How Much Does It Cost to Charter a Sailboat in the Caribbean?

If you’ve looked into chartering a sailboat in the Caribbean, you’ve probably realized quickly that pricing is all over the place. A basic bareboat can cost a few thousand dollars, while ultra-luxury crewed yachts climb well into six figures.

As former Caribbean charter crew, we’ve hosted hundreds of guests, and seen every type of charter from the bareboat adventure to the ultra-luxury all-inclusive experience. What you’re really paying for isn’t just the boat. It’s access to a different version of the Caribbean: secluded anchorages, quiet beaches, local beach bars, and the freedom to wake up somewhere new each morning.

This guide breaks down the real numbers behind Caribbean sailboat charters, what’s actually included, and what a week on the water looks like at every price point. There’s a lot to cover, so stick with us.

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Sailboat Charter Costs in the Caribbean (Quick Overview)

Average Weekly Prices by Charter Type

Keep in mind these are base charter rates, so the actual cost of your trip will include additional expenses that we’ll break down as we go.

Four main categories of sailboat charters in the Caribbean:

• Bareboat charters are simply the yacht itself. You operate the boat yourself.
• Skippered/captain charters add a professional captain to a bareboat charter.
• Crewed charters are the inclusive luxury experience with captain, chef, meals, drinks, and water toys.
• By-the-cabin charters allow couples or individuals to book a cabin on a shared boat instead of chartering the whole crewed yacht.

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Bareboat vs Skippered vs Crewed: What You Actually Pay For

The type of charter you choose is the single biggest factor in your overall cost.

Bareboat Charters (Lowest Cost Option)

A bareboat is exactly what it sounds like. You are renting the boat, just like you would a rental car.

No captain, no chef, no crew. You’re responsible for everything: sailing, navigation, provisioning, cooking, and anchoring/mooring. It’s the most budget-friendly entry point into a sailing vacation, but the true cost goes well beyond the charter rate.

There are fewer monohull bareboats available as catamarans increasingly dominate the charter market, but they remain the lowest-priced option to get you on the water. Catamarans offer double the living space of a similarly sized monohull, a more stable platform at anchor, and a more comfortable experience for guests who aren’t die-hard sailors. That livability comes with a higher price tag.

To rent a bareboat, you must have documented sailing experience. Charter companies will require a sailing resume and may ask for certifications and perform a checkout ride.

What’s Included:

The boat, dinghy, linens and towels, kitchenware, safety gear, and sometimes basic snorkel equipment.

What’s NOT Included:

• Insurance
• Fuel
• Water toys and fishing gear
• Provisions (like extra toilet paper!) and ice
• Moorings and dockage
• National park fees
• WiFi
• Cruising permits and taxes
• Customs and immigration fees if crossing borders
• Additional water if the boat does not have a watermaker
• Many bareboat charter companies charge mandatory end-of-charter fees that can add several hundred dollars (cleaning fees, base fees, checkout fees) that can surprise travelers. These can feel hidden until you’re looking at the final invoice. Read the fine print before you book.

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Skippered Charters (Mid-Range Option)

A skippered charter is a bareboat with a professional captain hired on. It’s generally the most budget-friendly option for non-sailors who still want to keep costs down, but there are other variables to consider.

Sleeping and living arrangements. The captain is coming aboard a bareboat with you, which means you’ll need to plan cabin allocation and meals. Many highly rated captains often require their own cabin and head. The tiny “coffin” crew quarters found on some bareboats are usually not acceptable for experienced professional captains, although this is not always the case.

In the Caribbean, professional captains generally cost around $250-$350 per day depending on experience and reputation.

A good captain is worth every penny. Not every certified captain is equal. Just because someone has the minimum qualifications to legally work onboard does not mean they have the experience, regional knowledge, or professionalism you actually want responsible for your safety.

