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From 1,690€ per person
From 1,690 € /person
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Adventure offered by Stephan

Between 12 and 13 days
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Very popular activity. Places usually sell out 115 days before the start
Discover the breathtaking diversity of the Caribbean islands on our unique sailing trip from St. Maarten to Puerto Rico.

From white sandy beaches and turquoise lagoons to colorful coral reefs, rainforests, and history – every day on this route is a Caribbean experience. During our journey, we enjoy the contrasts between lively sailing areas, colonial charm, small paradises, and the majestic nature of the Northeast Caribbean.

Dive into crystal-clear waters, discover the colorful underwater world, enjoy tropical sunsets and Caribbean joie de vivre: music, cocktails, flamboyant markets, relaxed bars, and the feeling that time stands still here. In the evenings, we raise a glass as the palm trees rustle and the surf gently rolls against our hull.

Our adventure begins on St. Maarten – the famous “Friendly Island” – and takes us on a leisurely cruise through the British Virgin Islands and the Spanish Virgin Islands to San Juan in Puerto Rico. We sail between the most beautiful bays of the Leeward Islands, explore national parks, enjoy snorkeling and shore excursions, and let ourselves drift between beach bars, anchorages, and the Caribbean island rhythm.

Highlights
St. Maarten – Two cultures on one island, a vibrant port of departure with international connections
St. Barthélemy – Caribbean elegance and French chic
Anguilla (optional) – Dreamlike, tranquil beaches and a Caye atmosphere
British Virgin Islands – Virgin Gorda (The Baths), Jost van Dyke (White Bay & Soggy Dollar Bar), Norman Island (Treasure Hunt & Caves)
Culebra & Vieques – Spanish Virgin Islands with secluded bays, Bio Bay and natural paradises
Puerto Rico – destination port San Juan with UNESCO Old Town, Caribbean-Spanish atmosphere and perfect return flight options

Territory
The northeastern Caribbean offers perfect sailing conditions in January.
Our sailing trip takes us from St. Maarten through the Leeward Islands, with short, sheltered distances, through the trade wind zone, and past coral reefs and tropical islands. Winter temperatures range between 25°C and 29°C, and the water remains pleasantly warm year-round (around 26–27°C).

The northeast trade winds, at force 4-5, ensure relaxed and safe sailing experiences. Short rain showers bring a pleasant coolness, and the overall climate is dry and sunny. The warm, cosmopolitan people of the region make life on board and shore excursions particularly enjoyable.
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  • Plan
    Our sailing adventure begins in St. Maarten, where, after boarding and a short safety briefing, we'll explore the island and restock our supplies. The first few nautical miles will take us to the sophisticated bays of St. Barth and on to the relaxed beaches of Anguilla (weather permitting).
    Further west we reach the BVI: Virgin Gorda and the famous "Baths", Norman Island with legendary caves for snorkeling, Jost van Dyke with its famous bars and Caribbean lifestyle.

    We leave the British Isles and sail west: Culebra and Vieques, the "Spanish Virgin Islands," captivate with sheltered bays, mangroves, turquoise waters, and picture-perfect beaches. A highlight is the famous "Bio Bay" of Vieques, where the water glows magically at night.
    The final leg takes us along the northeast coast to San Juan, Puerto Rico. There, our cruise concludes with a visit to the historic old town, experiencing Spanish life, enjoying music, and relaxing in the open harbor, which offers ideal return travel options. Crew changes at the beginning and end of the trip are particularly easy thanks to large international airports.
    The Caribbean way of life – from reggae and salsa to exotic spices, tropical fruits, and a relaxed zest for life – accompanies us on every leg of this extraordinary journey. The one-way route from St. Maarten to Puerto Rico embodies the joy of sailing, relaxation, Caribbean flair, and pure freedom.

    Wind & Climate
    Trade winds: Mostly from the northeast, 3–6 Beaufort, steady engine for fantastic sailing days
    Water temperature: Ø 27°C
    Air temperature: Ø 28–29°C
    January-April: Drier and pleasantly warm travel season, with occasional short showers providing welcome refreshment.

    yacht
    Our wonderful yacht is a very fast, spacious, and comfortable Hanse 575 – optimally equipped with four double cabins (each with its own bathroom and electric toilet), a separate skipper's cabin, Wi-Fi (Starlink, optional), multimedia system, 220V/7kW generator, washing machine, bread maker, Nespresso machine, extensive solar panels, watermaker, radar, AIS, hydraulic swim platform, and a dinghy with outboard motor. The yacht meets the highest standards of safety, comfort, and performance – allowing us to enjoy a stress-free and completely self-sufficient sailing trip.

