Ultimate Guide to a Caribbean Yacht Charter With Skipper

Thinking About Going on a Caribbean Yacht Charter With Skipper? Find Out Everything You Need to Know Here

Ultimate Guide to a Caribbean Yacht Charter With Skipper

Anyone can go on a Caribbean yacht charter with skipper if you have ample sailing experience or no sailing experience whatsoever you can still go. Everyone has to start somewhere and what better way to do so than by learning from a professional.

The Caribbean Sea is one of the world’s most popular tourist destinations with over 7,000 islands, islets, reefs, and cays, within the 28 nations it includes. A Caribbean yacht charter with skipper, no matter which country you visit the azure waters, white sandy beaches, and tropical climate make it the perfect Caribbean yacht charter with skipper destination. With islands in the Caribbean to small islands off mainland Belize, Colombia, Nicaragua, Mexico, and the Guyanas, the Caribbean Sea stretches far and wide.

The countries included in the 28 nations vary between a tropical savanna climate, tropical rainforest climate, and tropical monsoon climate varying with latitude and island placement. The Caribbean tends to have two distinct seasons – the dry season which takes place between December and April, and the wet season which goes from May to November.

The northern islands are also located within an area that is occasionally hit by hurricanes. Hurricane season lasts between June and November but the most prominent months are August and September. On a Caribbean yacht charter with skipper, you can expect a year-round average temperature of between 25-33c (77-90f).

Caribbean Yacht Charter With Skipper

Sailing with a skipper allows you to have a luxurious family sailing holiday, friends holiday, romantic getaway or a group sailing holiday without having to worry about planning an itinerary, researching the best places to moor or worrying about safety.

Caribbean Yacht Charter With Skipper

What Is A Caribbean Yacht Charter With Skipper?

What is a skippered charter? A Caribbean yacht charter with skipper is the perfect sailing holiday for families, couples or friends, of all sailing abilities. On a Caribbean yacht charter with skipper, you will book a yacht charter and then a skipper will accompany you on your charter. The skipper will sail the boat and offer expert knowledge of the location. You can set your own itinerary or the skipper can offer their expert advice and have as little or as much input as desired. A Caribbean yacht charter with a skipper allows you to relax while the skipper takes the helm, offering an easy and flexible yacht charter.

What Is It Like To Go On A Caribbean Yacht Charter With Skipper?

Relaxing Yacht Charter. When you go on a Caribbean yacht charter with skipper they are there to make your holiday easier and relaxing. The skipper will have their own cabin on the boat (allow for this when booking), you will also have to provide food and drink throughout the day, but the skipper doesn’t have to be involved in your meals, excursions or evening meals out if you don’t want them to.

Professional and Experienced Service. Each and every skipper is professional and experienced, with a large amount of knowledge of the areas. A skipper can be as discreet as required, you are to obliged to include them in your activities, they are there to make your holiday better, not to be in the way or make you feel uncomfortable.

Why Should You Go On A Caribbean Yacht Charter With Skipper?

Ample Benefits. The benefits of going on a Caribbean yacht charter with skipper totally dependent on the individual or families requirements. If skippering your own boat is what you want to do then go for it, but for those who want to spend more time on activities and have less stress then a skippered charter is an option. Caribbean yacht charter with skipper is great for every ability of sailing, if you don’t have any sailing qualifications or experience then a skippered yacht charter is you’re the only option. Many skippers will take the time to teach you valuable skills, or if you are experienced you can always learn more from the skipper.

Professional Skippers. On a Caribbean yacht charter with skipper, the skipper will take care of all the technical parts of the boat, safety, and moorings, you will be in capable hands. Skippers can provide unrivalled local knowledge of islands, the winds, the ocean, the best restaurants, the best marinas to moor at, the best anchoring spots, the condition of the sea bed and the forecasts.

The Caribbean Is A Top Sailing Destination

Lots of Countries to Explore. On a Caribbean yacht charter with skipper, all 28 nations are different, it is one of the most biodiverse ecosystems and areas in the world. The Caribbean has 8% of the world’s coral reefs as well as being culturally diverse, with a large number of different languages spoken, a variety of coastline landscapes, and diverse traditional cultures located throughout.

