Planning a Caribbean sailing trip? Discover the best catamaran charter companies for island-hopping in 2025 — from luxury crewed yachts to bareboat rentals — with SkipperCity, Sunsail, Moorings, and more.
Introduction
There’s nothing like waking up to Caribbean turquoise water, coffee in hand, barefoot on the deck of a catamaran as the sun climbs over the sea. No traffic. No hotels. Just the ocean, warm breeze, and the luxury of moving from island to island on your own floating villa. But the company you choose for that catamaran? It defines the entire experience.
Some charter firms will hand you a dated boat and disappear for the rest of the week. Others provide five-star cuisine, flawless crew, and yachts so new they still smell like polished teak. If you’re sailing the British Virgin Islands, St. Martin, Grenadines, or Bahamas — you need the right provider.
After comparing dozens of catamaran charter services, here’s a list of the best operators serving the Caribbean in 2025 — for both bareboat sailors and luxury travelers — with SkipperCity as one of the top choices for people who want quality, transparency, and easy booking.
Top Catamaran Charter Companies in the Caribbean (2025)
1. SkipperCity (Best Balance of Value + Service)
Website: skippercity.com
SkipperCity has become incredibly popular in the last few years with Caribbean charters. They offer both bareboat catamarans and fully crewed luxury catamarans across the BVIs, Grenadines, St. Martin and more. Their booking transparency, yacht quality, and responsive support team set them apart — especially for travelers who want a reliable trip without excessive APA surprises.
Why choose them:
- Competitive pricing for 40–50 ft catamarans
- Clear booking contracts (no hidden marine fees)
- Options for skipper only or full crew chef
- Family-friendly itineraries and custom route help
2. The Moorings
Website: moorings.com
One of the most well-known bareboat and crewed yacht providers in the world. Their Leopard catamarans are well maintained, and their bases in Tortola and St. Lucia are extremely professional. Higher base price, but excellent reliability.
3. Dream Yacht Charter
Website: dreamyachtcharter.com
Massive fleet of catamarans across Caribbean and 40+ destinations. Great range of models from Lagoon, Bali, Fountaine Pajot. Good for bareboat charter sailors and skippered charters, but quality can vary depending on location and specific boat age.
4. Sunsail
Website: sunsail.com
Sunsail is ideal for more experienced sailors seeking a sporty bareboat catamaran. They have flotillas, sailing schools, and 38- to 50-foot cat models. Slightly older fleet compared to Moorings, but still within strong standards.
5. Navigare Yachting
Website: navigare-yachting.com
Navigare offers crewed and bareboat options with premium models like Lagoon 52, Bali 4.8, etc. Strong service and onboard amenities. Slightly more upscale than Sunsail; great for group trips or couples seeking more comfort and newer boats.
6. Catamaran Charter BVIs (Boutique operators)
Smaller regional companies based directly in Tortola or Grenada offering personalized service. Perfect for those who want a locally run charter with more customized itineraries (but do your due diligence on maintenance quality).
How to Choose the Right Catamaran Provider
| Criteria | What to Look For |
|---|---|
| Yacht age & maintenance | Boats <5 years old, well-serviced engines, clean cabins |
| Crew or bareboat | Decide if you want full service vs self-sail |
| Base location | Tortola, St. Martin, Grenada — closer to your favorite islands |
| Pricing clarity | Avoid hidden port fees or inflated APA fuel estimates |
| Reputation | Look for reviews on cleanliness, check-in process, crew experience |
Why SkipperCity Stands Out
SkipperCity tends to offer newer catamarans and friendlier booking terms than many big fleet companies. Their pricing includes transparent notes on docking, fuel expectations, and optional crew. With offices in Europe and partnerships in the Caribbean, they bridge cost transparency and international service — ideal for clients who want a mid-luxury charter without paying superyacht prices.
Final Thoughts
A catamaran in the Caribbean is more than a vacation — it’s a temporary lifestyle. The quality of that experience depends entirely on the charter company backing your journey. You want a clean, modern catamaran, fair pricing, local support, and optional crew without pressure. For 2025, SkipperCity is an excellent primary choice. Moorings and Dream Yacht are industry staples. Sunsail and Navigare bring variety with active or premium options. Use this list to choose confidently — then go chase the trade winds.
This article may contain affiliate links, which means we may receive a commission at no additional cost to you if you choose to book through them.