    Services
    Sailing trip with skipper
    Berth on the yacht
    Sailing instructions
    Additional costs
    The onboard kitty depends on the crew's wishes (port fees, transit log, food and drink purchases, internet, security deposit insurance, diesel, etc.), usually around €350 per week per person. (The entry fee to the BVI is relatively high.)
    Arrival/Departure
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Other information
The skipper for this activity speaks english and german. To participate you must speak one of the languages spoken on board.

+ On-board cash of approximately €350 per person/week for food, shopping, port fees, diesel, etc. The skipper is usually provided for according to old tradition.
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Itinerary
Stephan
Meet Stephan, the skipper
2 reviews At Sailwiz since 2023
Every day I am thankful for this beautiful life. I would like to share that. Normally, as an organizational developer, I accompany companies in change processes. When it comes to sailing, I want to contribute to making this adventure more sustainable and environmentally friendly.
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Contact the skipper
Response rate: 93%
Response time: Less than a day

Boat details

Our yacht, a Hanse, stands for a comfortable and outstanding experience. It gives you a feeling of spaciousness, a calm atmosphere and offers the freedom you need for your activities. Nevertheless, it is fast, sporty and has great sailing performance. It was designed by Volvo Ocean Race Designers and is the fastest yacht in its class.

The large cockpit offers enough space for pleasant get-togethers and long conversations with a breathtaking panoramic view. On the sun deck you can be alone, take the time to read a book or enjoy the nature around you. The skipper's cabin has its own entrance. Even if you are supported by a professional crew, you still have your privacy.

The yacht is a modern Hanse 575. It has 4 double cabins and a cabin for the skipper. Each cabin has its own bathroom with electric toilet. Starlink, multi media, air conditioning, generator, 230 V in all cabins and Nespresso coffee machine. Solar panels, radar, AIS, watermaker, washing machine, bathing platform and a dinghy with an electrically powered outboard motor. Comprehensive safety and navigation equipment as well as many other equipment that you need to be self-sufficient.
The perfect yacht that meets the highest standards of safety, design, sailing characteristics and comfort.
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Specifications
  • Model: Hanse - 575
  • Capacity: 9 spots
  • Length: 17.15 m
  • Cabins: 4
  • Year: 2014
  • Bathrooms: 4
Features
  • GPS
  • Radar
  • Life jackets
  • VHF
  • Sounding line
  • Electric windlass
  • Autopilot
  • Wind equipment
  • EPIRB
  • Generator
  • Tender
  • Bow thruster
  • Shower
  • Bimini
  • Fishing rods
  • HI-FI equipment
  • Wifi
  • TV
  • Equipo de snorkel

Additional Information

Included
  • Professional skipper
  • Bed linens
  • Paddle Surf
  • Fishing equipment
  • Certificates
  • Equipo de snorkel
  • Towels
Not included
  • Costs of mooring and anchoring
  • Meals on board
  • Food and drink on land
  • Airport transfer
  • Gas
  • Flights
  • Skipper's food
Payment methods
  • Credit/debit card
  • Wire transfer

5 · 2 reviews

  • Wir entdecken die Welt: Die kleine Atlantiküberfahrt - Malaga zu den Kanaren
    avatar
    November of 2024
    Excellent trip from Gibraltar to the Canary Islands! The sailboat is super comfortable and safe and the skippers are very friendly and professional with lots of nautical experience. Highly recommended!
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  • Happy New Year in the Caribbean
    avatar
    December of 2023
    We have enjoyed some unforgettable days on board! The Caribbean really is a paradise.
    Captain Andy has been great, a very calm person who has allowed us to help him and pilot.
    The Hanse 575 is a modern, spacious and comfortable sailboat, with plenty of privacy as each cabin has its own bathroom.
    Read more
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Next dates

  • 11 Jan (2026) · 12 days
    Confirmed, 1 place left
    1690 € /person
  • 8 Mar (2026) · 13 days
    Confirmed, places available
    1790 € /person
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Response rate: 93%
Response time: Less than a day
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