Deckhand – Cycling Specialist

Bespoke Crew; United States; On-site; USD 36,000 - 43,000; Full time

Job summary

Bespoke Crew is seeking a Deckhand with a passion for cycling to join an 80m+ private MY with a strong crew culture. You will be responsible for the yacht's bicycles and equipment, ensuring readiness for frequent cycling trips and watersports.

The role requires excellent communication and a confident, guest-facing demeanor. The ideal candidate has a strong cycling background, maturity, and the ability to operate in close contact with owners.

Qualifications

• Strong cycling background with road cycling experience.
• Confident, mature and comfortable in owner-facing roles.
• Ability to plan and lead cycling trips and logistics.
• Visa and driving licence requirements as stated.

Responsibilities

• Plan cycling routes and guide guests on road trips.
• Maintain and organise cycling equipment and bicycles.
• Assist with supplies, water and logistics during excursions.
• Support day-to-day deck duties and tender operations.
• Engage guests with watersports and activities as needed.

Skills

Strong cycling background

Confident road cyclist

Maturity and confidence

B1/B2 Visa

Full driving licence

Job description

A fantastic 80m+ private MY with a well-established programme and an excellent crew culture is looking for a Deckhand with passion for Cycling!

The owners enjoy an active lifestyle, with cycling being a huge part of their routine – The successful candidate will play an important role in supporting and joining these trips.

The yacht carries an impressive selection of tenders and toys, including a 40ft Wally, 44ft Van Dutch and various RIBs, meaning there will be plenty of tender operations and watersports activity throughout the programme.

The yacht has a strong culture of fitness, cycling and outdoor activities, reflecting the owners’ lifestyle. There is a dedicated crew gym onboard, and the team regularly socialises together ashore.

THE ROLE

Cycling will be a key part of your role. You will take responsibility for the yacht’s bicycles and associated equipment, ensuring everything is maintained and ready for use.

You will also:

• Plan cycling routes
• Accompany and guide the guests on regular road cycling trips
• Assist with supplies, water and logistics during cycling excursions
• Maintain and organise all cycling equipment
• Support the wider deck team with day-to-day deck duties
• Assist with tender operations, watersports and general guest activities

This is a very owner-facing position, so strong communication skills, confidence and a personable nature are essential.

THE IDEAL CANDIDATE

• Strong cycling background
• Confident road cyclist with good knowledge of cycling routes and equipment
• They could except junior candidates with Strong cycling backgrounds also
• Maturity & Confidence in an owner-facing position
• Good previous longevity on a vessel
• B1/B2 Visa
• Full driving licence preferred

PACKAGE

Start Date: By end of November 2026

Rotation: 5:1

• $3,500 USD for a greener candidate
• salary increase after one year, subject to performance