The Best Caribbean Bareboat Charter Destinations

Best Caribbean Bareboat Charter Destinations

While far-off, exotic yacht charters might be intriguing, nothing beats a Caribbean bareboat charter destination right in our own backyard.

Tropical sandy beaches, steady trade winds, lazy beach bars, and convenient travel options characterize a visit to these many islands.

And if you’re limited to a week or 10 days, you’ll get to spend more time on your catamaran with a tropical beverage, and less stuffed into a crowded flight.

From Grenada to Puerto Rico, nearly every country in the leeward and windward islands has a Caribbean sailing vacation option for you.

If you are still early in your chartering journey, these are the top Caribbean bareboat charter destinations you need to explore.

You can visit each many times, and still find new fresh adventure on a return trip.

I’m on my 10th yacht charter (still in my 30s), and I’ve only visited one destination outside of these six (Key West and the Dry Tortugas).

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma) on a bvi catamaran charter
Sunset at North Sound, Virgin Gorda in the BVIs

British Virgin Islands

Yes, the British Virgin Islands is the obvious choice, but you have to put it first on the list. It’s the global yacht charter capital.

Not only is the BVIs the best place for first-timers, but you’ll find yourself returning year after year. There’s something about it that keeps drawing you back.

I’ve spoken with some old salts that have made over 30 trips!

It’s popularity owes itself to the unique geography, with many islands and bays to explore, sheltered from the trade wind driven swells.

The sailing is predictable and navigation is easy with short, line of sight passages.

Beach bars, restaurants, and amenities galore, the majority of BVI’s economy caters to charterers.

My BVI destination page is a good place to start to learn more about the BVIs.

Devil's Bay beach at the Baths in BVI
Boulders at Devil's Bay | the Baths, BVI
Lagoon and beach at Cow Wreck
Lagoon swimming on the north shore of Anegada
white bay east side jost van dyke
Beach bars line White Bay, Jost van Dyke

Highlights of a British Virgin Islands yacht charter

  • Hike through the gigantic granite boulders at the Baths to Devils Bay

  • Anchor in North Sound and enjoy the sights of one of the finest harbors in the Caribbean

  • Sail offshore to the sunken island, Anegada. Sip cold beverages at rustic beach bars on the beautiful north shore

  • Go Beach Bar hopping for painkillers at famous White Bay, Jost van Dyke

  • Jump into the water from the second deck of the floating pirate ship bar, Willy-T

Sandy Cany sandbar in the Exumas
One of the many sandbars in the Exumas, this one at Sandy Cay

Exuma, Bahamas

Yes, I know, it’s not technically the Caribbean, but it’s close enough.

I love the Exumas for the fishing, solitude, easy travel options from the USA, and those dreamy blues…

This is also more of an advanced sailing destination and I would not recommend it until you have 2+ charters under your belt. You’ll need to anchor more frequently and pay close attention to weather, tides, currents, and depths. We first visited the Exumas on my third sailing trip.

The water in the Exumas is absolutely stunning, with some of the most vibrant turquoise blues I’ve ever seen.

If you want to learn more about the Exumas, check out my cruising guide, or check out my Exuma destination page.

Pirate's Lair in the Exuma Bahamas on a Exuma Yacht Charter
Pirate's Lair at Warderick Wells in the Exuma Land and Sea Park
Wahoo caught on the drop in the Exumas sound
Catching wahoo on the drop in the Exumas
Staniel Cay anchorage near Thunderball Grotto
Navigating to the anchorage near Staniel Cay and the Thunderball Grotto

Highlights of an Exuma, Bahamas yacht charter

  • Visit the Exuma Land and Sea Park – our favorite mooring field is the Pirate’s Lair

  • Dinghy the mangrove river at Shroud Cay and hike up to Camp Driftwood

  • Pass through a cut to the Exuma Sound and fish the drop for mahi, tuna, and wahoo

  • Cross the Yellow Bank and stop for lunch at one of the many coral heads you’ll pass along the way

  • Grab a peanut colada at Staniel Cay Yacht Club and snorkel nearby Thunderball Grotto

Sunset at Green Beach Vieques
Sunset at Green Beach in Vieques

Spanish Virgin Islands

Part of Puerto Rico, they lie right next to the US Virgin Islands.

