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Caribbean Charter Yachts
  The Caribbean is without doubt one of the most perfect destinations to charter a yacht with your family and friends - it is the ultimate tropical paradise for a sailing holiday with stunning ...

Leeward Islands Yacht Charter Guide - Article
Sailing the Leeward Islands Discover the secrets of St. Martin, St. Barths, Anguilla, and Antigua as you vacation on your luxury yacht charter in the Leeward Islands St. Barths | St. Martin ... There are 2 additional articles in this category.

St. Barts Yacht Charter Guide 2025-2026 - Article
Stunning St. Barts Charter a Crewed Motor Yacht, Crewed Catamaran, or Bareboat Sailboat in St. Barts for an Epic Caribbean Vacation St. Barts Crewed Motor Yachts | St. Barts Crewed S... There are 6 additional articles in this category.

The Top St Barths Crewed Motor Yachts
Motor Yachts in Gustavia Harbor, St. Barths Explore Everything St. Barths Has to Offer and More Onboard Your 2025 or 2026 Luxury Crewed Motor Yacht Charter St. Barths is an island destinatio...

St Martin, Anguilla, St Barths Crewed Motor Yacht Itinerary - Article
Discover the Caribbean Leeward Island charm from St Martin to Anguilla and St Barths on the ultimate 7 day motor yacht itinerary The Leeward Islands are cooled by year-round trade winds, wi...

We have much more to tell you about! Click here to see another 7 articles

Discover our selection of yachts below and contact our Charter Experts at Boatbookings to receive a bespoke proposal and embark on the ultimate yacht charter vacation.

Let us take over and do the work for you by completing our enquiry form. Or, contact us directly at [email protected] with details of your group size, type of yacht, destination and budget. One of our Charter Experts will call you so please leave your phone number.

We look forward to hearing from you!

SORANA II - Princess 82 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
SORANA II
    Princess 82 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Princess 82 Luxury Crewed Motor Yacht
  • Length: 24 m
  • Year: 2018 (2023 Refit)
  • Cabins: 4
  • Berths: 8
  • From $35000 to $57600 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 24 m (81' )
  • Year: 2018 (2023 Refit)
From $35000 to $57600
per week

BOATBOOKINGS SAYS:
"You will surely be looked after by a passionate crew as you cruise the enchanting Caribbean islands on SORANA II."

ALLORA - Benetti 121 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
ALLORA
    Benetti 121 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Benetti 121 Luxury Crewed Motor Yacht
  • Length: 36.9 m
  • Year: 2011 (2022 Refit)
  • Cabins: 5
  • Berths: 10
  • From $110000 to $120000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 36.9 m (125' 6")
  • Year: 2011 (2022 Refit)
From $110000 to $120000
per week

BOATBOOKINGS SAYS:
"Grace the shores of the Caribbean Leewards luxurious comfort on ALLORA!"

ACCIDENTAL SUCCESS II - Sunseeker 95 - 5 Cabins - St Kitts - St Martin - St Barths - Leewards - Caribbean
ACCIDENTAL SUCCESS II
    Sunseeker 95 - 5 Cabins - St Kitts - St Martin - St Barths - Leewards - Caribbean
  • Sunseeker 95 Luxury Crewed Motor Yacht
  • Length: 28 m
  • Year: 2024
  • Cabins: 5
  • Berths: 10
  • From $95000 to $115000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 28 m (95' 4")
  • Year: 2024
From $95000 to $115000
per week

BOATBOOKINGS SAYS:
"Experience exclusivity on ACCIDENTAL SUCCESS II while exploring the Caribbean Leewards your round!"

REVE BLEU - Lagoon Sixty 5 - 4 Cabins - Antigua - St Martin - St Barths - Leewards - Caribbean
REVE BLEU
    Lagoon Sixty 5 - 4 Cabins - Antigua - St Martin - St Barths - Leewards - Caribbean
  • Lagoon Sixty 5 Luxury Crewed Catamaran
  • Length: 20 m
  • Year: 2023
  • Cabins: 4
  • Berths: 8
  • From €45000 to €50000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 20 m (68' 8")
  • Year: 2023
From €45000 to €50000
per week

BOATBOOKINGS SAYS:
"Explore calm coves and isles anew as REVE BLEU glides through the Caribbean’s hue!"

ARAOK - Fountaine Pajot Ipanema 58 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean VIEW 1 REVIEW 
ARAOK
    Fountaine Pajot Ipanema 58 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
  • Length: 17.8 m
  • Year: 2018 (2022 Refit)
  • Cabins: 3
  • Berths: 6
  • From €25000 to €29000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.8 m (60' 4")
  • Year: 2018 (2022 Refit)
VIEW 1 REVIEW
From €25000 to €29000
per week

BOATBOOKINGS SAYS:
"You will surely enjoy your time soaking up the Caribbean and Sardinian sun while bathing in luxury on ARAOK!"

