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 2 of 5

Brown Eyed Girl

Brown Eyed Girl

Bareboat

BVI, British Virgin Islands

8 berths3 cabins13 mCatamaran · 2019
from
$949
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Pegasus

Pegasus

Bareboat

BVI, British Virgin Islands

7 berths3 cabins13 mCatamaran · 2022
from
$999
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Time Thief

Time Thief

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2020
from
$7,000
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Idle Time

Idle Time

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2020
from
$7,000
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Penny Lane

Penny Lane

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2020
from
$8,000
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Vida

Vida

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2022
from
$7,000
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Fortunata

Fortunata

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2023
from
$7,000
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Pleasant Arbour

Pleasant Arbour

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2020
from
$7,000
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All the Perks

All the Perks

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2023
from
$7,000
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Rendezvous III

Rendezvous III

Bareboat

BVI, British Virgin Islands

10 berths4 cabins13 mCatamaran · 2025
from
$1,279
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Wayfinder

Wayfinder

Bareboat

Bahamas, Bahamas

6 berths3 cabins13 mCatamaran · 2023
from
$7,450
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Serenity Now

Serenity Now

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2024
from
$7,000
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Speakeasy

Speakeasy

Bareboat

Bahamas, Bahamas

6 berths3 cabins13 mCatamaran · 2023
from
$7,450
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Carrie Lee

Carrie Lee

Bareboat

BVI, British Virgin Islands

10 berths5 cabins16 mCatamaran · 2023
from
$14,500
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Hoylah

Hoylah

Bareboat

BVI, British Virgin Islands

10 berths5 cabins16 mCatamaran · 2023
from
$14,500
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Big Big Plans

Big Big Plans

Bareboat

BVI, British Virgin Islands

13 berths5 cabins16 mCatamaran · 2024
from
$14,000
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Last Mango

Last Mango

Bareboat

BVI, British Virgin Islands

8 berths4 cabins16 mCatamaran · 2026
from
$13,500
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Peace Out

Peace Out

Bareboat

BVI, British Virgin Islands

10 berths5 cabins16 mCatamaran · 2027
from
$14,500
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Freedom

Freedom

Bareboat

BVI, British Virgin Islands

11 berths5 cabins16 mCatamaran · 2024
from
$14,000
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Vienna

Vienna

Bareboat

BVI, British Virgin Islands

11 berths5 cabins16 mCatamaran · 2022
from
$14,000
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What's left

What's left

Bareboat

BVI, British Virgin Islands

12 berths6 cabins16 mCatamaran · 2023
from
$15,000
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Lune Rae

Lune Rae

Bareboat

BVI, British Virgin Islands

12 berths6 cabins16 mCatamaran · 2025
from
$15,000
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Alizee

Alizee

Bareboat

BVI, British Virgin Islands

12 berths6 cabins16 mCatamaran · 2025
from
$15,000
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Ingrid

Ingrid

Crewed

St. Martin, Caribbean

12 berths5 cabins16 mCatamaran · 2025
from
€21,000
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Valkyrie

Valkyrie

Bareboat

BVI, British Virgin Islands

12 berths6 cabins16 mCatamaran · 2026
from
$15,000
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Crude Escape

Crude Escape

Bareboat

BVI, British Virgin Islands

12 berths6 cabins16 mCatamaran · 2026
from
$15,000
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Aboat Time

Aboat Time

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2024
from
$8,500
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Wanderlust

Wanderlust

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2023
from
$8,800
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Nalu

Nalu

Bareboat

BVI, British Virgin Islands

11 berths4 cabins13 mCatamaran · 2022
from
$10,500
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Seeker

Seeker

Bareboat

BVI, British Virgin Islands

11 berths4 cabins13 mCatamaran · 2023
from
$10,500
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Winged Arrow II

Winged Arrow II

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2024
from
$10,500
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Lucky Traveller

Lucky Traveller

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2024
from
$10,500
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Arete

Arete

Bareboat

BVI, British Virgin Islands

11 berths4 cabins13 mCatamaran · 2024
from
$10,500
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Gelos

Gelos

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2021
from
$1,499
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Detour

Detour

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2022
from
$1,559
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Two Phish

Two Phish

Bareboat

BVI, British Virgin Islands

10 berths4 cabins13 mCatamaran · 2023
from
$10,500
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No Agenda

No Agenda

Bareboat

Bahamas, Bahamas

8 berths4 cabins13 mCatamaran · 2022
price on enquiry
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Free To Be

Free To Be

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2022
from
$10,800
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Pau Hana II

Pau Hana II

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2022
from
$10,800
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Morskie Oko

Morskie Oko

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2025
from
$10,800
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Alternate Current

Alternate Current

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2024
from
$10,500
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Pretty Penny

Pretty Penny

Bareboat

BVI, British Virgin Islands

8 berths4 cabins13 mCatamaran · 2026
from
$10,800
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Ogibni

Ogibni

Bareboat

BVI, British Virgin Islands

11 berths4 cabins13 mCatamaran · 2020
from
$8,500
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Debriefed

Debriefed

Bareboat

BVI, British Virgin Islands

9 berths4 cabins13 mCatamaran · 2022
from
$10,500
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Keep It Movin'

Keep It Movin'

Bareboat

BVI, British Virgin Islands

6 berths3 cabins12 mCatamaran · 2025
from
$7,000
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Scarlet Ibis II

Scarlet Ibis II

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2025
from
$8,600
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Selah

Selah

Bareboat

BVI, British Virgin Islands

6 berths3 cabins13 mCatamaran · 2025
from
$8,600
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Serenus

Serenus

Bareboat

BVI, British Virgin Islands

7 berths3 cabins13 mCatamaran · 2026
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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