If you want to seek out the old school Caribbean vibe, the Spanish Virgin Islands are for you. They are far less popular and developed than their Virgin Island neighbors to the east.

The SVIs consist primarily of Culebra, Culebrita, and Vieques. There are also a number of smaller cayos to explore as well.

You can find two of the most stunning beaches in all of the Caribbean here: Playa Flamenco and Playa Tortugas.

If you want to learn more about the SVIs, I suggest Stephen Pavlidis’ Guide to Puerto Rico. You can also check out my cruising guide, or SVI destination page.

View of Culebrita, one of the Culebra anchorages
Tortuga Beach and the lighthouse at Culebrita
Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
Epic sunset at a Carlos Rosario
Tank at Flamenco Beach
One of the abandoned tanks at Playa Flamenco

Highlights of a Spanish Virgin Islands yacht charter

  • Hike to the abandoned lighthouse at the top of Culebrita for incredible 360 views

  • Sip $2 Medallas from the vendors at Playa Flamenco

  • Snorkel the beautiful reef from your mooring ball at Carlos Rosario

  • Watch an epic sunset over the Puerto Rico mainland at Green Beach

  • Take a bioluminescence kayak tour at Mosquito Bay

Petit Rameau at Tobago Cays
The idyllic Tobago Cays, a must stop in the Grenadines

St. Vincent & the Grenadines

This is the only destination on my list I haven’t yet visited. We had plans, but were disrupted by Covid.

You’ll enjoy easy sailing, white sandy beaches, abundant marine life, and many vintage Caribbean beach bars to help cool you off.

You can do a roundtrip or a 1-way passage south to Grenada. This option avoids a potential uncomfortable upwind slog back to St. Vincent

Most people don’t spend much time on the main island of St. Vincent – the many unspoiled islands of the Grenadines to the south beckon.

If you want to learn more about the Grenadines, pick up a copy of the Sailor’s Guide to the Windward Islands.

Anchorage at Salt Whistle Bay
The anchorage at Salt Whistle Bay
Petit Tebac
Captain Jack Sparrow's island, Petit Tebac
The lone umbrella at Mopion Island
The lone umbrella at Mopion Island

Highlights of a St. Vincent and the Grenadines yacht charter

  • Visit the stunning Tobago Cays, snorkel the coral reefs, swim with turtles, and arrange for a lobster beach barbeque

  • Anchor at idyllic Salt Whistle Bay and walk along the beautiful palm-lined beach

  • Explore the island where Captain Jack Sparrow was marooned – Petit Tebac

  • Head to Mustique and grab a cocktail at the legendary Basil’s Bar

  • Get your picture taken with the umbrella on the castaway island, Mopion

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We have relationships with the Caribbean yacht charter companies and have personally chartered with many of them.
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Often photographed Trunk Bay at St. John, USVI

US Virgin Islands

During Covid, the US Virgin Islands made a resounding comeback due to travel restrictions elsewhere. Many long-time BVI visitors discovered the USVIs for the first time. Many were pleasantly surpised!

Why is the USVI appealing? Good provisioning options, cheaper prices, and direct flight options are a few reasons.

Consisting of St. Thomas, St. John, and St. Croix, most boaters spend the abundance of their time circumnavigating St. John and visiting the pristine National Park areas.

You can even use it as a jumping off point to explore the Spanish Virgin Islands. Read about how I did this in my recent USVI and SVI bareboat charter trip.

Epic sunset at Magen's Bay, St Thomas, USVI
The lovely bight of Magens Bay
Beautiful fall day at the Maho Bay mooring field on our US Virgin Islands bareboat charter trip
Beautiful day at Maho Bay in the Virgin Islands National Park
Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands
Christmas Cove anchorage and a sunset over St. Thomas

Highlights of a US Virgin Islands yacht charter

  • Lounge on the beach at Maho Bay and take in the spectacular surroundings

  • Be adventurous and conduct an offshore passage to St. Croix to visit the pastel-colored town of Christiansted

  • Stroll the lovely town of Cruz Bay and grab a bite to eat or do some shopping

  • Sail the north shore of St. Thomas to the bight at Magens Bay. Simply enjoy the magical scenery or head ashore for a drink at the beach bar

  • Enjoy the solitude of the Salt Pond Bay anchorage – lime away the afternoon or hike for the views at Ram’s Head

Shirley Heights on a Antigua yacht charter
Historic English Harbour in Antigua

Antigua & Barbuda

After spending a lot of time recently in the Virgin Islands and the Bahamas, our next trip is planned for Antigua & Barbuda in the southern Leeward Islands. Read about my plan here.

