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How to plan for an all-inclusive sailing trip

Friends toasting on a yacht during a sailing trip

You’ve done it, you’ve decided on a dream vacation to the Caribbean islands! While your mind might be ready to start soaking up the sun, the first step is to create a plan.

Sail Play Dine Yacht Charters is here to help you plan a trip you’ll never forget. We help you experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter yacht in the US and British Virgin Islands, Bahamas, and beyond! We take care of your every need to match you with the right boat and crew at the best rate guaranteed. We offer a large range of boats that suit every budget and our trusted service comes at no extra cost to you!

Let’s walk through the steps to help you plan a trip of your own.

Choose your destination and length of time

The first question is, where do you want to go and for how long? On our website, you can search by date, length of stay, number of passengers, and budget to find the perfect yacht for your needs.

Here are the destinations you can choose from:

  • The Virgin Islands

  • Bahamas

  • St. Martin - St. Barts

  • The Grenadines

  • Belize

Decide what you want from your vacation

What type of vacation are you looking for? Do you prefer relaxation, adventure, or a mix of both? In the Caribbean, there is no shortage of things to do: snorkeling, kayaking, paddle-boarding, tours, hiking, or relaxing at the beach to name a few. If you’re not sure, we’re happy to recommend some activities.

Pack your bags

To ensure a comfortable stay and to be fully prepared, there are some things that are absolutely essential to bring with you such as your passport, money, and phone.

When it comes to packing (and not over-packing) you’ll want to think about what activities you have planned to decide what to wear. For days on the water you’ll want swimwear, cover-ups, hats, sunglasses, and a waterproof phone case. For days on-shore or out adventuring, bring casual, quick-drying clothes, and comfortable shoes. Sweaters or long-sleeve shirts are also great to have for cool nights. And finally consider, do you want to have a nice dinner ashore? Pack a nicer outfit like a dress, nice blouse or collared shirts.

When it comes to personal toiletries and medications, stick to things that are already part of your daily routine. The Caribbean sun is strong, so make sure to bring reef-safe sunscreen and after-sun creams.

Don’t go overboard… with the packing

The other part of packing is knowing what not to bring along. Storage space is at a premium onboard and in your cabin. As a general rule of thumb, we recommend not to pack more than what you need for the length of your stay. Opt for items you can wear in multiple ways to pack lighter and save space.

Consider seasickness

For those prone to motion sickness, planning ahead will be your safest bet. We know that seasickness happens and we know that some people are more susceptible than others. If you’re worried, we recommend talking to your doctor before your trip about a prescription or other preventative measures.


Sail Play Dine offers custom itineraries in the Virgin Islands, Bahamas, St. Martin - St. Barts, The Grenadines, and Belize. We invite you to join us on a sailing adventure that promises a first-class experience, excitement, and the memories of a lifetime. Contact us today and start planning your dream vacation!

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