Chartering a Yacht in the Caribbean

A private boat charter for your family seems like a huge splurge but might not be as out-of-reach as you think. Nancy Van Winters of ENVY Yacht Charters explains why these dream trips are the perfect Covid-safe vacation.

By Maryann Jones Thompson.

Chartering a boat to explore the Caribbean is not just for the Kardashians anymore. Nancy Van Winter of ENVY Yacht Charters says normal families can do it too!

“Charters have remained an incredibly popular trip during the pandemic,” Nancy explains.  “Extended families and friends can be together but still be socially distant. Families found that even though doing school and work at home together was a drag, being on a charter served as a re-centering. The fresh air and water is very freeing. 

And the pampering is great—what parent is not sick and tired of cooking and cleaning after every meal?! Clients said it was way better than being at a resort where everyone runs off and does their own thing.”


Nancy talked to ROAM to explain the benefits of chartering a yacht way back in 2015. Bottom line? While not cheap, chartering a large catamaran or boat can be a cost effective way to have a personal and unparalleled experience tripping through tropical waters, especially when compared to the total cost of other high-end cruises and resort vacations.  (If you’re new to the whole concept of Caribbean boat charters like I was, read ROAM’s “Yacht Charter 101” article to get the basics.)

ROAM caught up with Nancy in March 2021 on how the pandemic has impacted the charter industry and get her expert insight on the best trips that families can take via charter these days.

ROAM: Your brokerage matches vacationers with boats to rent and ensures that everything runs smoothly. How did the pandemic affect your business?

Nancy: It’s been a very crazy year! Some yacht owners went bankrupt and left clients hanging.  I’ve been in business a long time so my clients all stood by me. I’ve done my fair share of “reschedules” but I’ve been lucky. Now we brokers have become even more discerning about who we work with and have added even more ways to protect customers and the crews on the boat, both financially and health-wise. 

Personally, the best part was that we rescued a sweet dog from Antigua. I was at the international boat show in Antigua in late 2019 and met a group of girls who were stewardesses on boats. They found the pup and saved her. We named her “Nellie” and she came to live with us in the U.S. She has been our saving grace over the past year! I created an instagram account for her to share photos with her rescuers @nellie_the_island_dog


ROAM: Awww, we love rescue pups!!! That’s awesome!!!  So tell us how the yacht charter market has changed because of the pandemic?

Nancy: Charters in the U.S. Virgin Islands have gone insane. For the past 30 years, the big cruise ships had taken over the market. You’d see 8 cruise ships in St. Thomas and that pushed the smaller yacht charters to the British Virgin Islands for a more intimate ports and experiences. The BVIs have the Baths and Anegada and the beach bars and that experience wasn’t available to charters in the USVI. 

But during Covid, the process for Americans to get to the British Virgin Islands became very difficult. The country is still open but it is a very strict and expensive process to get there. You must fly in—you can’t come in by ferry or boat. You must pay $175 per person for a Covid test on arrival, quarantine, wear a tracing bracelet, and take another test on the fourth day before you can depart. Because charters are typically a week long, that makes a boat trip nearly impossible.

(Now if you have a lot of time, the BVIs are a different story. I had a family who recently chartered a boat for three weeks in the BVIs. They were working and going to school from there so it was a great experience!) 

The USVI are American! The rules are that you need a negative test within 5 days of arrival but that’s it. Because it is a U.S. destination, you don’t have to do another test to return to the states. It makes it an easy destination during Covid. Getting everyone tested multiple times is not an easy or cheap option for families traveling with a lot of kids. 

And now that the cruise ships are gone, many charters moved to the USVIs from the BVIs. The crews have come up with some incredible itineraries in the USVI that include St. Thomas, St. John, and weather permitting, St. Croix. There are new bars, beach clubs, cabana rentals for the day – it’s unbelievable what has happened. The market has evolved to a point that no one anticipated. 

Customers are bummed to miss the BVIs but since the cruise ships left St. Thomas, the number of people has decreased dramatically and the water quality has become much bluer. 


ROAM: Where else is popular post-pandemic? Where would you go?