CAT TUA - Lagoon Seventy 7 - 4 Cabins - St Martin - St Barths - Leewards - Windwards - Caribbean
CAT TUA
    Lagoon Seventy 7 - 4 Cabins - St Martin - St Barths - Leewards - Windwards - Caribbean
  • Lagoon Seventy 7 Luxury Crewed Catamaran
  • Length: 23.28 m
  • Year: 2021 (2024 Refit)
  • Cabins: 4
  • Berths: 8
  • From €77000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.28 m (79' )
  • Year: 2021 (2024 Refit)
From €77000
per week

BOATBOOKINGS SAYS:
"Experience the serenity of nature amidst the Caribbean Leewards aboard the luxurious catamaran CAT TUA!"

HEEUS - Bering 145 - 6 Cabins - Monaco - Capri - St Barths
HEEUS
    Bering 145 - 6 Cabins - Monaco - Capri - St Barths
  • Bering 145 Luxury Crewed Motor Yacht
  • Length: 44.2 m
  • Year: 2023
  • Cabins: 6
  • Berths: 12
  • From €225000 to €275000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 44.2 m (150' 4")
  • Year: 2023
From €225000 to €275000
per week

DUGONGO II - Lagoon 52 - 6 Cabins - St Martin - St Barths - Leewards - Caribbean
DUGONGO II
    Lagoon 52 - 6 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Lagoon 52 Crewed Catamaran
  • Length: 15 m
  • Year: 2019
  • Cabins: 6
  • Berths: 12
  • From €9750 to €15600 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15 m (51' )
  • Year: 2019
From €9750 to €15600
per week

BOATBOOKINGS SAYS:
"DUGONGO II is an intimate crewed catamaran ideal for a family charter in the Caribbean!"

NOVA - Robertson and Caine 43 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
NOVA
    Robertson and Caine 43 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Robertson and Caine 43 Crewed Catamaran
  • Length: 13 m
  • Year: 2000 (2023 Refit)
  • Cabins: 3
  • Berths: 6
  • From $12500 to $15500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13 m (44' 4")
  • Year: 2000 (2023 Refit)
From $12500 to $15500
per week

BOATBOOKINGS SAYS:
"Feel your worries drop away as NOVA paints the Caribbean in shades of play!"

WESTERLUND - Lagoon 46 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
WESTERLUND
    Lagoon 46 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Lagoon 46 Luxury Crewed Catamaran
  • Length: 14 m
  • Year: 2020
  • Cabins: 4
  • Berths: 10
  • From €8394 to €10387 per week
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2020
From €8394 to €10387
per week

BOATBOOKINGS SAYS:
"The enormous flybridge will have your whole family immersed in the art of sailing on your Caribbean charter aboard WESTERLUND!"

LOBA DO MAR - Bali 4.6 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
LOBA DO MAR
    Bali 4.6 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Bali 4.6 Crewed Catamaran
  • Length: 14 m
  • Year: 2024
  • Cabins: 5
  • Berths: 10
  • From $24500 to $28500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2024
From $24500 to $28500
per week

BOATBOOKINGS SAYS:
"In the Leeward Islands, LOBA DO MAR sets the bar, carrying you through waters that sparkle like a guiding star!"

SARA - Leopard 46 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
SARA
    Leopard 46 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Leopard 46 Crewed Catamaran
  • Length: 14 m
  • Year: 2012 (2023 Refit)
  • Cabins: 3
  • Berths: 7
  • From $12000 to $17500 per week
Details Enquire
  • Berths: 7
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2012 (2023 Refit)
From $12000 to $17500
per week

BOATBOOKINGS SAYS:
"Your camera will never rest from the spectacular scenery of the Caribbean on SARA!"

BEYOND - Fountaine Pajot Aura 51 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
BEYOND
    Fountaine Pajot Aura 51 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Fountaine Pajot Aura 51 Crewed Catamaran
  • Length: 15 m
  • Year: 2022
  • Cabins: 4
  • Berths: 6
  • From $21900 to $28680 per week
Details Enquire
  • Berths: 6
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15 m (51' )
  • Year: 2022
From $21900 to $28680
per week

BOATBOOKINGS SAYS:
"A rare and unique opportunity to charter a new Fountaine Pajot Aura 51 in the Leewards and Grenadines in the Winter, and the Bahamas in the Summer."