Antigua and Barbuda is a single country, located in the southern Leeward Islands near Montserrat and Guadeloupe (potential offshore destinations for a longer yacht charter trip).

This destination has something for every type of crew. Gorgeous beaches (they attest to having 365 of them), offshore fishing, plenty of bars and restaurants, British naval history, reef snorkeling, and some adventure at offshore Barbuda.

Why else do I like this Caribbean bareboat charter destination? It has a great balance of the get-away-from-it-all anchorages that we enjoy, but it also has a great beach bar/nightlife scene.

pink beach in Barbuda
Quiet pink beaches await after an offshore sail to Barbuda
Carlisle Bay on a Antigua yacht charter
With 365 beaches, there's one for every day

Highlights of a Antigua & Barbuda yacht charter

  • Sail offshore to Barbuda, one of the Caribbean’s hidden gems; anchor in solitude anywhere along the Caribbean’s longest pink sand beach (11 miles)

  • Relax amongst the reefs at peaceful Green Island

  • Drag some fishing lines and catch mahi, wahoo, or tuna in the deeper water offshore

  • Hike to Shirley Heights for commanding views and some nightlife at their famous Sunday evening bbq parties

  • Gaze at 200 foot mega yachts in Falmouth Harbour or rub elbows with the rich and famous at the establishments ashore near historic Nelson’s Dockyard

  • Arrange for a tour of frigate bird sanctuary at Codrington Lagoon

Book your next yacht charter with us

We have relationships with the Caribbean yacht charter companies and have personally chartered with many of them.
Let us find you the best option - it doesn't cost you anything extra.

Thanks for reading my post about the best Caribbean bareboat charter destinations! If you enjoyed it, please subscribe or check out some of my other articles, like this one about how the British Virgin Islands’ vibe is changing.

When is the Best Time to Visit the British Virgin Islands?

A typical day representing the best time to visit the British Virgin Islands

If you’re planning a yacht charter to the British Virgin Islands, you should consider the four different sailing seasons:

  1. High season: December to March

  2. Shoulder season one: April to June

  3. Peak hurricane season: July to October

  4. Should season two: November

My recommendation? The best time to visit the British Virgin Islands is during shoulder season one (April to June). We enjoy predictable weather, longer days, steady wind speeds, fewer crowds, and cheaper charter prices.

Below, I summarize each to help you make your decision. If you want to learn more about weather and marine resources for the British Virgin Islands, check out this post.

BVI Climate and Average Weather by Month

Wind Speed (kts)
Wind Direction
Daylight (hrs)
Precipitation (in)
Avg. High Temp.
Avg. Water Temp.

BVI high season (December to March)

This is the busiest and most expensive time of the year. Hurricane season is over, and the annual pilgrimage of cruising boats has made it’s way from mainland U.S. and Europe to enjoy the warm Caribbean winter.

Expect crowded mooring fields and frustrated skippers who lost the Boatyball lottery.

Days are shorter (~11 hours vs ~13 hours in the summer).

Most notably, you can expect the Christmas Winds: several days of strong winds (15-30 knots) created by strong high pressure systems in the Atlantic. Make sure you know how to reef those sails!

Wind is usually out of the E to NE and less precipitation falls this time of year.

Double rainbow over Anegada in the British Virgin Islands
A typical BVI day in Anegada with some cumulus clouds and the occasional shower

BVI shoulder season 1 (April to June)

This is my favorite and I believe the best time to visit the British Virgin Islands for sailing trips. We’ve been to the BVIs 3x in May. The crowds have thinned out somewhat and the weather has become more settled.

Expect easy 10-15 knots from the E to SE and an occasional shower to cool things off.

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BVI peak hurricane season (July to October)

It can be hot, the trade winds lessen (5-15 knots), and tropical mischief can be brewing.

But, you might have the place to yourself. On the flip side, however, some establishments are closed, so keep that in mind if you are planning to hop around the beach bars.

This is the wet season thanks to developing low pressure systems.

