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A Virgin Islands charter vacation is something special and will create memories that will last a lifetime. Preparing for your trip and keeping things organized while on the water will maximize the enjoyment for you and your crew.

Planning your trip often starts months in advance and can be very enjoyable. But you may also discover an opportunity that opens up for an inexpensive charter package and airfare prompting a quick impromptu trip. As long as you have a passport and your time is flexible, you can be ready to leave for a Virgin Islands charter on short notice if the price is right.

Whether you are planning a year in advance or with two-weeks notice, following a checklist can help make your trip more enjoyable.

You may also have a few tips of your own. Please feel free to share them with us and other readers by commenting below.

Enjoy miles of white sand beaches.

Enjoy miles of white sand beaches.

6-12 Months Ahead

1. Select Your Dates

  • How many days can you afford to be away? A 10-day trip is ideal.
  • Allow for 1-2 days on each end of the trip for travel time. A hotel stay may be required on one or both ends due to arriving and departing flights and the charter schedule. This can be a enjoyable transition on either end of the trip.
  • Another option can be an early sleep-aboard where you may arrive late the day before your charter starts and arrange to stay aboard your charter boat for a nominal charge, less than the cost of a day’s charter. This allows you and your crew to get unpacked and settled onto the boat.
  • Fireballs at Trellis Bay

    Fireball Full Moon Party at the Cyber
    Café, Trellis Bay/Tortola

  • Maybe you've heard about some of the special events in the Virgin Islands. The monthly Full Moon Fireball Ceremony at Trellis Bay or Full Moon Night at the Bomba Shack may be on your list and may set your charter schedule. Or, you may want to experience Virgin Islands Carnival in St. Thomas or Spanishtown on Virgin Gorda. If your plans call for a late May charter, the BVI Music Festival in Cane Garden Bay is not to be missed. Or, knowing about some of the several sailboat racing events in the BVI may shift your dates. Knowing the dates of these events can add something special to your charter vacation. Check out the BVI Events or USVI Events on our site or visit local tourism bureaus web sites.
  • And don’t miss checking out the Itineraries we have developed for more ideas.

2. Select Your Crew

  • The crew could be simple with just two people or a small family. Or you could share the cost and experience with up to three additional couples in a four-cabin boat. If you have friends and family who love to cruise, you could even organize a small flotilla.
  • It is important to determine who will be the captain. This is typically the person who is signing the charter contract as they have responsibility for any damage to the boat. Discuss the possibility of damage to the boat and whether costs will be shared or if the person who caused the damage will pay. This could be as simple as the head backing up ($75-$100), losing a dinghy or at its worst grounding the boat. The Virgin Islands is relatively safe and there are rare chances of theft. But it's best to determine how your group will handle the unexpected—just in case.
  • It’s a good idea to select crew with like interests. Some see the Virgin Islands as a chance to let it all hang out and drink and dance until the wee hours. Some crews enjoy quiet anchorages. Some like to cook onboard and some like to dine out every night. Talking about crew and individual interests ahead of time can make sure all are on the same plan for your trip. Discuss provisioning—that will often reveal the interests of others on the trip. Also discuss sailing style. Some want lazy cruising with a drink in hand and others want to spend the days outside of the islands where the winds are strongest and with the rail buried in the water on a thrilling reach.
  • It’s not hard to get a group of friends or family to initially agree to join a Virgin Islands charter. When you have your dates set and need to pay a deposit, consider having the others pay their share of the deposit at that time as well. Paying for part of the charter has a tendency to lock in everyone’s commitment. Crew dropping out due to scheduling problems before a trip can create a lot of tension. One idea is to have a short list of potential backup guests who are interested in joining you in case someone is unable to go.

3. Select Your Charter Company and Boat

    Boat interior
  • You may have a particular boat already in mind. See Selecting Your Boat for more information. The size and interests of your crew will dictate sail or power, monohull or catamaran, two cabins, three or four. The charter companies’ web sites all have boat layouts. Charter costs will be dictated by the amenities a company offers, the season, the size and style of the boat and the age of the boats. In the Virgin Islands there is quite a selection of boats available. Perusing the different boats on the web can be a lot of fun.