A Place To Sail For Everyone. When sailing on a Caribbean yacht charter with skipper there is a country for everyone from beginner sailing areas to advanced long stretches of open ocean for professional sailors. The water temperature varies from 26c or 76f (wet seasons) and 30c or 87f (dry summer season), which make it an ideal sea for swimming, snorkeling, and discovering the underwater world, with a variety of marine life as well as the land which surrounds it, which is great for a Caribbean yacht charter with skipper.

Create An Itinerary. When you are on a Caribbean yacht charter with skipper, you and your skipper can create an itinerary depending on your desires and requirements. Your skipper can recommend islands to explore, marinas to moor in and restaurants to visit. They also have expert knowledge of how to book marinas and what needs to be done in advance and what places you can just arrive at without pre-booking on a Caribbean yacht charter with skipper.

Caribbean Itineraries

Sailing Itineraries. The Caribbean has an abundance of top sailing locations, the best snorkelling spots, and impossibly gorgeous cays, there is something for everyone. We have created an abundance of Caribbean sailing itineraries, to allow sailors to experience some of the best sites on a Caribbean yacht charter with skipper.

Ultimate Guide to a Caribbean Yacht Charter With Skipper

Contact Us to Book a Caribbean Yacht Charter With Skipper Today

Amazing Sailing Experiences

Our Amazing Customers


  • Great family vacation.

    I didn't think sailing with my family would be so much fun...

    Sailing for the first time.

    Alex
    Alex USA

  • I recommendate them !

    Everything went smooth, the paper processing, special requests and the specs of tht check-in procedure. Boat was also in good shape, so no complaints and a worry free holiday...

    We had a great experience with booking through sailchecker.

    <read more>

    Dick USA

  • Great service from Kate.

    Informative and looked for the best value for our family. Very good customer service on this side and in Greece. Great boat and skipper...

    Fantastic holiday from start to finish.

    <read more>

    Angela United Kingdom

  • Very professional outfit!

    They were very responsive and very quick to answer questions via email and instant chat. They had extensive knowledge of the area...

    We will most definitely use their services for our next bareboat sailing vacation.

    <read more>

    Kirsten W.
    Kirsten W. USA

  • Sail checker were professional from start to finish - we wouldn’t book through anyone else!

    Sailchecker were professional from start to finish - and were awesome dealing with a problem! Our first Yacht had serious issues and sail checker helped us to resolve it...

    They are easy to deal with, straightforward and honest and I would recommend them to anyone planning a charter holiday.

    <read more>

    Kat, H.
    Kat, H. UK

  • Coronavirus pandemic support has been brilliant!

    During the Coronavirus pandemic, Kate and her colleagues at Sailchecker have performed brilliantly. They have been considerate and highly efficient in re-organising our Turkey charter and also provided lots of assistance in getting our Yacht Security Deposit insurance policy transferred to match our revised charter dates.

    Truly worthy of a 5 star rating!

    <read more>

    Alan, R.
    Alan, R. UK

  • Sailing is the perfect family holiday.

    Would I go sailing again? OMG yes! Sailing is the perfect family holiday. Boys loved the activities, I enjoy relaxing as well...

    Sailchecker.com arranged a sailing cruise her family of 2 sons, daughter & hubby in the BVI with their own.

    Anne
    Anne USA

  •  Thank you sooo much! It was sail in the day… party at night. We couldn't have wanted a better skipper or a Spring Break!  Good times...

    Arranged for 6 friends to sail Spring Break in the British Virgin Islands for under $500 each.

    Tim
    Tim USA

  • We had an absolute blast !!

    All bookings and confirmations was always accurate with no delays. Our boat was also fabulously maintained and the Skipper new the area extremely well...

    Everything was down to the tee.

    <read more>

    Pieter Van R.
    Pieter Van R. Netherlands
SailChecker Yacht Charter and Sailing Worldwide Logo TrustPilot 4.9/5 Stars

Rated 4.9 out of 5 based on 215 reviews on Trustpilot

Got a Burning Question About Caribbean Yacht Charter With Skipper?

We’re Happy to Answer Any Yacht Charter & Sailing Question

Leave us a quick question here, or call your local office, the numbers are located in the footer below. When not arrange a call back?

girl at desk at yacht charter show
Recommended Posts

Leave a Comment

Start typing and press Enter to search

The Fastest Way to Our Award Winning Charter Service Starts Here >>>
Get Started
close-image
beach with a palm tree and the ocean on a Caribbean bareboat charterAmalfi coast with boats and mountains on a Europe yacht charter with skipper