Set sail on the adventure of a lifetime with Raisin Sail Island Charters aboard the stunning 45' Lagoon Catamaran, Whiskey Business, Captained by Wade and Chef Tippee Ball! Your charter of a lifetime includes a range of water activities, from snorkeling and paddleboarding to the thrill of the subwing, ensuring that every moment is filled with excitement and wonder. And with the onboard company of Bo the dog, your experience is sure to exceed all expectations. Whether you're beachcombing on secluded shores, exploring the historic trails of St. John National Park, or indulging in Chef Tippee’s 5-star meals made with local island ingredients, your custom-tailored vacation will be nothing short of extraordinary. Plus, with additional services like onboard live concerts, massage therapy, and even a floating taco bar, every detail of your trip will be crafted to create unforgettable memories.

If Whiskey Business isn't available for your preferred dates or if you're planning a larger gathering, we’ve got you covered with a selection of over 45 carefully curated yachts. Explore the fleet, available for charter in both the Virgin Islands and the Bahamas, and discover the included and additional activities tailored to enhance your experience. To find exactly what you're looking for, simply click the buttons below to jump to your desired section on this page. Don't hesitate to reach out with any questions—our team is here to assist you every step of the way!

Available Activities On Charter

Snorkeling

Sea turtles, rays, and tropical fish are just the minimum types of sea life you'll come face to face with during a snorkeling experience at one of the most magical places you've ever been. 

Subwing

Hold on because this is “snorkeling on steroids!” On the subwing you'll experience flight underwater and glide like a dolphin, perform acrobatics, or
just relax on the surface!

Hiking

St. John National Park is a quick sail away and is filled with historical sites and ruins dating back hundreds of years. We know all of the best spots to hike and will guide you along the way!

Beach Bar Hoppin’

We know the best spots in the USVI and the BVI to take you to put your feet in the sand and have island staples such as Painkillers and Bushwackers to keep the good times rollin'!

Paddle Boarding & Kayaking

Imagine a feeling of standing on water at the same time while exploring secret beaches! Whether you're a pro or a beginner, there's no wrong way to float & soak up the sun!

Sailing

Feel the Caribbean sea breeze on the bow as Captain Wade takes you on a sailing adventure from island to island! Let the beauty of the Virgin Islands wash your worries away! Jib up, stress down!

Floating Taco Bar

The famous 'Lime Out' is a floating taco bar located in Coral Bay and can absolutely be in your itinerary to dine at. Nothing beats a gourmet taco while lounging on their floats in paradise!

Beach Combing

We also like long walks on the beach! We'll take you to most incredible remote beaches you can ever imagine and supply you with awesome activities to have some fun in the sun!

Much Needed R&R

We can't think of a better way to totally disconnect and unwind than to be on a yacht on a private charter with some of your closest friends and family. It's the ultimate vacation!

Charter Add-Ons

Onboard Live Concert

Inquire with us prior to booking and we will schedule your very own band performance by a local favorite "After Irma" on the aft deck of Whiskey Business while you sip cocktails on enjoy our floats in the water! It is an absolute blast!

Massage Services

Inquire with us prior to your charter date and we will schedule our preferred and trusted masseuse to provide you and your party with a tranquil experience like no other.

Wedding In Paradise!

How much more dreamy can a wedding be onboard our yacht in the most beautiful Caribbean bay?! We'll show you! We can make your big day the most memorable with our wedding & engagement services. Inquire prior to booking for more info.