Benures Bay Sunset at Norman Island, British Virgin Islands
Don't worry, you can expect epic sunsets year round in the BVIs

BVI shoulder season 2 (November)

This is my second favorite time to sail in the Caribbean and the British Virgin Islands.

Again, the crowds haven’t arrived yet and the weather tends to be settled – similar to April-June.

Trades blow 15-20 knots with wind direction from the E to NE.

The biggest downside of this time of year is the shorter. It can make a difference if you plan to spend long days on the water. Otherwise, not a big deal!

Thanks for reading my post about the best time to visit the British Virgin Islands! If you enjoyed it, please subscribe or check out some of my other articles, such as this one about sailing to Anegada.

5 Ways the British Virgin Islands’ Vibe is Changing

Lounging on the trampoline in the British Virgin Islands
white bay east side jost van dyke
A typical day at White Bay, made busier by the visiting cruise ship

The British Virgin Islands were devasted by the hurricanes of 2017.

They since come roaring back only for the recovery to be held back by Covid.

But hang on, the 2021-2022 season looks to be a record breaker. Restrictions eased and crews leapt at the chance get back on the water.

Popular anchorages have been crowded, more than ever.

Legendary establishments such as the Bitter End Yacht Club are back in business.

The painkillers are flowing in White Bay, Jost van Dyke.

Despite this resurgence, the British Virgin Islands’ vibe is gradually changing. Good or bad? I’ll let you decide. If I sound like a pessimist, don’t be alarmed. I love the BVIs and I’ll be back for years to come.

BVI mooring fields are becoming more crowded

The British Virgin Islands is benefiting from a booming yacht charter industry. Interest in sailing vacations is higher than ever.

As the global bareboat charter capital, the BVIs are feeling those tailwinds strongly.

This is great news for the local economy and the industry as a whole.

But gone are the days of finding your own remote piece of paradise in the BVIs. I know of a couple secret spots, but I have to keep those to myself! I’ll let you in on a few others in this post about secret BVI anchorages.

If you’re in a mooring field, expect to have lots of neighbors, close at hand. So, choose your ball wisely.

Navigating the often crowded mooring field in Setting Point, Anegada

Boatyball is also a more recent development. Some would argue they haven’t added any new mooring balls, rather just replaced existing balls.

Regardless, expect balls to be packed in as tightly as might allow in the future.

Mooring fields that went into disrepair after the hurricanes are now coming back online.

Other beautiful places, such as Benures Bay, that used to be anchoring only…now have mooring balls. This is bad news if you prefer to anchor in (relative) solitude.

Best advice to avoid the crowds? Try and visit in the shoulder seasons (April-May, November). Or better yet, squeeze a trip in during the summer.

The old Saba Rock in the BVIs before the 2017 hurricanes
A view of the old Saba Rock on my first bareboat charter trip over 10 years ago

Resorts and iconic beach bars are catering to the masses or going upscale

I’m too young to have experienced what the undiscovered BVI vibe used to be 30+ years ago.

One symptom of development and progress? Many of the local, old school beach bars are disappearing or being replaced.

After the 2017 hurricanes, when places such as Saba Rock or the Loose Mongoose rebuilt, they went upscale, likely due to the capital that came in to make the rebuilding happen.

Other well known iconic spots such as the Soggy Dollar Bar or Foxy’s now cater to the crowds that often come with visits from cruise ships.

painkillers at the soggy dollar bar in white bay jost van dyke
Tour boats leaving at the end of the day in White Bay
Tipsy's by Ann on the north shore of Anegada, where you can still find that old school BVI vibe

If you’ve been to the Soggy lately, you’ll notice an abundance of USVI day tour boats that crowd the beach.

So can you still find that old school vibe? The good news is, yes! You just need to know where to look. The best spots are going to remain secret, for good reason, but they’re out there.

Anegada, however, is still clearly a winner in this category. The old school vibe, from what I understand, can still be discovered.

Local bars on the beautiful north shore beaches and at the anchorage in Setting Point still dominate, and defend that vibe.

Cape Air Cessnas, one of your options for the puddle jumper flight to BVI
Cape Air Cessnas at SJU, one of your options for a puddle jumper flight

Travelling to the British Virgin Islands feels more difficult

You might think ease of travel would be important for a country who’s GDP is supported by the yacht charter industry.