A great captain will:

• Plan your itinerary based on your expectations and weather, and have backup anchorages ready when the plan changes.
• Know the regional nuances that charts and apps simply don’t capture. The Caribbean trade winds are their own beast. The “Christmas winds” (strong sustained 30+ knot winds that arrive annually between mid-December and March) can turn a comfortable passage into a rough one for the unprepared. Even experienced sailors who know other sailing regions are often surprised by Caribbean conditions. Local knowledge of which bays are protected in different conditions, where to anchor versus where to pick up a mooring, and when to arrive to secure a spot comes from years of on-the-water experience, not something you can Google.
• Keep you safe. A good captain gives a thorough safety briefing, monitors everyone at all times, especially when snorkeling, getting in and out of the dinghy, or when alcohol is involved, and is trained to handle medical emergencies and knows the local emergency services.
• Stay sober. This should go without saying, but it needs to be said. We’ve seen hired captains getting drunk/high with their guests. It puts credentials, and more importantly, lives at risk. Non-negotiable.
• Think ahead. The most requested captains help with dinner reservations, activity planning, local recommendations. It’s not in the job description, but it’s what makes the difference between a good trip and an amazing trip.
• Have mechanical skills. Something always breaks on a boat. Always. It’s not a reflection of poor maintenance. It’s the reality of equipment floating in saltwater. A captain who can troubleshoot onboard systems means minor problems won’t derail your trip.

Even experienced sailors sometimes choose to hire a captain just to shed the responsibility and actually enjoy a hands-off vacation. And just because you hire a captain, doesn’t mean you can’t participate in hands-on sailing when you choose.

What’s Included:

Everything in the bareboat package, plus the captain.

What’s NOT Included:

All the same extras as a bareboat (fuel, provisions, moorings, insurance, park and permit fees, end-of-charter cleaning charges, etc. ), plus the captain’s food allowance and gratuity. Stay with us, these fees are explained more later.

Worth Knowing:

It is also possible to add a chef to a bareboat charter. The going rate is $250–$350/day plus gratuity, similar to a captain. Once you’re adding both a captain and a chef to a bareboat, it often makes more financial and logistical sense to shift your search toward privately owned, fully crewed sailboats rather than piecing together a crew through a large bareboat charter company.

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Fully Crewed Charters (All-Inclusive Experience)

Crewed yacht charters are considered the luxury end of the sailing world, and they are often far more attainable than people assume. By the time you hire a captain, provision the boat for a week, and budget for meals ashore, you may land squarely inside the range of a comfortable crewed yacht that handles all of it for you.

What Makes a Crewed Charter Different?

The biggest difference is that this is the crew’s home.

A crewed yacht usually feels far more personal and welcoming than a standard bareboat rental. You’ll feel the difference between a sterile bareboat and a space someone genuinely lives in and cares for the moment you step aboard. It shows in the personal touches, the well-stocked amenities, and a kitchen that’s actually used properly. Crewed yachts are not only being constantly maintained but also regularly updated.

Gourmet meals, snacks, drinks, cocktails, and happy hour hors d’oeuvres are chef-prepared, using the freshest local ingredients.

You are not worrying about provisioning, dishes, cooking, weather routing, or docking. Simply show up and enjoy the experience.

What’s Included:

• Everything in the bareboat package (your mobile hotel room), Plus…
• Captain and chef
• Gourmet meals
• Snacks and hors d’oeuvres
• Standard bar package (beer, wine, spirits, non-alcoholic drinks)
• Daily cabin cleaning
• Fuel/water
• Water toys and good snorkel equipment
• Sometimes scuba diving, and diving gear (yacht specific)
• Mooring fees and national park fees
• Cruising taxes, permits, and customs/immigration clearance fees (varies by region)

What changes as the price goes up? Top-shelf brand-name alcohol and wine labels, more and higher-end water toys, elevated onboard amenities (hot tubs start appearing in the luxury category), additional crew members, and service details such as the standard cleaning in the comfortable range becomes full turndown service and fresh flowers in the luxury-and-above tier.

What’s NOT Included:

Even all-inclusive charters still have some extra costs.