Virgin Islands Charter Yachts


2 & 3 Cabins

2015 45’ Lagoon “WHISKEY BUSINESS”

3 Cabins | 6 Guests

2016 52’ Lagoon “SHANGRI-LA”

3 Cabins | 6 Guests

2018 45’ Leopard “SISU”

2 Cabins | 4 Guests

2015 44’ Leopard “BLACKFISK”

3 Cabins | 6 Guests

2014 56’ Lagoon “MIRA SOL”

3 Cabins | 6 Guests

2020 50’ Leopard “SOUTHERN CHARM”

3 Cabins | 6 Guests

2020 50’ Lagoon “LA SPERANZA”

3 Cabins | 6 Guests

2018 45’ Lagoon “RAPSCALLION”

3 Cabins | 6 Guests

2016 45’ Lagoon “MAKIN’ MEMORIES”

3 Cabins | 6 Guests

2021 59’ Fountaine Pajot “OHANA”

3 Cabins | 6 Guests

2016 60’ Sunreef “EUPHORIA”

3 Cabins | 6 Guests

2019 51’ Leopard “SOGGY DOGGY”

3 Cabins | 6 Guests

2017 50’ Fountaine Pajot “IARA”

3 Cabins | 6 Guests

1999 (2018 Refit) 50’ Voyage “FEEL THE MAGIC”

3 Cabins | 6 Guests


4 Cabins

2016 62’ Lagoon “HEAVENLY”

4 Cabins | 8 Guests

2013 56’ Lagoon “ALTESSE”

4 Cabins | 8 Guests

2023 53’ Island Spirit “FLOR DE LUNA”

4 Cabins | 8 Guests

2022 57’ Royal Cape “ADVENTURE US”

4 Cabins | 8 Guests

2006 90’ Ferretti “INDULGE II’

4 Cabins | 10 Guests

2025 59’ Fountaine Pajot “CHRISTOS ANESTI”

4 Cabins | 8 Guests

2025 65’ Lagoon “REVERIE”

4 Cabins | 8 Guests

2020 50’ Lagoon “DELANA MAE”

4 Cabins | 8 Guests

2023 67’ Fountaine Pajot “INDULGENCE”

4 Cabins | 8 Guests

2023 48’ Bali “KASIOPEJA”

4 Cabins | 8 Guests

2024 53’ Royal Cape “WONDERWAY”

4 Cabins | 8 Guests

2016 72’ FP “SOME KIND OF WONDERFUL”

4 Cabins | 8 Guests

2016 58’ Leopard “DEEP BLUE”

4 Cabins | 8 Guests

2022 49’ Bali “SERENITY 4.9”

4 Cabins | 8 Guests

2020 74’ Sunreef “OCEAN VIBES”

4 Cabins | 8 Guests

2016 52’ Lagoon “OCELOT”

4 Cabins | 8 Guests

2022 54’ Bali “NAE KAE”

4 Cabins | 8 Guests

2025 55’ Lagoon “EVENSTAR”

4 Cabins | 8 Guests

2025 59’ Fountaine Pajot “PLUS 10”

4 Cabins | 8 Guests

2022 54’ Bali “LOCATION 5.4”

4 Cabins | 8 Guests

2002 62’ Leopard “DAYDREAM”

4 Cabins | 8 Guests


5 Cabins

2013 58’ Leopard “TOUCH THE SKY”

5 Cabins | 10 Guests

2023 Bali 5.4 “PERMABEAR”

5 Cabins | 10 Guests

2013 59’ Fountaine Pajot “PERPETUAL BLUE”

5 Cabins | 10 Guests

2024 53’ Island Spirit “PELICAN BLEU”

5 Cabins | 10 Guests

2023 Bali 5.4 “NO INHERITANCE”

5 Cabins | 10 Guests

2015 58’ Leopard “BAREFOOT COWBOY”

5 Cabins | 10 Guests

2013 75’ Two Oceans “HQ2”

4 Cabins | 10 Guests

2016 52’ Lagoon “ELATION”

5 Cabins | 10 Guests

2023 48’ Bali “MEMENTO AMORI”

5 Cabins | 10 Guests

2020 57’ Royal Cape “GET ALONG”

5 Cabins | 10 Guests

2019 60’ Sunreef “GYRFALCON”

5 Cabins | 10 Guests

 

Bahamas Charter Yachts


2019 62’ Lagoon “DREAM BEAUTY”

5 Cabins | 10 Guests

2022 52’ Xquisite “WILD RUMPUS”

