1. Summary of Planning a Caribbean Vacation
Planning a trip to the Caribbean should start with a few simple questions:
- Who’s going? Is this a couple’s trip? A family vacation? A getaway with friends? Some resorts cater to families, while others are couples-only, for example. Some destinations are far more gay-friendly than others. If you’re traveling with someone with limited mobility, it’s important to check whether your destination is handicapped-accessible.
- What do you want to do when you get there? Some islands are known for their nightlife, while others offer quiet seclusion, great watersports, diving, rich history and culture, or focus on ecotourism. Some have multiple casinos, while others ban gaming. Choose a destination that has the mix of atmosphere and activities that are right for you.
- When do you want to go? Mid-winter trips to the tropics are popular, but you can save big by going in the off-season or shoulder season, which actually extends to mid-December in the Caribbean. Hurricane season is also a cheaper time to travel.
- If you want to get a taste of real Caribbean culture when you’re traveling, consider checking out what events are scheduled when you want to visit; the holidays can be a great time for a family vacation in the Caribbean.
- How long will you stay? If you want a weekend getaway or another trip where you need to maximize your time away, look for destinations that are relatively close to the U.S. (such as Bermuda, the Bahamas, and the Cayman Islands) or have frequent, direct flights (like Nassau, San Juan, and Montego Bay). You’ll also want to find a hotel that’s close to the airport so you don’t spend hours in transit once you arrive.
- How much do you want to spend? Not all Caribbean destinations or resorts are created equal. You can stay in five-star luxury or a beach hut. Places in the Dominican Republic generally appeal more to budget-conscious travelers than, say, St. Barts. An all-inclusive resort can be a better value than a pay-as-you-go hotel. Airfare costs are another huge consideration.
- How will you get there? For the vast majority of travelers, this will be by air or cruise ship. The former is pure transportation, while the latter is an integral part of your vacation experience.
- Why are you going? Are you celebrating an anniversary, honeymoon, or another special occasion? Some destinations and resorts are better for a romantic getaway than others.
Planning a Caribbean Vacation: Choosing a Destination
What destination should you visit in the Caribbean? There are as many answers as there are islands in the Caribbean — thousands, in other words.
Want romance? Try St. Lucia. Family fun? Aruba. Nightlife? Cancun or San Juan. Ecotourism? Check out Dominica. For fine dining and sophisticated culture, it’s hard to beat Barbados. But no one island has a monopoly on any of these attractions.
Most Caribbean destinations are safe for travelers, but it’s wise to check the latest warnings (if any) about where you are headed. Always take some prudent steps to protect your loved ones and belongings.
Planning a Caribbean Vacation: Finding a Flight
The best hotel deal in the Caribbean won’t amount to much if you can’t get there, or if you have to spend a small fortune to do so. On one hand, certain Caribbean destinations — like Puerto Rico and the Dominican Republic — have a lot of flights and competition among airlines, which tends to keep costs low. However, other islands — particularly smaller ones and those off the beaten path — may have relatively infrequent air service and high prices.
Flight duration is another issue: You can spend a lot of time in the air depending on where you are coming from and where you are headed in the Caribbean. Look for a destination with direct flights from the U.S. and check out the approximate flight time from your departure city to your destination. For example, the Bahamas are right off the coast of Florida.
There is relatively little budget airline service to the Caribbean, so it pays to compare prices on flights before you go.
Planning a Caribbean Vacation: Where to Stay
The choice of hotel, resort, villa, B&B, or cruise line will play a huge role in shaping your Caribbean experience. This is typically where you’ll spend most of your time during your trip, especially if you choose an all-inclusive property or take a cruise.
Most Caribbean resorts are located on a beach somewhere, but the same is not always true for hotels, B&Bs, or villas. Be sure to check if sun, sand, and surf are high on your priorities.
All-inclusive trips are popular and usually offer good value for the money but might not interest you if fine dining is essential for your getaway.
Private island resorts offer seclusion and romance but may lack in nightlife, tours, or excursions.
Cruises allow you to visit multiple islands while always having a place to dine and rest at the end of the day. However, know upfront that your bar tab can add up. The biggest drawback to cruising is that you never seem to get enough time on shore to learn about the places you are visiting.
Plan Your Caribbean Vacation Activities, Tours, and Sightseeing
Many people go to the Caribbean with the main activity in mind: relaxing on a beautiful beach. For some, this is sufficient. However, most travelers want their Caribbean vacation to include activities on the water and perhaps a little adventure, such as jungle tours or zip lining.
Hotels and cruise lines have activity desks that make it easy for you to book tours; cruise lines allow advance bookings for popular tours that may fill up quickly. The downside is that you could be paying a hefty premium for that convenience.
You can also go online and book tours directly with vendors, or use the Internet to book vetted tours in advance with companies that work with transportation and tour companies in the Caribbean.
What kind of activities will you find in the Caribbean? In short, almost anything you can imagine, from tours of historic homes to swimming with dolphins. Selection varies from destination to destination; however, you’ll likely be able to dive, snorkel, take a boat ride, learn some local history, and book an island tour regardless of where you go.
Before you plan, check to see what comes free with your stay. All-inclusive resorts usually include non-motorized water sports and some packages may offer tours. If all you want is a general tour, it’s sometimes better to arrange for a vehicle and local driver who can act as your guide.
Plan Your Caribbean Vacation: Restaurants and Dining Out
If you’re staying at an all-inclusive resort or on a cruise, your meals are usually covered. However, you may want to research dining options in advance to avoid growing tired of the same place day after day.
While in the Caribbean, explore some authentic cuisine, such as street food that’s popular on many islands. Creole and Latin cuisine features flavors from around the world using local ingredients. Trying the local beer and rum is also a must if you enjoy some libation.
Tipping customs are generally the same in the Caribbean as in the U.S. — 15-20 percent is always appreciated. You’ll usually find menu prices in U.S. dollars alongside the local currency.
Plan Your Caribbean Vacation: Transportation and Car Rentals
One expense that often gets overlooked by Caribbean travelers is transportation, whether it is getting from the airport to the hotel or out to explore. Public transportation from airports to resort areas is limited, so you’re generally faced with renting a car or using a hotel shuttle or cab unless transfers are included in your hotel stay.
Your decision to rent a car or rely on cabs depends on how much you intend to explore once at your resort. Keep in mind that the activities desk at your hotel can arrange tours with transportation directly from the lobby. It’s also crucial to assess the relative safety of driving around, especially in destinations with significant crime problems or differing driving rules.
Plan Your Caribbean Vacation: Packing, Safety, and Weather Checks
Once you’ve sorted out your flights, hotel, activities, meals, and local transportation, it’s time to pack!
Before you head out, check the weather report for your destination and any relevant health alerts. Finally, ensure your home is secure while you’re away, and enjoy your Caribbean adventure!