• Meals or drinks ashore (not required but highly recommend experiencing the local food and culture)
• Premium or excessive alcohol above the standard bar (varies by price tier)
• Crew gratuity (Caribbean industry standard is 15–25% of the charter rate. Budget for it. It’s expected and well-earned)

Worth Knowing:

Unlike bareboat charters where check-in and check-out procedures eat into your time, a crewed charter’s 7-day rate is truly seven full 24-hour days. Other than a quick safety briefing when you arrive, you’re sailing shortly after arrival.

Crewed Charters (APA/Plus Expenses)

APA stands for Advanced Provisioning Allowance. This is where crewed yacht pricing starts getting very confusing.

Most Caribbean crewed sailboats are priced as all-inclusive; however, some (more common in the luxury motor yacht world and European charter markets, like French Caribbean territories) are priced under an APA model.

This means the charter rate covers the boat, crew, and amenities, but NOT provisions (including alcohol), moorings, park fees, or fuel. An APA fund (typically around 30% of the charter rate) is collected upfront, drawn down throughout the trip, and any remaining balance is returned to you at the end.

Sometimes these charters are instead marketed as “plus expenses,” meaning guests simply pay costs as they go. Make sure you know which model you’re booking.

What’s Included:

• Everything in the bareboat package (your mobile hotel room), Plus…
• Captain and chef
• Daily cabin cleaning
• Water toys and good snorkel equipment
• Sometimes scuba diving, and diving gear (yacht specific)

As pricing increases, see upgraded brand-name alcohol and wine selections, a wider range of higher-end water toys, enhanced onboard amenities (such as hot tubs in the luxury category), additional crew members, and upgraded service touches, such as full turndown service and fresh flowers in luxury categories.

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By-the-Cabin Charters (Crewed Charter Shared Option)

By-the-cabin charters are a completely different experience from privately chartering a yacht. Instead of renting the whole boat, you reserve a single cabin and share the yacht with other travelers.

Things to consider on a by-the-cabin charter: You’re not on a cruise ship with 100+ passengers and multiple venues to spread out across. You’re sharing both the yacht and itinerary with others, sleeping 20 feet from strangers, eating every meal together, and spending 24 hours a day in close quarters with people you’ve never met.

That said, it’s a solid option for the right person. If you’re easygoing, flexible, looking to meet new people, and want to get on the water affordably, this can work beautifully. We’ve seen by-the-cabin groups end up as genuine lifelong friends who continue to travel together. We’ve also seen… the other kind of situation.

Our friend once had guests on a by-the-cabin charter who thought the front of the boat was an appropriate place for a very intimate moment while the chef was preparing dinner and other guests were directly below them with open cabin windows.

What’s Included:

• Everything in the bareboat package (your mobile hotel room), Plus…
• Captain and chef
• Gourmet meals
• Snacks and hors d’oeuvres
• Standard bar package (beer, wine, spirits, non-alcoholic drinks)
• Daily cabin cleaning
• Fuel/water
• Water toys and good snorkel equipment
• Sometimes scuba diving, and diving gear (yacht specific)
• Mooring fees and national park fees
• Cruising taxes, permits, and customs/immigration clearance fees (varies by region)

What’s NOT Included:

• Meals or drinks ashore (although not required, highly recommended)
• Premium or excessive alcohol above the standard bar (varies by price tier)
• Crew gratuity (Caribbean industry standard is 15–25% of your charter rate. Budget for it. It’s expected and well-earned)

Best for: Easygoing solo travelers or couples on a tight budget who prioritize the experience over privacy. Go in with eyes wide open and a good sense of humor.

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What Determines the Cost of a Sailboat Charter?

Beyond the type of charter, several other factors move the number up or down. We know, there really are SO many factors!

Destination (Caribbean Focus)

Some Caribbean destinations are significantly more expensive due to taxes, demand, provisioning costs, marina infrastructure, and flight accessibility.

