visas required for U.S. citizens of any Caribbean basin nation. As for passports, the rules have changed, so pay attention. The U.S. government’s Western Hemisphere Travel Initiative is now in effect, and U.S. citizens flying to or from the Caribbean (and Canada and Mexico) need a passport. If traveling by land or sea, passports will be required beginning June 1, 2009. The only exception to this rule is Barbados, which has always required a passport from U.S. citizens regardless of mode of transport. If you plan to travel to the Caribbean and don’t yet have a passport, get one now. The only countries exempt from this requirement are Puerto Rico and the U.S. Virgin Islands, which are territories of the United States.

6. Insurance

Typically a Caribbean trip is an investment both in time and money. Don’t risk it. Last summer I was supposed to go to Turks & Caicos on Aug. 16. Due to a fall on Aug. 15, my beach chair and piña colada were replaced with a surgical table and a scalpel. Thankfully, I had travel insurance. While I was bummed about the trip, my wallet was happy and I was made whole.

7. Money, Language and Other Necessities

There are perhaps a dozen different currencies in the Caribbean; the U.S. dollar is widely accepted. I do recommend getting a small amount of local currency for taxi driver tips and small incidentals, but it is not necessary. The electricity is the same as the United States and is on a standard 120/240v system. Internet Wi-Fi hot spots are spotty, and your best bet is at an Internet cafe. Cell coverage is also spotty and very expensive. If your phone is unlocked by the cell carrier, it is usually less expensive to buy a new SIM card at your destination—they are usually available in airports and in news stores. English is also widely understood and spoken.

8. Flying In

The Caribbean is served by many airlines. Some islands are better than others. For the major islands, there likely will be nonstop service from the United States mainland. For the medium-sized islands, there may be an intermediate stop or two. And for the really small islands, be prepared for multiple connections, small planes, short runways and dramatic landings.

9. Where to Stay

The Caribbean boasts every type of accommodation imaginable. From sprawling luxury resorts to intimate thatch-roof shacks, the choice is yours. St. Lucia is home of Anse Chastanet and Ladera, two of the finest romantic hotels in the world. Jamaica is the queen of the all-inclusive resort with Sandals, Grand Lido, Beaches, Breezes and the naughty Hedonism resorts.

10. How Long

I have been to Jamaica for one night and it was no fun. While shorter stays are possible on the larger islands closer to the mainland, to really experience any island, I feel you need five days at a minimum. Remember, you could possibly lose two days just in traveling if your destination is in the Southern Caribbean. Three days will allow you to relax, unwind, sip a cool cocktail or two, soak up some sun, splash in the clear blue waters and explore the land a little.

One thing is certain, when you vacation in the Caribbean; it is never a bad thing. With a little planning and forethought, it can be the best experience imaginable. As they say in Jamaica—Irie Mon!

P.S.: Oh, and that relatively mosquito-free island? Aruba!

[Read Essential Caribbean Packing List for more information on how to pack for your Caribbean vacation.]

Destinations: Caribbean

Themes: Beach Vacations

User Comments

Where would be the best place to rent (charter) a power boat to island hop on relatively calm seas? We'd love to cruise on a boat with or without a captain to various interesting islands, diving, fishing, beaching along the way. Any suggestions?

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