As the horizon of 2026 unfolds, the call of the open sea grows louder. Sailing holidays in 2026 are no longer confined to summer: with the right route, a boat rental becomes a year-round way to explore new coastlines, islands and cultures — at your own pace.
Whether you’re a seasoned sailor, travelling with friends, or planning your first adventure with a skipper, this guide will help you choose the best sailing destination by month. From Caribbean trade winds to Mediterranean shoulder seasons and dreamy island hopping, here are the best places to go sailing in 2026 — one unforgettable month at a time.
Kick off the year with a British Virgin Islands sailing holiday, one of the easiest and most iconic spots for a winter bareboat charter or catamaran rental. Steady trade winds, short distances and protected waters create perfect conditions for stress-free island hopping. Swim at The Baths of Virgin Gorda, relax in postcard bays, and enjoy the laid-back atmosphere of Jost Van Dyke.
Top Tip: Visit Norman Island’s Treasure Caves early in the day for the best light and fewer boats.
Best Boat Type: Catamaran
Must-See: The wreck of the Rhone, a legendary dive site rich in marine life.
.
Boat Rental in the British Virgin Islands
February is perfect for a Grenada sailing trip, with warm temperatures, calm seas and reliable breezes. Known as the “Spice Isle”, Grenada blends vibrant culture with relaxed cruising: anchor in quiet bays, stroll around St. George’s, unwind on Grand Anse Beach, and snorkel at the famous Molinere Underwater Sculpture Park.
Top Tip: Stop by Grenada’s spice markets for a local experience that instantly sets the mood for your Caribbean charter.
Best Boat Type: Catamaran
Must-See: Levera National Park, a peaceful stretch of coastline with excellent swimming and wildlife.
.
.
March is one of the best months for sailing in Saint Vincent and the Grenadines. The sea is warm, visibility is high, and the island chain delivers the kind of route sailors dream about: Bequia, Mustique and the Tobago Cays, with lagoon-blue water and unforgettable anchorages.
Top Tip: Hike to La Soufrière volcano on Saint Vincent for incredible views — then reward yourself with a sunset swim back at the boat.
Best Boat Type: Catamaran
Must-See: The Tobago Cays Marine Park for snorkelling and sea turtle sightings.
.
Boat Rental in Saint Vincent & the Grenadines
.
Sail into spring with a Turkey yacht charter along the Turquoise Coast. April brings milder temperatures, quieter bays and a perfect balance between sailing and sightseeing. Explore Fethiye’s dramatic coastline, anchor near the Blue Lagoon, visit Lycian rock tombs and enjoy the atmosphere of coastal markets and marinas.
Top Tip: Sail to Butterfly Valley (boat access only) for a scenic hike among cliffs, waterfalls and wild flora.
Best Boat Type: Sailboat
Must-See: The ruins of Gemiler Island, steeped in Byzantine history.
.
.
May is one of the smartest months for a sailing holiday on the Amalfi Coast. The weather is already beautiful, the sea is welcoming, and the coastline feels less crowded than in summer. Cruise past colourful villages on the cliffs, anchor near hidden coves, and explore iconic towns like Positano and Ravello — with the freedom that only a boat can give you.
Top Tip: Enjoy a seaside dinner with fresh seafood and limoncello — then head back on board for the quietest night you’ll ever spend near the coast.
Best Boat Type: Sailboat or Motorboat
Must-See: Fiordo di Furore, a spectacular fjord-like cove with crystal-clear water.
Don’t Forget Visa Arrangements: If you’re travelling from outside the EU and planning to experience Naples by sea, remember to schedule your Schengen visa appointments well in advance. Peak travel seasons can fill up appointment slots quickly, so it’s best to secure your visa in plenty of time before setting sail.
.
Boat Rental on the Amalfi Coast
.
June is ideal for a Canary Islands sailing holiday, especially around Tenerife. Expect warm Atlantic days, consistent winds and dramatic volcanic scenery. It’s a great month for sailors who want a mix of longer passages and rewarding stops, with the bonus of incredible marine life and golden sunsets at anchor.
Top Tip: Plan a sail towards La Gomera for one of the best chances to spot dolphins and whales in the region.