Bahamas

The Bahamas currently carries some of the highest charter taxes in the Caribbean. Many charters do not include the Bahamas’ 14% VAT in the advertised base price, which can create major sticker shock later in the booking process.

Leeward Islands

The northern half of the Eastern Caribbean, including the Virgin Islands, St. Martin/Sint Maarten, Anguilla, St. Barths, Antigua, among others, is the highest-demand, highest-cost sailing region in the Caribbean.

The British Virgin Islands are considered one of the world’s sailing meccas and remains one of the most popular yacht charter destinations globally with protected channels, consistent tradewinds, and world-famous anchorages.

Windward Islands

The southern half of the Eastern Caribbean (St. Lucia, Martinique, the Grenadines, among others) are generally more affordable cruising grounds.

They also offer more “true sailing” with longer passages between islands and more open ocean conditions compared to the relatively protected waters of the Virgin Islands. Less infrastructure, more adventure.

Western Caribbean & Central America

The lowest-cost operators in the region. Still beautiful water, significantly lower overhead, and fewer options.

Why Some Islands Cost More

The cost differences come down to simple supply and demand, ease of access (daily direct flights from major US hubs drive up demand significantly), each territory’s government fee structures, and the cost and availability of provisions.

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Seasonality

The Caribbean charter season has very clear pricing fluctuations.

High Season

November through July with peaks around major holidays and spring break.

Shoulder Season

October/November and July/August bring less demand, more negotiating room, and more availability. Shoulder season can offer excellent value while still having good weather.

April is our favorite time of year in the Caribbean. The strong Christmas winds start to lay down, and it’s this sweet little shoulder season between the spring break crowds and the final summer rush before hurricane season.

Hurricane Season

August through October typically brings the lowest pricing.

This is where you’ll find the real deals, but with significant trade-offs. Many restaurants and businesses close. Northern charter fleets relocate south due to insurance restrictions. The weather risk increases substantially, so travel insurance is a must this time of year.

Holiday Weeks

Holiday pricing is its own premium category.

• Christmas week: expect roughly a 15% rate increase, a minimum 7-night booking, and sometimes fixed dates
• New Year’s week: expect a 25% increase with the same restrictions as Christmas.
• Easter and spring break: rates may not be officially marked up, but boats fill a year in advance.

One firm rule: there are no discounts during holiday weeks. No per-person rates, no short-trip deals. If you’re planning a holiday sailing trip, book 12 months out to get the yacht you want.

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Boat Type & Size

Monohull vs Catamaran

Catamarans offer roughly double the living space of a monohull of equivalent length. They’re more stable at anchor, appeal to a broader audience, and cost more across every category. Monohulls are for sailors looking for the quintessential sailing holiday.

Size Matters

Kind of. Bigger isn’t always better when it comes to charter boats.

A 62-foot yacht may only have 3 guest cabins designed for a high-end luxury experience, while a 50-foot catamaran might fit 5 cabins and spread the cost across more people. Same category, but a different vacation type and price point.

Older vs Newer Boats

This is more nuanced than it sounds, and it’s one of the most common misconceptions in charter shopping. Newer always means higher price, but it doesn’t always mean better.

A 25-year-old crewed yacht with an owner who treats it like their prized possession and upgrades it continuously can be in significantly better condition than a 2-year-old bareboat that’s been rented by dozens of groups.

Age matters more for bareboats (which are treated like rentals) than for fully crewed yachts (which are treated like a home). When shopping for a crewed charter, focus on crew profiles, reviews, and how well the boat is maintained, not the year it was built.

Luxury Amenities

As you move up in price, you start seeing hot tubs; premium wine cellars; larger and more powerful dinghies; expanded water toy collections such as e-foils, kiteboards, and sea scooters; turndown service; designer interiors; award-winning chefs with elevated fine-dining service.

At the ultra-luxury level, the yacht itself becomes part of the experience.

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Trip Length & Timing

7 days (nights): is the industry standard for weekly charter pricing. Almost all listed rates are based on this.

