Epic Sailing Trips You Must Experience This Year

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Sailing offers a unique way to explore the world, combining adventure with relaxation. Whether you’re a seasoned sailor or a first-time adventurer, these eight unforgettable sailing trips around the world will provide you with memories to last a lifetime. From the turquoise waters of the Caribbean to the enchanting Greek Isles, each destination promises an epic journey.

1. The Caribbean: Island Hopping Paradise

Photo by Jakob Owens on Unsplash

Itinerary Highlights

  • Day 1: Start your journey in St. Lucia, exploring its lush rainforests and stunning Pitons.
  • Day 2–3: Sail to the Grenadines, where you can snorkel in the Tobago Cays and visit the quaint island of Bequia.
  • Day 4–5: Head to Barbados, enjoying its vibrant culture and beautiful beaches.
  • Day 6–7: End your trip in Antigua, known for its historic sites and 365 beaches.

Must-See Sights

  • The Pitons in St. Lucia
  • Snorkeling in the Tobago Cays
  • Harrison’s Cave in Barbados
  • Nelson’s Dockyard in Antigua

Insider Tips

  • Best time to visit: December to April for calm seas and sunny weather.
  • Pack light, breathable clothing, and plenty of sunscreen.

Book Your Caribbean Sailing Adventure here

2. The Greek Isles: A Sailor’s Dream

Photo by orva studio on Unsplash

Itinerary Highlights

  • Day 1: Begin in Athens, visiting the Acropolis before setting sail.
  • Day 2–3: Sail to Mykonos, famous for its nightlife and stunning beaches.
  • Day 4–5: Explore Santorini’s iconic blue-domed churches and volcanic landscape.
  • Day 6–7: Discover the charm of Crete, with its rich history and beautiful beaches.

Must-See Sights

  • The Acropolis in Athens
  • Mykonos Windmills
  • Oia, in Santorini
  • Knossos Palace in Crete

Insider Tips

  • Best time to visit: late spring or early fall to avoid the summer crowds.
  • Try local delicacies like moussaka and souvlaki.

Plan Your Greek Isles Sailing Trip here

3. The French Riviera: Glamorous Sailing

Photo by Antoine Rakotozafy on Unsplash

Itinerary Highlights

  • Day 1: Start in Nice, exploring its markets and old town.
  • Day 2–3: Sail to Cannes, enjoying its famous promenade and luxury shops.
  • Day 4–5: Visit St. Tropez, known for its beaches and vibrant nightlife.
  • Day 6–7: End in Monaco, marveling at its opulent casino and royal palace.

Must-See Sights

  • Promenade des Anglais in Nice
  • La Croisette in Cannes
  • Pampelonne Beach in St. Tropez
  • The Prince’s Palace in Monaco

Insider Tips

  • Best time to visit: May to September for warm weather and a lively atmosphere.
  • Dress stylishly, especially if you plan to visit high-end restaurants or clubs.

Explore the French Riviera Sailing Routes here

4. The Amalfi Coast: Italy’s Gem

Photo by KaLisa Veer on Unsplash

Itinerary Highlights

  • Day 1: Begin in Naples, visiting Pompeii and the Amalfi Coast.
  • Day 2–3: Sail to Capri, exploring its Blue Grotto and charming streets.
  • Day 4–5: Visit Positano, known for its cliffside views and pastel houses.
  • Day 6–7: End in Sorrento, enjoying its stunning coastal views and lemon groves.

Must-See Sights

  • Pompeii’s ancient ruins
  • Blue Grotto in Capri
  • The beaches of Positano
  • Sorrento’s Piazza Tasso

Insider Tips

  • Best time to visit: April to October for pleasant weather.
  • Indulge in local dishes like pizza margherita and limoncello.

Book Your Amalfi Coast Sailing Experience here

5. The Seychelles: Tropical Paradise

Photo by Michaela Římáková on Unsplash

Itinerary Highlights

  • Day 1: Start in Mahé, exploring its beautiful beaches and vibrant markets.
  • Day 2–3: Sail to Praslin, home to the famous Anse Lazio beach.
  • Day 4–5: Discover La Digue, with its stunning granite boulders and secluded beaches.
  • Day 6–7: End your trip on Curieuse Island, known for its giant tortoises and mangrove forests.

Must-See Sights

  • Anse Lazio in Praslin
  • Anse Source d’Argent in La Digue
  • Giant tortoises in Curieuse Island
  • Victoria Market in Mahé

Insider Tips

  • Best times to visit: April, May, October, and November for calm seas and good weather.
  • Pack snorkeling gear to explore the vibrant coral reefs.

Discover Seychelles Sailing Trips here

6. The Bahamas: Crystal Clear Waters

Photo by Ryan Geller on Unsplash

Itinerary Highlights

  • Day 1: Begin in Nassau, exploring its historic sites and bustling markets.
  • Day 2–3: Sail to Exumas, swim with pigs, and visit Thunderball Grotto.
  • Day 4–5: Discover Eleuthera, known for its pink sand beaches.
  • Day 6–7: End in Grand Bahama, enjoying its beautiful beaches and underwater caves.

Must-See Sights

  • Swimming pigs in Exumas
  • Pink Sand Beach in Eleuthera
  • Lucayan National Park in Grand Bahama
  • Atlantis Resort in Nassau

Insider Tips

  • Best time to visit: November to April for warm weather and fewer crowds.
  • Bring an underwater camera to capture the vibrant marine life.

Book Your Bahamas Sailing Adventure here

7. The Whitsundays: Australia’s Treasure

Photo by Marcel Wiemers on Unsplash

Itinerary Highlights

  • Day 1: Start in Airlie Beach, the gateway to the Whitsundays.
  • Day 2–3: Sail to Whitehaven Beach, known for its white silica sand.
  • Day 4–5: Explore Hamilton Island, offering a mix of luxury and natural beauty.
  • Day 6–7: Visit the Great Barrier Reef, snorkeling among vibrant coral and marine life.

Must-See Sights

  • Whitehaven Beach
  • Hill Inlet lookout
  • Hamilton Island’s Marina
  • Great Barrier Reef

Insider Tips

  • Best time to visit: May to September for dry, cool weather.
  • Don’t miss the Heart Reef, best viewed from a seaplane or helicopter.

Discover Whitsundays Sailing Trips here

8. The Dalmatian Coast: Croatia’s Jewel

Photo by Alexey Savchenko on Unsplash

Itinerary Highlights

  • Day 1: Begin in Split, exploring its historic Diocletian’s Palace.
  • Day 2–3: Sail to Hvar, known for its lively nightlife and beautiful beaches.
  • Day 4–5: Visit Korčula, believed to be the birthplace of Marco Polo.
  • Day 6–7: End in Dubrovnik, the “Pearl of the Adriatic.”

Must-See Sights

  • Diocletian’s Palace in Split
  • Hvar’s nightlife and beaches
  • Korčula’s medieval architecture
  • Dubrovnik’s ancient city walls

Insider Tips

  • Best time to visit: May to September for warm weather and calm seas.
  • Sample local wines and seafood dishes.

Plan Your Dalmatian Coast Sailing Adventure here

Related Article: Top Summer Water Sports to Try Now


Embarking on one of these epic sailing trips will not only fulfill your wanderlust but also provide you with a lifetime of unforgettable memories. From the turquoise waters of the Caribbean to the historic charm of the Greek Isles, each destination offers unique experiences and stunning sights. So hoist your sails and set course for adventure!

Explore More Sailing Trips and Book Now here

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