4. Make Your Travel Arrangements

  • Depending on where you live, there are typically many options for air travel to the Virgin Islands. Keep an open and creative mind and read the air schedules posted online carefully. A great price may require an overnight stay in one city along the way. If your charter is leaving from Tortola you may want to fly into the small Beef Island airport at the east end of the island. You may see a fare that is $100 cheaper to fly into St. Thomas, where you could easily take a ferry to Road Town, Tortola. But the $100 savings may be consumed by the ferry fare and the extra time involved. If your schedule is flexible, check fares several different days before or after your trip. This may adjust your charter dates or a hotel stay. Airlines often charge more on the weekends. Arriving and departing with your charter boat can also be easier by avoiding the weekends at a charter base.
  • One option for low-cost travel is to use airline points. The Virgin Islands is one of the most popular destination for airline points but there are a few strategies that might work if the free flights appear full. Check on flying into St. Thomas (STT) instead of Beef Island, Tortola (EIS). It is considered a domestic destination from the U.S. and will require less reward points and offer more flight options. You may find a free flight as far as San Juan and then pay around $200 round trip for a commuter flight from San Juan to Beef Island. While not free, this can be a huge savings.
The Indians

One of the best spots for snorkeling! The Indians/Norman Island

2-3 Months to Go

About now you can almost feel the Virgin Islands sunshine.

Organize your crew and confirm.

  • The final payment will be due 60 or 90 days prior to your charter date and you should collect payments from all.
  • Consider what you want to bring. Remind your crew to make sure they have shopped for bathing suits. You and your crew may want to make sure they have a good mask for snorkeling. Most of the charter companies will provide masks and fins. The masks provided by the charter company may be of various quality. A good fit for a diving mask makes a big difference when enjoying some of the best snorkeling in the world. Consider a long sleeve shirt to protect your back and arms when snorkeling under the Virgin Islands sun. Wave runners or water shoes are also advised.
  • This is a good time to check that everyone on the crew has a valid passport. Have the crew each send you their passport number so you can be assured they have checked their passport. Your charter company may also require passport numbers.

NOTE: Passports within six months of expiration should be renewed as they may not be accepted.

1-2 Weeks to Go

Get organized to go.

  • The stores in the British Virgin Islands have limited stock. It is best to purchase all items you might need ahead of time like suntan lotion or memory cards for cameras. Pack a hand carry bag with all your essentials for the trip including your toiletries, swimsuit and a day or two of clothes—just in case your checked bag is delayed.
  • It is a good time to have everyone check their airline reservations one more time.
  • Find out if anyone will be bringing any prescription drugs. Everyone should make sure they have enough for the duration of the trip. It is good to know if there are any medical issues. A captain is responsible for his or her crew.

Organize your provisioning list

Determine whether you want to pre-order things like the heavy items such as water and beer in advance for delivery to the boat or if you want to order the first several days of provisions through either the charter company or directly through one of the local markets in Tortola. It is easy to do grocery shopping in Tortola the morning of departure.

Bobby's Market

Bobby's Market, Cane Garden Bay/Tortola

This is also a good time to start packing. Remember, most people over pack. T-shirts and swim suits or shorts are the most used items. For evenings out, one nice shirt for men and a nice dress for women and you are set. Consider putting all your essentials in your carry on bag. Don’t forget a long sleeve t-shirt and possibly skins to cover legs if you are prone to sunburning. Sunglasses and a hat are also advised.

If you plan to use your cell phone, check on the roaming rates in the British Virgin Islands for your cellular carrier. Local roaming rates can be as high as $3-$4 per minute to the U.S. while cruising in the BVI. If you have an iPhone or Smartphone also check the data rate. Don’t ruin your trip weeks afterwards with a thousand dollar cellular bill. There are a number of places that offer Wi-Fi service where you can check email or check-in at home using popular VoiP services like Skype. If you don’t have a Skype account, this would be a good time to sign up and learn how to use it.

Daily Check List

You made it to the Virgin Islands! Your boat is provisioned, water is full, all systems are operating and it is time to leave the charter company’s dock. First item on the list should be to relax and enjoy. To keep things enjoyable, create a short daily checklist of the basics. Think ahead in a two-day window of time and plan your itinerary and day stops accordingly. Try these items as a daily check list and add your own as needed.

Harbor with cruise ship

Try to make sure to go through your checklist before you head out of any harbor.

  • Check your fresh water levels. How long does it take to go through the first tank? Determine when you will need to fill your tanks and where you should go.
  • If you chartered a power boat, how is your fuel situation? Determine locations of next available fuel docks.
  • Check drinking water, ice, beer, soda, and provisions. There are stores throughout the Virgin Islands, but not everywhere.
  • Clothes need washing? Coin laundries are available but not everywhere. Our Cruising the Virgin Islands guide book has checkmarks showing where many are located.
  • Most restaurants, bars and grocery stores take credit cards. ATMs are located in most of the main towns.If you are going to Anegada, cash is preferred (there are no ATMs).
  • Where are you heading tomorrow? Will your supplies and other needs work for that location?

Relax and enjoy!

