• Wave icon Trip Type: Coastal
  • Speech bubble icon Instructors: 2
  • People icon Crew Size: Max 9 (10 for ocean)
  • Cake icon Ages: 18-70 ish
  • Pin icon Region: Caribbean & The Americas
Intermediate

Adventure Rating:
Intermediate

None

Experience Required:
None

Up to 11 Days from £2,199

Dates, Prices & Travel

Sailing vacation: Remote Caribbean Islands

This Caribbean sailing adventure is your chance to explore some of the region’s most remote and unspoiled islands – destinations that few other sailors ever reach due to their lack of modern infrastructure. This is Caribbean sailing as it used to be: raw, adventurous, and truly off the beaten track. With rugged coastlines, quiet anchorages, and the kind of untouched beauty that’s becoming increasingly rare, these islands offer a glimpse into the Caribbean of decades past.

Sailing to St. Kitts, Nevis, Statia, Saba, and Barbuda is a journey through spectacular landscapes but also an immersion into a way of life far removed from bustling tourist hubs. Each day brings a new adventure: anchoring off pink sand beaches in Barbuda, exploring the volcanic trails and underwater wonders of Saba, or navigating the historic harbours and reefs of Statia. Without the pressure of marinas or crowds, you’ll experience the freedom of true exploration, finding sheltered bays, dramatic coastlines, and the kind of peace that only comes from sailing into the unknown.

This trip is for sailors who want more than just a normal sailing holiday. It’s for those who crave a real adventure, where the trade winds guide you to places few have experienced, and every day feels like a discovery. Whether you’re a seasoned mariner or a first-timer, this is your chance to rediscover the Caribbean in its purest, most authentic form.

Ready for the trip of a lifetime with Europe’s #1 rated adventure sailors?

Rubicon 3 expeditions are genuine sailing adventures rather than a packaged sailing vacation. You will be off the beaten track, possibly out on the open ocean, depending on the route you choose and sailing to and exploring remote and beautiful places. The expert Rubicon 3 instructors will train you and ensure you are fully involved in all aspects of the experience, including navigating, helming, trimming sails, cooking and looking after the yacht. As a true sailing adventure, it is much less predictable (& much better!) than a packaged experience, with itineraries planned day by day and shaped by local circumstances and weather. To take part in the adventure, the crew must come with a great attitude, an open mind and a desire to be fully involved.

Want to join?

Go to the Dates & Prices button to see the dates this trip runs. It will also give you information on connecting travel, including where to fly and when and where to join the boat.

 

Sailing Area

Antigua area sailing map
Mystery caribbean islands sailing route map
The Yachts

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Key Information
What’s included
  • All food and accommodation on board

  • All fuel & berthing fees

  • Your own bunk and storage area

  • Use of oilskins

  • Use of lifejacket with PLB

  • All sailing tuition

  • RYA Competent Crew (supplementary fee)

What’s Not included
  • Your connecting travel to & from boat

  • Sailing & travel insurance

  • Meals you choose to eat ashore

  • Alcohol

  • Visas (where required)

  • Discretionary crew tip

Interested in dates & availability?

To see when this trip runs, its start and end locations, price to join the crew and availability, click on the ‘Dates, Prices & Travel’ button up top.

Discretionary tipping of the Rubicon 3 crew

We’ve priced this trip 5-10% lower than we otherwise would to allow you the option, at the end of your adventure, to offer a discretionary tip to the Rubicon 3 skipper and mate if you feel they’ve provided exceptional service. A combined tip of 5-10% is suggested but is entirely at your discretion and based on your satisfaction with their performance. See our FAQs here.

Got Questions? We’re Here to Help!

We get it – joining a major sailing adventure is a big decision, and it’s natural to have lots of questions before you book. Wondering who else will be onboard? What the experience will be like? These and many more questions are completely normal. While our homepage and FAQs provide loads of info, we know sometimes it’s best to talk it through. Don’t hesitate to contact us by phone, email, or live chat (at the bottom of the screen). Better yet, we’d suggest you schedule a call. Most crew who join do and find it really useful. We can discuss your options, answer every question, and make sure you’re booking on the perfect trip for you.