2 Cabins | 4 Guests

2022 44’ Bali “PENNY JO”

3 Cabins | 6 Guests

2009 62’ Sunreef “SERENDIPITY”

4 Cabins | 8 Guests

2022 54’ Bali “LOCATION 5.4”

4 Cabins | 8 Guests

2013 58’ Leopard “TOUCH THE SKY”

5 Cabins | 10 Guests

2016 68’ Sunreef Supreme “MIDORI”

4 Cabins | 8 Guests

Dive Charter Yachts


2013 56’ Lagoon “ALTESSE”

4 Cabins | 8 Guests

2016 58’ Leopard “DEEP BLUE”

4 Cabins | 8 Guests

2018 45’ Leopard “SISU”

2 Cabins | 4 Guests

2002 62’ Leopard “DAYDREAM”

4 Cabins | 8 Guests

Frequently Asked Charter Questions

  • Our main goal is your satisfaction and what is more satisfying than waking up knowing you’re about to embark on a week-long paradise vacation? All of our charters have the option to sleep aboard the night before your charter. Avoid the stress of having to find a hotel and transportation the day you arrive by staying on the boat the night before. The terms and pricing are unique and will be listed on each of the yacht brochures. 

  • During the Holidays, it is recommended to get to the airport 3-4 hours prior. During non-peak times, 2 hours will suffice. Bringing a carry on definitely recommended and due to the fact that you will be on a luxurious yacht in the warm Caribbean, overpacking is not needed.

  • Of course! Our charters are mostly design for older kids and adults to enjoy, but please feel free to inquire if you will be boarding with children under 5 and we can accommodate!

  • Yes, of course! They will be there 24/7 to cater to anything you need if desired. The have their own crew quarters and can adhere to any privacy requests you have. This is beneficial, not only for your overall vacation experience but for your safety as well.

  • Your charter is highly flexible and personalized:

    Crafted to Your Liking: Every day on your charter is designed to reflect your personal preferences, making each experience uniquely yours. We prioritize your interests to ensure every activity resonates with you and your group.

    Customized Itinerary and Cuisine: Through a detailed preference sheet and a discussion before the charter, we gather your inputs to tailor the menu and journey to your tastes, ensuring a bespoke experience.

    Adaptable Plans: Given the capricious nature of the weather and changing whims, our plans remain versatile. We're ready to modify the itinerary or activities to better match your current preferences, ensuring your charter experience remains in perfect harmony with your desires.

  • Our rates are all-inclusive unless otherwise specified on the brochures. This includes the use of all toys and amenities, a crew, taxes, cruising permits, licenses, standard onboard supplies, and food and beverage as specified in the charter agreement and on our menus are all included in our rates.

  • Flights

    Any onshore meals or excursions.

    Tip is in addition to the rate with 15% - 20% being standard.

  • The rates you will see on each brochure are all inclusive for the entire yacht for 7 days. For example, $25,000 is the total for 7 days and 8 guests. This roughly equates to $446 per person per night. Tip is in addition to the rate with 15% - 20% being standard.

  • The majority of our charters go out for 7 nights/8 days to maximize the experience, but if you have timing or pricing restrictions we can offer you a 6 or 5 night charter. In some instances, we may be able to accommodate 4 nights. Feel free to inquire with us and we will do our best!

  • Absolutely! 10 and even 14-night charters are common!

  • • Private Romantic Charters

    Many of our guests choose to celebrate special occasions such as weddings, honeymoons, anniversaries, Valentine’s Day, or even vow renewals! We have extensive experience in arranging wedding charters for both large and small parties. We work closely with the crew and local services such as bands and photographers to ensure that all your wedding celebration plans are taken care of. The crew we recommend are experts in providing a romantic experience for their guests, whether it’s creating a private and luxurious setting for couples to relax and enjoy each other’s company, setting up romantic meal settings, or organizing romantic celebrations.

