SailTiesSailTies
  1. Adventures
  2. Sail Libra

SailTies vetted operator

Sail Libra

Real offshore and blue water cruising with a great owner skipper.

Logbook App

  • Digital Logbook
  • SailTies Plus
  • Crew Match
  • Support
  • Sailor stories

Adventures

  • All adventures
See 12 trips
  • Vetted operators only
  • Secure booking

Upcoming trips with Sail Libra

12 trips to choose from, with berths from £2,875.

  • Sailing the Tropical Trail — Sailing Course in Bermuda & U.S. Virgin Islands
    Open to all

    Sailing the Tropical Trail

    Bermuda & U.S. Virgin Islands · Caribbean

    Next: 13 - 23 November 2026

    1 date in November


    $7,550

  • Wind & Waves Seminar — Sailing Course in U.S. Virgin Islands
    Open to all

    Wind & Waves Seminar

  • Caribbean Offshore Challenge — Sailing Course in U.S. Virgin Islands & Grenada
    Open to all

    Caribbean Offshore Challenge

  • Windward to Leeward Training — Sailing Course in Sint Maarten
    Open to all

    Windward to Leeward Training

  • To The South — Sailing Course in Sint Maarten & Grenada
    Open to all

    To The South

  • Eastern Caribbean Passage — Sailing Course in Grenada & Sint Maarten
    Open to all

    Eastern Caribbean Passage

  • Caribbean Offshore Intensive — Sailing Course in Sint Maarten & Grenada
    Open to all

    Caribbean Offshore Intensive

  • Rum & Ruins Passage — Sailing Course in Sint Maarten
    Open to all

    Rum & Ruins Passage

  • North Atlantic Intensive — Sailing Course in Sint Maarten & Bermuda
    Open to all

    North Atlantic Intensive

  • Gulf Stream Intensive — Sailing Course in Bermuda & United States
    Open to all

    Gulf Stream Intensive

  • The Portuguese Coast Passage — Sailing Course in Portugal
    Open to all

    The Portuguese Coast Passage

  • The Atlantic Islands Passage — Sailing Course in Portugal & Spain
    Open to all

    The Atlantic Islands Passage

Hear when Sail Libra adds trips

Leave your name and email for Mike's monthly email. It's where we announce new trips, so you'll hear when Sail Libra adds more.

Prefer to talk it through?

You'll get Mike's monthly email, which is where we announce new trips. Unsubscribe any time.

Privacy policy

Where you'll sail

The routes

See where each trip goes and when it next sails, then pick the one that fits your dates.

  • 1

    Sailing the Tropical Trail

     Sailing the Tropical Trail

    This 850 to 900-nautical-mile offshore passage from Bermuda to St. Thomas offers 6 to 7 days of steady tradewind sailing and real-world offshore experience.

    Route
    Bermuda to St. Thomas
    Next departure
    November 13 – 23, 2026
    Berths from
    £7,550
    See dates and prices
  • 2

    Wind & Waves Seminar

     Wind & Waves Seminar

    This 4-day sailing seminar in the U.S. Virgin Islands offers a practical introduction to coastal and offshore sailing.

    Route
    St Thomas to St. Thomas
    Next departure
    December 3 – 7, 2026
    Berths from
    £3,850
    See dates and prices
  • 3

    Caribbean Offshore Challenge

     Caribbean Offshore Challenge

    Embark on an unforgettable Bluewater journey from the heart of the US Virgin Islands to the lush spice island of Grenada.

    Route
    St. Thomas to Grenada
    Next departure
    January 14 – 23, 2027
    Berths from
    £5,250
    See dates and prices
  • 4

    Windward to Leeward Training

    Windward to Leeward Training

    This passage provides a classic northbound Caribbean training opportunity, traveling from Grenada to Sint Maarten with multiple potential island stops along the way.

    Route
    Grenada to St Maarten
    Next departure
    January 30 – February 6, 2027
    Berths from
    £5,200
    See dates and prices
  • 5

    To The South

    To The South

    This passage offers a classic southbound transit of the Lesser Antilles, traveling from Sint Maarten to Grenada with a focus on French-influenced islands along the way.

