Your Questions Answered
The Caribbean is one of the most popular and rewarding regions for a sailing holiday. From the steady trade winds to island-hopping adventures, there’s something for everyone. These FAQs cover essential information about chartering in the Caribbean including the Bahamas:the best times to go, choosing between islands, what’s included, and how to get started.
Explore Destination FAQs
Do I need a sailing qualifications to bareboat charter in the Caribbean?
In most of the Caribbean, you do not need a formal sailing qualification such as an ICC (International Certificate of Competence) or RYA certificate in order to take a bareboat charter. What you do need is to demonstrate sufficient sailing experience and practical knowledge to the charter operator Continue Reading...
What sailing qualifications are required to bareboat charter in the Caribbean?
Unlike some other regions, most Caribbean destinations do not require a formal sailing licence to charter a bareboat. However, you must demonstrate sufficient experience and competence to safely operate the vessel. Continue Reading...
When should I book a charter boat in the Caribbean and Bahamas?
The best time to charter in the Caribbean and Bahamas is from December through July, with peak season running mid-December to March. That’s when you’ll find the most settled weather and lively island atmospheres that are perfect for escaping southern hemisphere winters or northern chills. Continue Reading...
What do you recommend about boat chartering in the Caribbean?
Chartering a boat in the Caribbean - including The Bahamas - is one of the most rewarding sailing experiences you can have. We recommend the region for its warm climate, steady trade winds, short sailing distances, and abundance of beautiful anchorages. Continue Reading...
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...
Latest Blog Posts
-
Sailing Between US VI, British VI and Spanish VI
Step-by-step guide to current regulations for sailing between the British Virgin Islands and US Virgin Islands, and the US Virgin Islands and Spanish Virgin Islands.
-
A Short History of Chartering in Bay of Islands, NZ
Once home to over 40 bareboat charter yachts, the Bay of Islands stood proudly among the world’s sailing destinations. Kiwis and visitors alike could explore this subtropical paradise aboard locally managed fleets. Times have changed.
-
Getting to Vava'u, Tonga for your Sailing Holiday (2025)
Your 2025 guide to getting to Tonga—international flights, Fiji to Vava‘u direct service, domestic Saab 340B airlink from Tongatapu and ferry option via Haʻapai.
-
Why a Lot of Itinerary Advice Misses the Mark for Sailing Holidays
Learn why many bareboat sailing itineraries found online can be misleading, and how first-hand advice makes all the difference.
-
Modern Consumer Tech on Sailing Charter: do we really need it?
When thinking about a sailing holiday, it’s natural to wonder whether to bring our modern gadgets along for the ride - or leave them behind entirely. Technology is so deeply woven into the fabric of our daily routines. So should we pack our tablets and smartphones or is a sailing charter the perfect opportunity to fully disconnect and reset?
The Sail Connections Guarantee
One contact - every option - advice you can trust.
- Matching any competitive offer
- Sourcing boats with discounts available
- Personalising our proposal just for you
- Qualifying the operator as well as the boat
- Advising without bias based on 25+ years of experience
- We do more than just book yachts!
We will match any discount website offer on charter boat price, and still provide our customary high level of service.
Get in Touch