Longer trips (10 days, 2 weeks, etc.): Divide the weekly rate by 7, multiply by the number of nights. Straightforward. Sometimes discounts are given the longer the trip gets.

Shorter charters are where pricing gets tricky. A charter yacht has the same fixed turnaround costs whether it runs 4 days or 10 days (cleaning, provisioning setup, fuel, marina fees). Those costs don’t disappear on a shorter trip.

As a result, short charters often come with a surcharge. A common formula: a 5-day trip is priced by dividing by 6 (instead of 7), then multiplying by 5. Very short trips may add an additional $200–$500 on top. It’s not price gouging; it’s simple math.

One important note on pricing: There is no set price on yacht charter categories. The owner sets the rate on each yacht, and it’s the same rate across all booking platforms. Shopping the same yacht across multiple charter websites won’t yield a cheaper price.

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Group Size

Most charter yachts are priced by the yacht, not by the person, even if some listings break the cost down “per guest” for psychological reasons. In reality, you’re renting the entire boat and splitting the cost among everyone onboard. The only exception is a By-the-Cabin Charter.

That’s why sailing vacations often make the most sense for groups. A fully crewed, all-inclusive catamaran that costs $22,000 for the week comes out to about $3,667 per person with 6 guests onboard. And that price typically includes accommodations, meals, drinks, crew, and water toys which are expenses that would all be separate at a traditional resort.

Catamarans are especially popular for group travel because the layout naturally balances privacy and shared space. Multiple ensuite cabins, separate hulls, and large outdoor living areas make them comfortable for couples traveling together, families, or groups of friends sharing the experience.

What’s Included in the Base Price of a Sailboat Charter (and What’s Not) in a Snapshot

👉Have a peak at our Sailing Trip Essential Packing List to learn more⛵️

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Real Examples: What a 7-Day Charter Actually Costs

Most Economical: Shared by-the-cabin

Catamaran with crew | BVI 🇻🇬 | 2 guests

• Charter rate: $2,400–$3,200
• Crew gratuity at 20%: $480–$640

Estimated total: $2,880–$3,840 | Per person: ~$1,440–$1,920

Best for easygoing individuals or a couple looking to meet others.

Budget Option: Bareboat Adventure

Older monohull | BVI 🇻🇬 | 6 guests

• Charter rate: $3,500–$5,000
• DIY Provisions for the week: $2,000–$3,500
• Fuel: $300–$600
• Moorings and park fees: $400–$700
• End-of-charter fees: $200–$400

Estimated total: $6,400–$10,200 | Per person: ~$1,100–$1,700

Best suited for experienced sailors who want maximum independence and minimum overhead.

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Family or Friends Trip: Skippered Charter

Catamaran with hired captain | BVI🇻🇬 | 6 guests

Estimated total: $12,450–$19,000 | Per person: ~$2,100–$3,200

Great for groups who want to hand off the responsibility and focus on the experience and cook for themselves without the full crewed price tag.

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The Full Experience: Crewed Catamaran

Comfortable crewed catamaran | BVI🇻🇬 | 6 guests

• Charter rate: $20,000–25,000 (all-inclusive pricing; APA charters are priced similarly once provisioning is added)
• Crew gratuity at 20%: $4,000–$5,000

Total: $24,000–$30,000 | Per person: $4,000–$5,000

Perfect for guests who want a true resort on the water with chef-prepared meals, an open bar, water toys, and a crew whose entire job is to make your week extraordinary.

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Is a Sailboat Charter Worth It?

Let’s do an apples-to-apples comparison (7 days / 3 rooms / 6 guests) because this is where travelers finally see the full picture.

A charter yacht looks expensive at first glance, until you compare it to what people already spend piecing together Caribbean vacations through hotels🏨⛺️🛳️, provisions 🛒, restaurants🍕, and island🚕 and boat🚤 excursions.

