About
PlainSailing.com is an award-winning, UK-based yacht and catamaran charter agency that has been helping sailors plan their perfect sailing holidays since 2014. Whether you're an experienced sailor looking for a bareboat yacht, or a newcomer seeking a skippered or fully crewed catamaran, PlainSailing.com covers over 45 departure destinations spanning Greece, Croatia, Italy, France, Montenegro, and the Caribbean, including popular hubs like Athens, Split, Dubrovnik, Antigua, and the British Virgin Islands. The platform provides live pricing and availability search, making it simple to compare boats and find the right vessel for your trip. Customers benefit from a super-low 25% deposit to secure bookings, exclusive early-booking deals, and a dedicated team offering fast, friendly customer support throughout the entire process. PlainSailing works exclusively with hand-picked, trusted charter partners to ensure fleet quality and service standards remain high. Beyond booking, the site offers planning resources including a distance calculator, route planning guides, mooring fee information, transfer advice, security deposit insurance, and discounted Imray maps. With a 4.9/5 rating on Feefo and hundreds of returning customers, PlainSailing.com is a reliable one-stop shop for anyone planning a sailing holiday in Europe or the Caribbean.
Key Features
- Live Pricing & Availability Search: Instantly browse real-time pricing and availability for yachts and catamarans across 45+ destinations worldwide.
- Multiple Charter Types: Choose from bareboat, skippered, or fully crewed charters to match your experience level and preferences.
- Low Deposit Booking: Secure your sailing holiday with just a 25% deposit — one of the lowest on the market — with flexible payment options.
- Hand-Picked Charter Partners: PlainSailing works exclusively with vetted, quality-assured charter fleets to guarantee a high standard of vessels and service.
- Holiday Planning Resources: Access distance calculators, route guides, mooring fee info, transfer advice, and more to plan every detail of your trip.
Use Cases
- Experienced sailors booking a bareboat yacht holiday in the Greek islands or Croatian coast.
- Groups of friends or families planning a skippered sailing holiday without needing prior sailing experience.
- Couples seeking a luxury crewed catamaran experience in the Caribbean or Mediterranean.
- First-time sailors looking for guidance on planning, qualifications, and routes for their first charter trip.
- Repeat charter clients comparing multiple destinations and vessels to find the best value for their annual sailing holiday.
Pros
- Exceptional Customer Service: Rated 5/5 across 525 verified reviews, with customers consistently praising fast responses and attentive support.
- Wide Destination Coverage: Over 45 departure points across Greece, Croatia, the Med, UK, and Caribbean give sailors huge flexibility.
- Lowest Deposit Option: A 25% deposit to lock in bookings makes it accessible for early planners without heavy upfront financial commitment.
- Trusted & Award-Winning: Recognised as 'Best Yacht Charter Agent in Europe', providing confidence and credibility for first-time and returning customers.
Cons
- Not an AI-Powered Platform: The booking and search experience is conventional and does not leverage AI personalisation or smart recommendations.
- Paid Service Only: All charters are paid bookings — there is no free trial or complimentary sailing experience offered through the platform.
- UK-Centric Focus: While destinations are international, the service and support are primarily geared toward UK-based customers, which may limit appeal for non-UK sailors.
Frequently Asked Questions
What types of charter does PlainSailing.com offer?
PlainSailing.com offers bareboat charters (self-skippered), skippered charters (with a professional skipper), and fully crewed charters (including hostess or chef options) across all major destinations.
How much deposit do I need to book?
You can secure a yacht or catamaran charter for 2026 with just a 25% deposit, which PlainSailing.com claims is the lowest deposit available on the market.
Which destinations does PlainSailing.com cover?
PlainSailing.com covers 45+ destinations including Greece (Athens, Corfu, Kefalonia, Rhodes), Croatia (Split, Dubrovnik, Trogir), the wider Mediterranean (Sardinia, Corsica, Ibiza, Malta), and the Caribbean (Antigua, BVI, Bahamas, Grenada).
Do I need sailing qualifications to book a bareboat?
Yes, bareboat charters typically require recognised sailing qualifications. PlainSailing.com provides guidance on what qualifications are needed depending on your destination and vessel choice.
How do I find the right boat for my trip?
Use the live search tool on the website to filter by destination, dates, yacht or catamaran type, and whether you need a skipper, to view real-time pricing and availability across the fleet.
