Trip Planning


Sojourn Sailing coordinates customized charter yacht vacations for any size or type of group, personal or professional. In doing so, we focus on the following five facets of a successful charter yacht plan:

1. Your Dates:

Whether it is Christmas vacation, the end of a successful sales quarter or spring break, we can create an itinerary around your schedule. However, sooner you can commit, the more flexibility you have in choosing the best options available. Even if your just exploring the possibility of a charter trip, give us a call, as the availability of certain boats might help you decide.

2. Your Location:

We have broken the Caribbean Islands into four main cruising grounds. Where you choose to charter may depend on your goals for this trip or where you may have been before. From the turquoise tranquility of the Virgin Islands’ to the hottest on-shore clubs of St. Martin, we'll put you in places you love and in places you'll never forget.

3. Your Group:

The newly married; families; country club members; ladies only; business partners or political organizations. Whatever the make-up of your group, we make it work. And number of people is never an issue, as we can arrange the same itinerary for multiple yachts.

As you can imagine, group type is a strong driver of charter activities once at sea. Families may have different activity preferences than a reunion of college buddies. Business executives may want all the options while a newly married couple may only be seeking simplicity and solitude. The most important thing to remember is that the possibilities are endless.

4. Your Vessel:

As most clients know, “yacht” is a somewhat generic term that can be applied to wide range of boats. Typically, it refers to a vessel (usually ocean-going) used for racing or private cruising. We understand that the word often conjures images of exquisite, 200’ floating hotels with on-deck heli-pads. Well, that's true. But boats like that are only a fraction of what’s available for charter.

You can climb aboard a 30’ catamaran and experience an intimate sailing excursion in locales that no postcard can duplicate or travel guide could capture. Or maybe you want to streamline across the Caribbean in a sleek, classic monohull. It’s all up to you and the options are plenty. Sojourn is here to provide specific information on how these yachts differ and what will be most suitable for your charter group.

5. Your Price:

We represent only the best charter yachts in the Caribbean and each operation has points of strength that we align with your wants and desires. With an array of gorgeous yachts and exceptionally knowledgeable crews to choose from, we can easily partner your group with an outfit that is as equally invested in making sure your Caribbean vacation is as luxurious, adventurous and memorable as you want it to be. And maybe more so.

Obviously, different boats, crews and levels of service command an array of prices. However, there is little question that the value they all provide, in terms of memories, experience and attention to detail, cannot be assigned a dollar amount.

Other considerations…

After mailing down the fundamentals, we’ll hone in on the best charter menu options for your group and discuss itinerary specifics.

  • How about arranging a flight?

    Most major airports can get you to the Caribbean but having spent many years traveling to and around the Caribbean, we are aptly prepared to help you arrange the most convenient way to arrive in time and at the right place to access your charter.

    Talk to us about any flight preferences you have, relative to times of day or miles programs that may come into play and we’ll put together some options for you.

  • Menu and bar:

    Did we mention the private chef? That’s right, one of the best parts of a crewed charter vacation is the gourmet food and custom bar completely at your disposal. We can sit down with you, your family or group to plan an exceptional dining experience. We can accommodate an array of selections, preferences and we’ll be sure to address and document any allergy concerns.

  • Itinerary:

    This is where the personal touch and insight of Sojourn can provide the most impact. With our experience in the Caribbean, there are few activities we have not experienced or know how to make happen.

    From vibrant snorkeling adventures, island hopping, onshore hiking or simply soaking sun on remote beaches, we can help carefully plan everything you’ll remember about your charter trip.

    You can also let your captain decide on a daily sail, take advice from the crew or simply play it all by ear, letting spontaneity rule the day. Remember, you are in control and have the flexibility to do what it is that strikes you--and barring weather or extenuating circumstances--whenever you want to do it.

    Clients new to the charter world are always amazed at how easy it can be to plan a crewed charter vacation. Everything is taken care of by Sojourn Sailing, your captain and crew. All you have to do is get your group together, pack and the rest happens on the boat.

QUESTIONS? Give us a call… We can answer any question that you can come up with.

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Captain Dare Blankenhorn

Leigh Ann Nelson