Glamping (USVI)

The closest land-based comparison to bareboating is a simple, nature-focused trip with eco-cottages, shared amenities, self-catering, and only a few restaurant meals.

⛺️$5,400 + 🛒$2,500 + 🍕$1,000 + 🚤$6,000 = $14,900

No alcohol budgeted in provisions and restaurant totals.

Premium Cruise Line (Eastern Caribbean Itinerary)

This is the closest comparison to a “floating hotel room” vacation. While meals and accommodations are included, the costs start adding up once a group books excursions to actually experience the islands beyond the cruise port.

🛳️$11,400 + 🤿$5,000 = $16,400

Gratuities and meals are included, but alcohol is not included in this base cruise fare.

Villa & Basic Hotel (BVI)

When pricing both a private villa and a budget-friendly hotel, the base accommodation costs ended up the same for either three hotel rooms or a three-bedroom villa.

🏨$10,000 + 🍕$4,830 + 🚤$6,000 = $20,830

Includes pricing for two private boat tours to experience more than just the immediate hotel or villa area. Meals are based on average restaurant pricing with no alcohol included.

5-Star Resort (BVI)

This comparison uses a true five-star resort with breakfast only included. It’s upscale and polished, but not an ultra-luxury over-the-top experience. Basic water toys like snorkel gear, SUPs, and kayaks are included, but extreme water sports and off-property excursions are additional.

🏨$18,000 + 🍕$4,000 + 🚤$6,000 = $28,000

Pricing above includes two private boat tours plus average restaurant costs with no alcohol included.

All-inclusive with Butler Service (St. Lucia):

This is an ultra-luxury all-inclusive resort experience with butler-level service, where food and alcohol are fully included in the stay.

🏨$25,180 + 🚕$900 + 🚤$2,000 = $28,080

Includes one private boat excursion and one island tour since guests are otherwise limited to a stationary resort experience without off-property activities added.

The Experience Difference

Now let’s paint the picture of a day onboard a fully crewed yacht charter. This is an example of a day onboard our catamaran that chartered for $18,300.

You wake up to warm Caribbean light filling your cabin and the smell of fresh coffee drifting from the galley. By the time you step outside, your crew is handing you coffee exactly how you like it because by day two they already know your routine.

Breakfast is served in the shaded cockpit. Fresh fruit, warm pastries, a full savory spread, maybe even mimosas or Bloody Marys. Around you, the islands are just starting to wake up.

After a morning swim, the sails go up and you’re underway between islands. Flying fish skim the surface, birds soar in the sails’ slipstream, turtles appear alongside the boat, and if you’re really lucky, dolphins play in your wake.

By midday you’re anchored in a quiet bay. Paddleboards and snorkel gear are ready, and lunch is already being prepared. Fresh tropical dishes like tuna poke or fish tacos, and cocktails or mocktails, arrive without anyone needing to think about reservations or logistics.

The afternoon is all yours. Snorkeling reefs, hiking a ridge with panoramic views, simply floating in clear blue water, or head ashore to the local beach bar. It’s full of local families enjoying a beach day with freshly caught fish on the grill and a glass of Very Strong Rum (yes, that’s the name of it).

As happy hour approaches, cocktails are poured, hors d’oeuvres come out, and glorious smells come from the galley.

Dinner is a full experience. An elegant tablescape, steamed mussels in white wine and herbs, filet mignon and grilled lobster with grilled asparagus and sweet potato purée, finished with garlic butter. Dessert is molten lava cake. Each course is paired perfectly with wine from various regions.

The day ends anchored in total seclusion, under a sky full of stars.

No 5-star resort, cruise ship, or villa experience quite matches that feeling. After experiencing all of them firsthand, this is exactly why we fell in love with this lifestyle and why the value of the others isn’t even close to chartering a sailboat.

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Vacation Type Comparison at a Glance

By-the-cabin crewed charter not in the comparison because it’s only for two guests.

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How to Save Money on a Sailboat Charter

Go in Shoulder Season

October through mid-November, or July through August, offer lower rates, more availability to negotiate, and arguably better sailing conditions than the peak holiday crush.