    Route
    Sint Maarten to Grenada
    Next departure
    February 27 – March 6, 2027
    Berths from
    £4,550
    See dates and prices
  • 6

    Eastern Caribbean Passage

    Eastern Caribbean Passage

    This northbound passage offers an in-depth tour of the Windward and Leeward islands, starting with a tropical exploration of the Grenadines before transitioning into a series of…

    Route
    Grenada to Sint Maarten
    Next departure
    March 12 – 20, 2027
    Berths from
    £4,850
    See dates and prices
  • 7

    Caribbean Offshore Intensive

    Caribbean Offshore Intensive

    This passage focuses on extended offshore sailing, covering a direct non-stop leg from Sint Maarten to St.

    Route
    Sint Maarten to Grenada
    Next departure
    March 27 – April 3, 2027
    Berths from
    $4,850
    See dates and prices
  • 8

    Rum & Ruins Passage

     Rum & Ruins Passage

    This passage offers a mix of offshore sailing and historical exploration. Departing Grenada, the route features a layover in the historic town of St.

    Route
    Grenada to Sint Maarten
    Next departure
    April 10 – 17, 2027
    Berths from
    $4,850
    See dates and prices
  • 9

    North Atlantic Intensive

     North Atlantic Intensive

    Covering roughly 900 nautical miles nonstop from Sint Maarten to Bermuda, this passage takes you directly north into the open Atlantic.

    Route
    Sint Maarten to Bermuda
    Next departure
    May 6 – 15, 2027
    Berths from
    $7,750
    See dates and prices
  • 10

    Gulf Stream Intensive

    Gulf Stream Intensive

    This classic offshore passage covers approximately 650–700 nautical miles from St. George’s, Bermuda to Newport, Rhode Island, featuring a full Gulf Stream crossing and real-world…

    Route
    Bermuda to Newport
    Next departure
    May 21 – 29, 2027
    Berths from
    $5,850
    See dates and prices
  • 11

    The Portuguese Coast Passage

    The Portuguese Coast Passage

    Sail the Portuguese coast aboard Libra on a weeklong passage from Lisbon to the Algarve, combining coastal sailing, historic ports, dramatic headlands, protected anchorages and…

    Route
    Lisbon to Faro
    Next departure
    August 13 – 21, 2027
    Berths from
    $4,440
    See dates and prices
  • 12

    The Atlantic Islands Passage

     The Atlantic Islands Passage

    Sail offshore from Portugal to the Canary Islands aboard Libra on a 10 day Atlantic passage from Faro to Tenerife.

    Route
    Faro to Tenerife
    Next departure
    October 1 – 10, 2027
    Berths from
    $7,950
    See dates and prices

About the operator

Meet Sail Libra

We believe real seamanship can’t be learned at a marina. Libra was built for the open ocean — and so was this program. Whether you're looking to gain confidence offshore, log serious sea miles, or chase the horizon just for the hell of it, you're in the right place. ​​ For over a decade, we’ve helped sailors step beyond the dock and into a full-spectrum passage-making experience. It’s hands-on and sometimes it’s rough & loud — but it’s real. Every passage is a team effort. There’s no standing back and watching here — you’ll be on the helm, trimming sails, navigating, standing watch, and learning what it really takes to move a boat. We meet you at your level, then build you up from there.

See their trips
Sail Libra

What it's like on board

Your home at sea

The boat you'll sail on

Where you'll sleep, eat and learn the ropes for the whole trip.