Ready for a genuine sailing adventure? No Rubicon 3 route has a set itinerary and these islands in particular are less predictable and less developed. The skipper and mate will look at the wind and weather at the time and make a plan with you. You may discover a fantastic place and want to spend an extra few hours exploring, or the wind is from the wrong direction, so you sail somewhere off the initial plan. Making the adventure up as we go is all part of the magic of these trips. Below are some of the highlights of these lesser visited gems. The trip is perfect for beginners or more experienced sailors. It has sailing every day, time to explore ashore, lots of training, and short distances, so there is no need to rush anywhere.

sailing

Antigua

Along Antigua’s southern coast is the bustling Jolly Harbour where this route starts and ends. As we navigate past Willoughby Bay and Falmouth Harbour, you’ll really appreciate the island’s mountainous landscape. On arrival, we can explore the town or relax on Jolly Beach. For those who wish to, you can often sign up to a scuba excursion to discover the rich underwater world around Jolly Harbour.

Caribbean beach anchorage

Montserrat

Montserrat, sometimes called the Pompeii of the Caribbean, is a captivating island shaped by its dramatic history and natural beauty. Once a thriving hub of Caribbean culture, Montserrat’s fate changed with the eruption of the Soufrière Hills Volcano in 1995, which buried the capital, Plymouth, under layers of ash. Despite this, the island has risen again, offering a unique blend of wild green landscapes, pristine beaches, and the haunting beauty of its volcanic legacy.

We likely anchor in Little Bay, Montserrat’s main harbour and have a rest under the stars. As the sun rises, we can head ashore to explore the island’s highlights. It’s fascinating to visit the Montserrat Volcano Observatory, where you’ll gain insight into the island’s geological history and the 1995 eruption. A guided tour of the Exclusion Zone is a rare chance to witness the buried remains of Plymouth, a modern-day Pompeii.

There’s also the chance of a hike to Rendezvous Bay, Montserrat’s only white sand beach, and a secluded paradise perfect for snorkeling or simply exploring. For a slower pace, we can visit Woodlands Beach or stroll through the island’s Botanical Gardens, and really take in Montserrat’s natural beauty. We can also get a Caribbean-inspired meal at Hilltop Coffee House, where local dishes are served alongside panoramic views and a touch of island history, before heading back to the yacht.

Montserrat

St Kitts

St. Kitts, officially known as Saint Christopher Island, is often referred to as the ‘Mother Colony of the West Indies’ due to its status as one of the earliest British and French settlements in the Caribbean. The island’s rich history dates back to 1624, when it became a vital hub for sugar production. St. Kitts was central to the rise of the colonial plantation economy, and its strategic location made it a battleground for European powers vying for control.

We’ll likely anchor in Basseterre, the island’s capital and cultural heart. After heading ashore and clearing in, we can stroll through Independence Square, where the echoes of colonial life meet the rhythms of a modern day and busy Caribbean town. There’s a real insight into the island’s history with a visit to Brimstone Hill Fortress, a UNESCO World Heritage Site offering spectacular views of the coastline and a reminder of the island’s military significance. Maybe a lunch of local seafood at a local eatery, then we may be able to fit in a snorkel at White House Bay, where shipwrecks and coral reefs create an underwater paradise. There are also black sand beaches of South Friars Bay or we can partake in the lively and fun atmosphere of Frigate Bay.

St Kitts

Nevis

Nevis, the smaller and quieter of the two islands of St Kitts & Nevis, is famous for its lush landscapes and serene beauty. The island’s name comes from the Spanish word “Nuestra Señora de las Nieves” (Our Lady of the Snows), a reference to the white clouds that often crown its central peak, Nevis Peak. Steeped in history, Nevis is the birthplace of Alexander Hamilton, one of the founding fathers of the United States, and was once a hub for wealthy planters and their sugar estates. The island has retained its tranquil charm, making it perfect for those who enjoy a slower pace and authentic Caribbean culture.