WIND DANCER - Robertson and Caine Leopard 50 - 3 Cabins - St Martin - St Barths - Anguilla - Leewards - Caribbean
WIND DANCER
    Robertson and Caine Leopard 50 - 3 Cabins - St Martin - St Barths - Anguilla - Leewards - Caribbean
  • Robertson and Caine Leopard 50 Crewed Catamaran
  • Length: 15 m
  • Year: 2021
  • Cabins: 3
  • Berths: 6
  • From $21000 to $23000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15 m (51' )
  • Year: 2021
From $21000 to $23000
per week

BOATBOOKINGS SAYS:
"Wave your body smoothly while dancing to the rhythm of the gentle Caribbean waters on WIND DANCER!"

LADY MARIGOT - Privilege Alliaura Marine Group 58 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
LADY MARIGOT
    Privilege Alliaura Marine Group 58 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Privilege Alliaura Marine Group 58 Luxury Crewed Catamaran
  • Length: 17 m
  • Year: 2004
  • Cabins: 4
  • Berths: 8
  • From $25500 to $28500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17 m (57' 8")
  • Year: 2004
From $25500 to $28500
per week

BOATBOOKINGS SAYS:
"LADY MARIGOT is your gateway to unforgettable adventures in the Caribbean year-round!"

ALLURE 64- Privilege S6 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
ALLURE 64
    Privilege S6 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Privilege S6 Crewed Catamaran
  • Length: 19 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $40000 to $45000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 19 m (64' 4")
  • Year: 2020
From $40000 to $45000
per week

BOATBOOKINGS SAYS:
"Pure happiness and excitement await in the Leeward Islands on ALLURE 64!"

AVANTI - Privilege 745 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
AVANTI
    Privilege 745 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Privilege 745 Crewed Catamaran
  • Length: 22 m
  • Year: 2005
  • Cabins: 4
  • Berths: 8
  • From $46000 to $49000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22 m (74' 4")
  • Year: 2005
From $46000 to $49000
per week

BOATBOOKINGS SAYS:
"Where the gentle winds and laughter align, aboard AVANTI, the Caribbean Leewards feel divine!"

A PLAN - Sunreef 80 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
A PLAN
    Sunreef 80 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Sunreef 80 Luxury Crewed Catamaran
  • Length: 23 m
  • Year: 2025
  • Cabins: 4
  • Berths: 8
  • From €90000 to €120000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23 m (78' 8")
  • Year: 2025
From €90000 to €120000
per week

BOATBOOKINGS SAYS:
"Live bright and tan as you drift from cay to cay across the Leewards aboard A-PLAN!"

MAMMA MIA - Benetti Classic 120 - St Martin - St Barths - Leewards - Caribbean
MAMMA MIA
    Benetti Classic 120 - St Martin - St Barths - Leewards - Caribbean
  • Benetti Classic 120 Luxury Crewed Motor Yacht
  • Length: 36.58 m
  • Year: 2007 (2022 Refit)
  • Cabins: 5
  • Berths: 10
  • From $95000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 36.58 m (124' 10")
  • Year: 2007 (2022 Refit)
From $95000
per week

BOATBOOKINGS SAYS:
"Party and sing along as you cruise throughout the Caribbean Leewards on MAMMA MIA!"

ABIDE - Jongert 138 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
ABIDE
    Jongert 138 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Jongert 138 Crewed Sailing Yacht
  • Length: 42 m
  • Year: 2002 (2024 Refit)
  • Cabins: 3
  • Berths: 6
  • From $90000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 42 m (142' )
  • Year: 2002 (2024 Refit)
From $90000
per week

BOATBOOKINGS SAYS:
"Glide on enchanting waters and have an exhilarating exploration of the Caribbean waters on ABIDE!"

ORION - Catana 90 - 4 Cabins - St Martin - St Barths - Anguilla
ORION
    Catana 90 - 4 Cabins - St Martin - St Barths - Anguilla
  • Catana 90 Luxury Crewed Catamaran
  • Length: 27.432 m
  • Year: 2008
  • Cabins: 4
  • Berths: 8
  • From $46000 to $57500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 27.432 m (93' 7")
  • Year: 2008
From $46000 to $57500
per week

BOATBOOKINGS SAYS:
"Boatbookings favorite boat from the 2013 BVI Charter Yacht Show!"

Princess V65 - Day Charter - St Barths - Anguilla VIEW 1 REVIEW 
Princess V65
    Day Charter - St Barths - Anguilla
  • Day Charter Crewed Motor Yacht
  • Length: 0 m
  • Year:
  • Cabins: 4
  • Berths: 0
  • From €4590 to €5495 per day
VIEW 1 REVIEW  Details Enquire
  • Berths: 0
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 0 m (0' )
  • Year:
VIEW 1 REVIEW
From €4590 to €5495
per day

BOATBOOKINGS SAYS:
"Princess 65 available to charter with 14 guests around the beautiful island of St Barths."