Travel as a Group

This is the single biggest saver. Splitting a charter among multiple couples or family members dramatically improves the value per person.

Choose Older Boats

As discussed above, a 25-year-old crewed yacht with a meticulous crew is often in better shape than a 2-year-old bareboat that’s been through 60 charters. Look at the reviews, photos, and how the crew talks about their boat, not the model year.

Pick Budget-Friendly Destinations

USVI generally runs 10% cheaper than BVI. The Grenadines offer lower overall costs than regions that include St. Barths or Anguilla. Budget sailing adventures can be found in the Western Caribbean.

Consider By-the-Cabin Charters

If it’s just you and a partner, and you’re genuinely easygoing about shared spaces, a by-the-cabin charter is the most affordable entry point to the sailing experience. It’s not for everyone, but for the right traveler, it’s perfect.

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FAQs

How much does it cost to charter a sailboat for a week?

In the Caribbean, weekly sailboat charter costs range from around $2,000 for basic bareboat monohulls to well over $150,000 for ultra-luxury crewed catamarans. The sweet spot for most first-time charter guests (a comfortable crewed catamaran in the BVI, split among 6 people) runs $3,500–$5,000 per person all-in.

Is it cheaper to charter a sailboat or stay at a resort?

A by-the-cabin charter will come in cheaper than a resort stay for a week in the Caribbean.

For just two people, a resort is almost always the more cost-effective option when you compare similar levels of comfort and convenience on a private charter boat. Chartering a sailboat has a high fixed weekly cost, so it doesn’t scale down well for couples.

Where chartering starts to become comparable is with groups. Once you divide the cost between several people and add in meals, drinks, and excursions on the resort side, the gap narrows significantly. In many group scenarios, the total spend ends up surprisingly close.

What’s the cheapest way to charter a sailboat?

By-the-cabin charters are the cheapest option overall.

For private charters, older monohull bareboats are typically the most affordable.

How much should you tip a charter crew?

The Caribbean industry standard is 15–25%. Budget for 20% from the start.

Crewed yacht: ~20% of the full charter rate

Skippered/captain bareboat: ~20% of the total captain’s fee (If adding a chef, add 20% of the total chef fee for gratuity as well)

Gratuity should always be factored into your total trip cost, and a great crew earns every bit of it.

What’s included in an all-inclusive sailboat charter?

Captain and chef, all meals (three times a day plus hors d’oeuvres and snacks, chef-prepared), standard bar, fuel, water toys, national park and mooring fees, cruising permits and taxes (varies by region), a private air-conditioned cabin with en-suite bathroom, and daily cleaning service.

What’s never included: airfare and ground transfers, meals ashore, third-party excursions, and crew gratuity.

Do you need sailing experience to charter a sailboat?

Yes for bareboat charters. Documented experience and possibly certifications are required.

No, not at all for skippered or fully crewed charters. The captain and crew handle everything. Many of our charter guests have never set foot on a sailboat before.

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Is a Sailboat Charter for You?

Let’s be real, this is not exactly a budget vacation in the traditional sense. Even at the lower end of the range, a sailboat charter is an investment. But for those who are already considering five-star resorts, all-inclusives, or cruise ships, the value changes dramatically when you compare what you actually get.

A sailing charter shows you the Caribbean that many travelers may never see. What you’re really paying for is access to a different version of the Caribbean. Not cruise ports or resort buffets, but secluded bays, bioluminescent nights, local fish fries, and turtles and spotted eagle rays gliding through impossibly clear water, all with the wind filling the sails.

We’ve shared this type of vacation with hundreds of guests over the years because we genuinely believe this is one of the most incredible ways to experience the Caribbean, and we want anyone who’s curious to know that it’s within reach.

Want to learn more about sailboat charters? Come join us on our Caribbean Travel Help Facebook group where we share all things Caribbean and answer YOUR questions.