I’ve done plenty of travelling by boat over the years: ferries out to Sark and Rathlin Island, the Spirit of Tasmania, and the Drake Passage to Antarctica, which I’m still recovering from. None of those trips were warm. If you want sunshine on the water, though, you have to plan around the calendar. Croatia in July is brilliant. Croatia in January is grey and closed.
So this post is about warm-weather yacht travel destinations that stay good for most of the year, not just for a few summer weeks. Each comes with the best months and the season to avoid.
Male to Vadoo boat
First, Decide on Your Boat: Charter or Own?
For a one-off trip, chartering is hard to beat. I made the case for it in Plain Sailing – Advice for Stress-Free Travel. But if you keep going back to the same waters every winter, owning starts to make more sense. You keep your own gear on board, travel on your own schedule and don’t have to learn a new boat every trip.
What surprises many first-time buyers is that you don’t have to buy locally and then spend weeks moving the boat south. Browse luxury yachts for sale and you’ll find plenty already sitting in Florida, Mexico or the Caribbean. If you’re Canadian, working with a yacht broker in Toronto doesn’t limit you to Great Lakes boats either.
Luxury Yacht Sales Toronto, for example, lists new and pre-owned vessels across Canada, the US, Mexico and the Caribbean. It also helps coordinate the parts that trip up first-time buyers: surveys, boat history reports and financing through a network of more than 100 lenders. Buying a boat thousands of kilometres away is a lot less stressful when someone is checking the details for you.
Then, Know Your Storm Season
The Atlantic hurricane season runs from 1 June to 30 November and peaks from mid-August to October. On the Pacific side of Mexico it starts earlier, on 15 May. Nearly every year-round boating destination in the Americas has good months and risky months. The trick is to move with the seasons.
1. The Bahamas
Bimini is only around 50 miles from the Florida coast, which makes the Bahamas the easiest first step into tropical cruising for North Americans. The Exumas are the highlight: a chain of cays with water so clear you can watch your anchor dig in.
Best months: December to May.
Watch out for: Shallow water. Draft matters here, so catamarans and shallow-draft powerboats have the advantage. You’ll also need a cruising permit, and the Gulf Stream crossing should only be made with a settled forecast. Never cross when a north wind is blowing against the current.
2. British Virgin Islands
If you’re after sailing destinations for beginners, start here. The islands sit close together around the sheltered Sir Francis Drake Channel, so most passages are short and you can usually see your next stop. Moorings are easy to find, and the trade winds are fairly reliable in winter.
Best months: December to May.
Watch out for: Peak-season crowds around Christmas, and the hurricane months. If you’re flying in, I’ve written about getting a visa on arrival on Beef Island.
3. Grenada and the Grenadines
Grenada is the closest thing the Caribbean has to a year-round option. It sits near the southern edge of the hurricane belt, and many boat insurers set latitude limits for the storm months, so plenty of owners bring their boats south to spend the summer here. From Grenada you can hop north to Carriacou and the Tobago Cays, where you’ll snorkel with turtles.
Best months: All year, with the calmest trade winds from December to June.
Watch out for: “Lower risk” doesn’t mean no risk. Keep an eye on the forecasts from August to October.
4. The Florida Keys
The Keys are warm all year and easy to reach. For Canadian boaters, they’re the natural end point of the trip south along the Intracoastal Waterway. Marinas, fuel and repairs are never far away, so it’s a good place to get to know a new boat.
Best months: November to May.
Watch out for: Summer heat, afternoon thunderstorms and hurricane season. Winter marina rates climb, so book ahead.
5. Sea of Cortez, Mexico
This is the wild card. Based out of La Paz, you can anchor off Isla Espíritu Santo, swim with sea lions and go days without seeing another boat. It suits boaters on the Pacific side of North America.
Best months: October to June.
Watch out for: The Pacific hurricane season, and summer heat that’s brutal inside the gulf.
6. Bonaire and Curaçao
These two sit south of the main hurricane belt, which makes them some of the most dependable tropical yacht vacation spots in the region. Bonaire’s waters are a protected marine park, so anchoring isn’t allowed and you tie up to a public mooring.
Best months: All year.
Watch out for: Strong, steady trade winds, and limited provisioning compared with bigger islands.
Yacht Travel Tips for Following the Sun
- Check your insurance first. Many policies restrict where the boat can be during hurricane season. That clause may decide your summer plans for you.
- Match the boat to the water. A deep-keel sailboat that suits Georgian Bay may struggle in the Bahamas.
- Sort out paperwork early. Cruising permits, customs check-ins and crew documents vary from country to country and can take time.
- Plan for heat. Shade, fans and plenty of water matter more than you’d think.
Keep Chasing the Sun
The best warm-weather cruising comes down to timing. Get the season right and the Caribbean, the Keys or the Sea of Cortez can give you warm water in almost any month. Get it wrong and you’ll spend the trip watching forecasts.
If you’re planning island time, have a look at the rest of my Caribbean travel stories for beaches, food and border crossings from across the region. Don’t stop living!