We have bareboated previously out of Tortola and found provisioning in the marinas quite wide ranging. Now, my wife has specific eating requirements and we'd like to know whether to bring these items or if they can be acquired once arrived in Port Purcell (BVI charters): almond milk and organic fruits and veggies. We arrive 6/12/11. Thank you

The Riteway market, just across the road from BVI Charters, is now a superstore the size of a warehouse. They stock just about anything you could want including many gourmet items. The store is impressive, even by our US standards.

I would call them at 284-340-6112 (store managers office). I suspect they will have everything you need, depending on how specialized the food requests are.

Have a great trip!

Hey Mark, Were headed to the BVI in the spring. Wheres a good place to start. Ryan

What is the make up of your crew?
Kids? Adults?
How many?
How many days are you thinking of being on the water?
Do you need to time your trip with your children's spring break?
Do you prefer power or sail?


Mark- My crew will be my family, my wife and boys, 11 and 16.It would be about a week and yes its spring break.We would be coming from the NYC area late April to early May. We don't have an unlimited budget but want a memorable vacation for the kids and relaxation for us. We have sailed before and would love to try a catamaran if we can afford it. What do you think? Ryan

It can be a bit like a puzzle to get the different pieces in all the right places. If you have a little flexibility you can save some money too!

Your dates are a very popular time. The weather is excellent, a good break from any lingering cold spring weather in the Northeast. I like to start by first planning my airline connections. By going on today, I see there are plenty of flights from the NYC area to St. Thomas and Tortola.

Note - the cheapest fares include a layover in San Juan, Puerto Rico for flights to EIS (Beef Island, Tortola). Besides the overnight, this will require an overnight stay in a hotel in San Juan adding costs to your trip. The flight time should be 5+ to 8+ hours. Anything more than this for an afternoon flight or evening flight requires a layover. The best flights to EIS seem to be about $620 each.  You will have about a $30 cab fare from the EIS airport to your charter company or they may have a lower price for their shuttle.

But if you fly non-stop from JFK to STT (St. Thomas), a 4 hour and 20 minute flight, the airfare drops to $427. Add $55 for the Ferry to Tortola each and about $10 each for the cab from the airport to the ferry in Charlotte Amalie, St. Thomas and then in Tortola to your charter base. By the way, playing with the dates to fly one of the legs on a non-weekend flight can drop the airfare to under $400. I sometimes do my shopping on and then go to the airline website and I am able to find a cheaper fare. Once I have an airfare, on the airline web site, I put a HOLD on the reservation. This gives me 24-48 hours to work out my charter reservations.

Next, I start looking on the web at the different charter companies to see rates and what boats they have.
Looking at the Footloose Charters (Same parent company as The Moorings and Sunsail) Price Sheet for a catamaran shows their smallest at $1045 per day. This may be too costly for you. The catamaran has 4 sleeping cabins and is more room than you need for your family. At the other end of the spectrum a 32 foot monohull sailboat with two sleeping cabins will cost you $385 per day, plus insurance and national park fees.

Conch Charters calls this their shoulder season, meaning the rates are a little cheaper and has a 38' catamaran for $642/day if you really want to rent a cat. The key to keeping costs low on a cat is to consider sharing the charter with friends or family to fill the other cabins. If you can share the costs, a Virgin Islands vacation can be very economical when compared to comparable tropical hotel vacations.

Conch Charters also has a 2 cabin monohull sailboat for $271/day that could fit your needs.

There are many other good charter companies in the Virgin Islands with a variety of boats.You could consider the convenience of leaving on your charter directly from St Thomas with CYOA Charters. You can be from the airport to your charter boat in about :20, and plan a visit to the US VI (St. John) on your way to the BVI. CYOA's rates for their 2 cabin monohull sailboat are about $400-$460 per day. The range in charter rates is variable based upon the age of the boat and other amenities a charter company may offer. It is not an easy apples versus apples comparison.

Also, call the charter company you tend to prefer. There may be other discounts they can apply, or costs they need to make you aware of. Sometimes there are last minute, or off-season deals, though the dates that work for you are close to prime time.

After you know the dates you will be in the Virgin Islands you can start to look at the schedule of events for different places. We list many on the site (top right, in blue bar). You will miss the April 18th Full Moon Fireball Celebration at Trellis Bay, but you may want to see what activities they have going at the Bitter End Yacht Club. Around Easter they have their Family Fun Weeks. While on their web site note that they also have a great sailing program for your boys.

There are many other events you can schedule. Keep your plans loose with just one or two planned activities. For a weeks cruise plan on cruising to just a few islands and you will have a great time. Leave plenty of time for snorkeling and make sure you have sun protection for your boys. Snorkeling in the VI sun can lead to major sunburns on the back and legs. Consider shirts and light pants, or skins (available at your favorite sporting goods stores) to protect the skin when snorkeling.

Have a great time and enjoy planning your VI charter trip, and your time on the water in the islands with your family!


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