From mastering essential skills like anchoring and watch-keeping to streamlining meal prep and tackling the many collaborative tasks involved, we’ve been there and can guide you. We’ll work with you to build the skills and confidence you need, and for more complex needs, we partner with industry experts to provide comprehensive support. If your dream is to experience the adventure of long-distance cruising, we can help you make it a reality.
All photos come from Mike’s personal library
✓ RELOCATION
✓ CHARTER
✓ CONSULTING
The Mission: Adventure
We work with sailors to make their dreams come true.
Relocation Services / Yacht Delivery
Tired of the hassles of relocating your yacht?
Imagine simply arriving at your dream destination. Long passages can be challenging and uncomfortable, especially for less experienced crew. Kalypso Yacht Services specializes in yacht deliveries along the East Coast, including the Bahamas and the US Virgin Islands. Let our experienced team handle the journey, so you can enjoy your yacht where you want, when you want.
Charter Captain
Dreaming of a secluded island getaway on a yacht?
Let us take the helm. Our extensive experience in the islands means we know all the best-kept secrets – from perfect anchorages and snorkeling spots to adventurous hikes and prime lobster grounds. We’ll work with you and your crew to craft a truly personalized experience, handling every detail from excursions and provisioning to meal preparation and even movie night. Relax and enjoy your dream vacation; we’ll make it seamless and unforgettable. Simple and Comfortable is what we strive for.
Consulting / Coaching
Ready to captain your own yacht but lacking experience?
Preparing for your first extended cruise and unsure about provisioning? Kalypso Yacht Services can help. From engine room checks to hull inspections, we handle the less glamorous tasks. Leveraging our industry connections, we assist with everything from short hauls and surveys to yacht delivery and comprehensive ownership coaching. Let us prepare you for smooth sailing.

RATES
✓Delivery: From $350/day +exp
✓ Charter: From $300/day +exp
✓Consult / Coach: From $50/Hr
Putting it all together
You tell us what you want, and we’ll deliver. We can create a custom package for you, drawing from our Yacht Delivery/Relocation, Charter, and Consulting/Coaching services, to ensure you get exactly what you’re looking for.
Flexible
There is no one single solution – let us help you build the perfect package
Seamanship
Giving you the basic skills to maintain your yacht and crew
Buying or selling?
Kalypso Yacht Services offers complete support throughout your yacht sale or purchase. For sellers, we handle everything from preparation (cleaning, staging, professional photography) to listing with our brokerage partner, Bay Harbor Brokerage. For buyers, we assist with evaluation, surveys, sea trials, and all the paperwork. Post-purchase, we provide relocation, consulting, and coaching, including outfitting, provisioning, and maintenance planning.
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What our customers say

★★★★★
“Capt Mike was extremely professional with the delivery of my new Leopard 42 from Virginia to the Bahamas. I highly recommend him and will definitely use him again”
Chas M.
Owner, Leopard 42

★★★★★
“Mike sailed with us down the coast to Florida and then across the Gulf Stream. He was a pleasure to travel with, and is great at Navigation! He was quick to react to issues on the boat and is also great in the kitchen! Captain Mike would be an asset on any boat.”
David M
Owner, Caliber 42

★★★★★
“Mike is an excellent boat coach who helped me gain the confidence to ensure that I am asking the right questions with my boat purchase. We focused on my sailing goals, and he made sure I was factoring in everything I needed in my future dream boat.”
Lauren S.
Aspiring Owner
Frequently Asked Questions
Simply reach out to our team, providing us with your vision, and we will swiftly develop a plan that will transform your dreams into lasting memories.
Is it possible to change my date?
Yes, we understand that things change; weather, work, maintenance, budgets, etc. We’ll work with you, as long as you work with us.
Can owners participate with relocating?
Absolutely! We highly encourage owners to make the voyage. This builds confidence and knowledge of their vessel.
How does the billing process work?
For each mission, a transparent down payment is required to ensure we can cover necessary expenses such as travel, provisioning, and safety gear. You’ll receive a comprehensive final invoice upon trip completion.
What is the process for getting started?
We focus on the personal aspect of each and every customer. Expect multiple video conference meetings to establish a basic rapport and understanding of the journey.
What other services do you provide?
We’re embedded with a Brokerage company to help buy or sell your vessel. We have staging services to highlight your listing. We also partner with state of the art products to enhance your yacht experience.
Need further assistance?
Need help finding the answers you need? Let’s have a conversation.