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Mermaids, Pirates and Poets (Caribbean Sail)

Hosted by Stacy Earl

From $4,550 · 15–22 Jan 2028 · Book by 15 Jul 2027

History and cultureLiterary travelReading retreatsSailing

Seven nights on the Royal Clipper, a five-masted tall ship with 42 sails and the largest full-rigged sailing ship in the world. We sail round trip from Bridgetown, Barbados, and stop at a different island every day. On the way to Dominica she sails alongside her sister ship, Star Flyer.

Before we go, the group reads and watches together online from August 2027: one book a month, each tied to an island we visit, with film nights, a playlist and two video calls a month, just for the group. Caribbean novels, a pirate classic, a mermaid love story, and the films shot on these islands. The books we're planning around: The Mermaid of Black Conch by Monique Roffey, Captain Blood by Rafael Sabatini, Wide Sargasso Sea by Jean Rhys, A Small Place by Jamaica Kincaid and Windward Heights by Maryse Condé.

The ship sails at night and anchors by morning. Each day has one story stop on shore, and the rest of the day is yours: a beach, a swim off the ship's marina platform, or a deck chair under the sails. Pigeon Island on St Lucia, next to the fishing village in Derek Walcott's Omeros. A rowing boat up Dominica's Indian River, where Pirates of the Caribbean: Dead Man's Chest filmed. Nelson's Dockyard on Antigua. Brimstone Hill Fortress on St Kitts. Fort Napoléon on the Îles des Saintes, above the waters of the 1782 battle.

I'm on board with you all week. The final days and the solo cabin prices go to the waiting list first.

Stacy Earl

About your host

Stacy Earl

I lived just outside Harrogate, for several years. I know which lane gives the best view at dusk and which pub has the corner table worth claiming.

Website: twicetoldstories.com (opens in a new tab)

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The details

About the trip

Style
Upscale · about $650 a night
How active
Moderate
Getting around
Sailboat or yacht
Nearest airport
Bridgetown, Barbados (BGI)
Setting
At sea · Island · Beach

The ship

Ship
Royal Clipper · Star Clippers
Cruise
Sailing or yacht cruise · Our group on a regular sailing
Leaves from
Bridgetown, Barbados

What's included

Included
7 nights on the Royal Clipper in a cabin with a window · all meals on board · one story stop on shore on each island · the reading months from August 2027 · with two video calls a month · your host on board all week
Not included
Flights · Travel insurance · Tips · Drinks · port charges · personal spending. Travel insurance is required.
Rooms
Shared rooms
Alcohol
Drinks available to buy

Who it suits

Suits
Solo-friendly · Couples welcome

Day by day

  1. Sat: Bridgetown, Barbados. Board in the afternoon; the sails go up as we leave harbour
  2. Sun: Rodney Bay, St Lucia. Pigeon Island and Gros Islet, the village in Omeros
  3. Mon: Cabrits, Dominica. Sail alongside Star Flyer, then the Indian River and Fort Shirley
  4. Tue: Falmouth Harbour, Antigua. Nelson's Dockyard
  5. Wed: St Kitts. Brimstone Hill Fortress, then a beach afternoon at South Friar's Bay
  6. Thu: Îles des Saintes. Fort Napoléon and the story of the 1782 battle
  7. Fri: Martinique. A beach stop, the last night under sail and a farewell dinner
  8. Sat: Back in Bridgetown in the morning, and home

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