We can explore Charlestown, the island’s wonderful capital. You could vitis the historic Bath Hotel and Hot Springs, once the Caribbean’s first luxury resort, and enjoy the town’s colonial architecture and laid-back atmosphere. Treat yourself to a leisurely lunch at Sunshine’s Beach Bar & Grill, famous for its Killer Bee cocktail and beachside views and then relax on the golden sands of Pinney’s Beach, where the turquoise waters and soft breezes make an idyllic experience. For a touch of adventure, you could hike part of Nevis Peak earlier in the day or join a local guide to explore the island’s hidden trails.

Nevis

Statia (St Eustace)

St. Eustatius, affectionately known as Statia, is a small island with a fascinating history and loads of charm. Once a bustling hub of commerce in the 18th century, Statia was called the Golden Rock due to its significant role in Caribbean trade. Its free port status made it a vital node in the transatlantic trade routes, and its deep-water harbour was crowded with ships from around the world. The island’s historical significance is further cemented by its role in the American Revolution, as it was the first foreign entity to salute the United States’ flag.

Today, Statia offers visitors a glimpse into its storied past while providing an  escape from the busier Caribbean islands. The historic town of Oranjestad, with its cobblestone streets and well-preserved ruins is fascinating. The island’s dormant volcano, The Quill, is perfect for adventurous hikers to explore its lush interior and panoramic views.Statia

Saba

Saba, is truly the unspoiled Queen of the Caribbean. A striking volcanic island, it rises dramatically from the sea. Its towering peak, Mount Scenery, is the highest point in the Kingdom of the Netherlands, and the island’s steep, lush terrain is a haven for nature enthusiasts. Unlike many of its Caribbean neighbours, Saba has resisted large-scale tourism, preserving its pristine environment and old-world charm. The island’s friendly inhabitants, quaint villages, and incredible biodiversity make it a hidden gem for sailors and adventurers alike.

Ashore, adventurous hikers can tackle the trails leading up Mount Scenery, where a misty rainforest awaits at the summit, along with sweeping views of the Caribbean. For a more leisurely stroll, you an explore the charming streets of The Bottom or Windwardside, where quaint cottages, local eateries, and shops selling Saban lace and crafts provide a taste of the island’s unique culture. History enthusiasts can visit the Dutch Museum Saba or the Harry L. Johnson Museum, both offering insights into the island’s colonial past and daily life. We must try and eat in one of the local eateries, where we can try fresh seafood with a distinctive Saban twist. The Saba Marine Park offers unparalleled diving and snorkeling opportunities. Renowned sites like Third Encounter and Ladder Labyrinth have dramatic underwater pinnacles and reefs teeming with marine life.

Saba

St Barts

Ok – Saint Barthélemy, or St. Barts, is not a mystery island – in fact, it is renowned as a super glamorous retreat for the elite, but this small French island offers much more than its reputation for luxury. With its pristine beaches, turquoise waters, and charming villages, St. Barts embodies a perfect blend of sophistication and natural beauty. Historically, the island has a rich past, having changed hands between the French and Swedish, which is reflected in its unique culture and architecture. The capital, Gustavia, named after a Swedish king, is a really picturesque harbor town with red-roofed buildings, chic boutiques, and a relaxed feel.

Ashore, history enthusiasts can explore the remnants of Swedish colonial rule at Fort Gustave or visit the Wall House Museum to learn about the island’s past. Wander the cobblestone streets of Gustavia, where high-end shops and charming cafés line the waterfront, offering everything from designer fashion to local artisanal goods. For a quieter experience, visit one of the island’s many stunning beaches. Shell Beach, within walking distance of Gustavia, is perfect for swimming, while Anse de Grande Saline and Anse du Gouverneur offer quieter escapes with crystal-clear waters and powdery sands.

Water lovers will find a paradise in St. Barts’ sheltered bays, perfect for snorkeling, paddleboarding, or diving among vibrant coral reefs. In the evening, you can treat yourself to some world-class dining at a beachfront restaurant or enjoy a quieter meal at a local bistro serving French-Caribbean fusion cuisine.

