Sailaway Charters
Caribbean sailing

Caribbean

Sail the Caribbean.

Yacht charter across the Caribbean — Bahamas and British Virgin Islands.

See the fleetTalk to an expert
Season November–July2 countries

Destinations

Where to sail in the Caribbean.

Bahamas

November–July

Bahamas

British Virgin Islands

November–July

British Virgin Islands

St. Vincent

November–July

St. Vincent

Guadeloupe

November–May

Guadeloupe

Martinique

November–May

Martinique

St. Martin

Caribbean

St. Martin

Grenada

Caribbean

Grenada

Live fleet

Yachts available across the Caribbean.

233 yachts · page 3 of 5

Raven

Raven

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2026
from
$8,600
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Emma Rose

Emma Rose

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2026
from
$11,000
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Magic Hour

Magic Hour

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2026
from
$10,000
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Hoppy Choppy

Hoppy Choppy

Bareboat

BVI, British Virgin Islands

6 berths3 cabins12 mCatamaran · 2022
from
$5,500
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Rockabye

Rockabye

Bareboat

BVI, British Virgin Islands

6 berths3 cabins12 mCatamaran · 2023
from
$5,500
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Dellis Rae

Dellis Rae

Bareboat

Bahamas, Bahamas

6 berths3 cabins12 mCatamaran · 2022
from
$6,250
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Pizza My Heart

Pizza My Heart

Bareboat

BVI, British Virgin Islands

6 berths3 cabins12 mCatamaran · 2023
from
$899
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Déjà Vu

Déjà Vu

Bareboat

BVI, British Virgin Islands

9 berths4 cabins12 mCatamaran · 2022
from
$6,000
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Firefly

Firefly

Bareboat

BVI, British Virgin Islands

8 berths4 cabins12 mCatamaran · 2023
from
$5,500
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Seas The Day

Seas The Day

Bareboat

Bahamas, Bahamas

8 berths4 cabins12 mCatamaran · 2023
from
$2,200
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Wish You Were Here

Wish You Were Here

Bareboat

BVI, British Virgin Islands

8 berths4 cabins12 mCatamaran · 2020
from
$5,000
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Red Lyon

Red Lyon

Bareboat

Bahamas, Bahamas

6 berths3 cabins12 mPower Catamaran · 2022
from
$8,050
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Stephana

Stephana

Bareboat

Bahamas, Bahamas

7 berths3 cabins12 mPower Catamaran · 2024
from
$8,450
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Valhalla

Valhalla

Bareboat

BVI, British Virgin Islands

12 berths5 cabins15 mCatamaran · 2020
from
$11,000
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Soleil Rae

Soleil Rae

Bareboat

BVI, British Virgin Islands

11 berths5 cabins15 mCatamaran · 2019
from
$14,000
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Singing Winds

Singing Winds

Bareboat

BVI, British Virgin Islands

11 berths5 cabins15 mCatamaran · 2019
from
$11,000
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Serenata

Serenata

Bareboat

BVI, British Virgin Islands

14 berths6 cabins15 mCatamaran · 2020
from
$11,000
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Impossible Dream

Impossible Dream

Bareboat

Bahamas, Bahamas

6 berths3 cabins14 mCatamaran · 2021
from
$6,850
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Three Sheets

Three Sheets

Bareboat

BVI, British Virgin Islands

11 berths5 cabins14 mCatamaran · 2019
from
$10,000
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Barefoot Oasis

Barefoot Oasis

Bareboat

BVI, British Virgin Islands

11 berths5 cabins14 mCatamaran · 2020
from
$10,000
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Blue Vibes

Blue Vibes

Bareboat

BVI, British Virgin Islands

11 berths5 cabins14 mCatamaran · 2024
from
$12,000
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Dragonfly

Dragonfly

Bareboat

BVI, British Virgin Islands

10 berths5 cabins14 mCatamaran · 2023
from
$11,000
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Runny Babbit

Runny Babbit

Bareboat

BVI, British Virgin Islands

10 berths5 cabins14 mCatamaran · 2023
from
$11,000
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Cattitude

Cattitude

Bareboat

Bahamas, Bahamas

10 berths5 cabins14 mCatamaran · 2023
from
$9,650
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Stargazer