    • Multiple Yachts aka "Flotilla"

    Chartering multiple yachts is an incredibly enjoyable way to bring together large groups for an exciting island-hopping adventure! When chartering multiple yachts, it’s often possible to raft up together at anchor. If members of the group want to do different activities, such as fishing or scuba diving, while others prefer sunbathing or going ashore, the yachts can always split up and rendezvous later. Meals and social gatherings can be enjoyed together, whether it’s on the yacht, at the beach, or at a local establishment.

    •Single Family Charters

    Our charter yachts provide an ideal setting for an unforgettable family vacation, catering to the needs of families with young kids, teenagers, or young adult children. Our crews are well-equipped and experienced in handling kids that are old enough to swim, ensuring they have a blast while exploring the charter destinations to the fullest. They will even prepare meals tailored to each person’s preferences, accommodating even the pickiest eaters. If you’re a parent, you can unwind and witness your kids having the time of their lives. Cherish the adventures and precious moments together, as there are abundant activities and experiences for everyone to enjoy during this exceptional island-hopping vacation.

    • Onboard Diving Charters

    With a personalized itinerary that caters to your preferred schedule and pace, you have the flexibility to scuba dive at your own leisure and visit the dive sites of your choice. One of the advantages of chartering a yacht is that many of these dive sites are located in remote areas only accessible by smaller vessels, ensuring you can explore pristine coral reefs teeming with vibrant marine life. Even if some members of your group do not dive, they won’t feel left out as most dive sites also offer excellent snorkeling opportunities. Alternatively, they can partake in the numerous onboard activities offered by the yacht or venture ashore while you indulge in your diving adventures.

  • 1. Once your charter dates and cruising area are determined, A working hold is placed, so you can reserve flights and finalize the last details with your group. The hold is valid for two weeks. This timeframe allows you to execute the charter agreement and transfer the charter deposit into escrow.

    2. The Charter Yacht Brokers Association Inclusive Charter Agreement, detailing all charter terms, is electronically drafted, and signed by all parties. Upon signing the agreement, a 25% charter fee deposit is due, to be wire-transferred into the charter escrow account. These funds are managed according to the charter agreement terms.

    3. Six months prior to the charter an additional 25% deposit is due, to be wire-transferred into the charter escrow account.

    4. At 60 days prior to the charter, guest preference sheets are sent to all guests for completion. This information is critical for the crew so we can best serve all guests according to their individual needs or preferences.

    5. 30 days before the charter, the remaining 50% balance is due via bank wire transfer into the charter escrow account. Once funds are received, welcome letters are sent to guests by the crew, and preference sheets are requested back, if not already submitted. Also at this time, the crew will conduct a phone call with the primary guest to discuss the itinerary, menu, and address any pending changes or unaddressed needs or preferences.

    6. In the week leading up to the charter, the crew reconfirms all details with the primary guest and coordinates ground transportation from the airport to the marina.

    7. On the day of the charter, the crew remains in constant contact with the primary guest to facilitate the arrival of all guests and provide a warm welcome aboard!

  • If your itinerary involves stops outside of the U.S. Virgin Islands, you will need a passport. So ,for the British Virgin Islands and the Bahamas. Not for the U.S. Virgin Islands.


  • For charters in the USVI and/or BVI, you will be flying into Cyril E. King (STT) on St. Thomas, USVI. There are two main marinas we sail out of, both on St. Thomas. Yacht Haven Grande (YHG) in Charlotte Amalie and American Yacht Harbor (AYH) in Red Hook. YHG is closer to the airport and more developed, so that is usually the preference, but if you wanted to come in the night before and explore the local scene, Red Hook has more of a night life and restaurants. The crew can help arrange a taxi to meet you at the airport and take you to the yacht and then throughout the trip the boat will take you ashore using their dinghy/tender. If you prefer to fly into the BVI, let us know and we can accommodate depending on the yacht.

    For the Bahamas, you will fly in and out of Nassau.

  • Yes! All of our yachts come equipped with WiFi - some even have Starlink! There may be dead zones depending on your location, but that’s a great excuse to unplug!