Nancy: Hands down, the Exuma islands of the Bahamas. No quarantine is needed and you need a negative test on the fifth day. That test will count for your re-entry test to the U.S. And there is testing on every island in the Bahamas.

The bigger islands had bigger outbreaks so all the inter-island ferries got shut down.  Now the charters head to the Exumas. You fly into Nassau and have to spend a bit of time to get out there—about 4-5 hours on a power yacht—to reach your first night’s anchorage. 

But when you arrive, it’s amazing! So many colors of blue. So remote. It is a very special place. Families here need to “make their own fun” here— by that I mean there are not a lot of beach bars or shopping spots like those found in the BVIs so you’re swimming, snorkeling, beach combing. Doesn’t sound too bad, does it?


Another cool opportunity for charters is in New England. Because Americans were looking for a place to go last summer, charters in New England became popular. We couldn’t get enough boats there!  In New England, you have mostly yachts and they’re going to Martha’s Vineyard, Nantucket, Newport—fantastic places! 

ROAM: Now it’s time to talk money. How much we talking for each of these destinations?

Nancy: As we discussed in 2015, yacht charters aren’t inexpensive but when you factor in all the food, drink, transport, and activity costs of a cruise or resort vacation, very often, a week of full-board sailing in the Caribbean with your family can be very cost effective. 

As a broker, I am paid by the yacht owners so clients don’t pay extra for my services on top of the weekly charter fee. Brokers offer insurance and guarantees that the crew and the boat will be the right one for your group. We know all the captains and ports and boats and can make sure you are in the right charter. (Read our Yacht Charter 101 from 2015 for more info about the benefits of yacht brokers.) 

In 2021, the U.S. Virgin Islands is one of the least expensive options. A full-board charter for six people starts at $17,000. I recently had two families rent a 10-person, 52-foot boat that cost $23,000 for the week, but of course, that was a good deal given it was mid-pandemic. There are no additional taxes to pay in the U.S.V.I.

The British Virgin Islands run $28,000 for the week, all-inclusive, for six people. Ten people will start around $49,000.

New England pricing varies. For an example, I have a new captain with a 46-foot catamaran in the market. He’s got a great itinerary that runs $20,000 a week for 6 people, full board.

A Bahamas charter will cost a lot more. Rather than catamarans, the charters are typically mid-range power yachts and power catamarans.  A week’s charter for 6 people begins at $25,000-$30,000 but these rates are not all-inclusive. You need to pay an additional 30 percent up-front for expenses such as fuel, food, drinks, alcohol, or a splurge like docking at the Atlantis. Any money that you don’t use is refunded at the end of the trip.  There is also a 4 percent tax in the Bahamas. On the upside, the charters are equipped with a lot of amenities, such as jet skis, water trampolines and other fun features. 


ROAM: How far out do you need to book?  

Nancy: The USVI season runs from mid-November to August 1. High season in the Bahamas is from the end of March through September. And of course, the season in New England is very short, from June to the end of September. 

These charters are something to think of for 2022, 2023 and beyond. There are still dates available for 2021 but it is getting tight because so many 2020 sailings had to be cancelled and pushed to this year. Serious customers need to act quick!

And yes, whatever is on your bucket list for the next few years, whatever destination, book now! Pandemic reschedules are all being moved to 2021 and 2022 so bookings are tight. 

But if you can’t get a boat in the Caribbean this year, don’t worry. We can book you a charter in the Mediterranean—say, Greece or Croatia—Fiji, Thailand, or some other fabulous destination! 😉 



Maryann Jones Thompson  – March 2021

ROAM Founder & Editor   

After a thousand years in publishing as a business journalist, ghostwriter, content strategist and market researcher, Maryann brings her experience traveling as a backpacker, businessperson, expat and mom to writing and editing for ROAM.

© ROAM Family Travel 2021 – All rights reserved


ROAM with us! Read the latest REAL family adventures



Don’t miss a single trip! Enter your email address in the box below to subscribe to ROAM and receive notifications of new posts by email. Check your inbox for an email to confirm your subscription, click the link and you’re ready to ROAM!