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

12 days
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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 itinerary is a Caribbean experience. During our voyage, we'll enjoy the contrasts between vibrant sailing waters, colonial flair, small paradises, and the majestic nature of the northeastern 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 evening, we toast to the sound of the palm trees rustling and the surf gently lapping against our hull.
Our adventure begins on St. Maarten—the famous "Friendly Island"—and takes us leisurely through the British Virgin Islands and the Spanish Virgin Islands to San Juan, Puerto Rico. We sail between the most beautiful bays of the Leeward Islands, explore national parks, enjoy snorkeling and shore excursions, and drift between beach bars, anchorages, and the Caribbean island rhythm.

Highlights
St. Maarten – Two cultures on one island, a lively departure port with international connections
St. Barthélemy – Caribbean elegance and French chic
Anguilla (optional) – Beautiful, quiet beaches and a Cay feeling
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 of 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 cruise takes us from St. Maarten through the Leeward Islands, with short, sheltered stretches, through the trade winds, and past coral reefs and tropical islands. Temperatures range between 25°C and 29°C in winter, and the water remains pleasantly warm year-round (approx. 26–27°C).

The northeast trade winds with 4–5 Beaufort winds ensure relaxed and safe sailing. Short rain showers bring pleasant coolness, and the climate is generally dry and sunny. The region's warm, cosmopolitan people make life on board and shore excursions particularly pleasant.
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  • Plan
    Our sailing adventure begins in St. Maarten, where, after boarding and a brief safety briefing, we explore the island and replenish our supplies. The first nautical miles lead to the sophisticated bays of St. Barth and further to the relaxed beaches of Anguilla (weather permitting, depending on your wishes).
    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, delight with sheltered bays, mangroves, turquoise waters, and picture-perfect beaches. A highlight is Vieques' famous "Bio Bay," where the water magically glows at night.
    The final leg takes us along the northeast coast to San Juan, Puerto Rico. Our cruise concludes there with a visit to the historic old town, Spanish lifestyle, music, and an open harbor, providing an ideal return journey. Crew changes at the beginning and end are particularly easy thanks to major international airports.
    The Caribbean way of life—from reggae and salsa to exotic spices, tropical fruits, and a relaxed joie de vivre—accompanies us on every leg of this extraordinary travel experience. The one-way route from St. Maarten to Puerto Rico represents sailing pleasure, relaxation, Caribbean flair, and pure freedom.

    Wind & Climate
    Trade winds: mostly from the northeast, 3–6 Bft, constant engine for dream sailing days
    Water temperature: Ø 27°C
    Air temperature: average 28–29°C
    January: Drier and pleasantly warm travel season, with occasional short showers as a welcome refreshment

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

    Services
    Sailing trip with skipper
    Bunk on the yacht
    Sailing instructions
    Additional costs
    Onboard cash, depending on the crew's wishes (port fees, transit log, food and beverage purchases, internet, deposit insurance, diesel, etc.), usually around €350 per week per person. (The entry fee for 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: 92%
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
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Response rate: 92%
Response time: Less than a day
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