St Barts

Barbuda

Barbuda, the quieter and less developed sister island of Antigua, is often referred to as the Hidden Treasure of the Caribbean. Known for its unspoiled natural beauty, this island is a haven of tranquility, offering pink and white sandy beaches that stretch for miles, crystal-clear waters, and a rugged, untouched landscape. Historically, Barbuda has been sparsely populated, with much of the land owned communally by its residents. This unique arrangement has preserved the island’s pristine charm, making it a perfect island to explore.

Ashore, a visit to Codrington Lagoon is a must, where we can explore the Frigate Bird Sanctuary, home to one of the world’s largest colonies of these magnificent birds. Nature lovers can enjoy long walks along the island’s deserted beaches, such as Low Bay or Princess Diana Beach, both offering powdery sands and waters perfect for swimming or snorkeling. For history enthusiasts, the ruins of the Martello Tower provide a glimpse into the island’s colonial past and offer panoramic views of the surrounding landscape.

Frigate bird

Dates, Prices & Travel

Start Date & Location

March 18, 2025
Antigua

End Date & Location

March 28, 2025
Antigua

Price

£2,199

Deposit

£999

Availability

Available

Trip Information

Start Date: March 18, 2025

Start Time: 09:00

Start Country: Antigua

Start Port: Jolly Harbour

Start Marina: Marina TBC

End Date: March 28, 2025

End Time: 09:00

End Country: Antigua

End Port: Falmouth Harbour

End Marina: Marina TBC

Find Flights For This Trip
Fly Into: Antigua (IATA code: ANU)
Fly Out of: Antigua (IATA code: ANU)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Jolly Harbour, Antigua
  • The trip starts at 9:00 AM on March 18 2025, so you will need to be in Antigua by March 17 2025.
  • You have two options for accommodation on the night before the start date: Stay in a hotel or AirBnB.
  • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in Jolly Harbour, Antigua
  • The boat is scheduled to arrive into Jolly Harbour on the evening of March 27 2025, and you will need to disembark by 10:00 March 28 2025
General Notes
  • It is not possible to stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.
Add Trip Extras

Sub total:

Start Date & Location

February 17, 2026
Antigua

End Date & Location

February 26, 2026
Antigua

Price

£2,199

Deposit

£999

Availability

Available

Trip Information

Start Date: February 17, 2026

Start Time: 09:00

Start Country: Antigua

Start Port: English Harbour

Start Marina: Marina TBC

End Date: February 26, 2026

End Time: 09:00

End Country: Antigua

End Port: Falmouth Harbour

End Marina: Marina TBC

Find Flights For This Trip
Fly Into: Antigua Airport (IATA Code: ANU)
Fly Out of: Antigua Airport (IATA Code: ANU)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in English Harbour, Antigua
  • The trip starts at 9:00 AM on February 17 2026, so you will need to be in Antigua by February 16 2026.
  • You have two options for accommodation on the night before the start date: Stay in a hotel or AirBnB.
  • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in English Harbour, Antigua
  • The boat is scheduled to arrive into English Harbour on the evening of February 25 2026, and you will need to disembark by 09:00 February 26 2026
General Notes
  • It is not possible to stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.
Add Trip Extras

Sub total:

Start Date & Location

March 17, 2026
Antigua

End Date & Location

March 27, 2026
Antigua

Price

£2,299

Deposit

£999

Availability

Available

Trip Information

Start Date: March 17, 2026

Start Time: 09:00

Start Country: Antigua

Start Port: English Harbour

Start Marina: Marina TBC

End Date: March 27, 2026

End Time: 09:00

End Country: Antigua

End Port: Falmouth Harbour

End Marina: Marina TBC

Find Flights For This Trip
Fly Into: Antigua (IATA Code: ANU)
Fly Out of: Antigua (IATA Code: ANU)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in English Harbour, Antigua
  • The trip starts at 9:00 AM on March 17 2026, so you will need to be in Antigua by March 16 2026.
  • You have two options for accommodation on the night before the start date: Stay in a hotel or AirBnB.
  • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in English Harbour, Antigua
  • The boat is scheduled to arrive into English Harbour on the evening of March 26 2026, and you will need to disembark by 09:00 March 27 2026
General Notes
  • It is not possible to stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.
Add Trip Extras

Sub total:

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