Libra

Bill Tripp Custom Ketch

Type
Sailing yacht
Length
60 ft (18.2 m)
Built
1969
Flag
United States

Vessel Overview: Libra is a 60-foot custom center-cockpit ketch built in 1969 by Abeking & Rasmussen and designed by William H. Tripp Jr., one of America’s most respected yacht designers of his era. From her elegant lines to her rugged fiberglass construction and capable offshore performance, Libra has always stood apart. Over five decades and many tens of thousands of offshore miles, she has proven herself as a serious sailing vessel. Originally commissioned for global voyaging, Libra now serves as the flagship of Sail Libra’s offshore training program, carrying sailors on passages from the Caribbean to North America and across the Atlantic to Europe. ​ Refitted and continuously upgraded, she blends the enduring qualities of classic yacht design with modern systems and real offshore capability. Design Heritage: Libra was born from the work of one of the most influential American yacht designers of the twentieth century and built by a shipyard known for uncompromising craftsmanship. ​ William H. Tripp Jr. was a Long Island–based naval architect whose designs helped shape modern offshore sailing. He was known for boats that balanced performance, strength, and practicality at sea, favoring seakindly motion and manageability over trends or dockside appeal. Tripp was an early advocate for fiberglass as a serious offshore construction material and played a significant role in its acceptance for large ocean-going yachts. ​ Among his most notable works is Ondine, a custom racing yawl whose hull form and proportions became legendary in offshore sailing circles. Ondine’s success in ocean racing, including repeated victories in the Newport to Bermuda Race, established Tripp’s reputation for fast, powerful, and well-balanced hulls that could perform across a wide range of conditions. That racing pedigree directly informed his later cruising designs. ​ Tripp’s influence extended well beyond custom race boats. He worked closely with Hinckley to develop the Block Island 40, which evolved into the Hinckley Bermuda 40, one of the most enduring and respected cruiser-racers ever produced. He also designed several major production yachts for Columbia Yachts, including the Columbia 57, blending offshore capability with interior volume in a way that was ahead of its time. ​ Libra’s hull was drawn from this same design lineage. She carries the DNA of Ondine’s powerful yawl form, adapted for long-range cruising and extended offshore work. The result is a balanced hull with a long waterline, generous displacement, and proportions that favor speed, comfort, and control in open ocean conditions. ​ That design was executed by Abeking & Rasmussen in Bremen, Germany. Founded in 1907, the yard has more than a century of experience building high-quality yachts and specialized seagoing vessels. Their reputation rests on structural integrity, precision craftsmanship, and vessels built to operate reliably in demanding environments. Libra reflects that tradition, combining German engineering with Tripp’s offshore-focused design philosophy. ​ Libra was one of Tripp’s later custom designs, completed shortly before his death in 1971. Today, after decades of sailing and continuous refit, she remains true to that original intent. She is not a reinterpretation or a modernized copy. She is the real thing, refined and maintained, still doing exactly what she was designed to do: sail offshore, carry her crew safely across open water, and reward good seamanship.

Meet the crew

Who you'll sail with

The people behind Sail Libra, with every mile they've logged on SailTies to back them up.

  • RR

    Ryan Rayfield

    @rrayfield

    Owner · United States

    View profile
    NM logged
    542
    Voyages
    1
    Days at sea
    6

    Latest voyages

    • Port Washington to LunenbergPort Washington to Lunenberg

Book with confidence with SailTies

A team of sailors who have your back

We will help you pick the right trip and be there if anything unexpected happens.

  • Every operator vetted

    We only list operators we know personally or have been recommended by past customers. All trips are checked before they go live.

  • Terms published upfront

    Cancellation and refund terms shown on every trip page before you pay a deposit.

  • Talk to a sailor

    Our team sail, and they'll tell you honestly what a trip is like and whether it's right for you.

The SailTies community

From the logbooks

SailTies is the leading digital logbook and sailor network. These are stories from the sailors who use it.

All sailor stories
Three Volcanoes and a Cracked Shroud: Racing Offshore with Robert Šarić

Three Volcanoes and a Cracked Shroud: Racing Offshore with Robert Šarić

A cracked shroud 250 miles from the Rolex Middle Sea Race finish, three volcanoes in one campaign, and why Robert Šarić of Veruda Sailing School trains his crews on the Adriatic.