  • Please pack lotion-based and reef-friendly, SPF of your choosing, sunscreen. Spray-on sunscreens or Coppertone products are not allowed on board because they can discolor the deck and create slippery conditions. We strictly forbid these products to prevent damage to our vessels. Additionally, please refrain from using sunscreens that contain self-tanners or bronzers, as they can stain fabrics and harm the boat. It's important to note that in the USVI, sunscreens containing harmful chemicals known as the Toxic O’s, which are detrimental to coral reefs, are banned.

  • We recommend traveling light for maximum enjoyment. Opt for a soft-sided duffel bag instead of cumbersome hard luggage, as it's easier to stow and will ensure a more comfortable experience. Below is a sample packing list to assist you:

    -Four to five shirts

    -Four to five shorts or dresses

    -Three or four swimsuits

    -Beach cover-ups - the Caribbean sun can be deceptive. Don’t get burned!

    -Two pairs of shoes: a pair of flip flops and, either a pair of hiking shoes, tennis shoes, or water shoes (whatever you prefer to walk in if you are planning on doing some of the beautiful hikes ashore). Remember you will be spending most of your vacation barefoot :)

    -Phone or camera and charger (we have travel adapters on board if needed)

    -Hat and sunglasses

    -Seasickness remedies, if anyone in your party is prone to this ailment

    -Cash for purchasing souvenirs, cocktails on shore, etc. We will most likely not be passing any ATMs once we are on charter. We recommend obtaining Eastern Caribbean Dollars at the marina ATM if possible. Most locals will accept USD but ECD is easier and will give you better value.

    -Passports

    -Personal cosmetic and toiletry items

    -An easy-going, fun, and adventurous attitude! :)

  • -Snorkel gear - we have fins, masks and snorkels on board. We recommend that you bring your own mask and snorkel if you have them, as this tends to be the best fitting gear.

    -Spray-on, Coppertone, self-tanning or bronzing sunscreens are not allowed on board because they can discolor the deck and create slippery conditions. We strictly forbid these products to keep you safe and to prevent damage to our vessels.

    -Bath & Beach Towels - we provide both for each guest. We will supply a fresh set of towels mid-charter.

    -Soap, shampoo & conditioner are provided in each shower. Some guests prefer to bring their own which is totally up to you. Whatever you decide to pack, be sure to bring along all of the items that are going to make sure you are comfortable.

  • With how calm the bays are it is rare, however if you are sailing and the seas are high, you could. It is recommended that if you are unsure, or if you have a tendency to get motion sickness, you bring a preventative medication like Dramamine or Scopolamine patches. Our crews are experts at avoiding and assisting with this as well!

  • Absolutely! We understand this can be a sensitive issue and we want to accommodate however we can.

    Our Chefs are able to accommodate some dietary restrictions depending on what they are and which islands we are visiting. Typically, they can accommodate all but proper Kosher.

  • For the Virgin Islands, the chartDr season runs from November through July with December through May being absolutely beautiful with January through March being exceptional. In the summer, the yachts transit out of the Caribbean Hurricane Belt from August through October to avoid Hurricanes, so they are not available.

    For the Bahamas, April through August are primetime!

  • The standard is for charters to be ‘FULL BOARD’ meaning all meals on board the yacht, but we also offer:

    HALF-BOARD OPTION: Includes 7 breakfasts, 4 lunches & 3 dinners, happy hour canapes, standard ships bar and snacks.

    LOCAL FARE OPTION: Includes 7 breakfasts, 5 lunches & 6 dinners, happy hour canapes, standard ships bar and snacks. Any onshore meals are additional. We absolutely can abide by your dietary restrictions and desires.

    As dining onshore is additional, keep in mind, your chef will be able to create a menu to suit everyone in your group. Whether you are Kosher, vegan or one of your party is gluten or lactose intolerant, your Chef will cater to your group’s individual needs. Our focus is on fresh local ingredients when possible, and all types of diets are expertly catered for.

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