Planning a charter vacation in 2020? From watching the Monaco Grand Prix in Monte-Carlo to heading to St Barths for the Bucket regatta, take a look at the best destinations to visit by boat each month with our ultimate charter calendar for 2020.

January: Ring in 2020 in Phuket

Shun the crowds of St Barths and start your New Year with a January cruise around Thailand’s largest island, Phuket.

Once you have seen in the New Year in style, head to Phang Nga Bay or further afield to Koh Lipe and Koh Rok while the masses head back home after the holidays. “In one week you can do a 130nm trip and see lots of different islands,” says Captain Alessio Donia of 26-metre Maxxx, available for charter with Northrop & Johnson. “The best waters are in Koh Lipe and [there are] good local dive companies to take out guests.”

Every year, from January to March, more than 2,500 humpback whales gather in Samaná Bay to breed, so observe what Worth Avenue Yachts’ Graham Sullivan calls “the most magnificent thing Mother Nature can offer you”.

With its secluded anchorages in front of white-sand beaches flanked by lush mountains, Samaná Peninsula is the perfect base for exploration. While there, take the tender to visit the karst formations of Los Haitises National Park.

If superyacht racing is on your agenda, there is nowhere better to be in March than St Barths for the Bucket, as the biggest and most beautiful sailing superyachts fight it out. Either charter a sailing yacht to compete, or opt for a motor yacht and enjoy spectating from the sundeck.

After a hard day’s racing, make sure you sample the food at Bonito in Gustavia. “They have the most amazing Chilean sea bass with a vanilla rum beurre blanc sauce,” says Ami Ira of Bluewater. “And don’t miss going to Colombier Beach to snorkel with the turtles.”

Before the new foiling monohull sailing yachts line up in Auckland for the 36th America’s Cup in 2021, the five teams will be put to the test in World Series competitions around the globe. The first America’s Cup World Series regatta will take place in Cagliari, Sardinia.

“With a charter like this, booking early is a must,” says Edmiston’s Matthew Gant. “You want to make sure you get the right berth so that you are in the right area for all the after-race parties.” Post-racing, stretch your sea legs and explore the natural beauty of this Italian island. “The shallow, transparent waters of Cala Luna allow the sunlight to reflect on the golden sand, and deep caves are carved into the limestone cliffs, perfect for snorkelling,” says Irini Sarantis of IYC.

This historic highlight of the Formula 1 season packs wheel-to-wheel racing, high-octane speed and celebrity-filled parties into one epic weekend.

As the circuit runs right along the quayside in Monaco, there is no more glamorous a spot from which to take in all the action than a yacht moored in Port Hercules. “Book a boat that is berthed on Quai Kennedy,” advises Pierre Hurel of Camper & Nicholsons. “Other berths in the port do not allow a decent view of the race. For this event it is more important to get a berth with a view than a yacht with the precise characteristics you desire.” Berths and yachts get booked up far in advance, so put your foot on the gas to make it there this May.

Beat the heat, the crowds and the meltemi by heading to the Greek cruising grounds of the Cyclades early in the summer. “In Mykonos in June there are no meltemis, those strong northern winds, and no crowds,” says Popy Kaia of Atalanta Golden Yachts. The Greek island might be known for its party culture, but there is much more to this beautiful spot. Kaia recommends visiting the ancient ruins of nearby island Delos to experience some culture. When you want to soak up the sun, however, book a berth at Psarou Beach in front of the famed Nammos beach bar. “And then head to Scorpios to chill at sunset,” adds Kaia.

The sailing capital of the world, this historic town comes alive in the summer with parties and polo matches. On your visit, don’t miss picturesque Block Island, a short cruise from Newport. Work up an appetite on the Newport Cliff Walk, winding nearly six kilometres along the shoreline and taking in views of the Bellevue mansions.

“Have sunset drinks looking over the harbour from the Vanderbilt hotel’s Roof Deck bar,” says Eva Hiebert of Denison Yachting. “Another great location for sunset drinks and a meal is the Lawn at Castle Hill Inn, where you can watch sailing regattas as well as the signature Newport sunset.” If you’re settling into Rhode Island life, you could even stick around until August for Newport Jazz Festival.

The oldest film festival in the world is also the most glamorous. It has all the screenings and celebrity attendees that you would expect from a leading film festival (it’s considered one of the “big three”, along with Cannes and Berlin) but guests arrive on Rivas, and the parties are upgraded to fabulous balls.

Once the festivities have finished there is plenty to hang around for. “Obviously there are the major landmarks like the Basilica and Piazza San Marco, but we always advise clients to explore the little alleys, bridges and quieter areas that make up Venice’s charm,” says Sophie Holmes of Burgess. “In terms of restaurants, we suggest Antico Martini, In Acqua and the Cipriani hotel.” If you are feeling thirsty you can also head to Harry’s Bar for some carpaccio and a Bellini, both of which are said to originate from this Venetian mainstay.

Just because the Mediterranean charter season draws to a close in Autumn, it doesn’t mean superyachts should rush off. The sun-drenched Les Voiles de Saint-Tropez regatta on the C?te d’Azur is the perfect September stop-off.

Charter a sailing boat and take your place at the starting line or watch the J Class and Maxi fleets race from the deck of your motor yacht. “Most of the competing yachts arrive ahead of time so this is a great opportunity to stroll around and view them docked,” advises Ocean Independence’s Enora Vern. “Your captain will be able to choose a spot on the water to get a good view of the action during racing. It is the perfect way to get close and soak up the atmosphere. You can return to port in the afternoon when happy hour begins.”

Come October, New York City folk flock north-east to see the leaves change in bright explosions of red, yellow and burnt orange. It’s a sight to behold, and goes hand in hand with enjoying the other autumnal delights of warm apple cider, pumpkin-flavoured everything and taking the kids for a jovial ride on a tractor-pulled trailer.

Most people drive to see the leaves changing but a much better way to go is by boat, sailing into Camden Harbour and taking in views of the lighthouse-strewn Maine coast. “Camden is framed against the Camden Hills State Park mountains. With its postcard-perfect harbour, it is one of the state’s most charming locations, and the autumn foliage will be stunning to see from here,” says Burgess’s Holmes. “It is simply a picturesque cruising ground with incredible panoramic vistas from every vantage point.” Holmes recommends getting off the yacht for dinner to dine at Natalie’s, a French restaurant at Camden Harbour Inn, or tendering to Pilgrim’s Inn on Deer Isle.

Considering buying your own yacht? Where better to start than the biggest boat show in the world? The Fort Lauderdale International Boat Show is an ideal place to see new superyachts, tenders and everything in between. Snag an invite to the BOAT International party if you can.

Although South Florida is obsessed with whatever is the latest and greatest, the best restaurants are actually those that have been around forever. For enjoying a meal close to the boat show, “the best restaurant hands down is Canyon, but a very close second is Valentino,” says Ira of Bluewater. After the show, cruise down to the Florida Keys to carry on enjoying the warm winter weather.

Some people dream of a white Christmas, others dream of a white sandy-beach Christmas. If you fall into the latter category, be sure to book a Yuletide charter in the BVIs. These popular cruising grounds have something for the entire family, from excellent diving and sailing to famous beach bars and five-star dining.

“Jost Van Dyke is the smallest of the BVIs with the biggest personality,” says Sarantis of IYC. “Although it only has 25 permanent residents it is a lively destination, filled with great bars and eateries. In the Great Harbour alone you will find five restaurants. Try Corsairs for a lobster dinner, then head to Foxy’s Tamarind Bar to get the night started with a rum cocktail.”