• 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

From the sheltered mangrove bays of the Dominican Republic to the remote atolls of the Bahamas, this legendary voyage blends island exploration with true Caribbean passage making. We’ll sail through waters where humpback whales migrate, and step ashore on desert islands where yours are the only footprints. The route can stop at lagoons filled with thousands of flamingos, where we can snorkel coral walls alive with colour, and explore a legendary blue hole. The voyage is expected to be day sailing and island explorationwith one or two overnight passages under the stars.

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.

The exact route we take from the Dominican Republic to Nassau will depend on the wind angles and weather at the time. Your skipper will work with the crew to choose the best plan and together the crew can pick from a range of stunning stops along the way. We expect that there will be a mix of day sailing and one or two longer passages sailing through the night under the Caribbean stars. This is a list of some of the best loved highlights that we can build a route from.

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

The southernmost island of the Bahamas, Great Inagua lies closer to Cuba and Haiti than it does to Nassau. Dry, flat, and wind-swept, it feels very different from the low cays and shallow banks further north. It is home to one of the largest flamingo colonies in the world with tens of thousands of pink birds feeding and nesting in the island’s vast shallow lakes. Parrots, herons, and pelicans are also common. The beaches here run for miles, often without another footprint, and the surrounding waters are deep and amazingly clear.

flamingo cuba

Hogsty Reef

Hogsty Reef is a Caribbean anomaly being one of only three true atolls in the entire western hemisphere. Rising from 6,000 feet of ocean to break the surface in the middle of nowhere, it forms a perfect ring-shaped reef enclosing a shallow lagoon. Scientists believe atolls form from extinct volcanoes that subside over time, leaving only the reef behind, making Hogsty’s presence in the otherwise non-volcanic Bahamas all the more remarkable. The reef has claimed its share of ships over the years, with two wrecks visible above the water and another resting in just 25 feet. In calm weather, the water is so clear you can see coral heads, sandy patches, and the sharp outlines of the wrecks from the deck. The coral walls here are alive with colour with sponges, fans, and shoals of reef fish.

Hogsty reef

Turks and Caicos Islands

The Turks and Caicos are a string of low-lying islands and cays, ringed by dazzling shallows and deep-blue drop-offs. If the wind takes us here, likely stops are Grand Turk, South Caicos, or Providenciales (“Provo”). Smaller islands like Grand Turk feel quite untouched by time with streets lined with old colonial buildings, donkeys wandering by, and quiet local bars serving the much loved cold Turks Head beer. Offshore, the water here is rich with life: turtles grazing in the seagrass, eagle rays gliding over the reef edge, and wrecks that tell of the islands’ long history at the crossroads of Atlantic trade.

Caribbean beach anchorage

Acklins and Crooked Islands

A thin arc of land curves around these shallow banks, sheltering some of the most untouched waters in the Bahamas. Life here is unhurried with just a scattering of small settlements, fishing skiffs pulled up on the sand, and long stretches of beach with no one else in sight.Tthere are only a handful of places to anchor, like French Wells or the edge of the Bight of Acklins, and reaching them means careful navigation in good light so only possible when the weather is very settled. if we make it here, you’ll have the feeling that you’ve reached the outer edge of the world. It’s remote, beautiful, but entirely on nature’s terms.

caribbean sailing crew

Long Island

Eighty miles from north to south, Long Island is a mix of two coastlines. Cliffs and crashing surf to the east, calm beaches and anchorages to the west.  The island’s interior and shores hold plenty of discoveries. Dean’s Blue Hole, the world’s second deepest, drops to over 200 metres just a few steps from the sand. Its surface is a perfect circle of deep indigo, surrounded by pale shallows and limestone cliffs where locals and visitors leap into the water for the experience of a lifetime. Cape Santa Maria’s beach runs unbroken for miles, while smaller coves hide tidal pools and rock formations. Inland, Hamilton’s Cave hints at the Lucayan people who lived here centuries ago, and at Columbus Point the view over the ocean is spectacular.

blue hole long island bahamas

Exuma Cays

A string of 365 islands and cays stretching over 100 miles, the Exumas are where impossibly blue water meets a slower, friendlier pace of life. Great Exuma and Little Exuma are linked by a bridge, while hundreds of smaller cays scatter to the north, many only reached by boat. The main settlement, George Town, has everything from the lively Chat ‘n’ Chill beach bar on nearby Stocking Island to the Straw Market, where local craftspeople sell handwoven baskets and conch shell carvings. Exploring by boat unlocks the real treasures: Thunderball Grotto’s underwater caves, the famous swimming pigs at Big Major Cay, iguanas on Bitter Guana, and Compass Cay’s nurse sharks. On shore, beaches like Coco Plum and Hooper’s Bay offer long walks and the chance to see sea turtles in the shallows. Inland, small farming communities and historic sites such as the Pompey Memorial tell the story of the islands beyond their beaches.

Swimming Pigs

The Longer Passage
At least once on this trip, we’ll stretch out into a true offshore run, making 200 to 300 miles under sail, through the night and into the next day. It’s a magical experience in the warmth of the Caribbean, from the slow fade of the afternoon light and the sea changing character as the sun drops behind the horizon.  As darkness falls, the deck is lit only by the glow of the compass and the sweep of the instruments. On a clear night, the sky above opens into a blanket of stars, with the Milky Way often amazingly sharp and clear. Every so often, the water itself lights up with phosphorescence streaming away in the wake, breaking into sparks with each splash against the hull. Through the watches, navigation is a quiet rhythm of plotting positions, checking sails, and scanning the horizon. In the early hours, the first glow of dawn builds astern until the sun breaks free of the horizon and you’re left with the satisfaction of having sailed through the night – a magical experience.

Bahamas cay

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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