But that’s just not the case! In recent months, it’s actually trending worse. BVI’s fault? No idea, but I would make it a priority.

Getting to the BVIs has always been about jumping through hoops. And yes, there is still no direct flights from the USA, chiefly because the airport runway is too short. (Update: as of December 2022, American Airlines announced they will begin a direct flight from Miami to Tortola in June, 2023. But don’t expect this to fix the problem, there will only be one flight daily for ~80 passengers.)

You’re committed to a full day travel affair on both ends of your trip.

Recently, the smaller regional airlines have encountered staffing difficulties, leading to many delayed and cancelled “puddle jumper” flights – these are the short trips from nearby San Juan or St. Thomas, USVI.

With only a few of these a day, a cancelled flight can lead to an entire lost day sailing the British Virgin Islands. Ouch! Throw that planned itinerary out the window.

Axopar water taxi

Alternatives to flying into the British Virgin Islands

So is there a better way to arrive? Yes, and here’s your best option.

Many people prefer a direct flight from the USA to St. Thomas. Once you arrive, skip the public ferries who’s schedules are difficult to keep up with and are often late.

Book a direct water taxi from the likes of Island Time or Chillout Charters. They will pick you up in Red Hook, handle clearing you into BVI Customs while you stay on the boat, and then deliver you directly to your marina.

It will all take 1-1.5 hours.

Sit back, relax, and enjoy a cold beverage along the way.

A couple words of caution:

  • You’ll pay up for this option $$$$

  • Some are limited to 6 passengers, so if you have a larger crew, you may need to book two

Eustatia Sound Anchorage
One of the recent catamarans I took out in the BVIs, a Lagoon 450

Larger catamarans are taking over the British Virgin Islands

OK, not literally, but the trend is your friend.

It seems to be two-fold:

  1. Catamarans in favor of monohulls

  2. Bigger is better

I get it, and I tend to fall into the group that prefers a bareboat charter aboard this type of sailing yacht. I explain my feelings in this catamaran vs monohull post.

The market is simply responding to what crews prefer these days.

Bareboat charter in the BVIs on a monohull
The first boat I skippered in the BVIs: a 33 foot monohull

I captained my first sailboat on a 33 foot monohull, and my latest: a 54 foot catamaran. Every yacht charter since the first has been on a 45 foot cat or larger.

We find the bigger cats more appealing for a number of reasons:

  • Extra lounge space: flybridge, trampolines, etc.

  • Large crews that can spread out

  • Better stability, and galley above the waterline

  • Most will come with the features to keep the crew at ease: AC and water makers

So if you’re with me, this is a great development.

Here’s why you might not like it: things that go bump in the night. Mooring fields are getting increasingly crowded and catamarans, by nature, have a much wider beam.

In most trade wind prevailing conditions, this is not an issue. But if the breeze falls or there is a back winding scenario, it’s possible for yachts to get rather close for comfort.

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BVI and the USVI, a view of the Narrows
A view of the Narrows, with BVI on the left, and USVI on the right (St. John)

BVI-flagged charter vessels only

This might be a lesser point, but it’s worth taking into account.

It’s not impossible, but recent BVI regulations have made it extremely difficult for charter yachts to clear into the country.

They’ve created enough paperwork and bureaucracy to make it not worth the effort (Update: Waypoints has since cleared the majority of their USVI fleet to visit the BVIs)

Why would this be an issue? Some crews used to charter out of the USVI (or elsewhere) and cruise throughout the Virgin Islands (Spanish, US, BVI), clearing in and out of customs along the way.

So if that was your plan, just make sure you have the latest information.

Why did the BVI government do this? I think they lost a lot of revenue during Covid when the USVI enjoyed a resurgence of yacht charter tourism. The BVI charter vessels mostly remained dockside. It was simply a move to protect their vital industry.

Thanks for reading my post about 5 ways the British Virgin Islands’ vibe is changing! If you enjoyed it, please subscribe or check out some of my other articles, like this one about the perfect week-long BVI sailing itinerary.

Sailing in Hawaii: Is a Bareboat Charter Possible?

Sailing in Hawaii on a bareboat charter

You might, as I have, dreamed of a bareboat charter yacht trip to go sailing in Hawaii (and no, I don’t mean a sunset sail on a crowded catamaran at Waikiki Beach).

