Sail through 2021: Boat Holidays for Every Month of the Year

sailing holiday calendar

Get ready (and get excited!) for sailing in 2021 with our calendar guide on the best sailing destinations per month — twelve months of the year, twelve fantastic locations to visit on a boat holiday.

Where to go sailing in 2021

Where to take a sailing holiday in January:

Kick off the year with a Caribbean sailing holiday in Martinique: sandy beaches, stunning scenery, and superb weather for escaping the winter cold.  

sailing in martinique


  • Les Salines beach
  • The Islet of Chevalier
  • The canyon at Fort-de-France

Average daily high/low temperatures: 83°F/73°F

Where to take a sailing holiday in February: The Bahamas

February is within The Bahamas’ dry season, making it the perfect time to enjoy this ecological oasis known for its crystal-clear waters and laid-back vacation vibes.

sailing holiday in the bahamas


  • The pineapple fields and pink-sand beaches of Eleuthera
  • The tropical, bright city life of Nassau
  • Sunken ships and forest-like coral reefs

Average daily high/low temperatures: 78°F/67°F

Charter a boat in The Bahamas

Where to take a sailing holiday in March:
The British Virgin Islands

60 pristine Caribbean islands offer the perfect March getaway with endless blue skies, inviting waters, and chill beach-side dining spots.

sailing the bvi


  • Island hopping from Tortola
  • Diving at the wreck of the RMS Rhone
  • The Baths on Virgin Gorda

Average daily high/low temperatures: 84°F/74°F

Charter a boat in The British Virgin Islands

Where to take a sailing holiday in April: Greece

As April marks the start of Greece’s sailing season, you’ll beat the summer crowds but still enjoy lovely sailing conditions, plus that famous Hellenic Mediterranean culture.

sail greece


  • UNESCO World Heritage Sites in cities including Athens and Rhodes
  • Traditional fishing villages in the Cyclades
  • Countless beautiful beaches

Average daily high/low temperatures (Athens): 72°F/54°

Charter a boat in Greece

Where to take a sailing holiday in May:

Head to Seychelles in May for ideal sailing conditions. Swimming and snorkeling are also superb at the start of the month, while the natural beauty of the islands is breathtaking year-round.

sailing in seychelles


  • Exquisite white sandy beaches
  • Arulmigu Navasakthi Vinayagar Temple in Victoria 
  • Morne Seychellois National Park

Average daily high/low temperatures: 85°F/79°F

Charter a boat in Seychelles

Where to take a sailing holiday in June:

Italy in June is unbeatable: warm weather, thinner crowds, and everything that makes the “Bel Paese” a sailing holiday dream, from diverse coastal landscapes to Neapolitan-style pizza.

sailing holiday in Italy


  • Calabria’s beaches, especially Capo Vaticano
  • Flowers in bloom on Sardinia
  • The ruins of Pompeii

Average daily high/low temperatures (Calabria): 84°F/72°F

Charter a boat in Italy

Where to take a sailing holiday in July:

For a sailing trip that combines an agreeable Scandinavian lifestyle with unspoiled coastlines, celebrated Nordic seafood, and seemingly never-ending daylight, head to Sweden in July.

sailing holiday sweden


  •     The capital city of Stockholm
  •     Historic Visby on the island of Gotland
  •     The Gulf of Bothnia

Average daily high/low temperatures: 71°F/55°F

Charter a boat in Sweden

Where to take a sailing holiday in August:

With its 1,000 islands, rich cultural heritage, and postcard-perfect seascapes, cityscapes, and landscapes, Croatia is easily one of our top destinations for sailing — and there’s no better time to visit than late summer.

sailing calendar croatia


  • The beautiful cities of Dubrovnik and Split
  • Kornati National Park
  • Spectacular array of diverse beaches

Average daily high/low temperatures: 84°F/65°F

Charter a boat in Croatia

Where to take a sailing holiday in September:

Early fall is a great time for a US sailing holiday, whether you’re looking to experience New England’s brilliant foliage or to draw out the summertime in the Gulf of Mexico’s sunshine.

sailing in the USA


  • Palm-lined beaches of the Florida Keys
  • Lobster fishing ports in Maine
  • Whale watching in Northern California

Average daily high/low temperatures (Florida Keys): 87°F/79°F

Charter a boat in the USA

Where to take a sailing holiday in October:

Between the incomparable beauty of the Mediterranean and Aegean Seas and Turkey’s vibrant culture, the “Turquoise Coast” in October makes for a fantastic sailing trip.

sailing in turkey


  • Butterfly Valley
  • The bustling capital of Istanbul
  • Snorkeling in Hidayet Bay

Average daily high/low temperatures: 71°F/58°F

Charter a boat in Turkey

Where to take a sailing holiday in November:

There are many reasons to visit Thailand in November — the balmy weather and dry season make for enjoyable sailing, while the Loi Krathong Festival and blooming of the Bua Tong Blossom Fields make the month truly special.

sailing in thailand


  • Patong on Phuket Island
  • Ko Samet Island near Bangkok
  • Spas at Ko Samui

Average daily high/low temperatures: 87°F/76°F

Charter a boat in Thailand

Where to take a sailing holiday in December:
Antigua and Barbuda

Finish off a year of sailing in 2021 by relaxing in a Caribbean paradise complete with a tropical climate, dazzling blue-green waters, and beaches as soft and white as powdered sugar.  

sailing in antigua and barbuda


  • Frigate Bird sanctuary in Barbuda
  • Swimming with stingrays in Antigua
  • Antigua rainforest canopy

Average daily high/low temperatures: 83°F/75°F

Charter a boat in Antigua and Barbuda

Enjoy your holidays sailing in 2021

And there you have it — our list of the best sailing destinations per month. We wish you a happy year of sailing!