Stargazer

Bareboat

BVI, British Virgin Islands

10 berths5 cabins14 mCatamaran · 2023
from
$11,200
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Ramble On

Ramble On

Bareboat

Bahamas, Bahamas

7 berths3 cabins14 mCatamaran · 2024
from
$8,900
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Ithaka

Ithaka

Bareboat

BVI, British Virgin Islands

6 berths3 cabins14 mCatamaran · 2022
from
$9,000
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La Bella Vita

La Bella Vita

Bareboat

BVI, British Virgin Islands

6 berths3 cabins14 mCatamaran · 2024
from
$10,000
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Playful

Playful

Bareboat

BVI, British Virgin Islands

6 berths3 cabins14 mCatamaran · 2025
from
$10,000
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Altair

Altair

Bareboat

St. Vincent & Grenadines, Caribbean

8 berths4 cabins13 mCatamaran · 2018
from
$8,395
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Silvergirl

Silvergirl

Bareboat

BVI, British Virgin Islands

6 berths3 cabins16 mSailing Yacht · 2019
from
$5,800
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Paradise Found

Paradise Found

Bareboat

St. Vincent & Grenadines, Caribbean

6 berths3 cabins16 mSailing Yacht · 2017
from
$5,195
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Casbah IV

Casbah IV

Bareboat

BVI, British Virgin Islands

8 berths4 cabins17 mSailing Yacht · 2025
from
$1,599
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Saint Blue

Saint Blue

Bareboat

BVI, British Virgin Islands

8 berths3 cabins12 mCatamaran · 2019
from
$4,800
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Arcane

Arcane

Bareboat

Guadeloupe, Caribbean

10 berths4 cabins12 mCatamaran · 2016
from
€3,000
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Mr T

Mr T

Bareboat

BVI, British Virgin Islands

10 berths4 cabins12 mCatamaran · 2019
from
$4,800
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Doudou

Doudou

Bareboat

Guadeloupe, Caribbean

10 berths4 cabins13 mCatamaran · 2025
from
€3,500
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New-27

New-27

Bareboat

Guadeloupe, Caribbean

10 berths4 cabins13 mCatamaran · 2027
from
€3,700
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Providence

Providence

Bareboat

Guadeloupe, Caribbean

10 berths4 cabins12 mCatamaran · 2016
from
€3,100
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Last One

Last One

Bareboat

Guadeloupe, Caribbean

7 berths3 cabins12 mCatamaran · 2025
from
€3,500
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Laurelli−20% · Last minute

Laurelli

Bareboat

Grenada, Caribbean

12 berths4 cabins12 mCatamaran · 2020
from
€4,089
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Star of the seas 2

Star of the seas 2

Bareboat

BVI, British Virgin Islands

12 berths4 cabins12 mCatamaran · 2023
from
$6,000
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Bubbles Up

Bubbles Up

Bareboat

BVI, British Virgin Islands

12 berths4 cabins12 mCatamaran · 2024
from
$6,000
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Cloudwalker

Cloudwalker

Bareboat

BVI, British Virgin Islands

7 berths3 cabins12 mCatamaran · 2024
from
$799
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Oasis

Oasis

Bareboat

BVI, British Virgin Islands

7 berths3 cabins12 mCatamaran · 2025
from
$899
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Akala

Akala

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2025
from
$6,500
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Stella

Stella

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2018
from
$7,000
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Island Riff

Island Riff

Bareboat

BVI, British Virgin Islands

11 berths4 cabins13 mCatamaran · 2025
from
$1,329
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Caribbean questions

Asked and answered.

Which countries can I sail in the Caribbean?
We charter in Bahamas and British Virgin Islands. Each country has its own page with its sailing areas and the live fleet for your dates.
How do I choose between them?
Tell us your week, your crew and your vibe. We know every base in the region and will steer you to the right one — no hard sell.
How do I get a quote?
Send us your dates and group. Same day, we reply with three real options, three prices and the honest trade-offs.
Talk to a real charter expert

Instant quotes, fast replies

Email us — we come back fast

Send the dates, the group and the sea you have in mind. Real boats with real prices come back the same day, usually within hours.

  • Three matched boats, priced, in your inbox the same day
  • Advice from sailors who know the boats and the waters
  • Email or WhatsApp — reply by whichever suits you
  • No spam, ever

Talk to an expert

Get three options.

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