Perfect year-round weather. Tropical, white-sandy beaches. Stunning, mountainous terrain. Numerous flights to the US mainland. Abundant provisioning options.

Sounds like ideal conditions for a perfect sailing trip.

But not so fast.

There’s good reason why the Hawaii bareboat charter industry doesn’t exist: exposed anchorages, few marinas, and treacherous conditions in the channels are some of the contributing factors.

I’ll explain more and explain how you might still be able to pull off this dream trip.

Here’s what I’ll cover:

Stunning Napali Coast
The stunning Napali Coast in Kauai

Where to go sailing in Hawaii?

I think a good strategy for a week-long trip would be to pick an island: Kauai, Oahu, Maui/Molokai/Lanai, or even the Big Island. You don’t want to spend a good portion of your trip on rough passages in between the islands (see my section on cruising conditions).

Rely on your charter company or yacht crew for itinerary advice.

So where would I go?

I’m going to circumnavigate Kauai and sail down the magnificent and Napali Coast of Kauai.

I first got to experience this 10 years ago when I kayaked the length of it down to Polihale Beach. What an experience!

It is simply the most stunning place I have ever visited.

I also want to park myself in Hanalei Bay and watch the afternoon waterfall show. This is also one of the most beautiful settings I have experienced.

With help from the Mehaffy’s Cruising Guide to the Hawaiian Islands, I was able to sketch out a plan with anchorages they have tested themselves.

Sailboats at anchor in Hanalei Bay
Sailboats at anchor in beautiful Hanalei Bay

Week-long Kauai sailing itinerary:

Day 1: Cross Kauai Channel, anchor at Hanalei Bay

I’m going to assume that we start in Oahu, but your charter yacht might be able to pick you up in Kauai.

I, however, think a spirited channel crossing in moderate conditions would be fun (it’s downwind from Oahu to Kauai). Good chance to go fishing as well.

Day 2: Hanalei Bay

Full day to explore and relax in beautiful Hanalei Bay.

possible anchoring locations at Tunnels Beach in Kauai
Possible anchorages inside and outside Makua Reef
The Bali Hai cliffs at Tunnels Beach
The spectacular Bali Hai cliffs at Tunnels Beach

Day 3: Ha’ena and Tunnels Beach

Tunnels Beach might be the most stunning beach I’ve visited with it’s setting just below the famous Bali Hai cliffs.

There is even an anchorage inside the magnificent Makua Reef. I can’t think of a better place to enjoy a sunset.

Honopu Beach at the Napali Coast
Famous Honopu Beach
Nualolo from above
Nu'alolo and the reef from above

Day 4: Off to explore Napali Coast

Slowly soak up the incredible Napali Coast scenery and stop at Nu’alolo. Along the way visit the famous Honopu Arch. You may remember it from Pirates of the Caribbean: On Stranger Tides.

This is one of the most popular attractions for day tours along the Napali Coast, but it’s possible to find some space in the evening.

Snorkeling and admiring the scenery are top attractions here.

The cliffs at Polihale Beach

Day 5: Polihale Beach

Polihale is one of the longest beach stretches in Hawaii, at ~2.5 miles. This is also where the Rugged mountains of the Napali Coast turn inland.

It’s known for the mysterious barking sands and goats you will surely hear on the cliffs above your anchorage.

Ni'ihau Island in Hawaii
Ni'ihau - the forbidden island, as seen from Kauai

Day 6: Go visit the forbidden island, Ni’ihau

Ni’ihau is actually a private island, and it’s off-limits to visitors.

But, you can still admire it’s beauty from it’s shores. How many other tourists do you think get to come here?

The fishing is supposed to be excellent here, as is the snorkeling.

Day 7: Cross back to Oahu or disembark

If conditions in the Kauai Channel are treacherous, you may want to consider disembarking and flying back to Oahu.

Remember, you will be beating upwind going back the other direction. Your charter captain may have more flexibility on timing the passage in more comfortable conditions.

Nawiliwili small boat harbor would make a convenient place to catch a taxi to the nearby airport.

Let’s read on to find out how to plan a Hawaii sailing trip.

sailboat off the Maui coast
Sailboat anchored on a roadstead off the Maui coast

What is it like to go sailing in Hawaii

The biggest reason it’s hard to pull off a Hawaii bareboat charter trip?