CANCELLI DEL CIELO - Bali 4.6 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean - Ibiza
CANCELLI DEL CIELO
    Bali 4.6 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean - Ibiza
  • Bali 4.6 Crewed Catamaran
  • Length: 14 m
  • Year: 2024
  • Cabins: 5
  • Berths: 10
  • From $24500 to $28500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2024
From $24500 to $28500
per week

BOATBOOKINGS SAYS:
"Hear the hymn of the Caribbean Sea aboard the stylish catamaran CANCELLI DEL CIELO!"

MONDANGO - Lagoon 46 - St Martin - St Barths - Leewards - Windwards - Caribbean
MONDANGO
    Lagoon 46 - St Martin - St Barths - Leewards - Windwards - Caribbean
  • Lagoon 46 Crewed Catamaran
  • Length: 14 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $16500 to $18500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2020
From $16500 to $18500
per week

BOATBOOKINGS SAYS:
"Party all night and dance tango with your loved ones on the Lagoon 46 MONDANGO!"

INFINITY - Lagoon 46 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
INFINITY
    Lagoon 46 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Lagoon 46 Crewed Catamaran
  • Length: 14.02 m
  • Year: 2023
  • Cabins: 3
  • Berths: 6
  • From $20000 to $22500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14.02 m (47' 10")
  • Year: 2023
From $20000 to $22500
per week

BOATBOOKINGS SAYS:
"Sign up for an infinite number of surprises as you cruise the Caribbean Leewards on INFINITY!"

ANDIAMO - Leopard 50 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
ANDIAMO
    Leopard 50 - 3 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Leopard 50 Crewed Catamaran
  • Length: 15.24 m
  • Year: 2023
  • Cabins: 3
  • Berths: 6
  • From $25500 to $28000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15.24 m (51' )
  • Year: 2023
From $25500 to $28000
per week

BOATBOOKINGS SAYS:
"Hurry up and book a remarkable cruise in the Caribbean on ANDIAMO!"

BLUE LAGOON - Bali 5.4 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
BLUE LAGOON
    Bali 5.4 - 5 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Bali 5.4 Luxury Crewed Motor Yacht
  • Length: 16 m
  • Year: 2022
  • Cabins: 5
  • Berths: 10
  • From $28500 to $32500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 16 m (54' 4")
  • Year: 2022
From $28500 to $32500
per week

BOATBOOKINGS SAYS:
"A cruising vacation full of eye-candy surprises awaits amidst the beautiful Caribbean Leewards on BLUE LAGOON!"

OKINAWA - Fountaine Pajot Samana 59 - 5 Cabins - St Martin - St Barths - Leeward Islands - Caribbean
OKINAWA
    Fountaine Pajot Samana 59 - 5 Cabins - St Martin - St Barths - Leeward Islands - Caribbean
  • Fountaine Pajot Samana 59 Crewed Catamaran
  • Length: 18 m
  • Year: 2024
  • Cabins: 5
  • Berths: 10
  • From $42000 to $62000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18 m (61' )
  • Year: 2024
From $42000 to $62000
per week

BOATBOOKINGS SAYS:
"Tasty dishes, out-of-this-world tropical vistas, and euphoric onboard parties await in the Caribbean on the stunning catamaran OKINAWA!"

Princess V55 - St Barths
Princess V55
    St Barths
  • St Barths Crewed Motor Yacht
  • Length: 18.19 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From €4000 per day
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 18.19 m (61' 7")
  • Year:
From €4000
per day

BOATBOOKINGS SAYS:
"One of the finest small motor yachts to cruise around St Barths this winter."

THE BLUE PETER - Classic Yacht - 4 Cabins - English Harbour - St Barths - St Martin VIEW 1 REVIEW 
THE BLUE PETER
    Classic Yacht - 4 Cabins - English Harbour - St Barths - St Martin
  • Classic Yacht Crewed Sailing Yacht
  • Length: 19.65 m
  • Year: 1930
  • Cabins: 4
  • Berths: 7
  • From €2500 to €3000 per day
VIEW 1 REVIEW  Details Enquire
  • Berths: 7
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 19.65 m (66' 8")
  • Year: 1930
VIEW 1 REVIEW
From €2500 to €3000
per day

BOATBOOKINGS SAYS:
"The Blue Peter is fast, fun and full of character, perfect for regatta charters!"

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