Read the story
Seven of Thirteen: Elouise Pemberton's Challenge Fleet Quest

Seven of Thirteen: Elouise Pemberton's Challenge Fleet Quest

A Tall Ships bursary put Elouise Pemberton to sea at 19. Twenty years on she is working through all thirteen Challenge yachts, logging every mile on SailTies.

Read the story
46 Legs Round Britain: Jenny Whelan's Voyage with Dogsail

46 Legs Round Britain: Jenny Whelan's Voyage with Dogsail

Jenny Whelan sailed 46 legs and 1,800 nautical miles around Britain with her partner Pete, their dog Svea, and an AI chatbot, logging every leg on SailTies.

Read the story

Questions people ask before booking a sailing trip

A sailor looking out from the foredeck
  • Can I book on my own?

    Yes, and most people do. Trips are sold by the berth, so you join a crew rather than needing to bring one. Cabins are shared with someone of the same sex unless you book a whole cabin.

  • Do I need sailing experience?

    It depends on the trip, and every listing says which level it is written for. Beginner trips assume you have never sailed; advanced trips assume you can stand a night watch without supervision.

  • What's included in the price?

    The berth, the skipper and crew, and the running of the boat. Flights, insurance and most meals ashore are not. Every trip page lists what is and is not included before you pay.

  • What happens if I need to cancel?

    The operator's cancellation terms are published on the trip page before you pay a deposit, so you can read them before you commit. They vary by operator and by how close to departure you cancel.

  • What if the weather is bad?

    The skipper decides the route, and changing it is normal seamanship rather than a problem. Trips are very rarely cancelled outright; when they are, the operator's terms say what happens.

  • Who are the operators?

    Independent charter businesses and skippers we either know personally or have been recommended by past customers. Their registered business details are available upon request. All trips are checked before they go live.

Ready to sail with Sail Libra?

Pick your trip, or ask a question first. We'll get you an answer before you book.

See trips
  • Destinations
  • Expeditions
  • Racing
  • Mile building
  • Co-Charter
  • Gift vouchers
  • Sailing trips

    • Caribbean sailing
    • Mediterranean sailing
    • Co-charter in Greece
    • Americas sailing
    • UK sailing
    • Indian Ocean sailing
    • Arctic sailing
    • Atlantic crossings
    • Fastnet Race 2027
    • Caribbean regattas
    • Yachtmaster mile building
    • Offshore passage making

    For Businesses

    • Operators
    • Sailing schools
    • Instructors
    • Clubs & groups

    About Us

    • About SailTies
    • Blog

    Follow us

    SailTies
    Download on the App StoreGet it on Google Play

    © SailTies

    • Privacy
    • Terms
    • Cookies
    • Contact us
    U.S. Virgin Islands · Caribbean

    Next: 3 - 7 December 2026

    2 dates in December


    $3,850

    U.S. Virgin Islands & Grenada · Caribbean

    Next: 14 - 23 January 2027

    1 date in 2027


    $5,250

    Sint Maarten · Caribbean

    Next: 30 January - 6 February 2027

    1 date in 2027


    $5,200

    Sint Maarten & Grenada · Caribbean

    Next: 27 February - 6 March 2027

    1 date in 2027


    $4,550

    Grenada & Sint Maarten · Caribbean

    Next: 12 - 20 March 2027

    1 date in 2027


    $4,850

    Sint Maarten & Grenada · Caribbean

    Next: 27 March - 3 April 2027

    1 date in 2027


    $4,850

    Sint Maarten · Caribbean

    Next: 10 - 17 April 2027

    1 date in 2027


    $4,850

    Sint Maarten & Bermuda · Caribbean

    Next: 6 - 15 May 2027

    1 date in 2027


    $7,750

    Bermuda & United States · Americas

    Next: 21 - 29 May 2027

    1 date in 2027


    $5,850

    Portugal · Europe

    Next: 13 - 21 August 2027

    1 date in 2027


    $4,440$5,550

    -20%20% off

    Portugal & Spain · Europe

    Next: 1 - 10 October 2027

    1 date in 2027


    $7,950

    Photos & videos from our sailing trips

    Taken by the people who were there, attached to the reviews they left.