Best Boat Type: Sailboat or Catamaran
Must-See: The Tenerife–La Gomera channel for unforgettable wildlife encounters.
.
.
July in Mallorca is made for a classic Mallorca sailing holiday: warm water, long days and plenty of anchorages to choose from. Sail the rugged coast, pause in charming ports like Port de Sóller, and spend your afternoons swimming in calm coves before heading ashore for tapas and late sunsets.
Top Tip: Explore the sea caves of Cova des Coloms for an adventurous swim (conditions permitting).
Best Boat Type: Sailboat
Must-See: Cala Deià, a small, photogenic cove with bohemian vibes.
.
.
August brings the best of Croatia’s Kornati Islands: a spectacular archipelago of over 140 islands with protected waters and moon-like landscapes. A Kornati Islands yacht charter is perfect for sailors who want scenic navigation, swimming stops and unforgettable nights under the stars — all within easy daily distances.
Top Tip: Book a table in a local konoba reachable only by boat for the most authentic Kornati evening.
Best Boat Type: Sailboat
Must-See: Levrnaka Island’s Lojena Beach, one of the best swimming spots in the area.
.
Yacht Charter in the Kornati Islands
.
September is a favourite for sailors planning a Sardinia boat rental. The sea is still warm, the winds are pleasant, and the atmosphere becomes calmer after peak season. Cruise turquoise bays, visit chic marinas, and enjoy the island’s famous beaches with more space — and more serenity.
Top Tip: Anchor near the Maddalena Archipelago for swimming in unbelievably clear water.
Best Boat Type: Sailboat
Must-See: Cala Corsara on Spargi Island, a jewel-like beach framed by dramatic rocks.
.
.
October is a brilliant time for a Sporades Islands sailing holiday. The sea is calm, the islands are quieter, and the landscapes feel even more vivid. Explore Skopelos’ lush coastline, discover Alonissos’ hidden coves, and enjoy the charming atmosphere of Skiathos without the summer rush.
Top Tip: Sail to the Blue Cave near Alonissos for magical light at sunrise.
Best Boat Type: Sailboat
Must-See: Lalaria Beach on Skiathos, famous for its white cliffs and crystal water.
.
Boat Rental in the Sporades Islands
.
November in the Seychelles is ideal for a Seychelles catamaran charter, with warm waters, stunning visibility and island-hopping routes that feel like a dream. Sail between granite islands, snorkel vibrant reefs, and anchor off beaches that look untouched — where every day starts with turquoise water and ends with a glowing sunset.
Top Tip: Visit Praslin’s Vallée de Mai (UNESCO World Heritage) to see the rare coco de mer palms.
Best Boat Type: Catamaran
Must-See: Anse Lazio, one of the most iconic beaches in the Seychelles.
.
Catamaran Rental in the Seychelles
.
End the year with a Martinique sailing holiday, one of the best choices for a festive winter catamaran rental in the Caribbean. Enjoy steady trade winds, warm days, and a unique blend of French-Caribbean flavours — from colourful seaside villages to lush nature and calm anchorages.
Top Tip: Add a rum distillery stop to your itinerary for a truly local taste of Martinique.
Best Boat Type: Catamaran
Must-See: Anse d’Arlet, with its iconic beachfront church and postcard anchorage.
.
Catamaran Charter in Martinique
.
.
€ 4,040
price of the whole boat
€ 2,240
price of the whole boat
€ 1,575
price of the whole boat
€ 4,200
price of the whole boat
€ 4,725
price of the whole boat
€ 1,655
price of the whole boat
€ 1,105
price of the whole boat
€ 2,325
price of the whole boat
Our regular email newsletters include information about our boats, holiday ideas, destination insights and cultural briefings. You can unsubscribe at any time and we'll treat your data with respect, never passing on your details to third parties. Find full details of our data management in our Privacy policy page
By signing up, I agree to Sailogy's T&C's and Privacy policy
Looking for inspiration for your next sailing holiday? Packed with insights on trending sailing destinations plus stories from expert sailors and first-timers, our brand new digital magazine - Magister Navis - will guide your way to your next sail.
View magazine
