There are many flights available to every island in the Caribbean. Some of the islands have several connections in order to get there. Consider searching out private plane charters. They are a great way to cut out some of the many connections, and they are not very expensive. Many private air charters will pick up in San Juan Puerto Rico, or St. Thomas and fly to places like Martinique or St. Vincent and Union. The pilots on these charters are extremely accommodating and assist your party right through customs.

Whether you motor boat or sail, there are many boats and companies to choose from. Bear in mind that one entire day is dedicated to travel, provisioning and boat orientation. You will leave the dock by the following morning and begin your exciting journey. Many charter companies will allow sleep aboard the day before a charter begins. Ask about availability and fees. There are also many land-based venues to choose from and your charter company will know them as well.

If a crewed charter is your preference, there are many to choose from in all locations of the Caribbean. Having a local skipper on board will ensure that your charter experience will be more carefree. A local skipper will know how to negotiate the anchorages and coral reefs that are evident around many of the islands. He will also know the best beaches and the best restaurants and markets. Depending on the size of the charter boat, one may not want to take up valuable space on a tight ship and add a cook to the crew. But again if you want a carefree vacation with no dishes or cooking, then a hostess/cook will be a valuable asset to the perfect vacation.

For most of the Caribbean, only a sailing resume is required to bareboat. However, it is crucial to confirm that the charter company deems your resume acceptable, and to have in writing that confirmation. Certain winter weather periods in this region create challenging sailing conditions. If a novice, you may want avoid open water sailing.

Many parts of the Caribbean have mooring systems in place in order to protect the fragile ecosystem. Depending on the location and time of year, usually holiday weeks, arriving at an anchorage by mid afternoon is wise in order to get a mooring or drop anchor before the crowds arrive. Make sure that you are familiar with rules regarding anchorages/moorings for your particular islands. Moorings are an additional fee at many locations, be prepared to pay at least $25 per night.

During the November through January winter months; the prevailing wind is 15-20 knots from the northeast. This provides for calm pleasant conditions at anchor. On and off all winter, the famous "Christmas Winds" blow at 25-30 knots for several day periods. Beginning in February and finishing in June, the winds move from a northeast direction to southeast when 10-15 knots can be expected.

Late summer through fall (August through November) is the Caribbean’s rainy season. However, rainsqualls can occur at any time, and they are usually short lived. During September and October, the trade winds are unsettled and weakest. These months are considered the height of hurricane season, although the nominal season is June through November. Check charter company policies in regards to hurricanes. Average high temperatures range from 85° to 90° with the highest in July through October; average low temperatures are about 10° less.

Depending on the amount of time you have set aside, one-way options are popular in many locations. Martinique to St. Lucia, St. Vincent to Grenada, St. Lucia to Union are just a few examples of one-way itineraries. Inquire with your Charter Company or broker to find availability and the fee schedule.