These islands just aren’t like the Virgin Islands with it’s numerous islands and many sheltered bays.

The cruising conditions are challenging, presenting unique risks to sailboat skippers.

Let’s dive into the details.

Hawaii cruising conditions

Hawaii anchorages & marinas

Challenge #1.

The islands of Hawaii are much larger and have fewer protected anchorages. Depths tend to drop off sharply from shore. You can sail for miles along the coastline without finding shelter.

They are also stretched out across nearly 400 miles in the middle of the Pacific Ocean.

Where anchorages do exist, many tend to be exposed roadsteads. A change in the weather or a swell can make these dangerous and untenable.

There are few moorings.

Access to marinas is also more limited – there aren’t as many available. Most also simply don’t have much drop-in slip availability.

Pacific trade winds

Challenge #2.

While the trade winds that do blow in the summer can be quite consistent, they vary in strength.

It might be light or blowing up to 30 knots. Usually they fall into a pattern, blowing strongly for a few days before backing off.

Where this can disrupt your plans would be in the channels in between islands, where the wind funnels between the mountainous terrain and strengthens.

If the trades are 15 knots, they might increase to 25 knots in the channels!

This makes treacherous conditions with 8-10 foot wind waves. Not something I want to deal with upwind on a sailing vacation.

Rugged Napali Coast
The rugged coastline of Napali, exposed to northerly swells


Challenge #3.

If you visit between August and October, the large northerly swells can be mitigated.

But swells can occur any time of year, even in the summer.

Be prepared to adjust your plans depending on weather reports – the good news is they are well forecasted.

Take for example the recent historic summer swell that occurred in July 2022. Waves crashed over condos. A wedding was washed out. And surf breaks that have slept for years erupted.


The weather is perfect and beautiful year-round in Hawaii, that is, if you plan to park yourself at a beach resort.

If you plan to put some miles behind you on the water, you’ll need to pay closer attention.

Some suggest there are generally two seasons in Hawaii: summer and winter.

Hawaii’s summer season

This would be my preference for a yacht charter trip in Hawaii (specifically Aug-Oct). It’s also the best time to do some whale watching.

Between May and October, the trade winds blow more consistently (up to 90% of these days).

Leeward sides of the island (where you might spend much of your time) receives little rainfall.

The fabled winter swells that attract surfers from all over the world, have yet to arrive.

Hurricane’s can brush closely to Hawaii’s islands, but landfalls are rare (but you may still experience affects from the associated swells).

Hawaii’s winter season

In November through April, the trade winds don’t blow as consistently, but the temperature might be more pleasant.

Fronts can push in from the north creating heavy rain on the leeward sides.

You also get those large swells that will make northerly exposed areas off-limits at times.

Tides and current

This is generally not a big deal. It’s a small tidal range and you can expect most currents to be less than 1 knot.

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Kaneohe Bay home to a yacht club
Kane'ohe Bay, home of the local yacht club

How you can take a Hawaii yacht charter trip

OK, so how do we pull one of these trips off?

If you’re anything like me and my crew, we prefer to do all of the work ourselves: plan, skipper, cook, clean, etc.

But frankly speaking, I wouldn’t be comfortable sailing in Hawaii with these challenging conditions and unique risks.

I want someone with local knowledge aboard.

So a Hawaii bareboat charter is off the table for me anyway.

I’ve yet to find a company in Hawaii that offers a bareboat charter option. If you know one, please let me know!

The good news is there are a limited number of crewed charters available. The Hawaii charter industry is a tiny fraction of the one in the Caribbean, but, it exists.

I’ve reached out to several companies. Here’s who you might check out:

Hawaii Sailing Adventures: Broker with access to 11 yachts and coverage for all the islands

Honolulu Sailing Company: Charter company with three yachts offering inter-island sailing adventures

Hawaii Catamaran Charters: Broker offering several catamarans

Sail Hawaii: Offers a chance to go aboard as part of an ASA certification

Tradewind Charters: Charter company offering inter-island trips

Final note? Be prepared for sticker shock. Some quotes I’ve seen are much higher than what you’d expect for similar crewed charter trips in the Caribbean.

Thanks for reading my post about sailing in Hawaii and finding out whether bareboat charters are possible! If you enjoyed it, please subscribe or check out some of my other articles, like this one about the top 10 mistakes to avoid on a yacht charter.