• Wave icon Trip Type: Offshore
  • 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
High

Adventure Rating:
High

Low to some

Experience Required:
Low to some

12 Days from £2,399

Dates, Prices & Travel

Sailing vacation: Trade WInd Trail

Embark on an epic journey along the Trade Wind Trail, following in the wake of early explorers, pirates, and traders who navigated these routes centuries ago. This is no ordinary sailing holiday. It’s a true adventure into some of the most remote and unspoiled corners of the Caribbean. The winds that once carried Spanish galleons and buccaneers will power you through crystal-clear waters, past untouched islands, and into a world far removed from bustling tourist hubs.

Starting in the Dominican Republic, a land rich in history and rugged beauty, we set sail for the Bahamas, navigating through the vast blue of the Caribbean. Along the way, discover secluded anchorages, hidden blue holes, and dramatic coastlines. Each stop offers a chance to discover the authentic Caribbean, much as those who first explored these waters did: raw, untamed, and utterly captivating.

This trip is for those with a taste for true adventure, seeking more than just the comforts of a marina. It’s for sailors who want to experience the thrill of navigating by the trade winds, discovering hidden gems along routes that shaped the history of the Caribbean. Whether you’re exploring pirate hideouts, anchoring off deserted beaches, or marveling at the untouched beauty around you, every day feels like stepping into the pages of a maritime history book.

Ready to follow the trade winds and explore the unknown?

Rubicon 3 expeditions are genuine sailing adventures. Our expert instructors will guide you through every aspect of the journey, from navigating and helming to cooking and maintaining the yacht. Flexible itineraries shaped by weather and local conditions ensure that every trip is unique and deeply rooted in the spirit of exploration. All you need is an open mind, a love of adventure, and a willingness to dive into the unknown.

Want to join?

Check the Dates & Prices section for trip details, including connecting travel, where to join, and the best flights for this extraordinary journey.

Sailing Area

Sailing route map dominican republic to bahamas
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 possible highlights on this route (we won’ take them all, but let’s see which of them the weather allows – we’ll do as many as possible!)

Puerto Plata, Dominican Republic

The adventure begins in Puerto Plata, where crew members join the boat and prepare for the journey ahead. This city, known for its colonial charm and rum heritage, is the perfect starting point. After provisioning and safety briefings, we set off for some training and then sail along the Dominican coast, heading into the open waters of the Windward Passage.

Puerto Plata

Luperón Bay

Luperón Bay is regarded as the most important and naturally beautiful harbor in the entire Caribbean. Nestled between mangroves and lush green hills, this beautiful bay provides exceptional protection and calm waters, making it a favorite among sailors. Nearby, the golden sands of Playa Grande are just a short ride from the marina, offering a perfect spot to relax. For those interested in history, a visit to La Isabela, the first Spanish settlement in the Americas, provides a fascinating glimpse into the region’s past.

Luperon Bay

Great Inagua, Bahamas

Oiur first overnight passage takes us to Matthew Town on Great Inagua, the southernmost island of the Bahamas and our first port of entry. Known for its salt ponds and flamingo sanctuary, Great Inagua is a haven for wildlife enthusiasts. After clearing customs, there should be time to explore the natural beauty of the island or simply relax and soak in the peaceful surroundings.

flamingo cuba

Hogsty Reef

North east is Hogsty Reef, an isolated atoll renowned for its crystal-clear waters, stunning coral reefs, and historic shipwrecks. Weather permitting, we anchor here to snorkel and dive, exploring the reef’s pristine marine ecosystem. The sense of isolation and untouched beauty makes Hogsty Reef a highlight of the journey.

Hogsty reef

Marina at Emerald Bay, Great Exuma

The Marina at Emerald Bay is a destination where luxury meets adventure. Perfectly positioned on Great Exuma, it offers a seamless blend of comfort and natural beauty.

Relax on pristine beaches, snorkel vibrant coral reefs, or simply enjoy the stunning marina setting. With turquoise waters and the charm of the Exumas all around, it’s an ideal stop for anyone looking to soak up the magic of island life.

Bahamas cay

Staniel Cay

The spectacular Staniel Cay has been the set for more than one James Bond movie. The underwater caves of the “Thunderball Grotto,” which gave its name to one of the secret agent films, are an absolute must. You can visit the wonderful swimming pigs in Big Major Cay, which is very close to Staniel Cay. They are the Bahamas’ most representative icon!

Shroud Cay: Possibly the most beautiful island in the world 

It’s difficult to describe how beautiful Shroud Cay is, but it is the stuff of legend, and we are effectively visiting on our private yacht! There are tropical mangroves, virgin white sand beaches, and crystal clear blue waters. You can explore Driftwood Beach, where you can walk to the island’s highest point and share one of the best sunsets in the Caribbean. The mangroves are lovely to explore, or you can swim among sea turtles, lobsters, and tropical fish in Coral de Fuego or Wax Cut Drift Dive.

 

escobar plane bahamas

Norman Cay

Norman Cay is a captivating destination in the northern Exumas, steeped in history and surrounded by natural beauty. Once a hub for the infamous drug trade, it’s now a haven for adventurers and nature lovers alike.

Anchor in its calm waters and explore the sunken remains of a drug smuggling plane, now a vibrant reef teeming with marine life. Stroll along its secluded beaches, kayak through mangroves, or simply soak in the island’s tranquil atmosphere.

With its unique blend of history and pristine surroundings, Norman Cay offers an unforgettable slice of the Exumas’ charm.

warderick cay

Clifton Bay, New Providence Island

Clifton Bay is a hidden gem on New Providence Island, offering a tranquil retreat with a touch of adventure. Known for its calm, clear waters and lush surroundings, it’s a perfect destination for those looking to explore or relax in paradise.

Just a short sail from Nassau, Clifton Bay provides easy access to the stunning coral reefs of Clifton Heritage National Park, ideal for snorkeling and diving. For history lovers, the bay is steeped in cultural significance, with remnants of Lucayan villages and colonial-era ruins nearby.

Whether you’re diving into its underwater wonders or simply enjoying the serene beauty, Clifton Bay is a must-visit destination for a memorable Bahamian escape.

exumas anchorage

Nassau 

The passage finishes in Nassau. Stroll through the center of Nassau, with its colorful English colonial style, or finish your holiday early on one of its most famous beaches, such as Cable Beach, Jaws Beach, or Love Beach.

Dates, Prices & Travel

Start Date & Location

March 31, 2026
Dominican Republic

End Date & Location

April 11, 2026
Bahamas

Price

£2,399

Deposit

£999

Availability

Available

Trip Information

Start Date: March 31, 2026

Start Time: 09:00

Start Country: Dominican Republic

Start Port: Puerto Plata

Start Marina: Ocean World Marina

End Date: April 11, 2026

End Time: 10:00

End Country: Bahamas

End Port: Nassau

End Marina: Palm Cay Marina (TBC)

Find Flights For This Trip
Fly Into: Gregorio Luperón Airport (IATA code: POP)
Fly Out of: Lynden Pindling Airport (IATA code: NAS)

* Flights are not included in the trip price.

Important Notes
Joining the Boat

You will join the boat in Ocean World Marina, Puerto Plata, Dominican Republic.
The trip starts at 9:00 AM on March 31, 2026, so you will need to be in Puerto Plata by March 30, 2026.

You have two options for accommodation on the night before the start date:

  1. Stay in a hotel or AirBnB.
  2. 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 at Palm Cay Marina (TBC), Nassau, Bahamas.
    The boat is scheduled to arrive in Nassau on the evening of April 10, 2026, and you will need to disembark by 10:00 AM on April 11, 2026.

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.
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