It’s the sailor’s eternal debate: Caribbean or Mediterranean?

Both regions offer incredible beauty, history, and sailing experiences - but they deliver them in very different ways. Whether you’re drawn to the barefoot freedom of the Bahamas or the coastal charm of the Greek islands, here’s what to expect from each paradise.

The Caribbean - Easygoing, All-Inclusive, and Unforgettable

The Experience

The Caribbean is all about warm blue waters, constant sunshine, and relaxed island vibes. It’s where you kick off your shoes, dive off the stern, and spend your days exploring coral reefs and white-sand beaches. Life happens outdoors - snorkeling, paddleboarding, and sunsets at beach bars with your feet in the sand.

Most charters here are more all-inclusive, so your captain, onboard food, fuel, yacht costs, and activities are part of the experience. 

Sailing in the Bahamas

At Vagabonde Adventures, our home waters are the Bahamas, one of the most stunning and accessible sailing destinations in the world.

Where You’ll Sail:
We primarily explore the Abaco Islands, a pristine chain of cays just an hour’s flight from Florida. Your week may include:

• Marsh Harbour - your arrival port and gateway to adventure.

• Guana Cay - famous for its beach bars and vibrant coral reefs.

• Man-O-War Cay - a charming boat-building village.

• Hope Town - climb the candy-striped lighthouse for panoramic views.

• Tahiti Beach - walk the sandbar that appears at low tide.

• Sandy Cay - snorkel the protected national park reef.

• Little Harbour - grab a drink at Pete's Pub and explore the bronze sculpture gallery.
  

Where You’ll Fly Into:

• Marsh Harbour (airport code MHH)

Costs on Land:
The Bahamas are relaxed, think $25–$50 USD for a casual dinner, $5-$8 for a local beer, and $20–$30 for a taxi ride around town. We usually eat all breakfasts and lunches, plus 2 dinners on board,, and the rest are spent dining on shore. 

Best For:

• Warm weather sailing November to May

• Water life like turtles, stingrays, and tropical fish

• World class fishing

• Snorkeling, diving, and beach hopping

• Private, all-inclusive yacht charters with minimal logistics

• Easy travel from the US

If your dream is bright blue waters, sandy toes, and sunrise sails then the Caribbean calls your name.

The Mediterranean - History, Culture, and Coastal Charm

The Experience

Sailing in the Mediterranean is about coastal discovery, history, and culture. Oh and the incredible food and wine! You’ll spend days cruising between ancient ports, swimming in hidden coves, and evenings wandering cobblestone streets to find the perfect local taverna.

Unlike the Caribbean, most Mediterranean charters are “pay-as-you-go” - your yacht includes the vessel but meals, boat costs and marina fees are settled along the way. Expect more time exploring on land and dining ashore.

Some of our favorite countries to sail in are Croatia and Greece.

Croatia – The Dalmatian Islands

Croatia’s Dalmatian Coast is a sailor’s paradise with its cobblestone towns and hundreds of islands sprinkled along the Adriatic.

Typical Route (7 days):

• Split: Fly into Split Airport (SPU) - our main sailing hub.

• Brač: First stop for swimming and exploring charming harbors.

• Hvar: Famous for nightlife, lavender fields, and excellent restaurants.

• Vis: Remote and peaceful, with wineries and the legendary Blue Cave.

• Korčula: Birthplace of Marco Polo and home to beautiful Venetian streets.

• Trogir or Šolta: A relaxing final stop before returning to Split.
  

Costs on Land:
Croatia has some excellent local food and wine, expect €20–€40 per person for a waterfront dinner, €5-€10 for local wine or beer, and €30-€60 for marina fees per night (shared among your group).

Best For:

• Experiencing a unique side of the Mediterranean

• Historic towns and island hopping convenience

• History, culture, quality food, and calm waters
  

Greece - Ancient Beauty and Endless Islands

Few places rival Greece for sheer variety and beauty. Sailing here feels like drifting through history, temples on cliffs, whitewashed villages, and fresh Greek food everywhere.

Typical Route (7 days):
Most travelers fly into Athens (ATH) and depart from Lavrio or Alimos Marina, just 30-45 minutes from the airport.

In one week, you might explore the Saronic Islands, a favorite for steady winds and short passages:

• Aegina: Famous for pistachios and lively markets.

• Poros: Pine-covered hills and pretty harbor walks.

• Hydra: A highlight. No cars, just donkeys and timeless charm.

• Spetses: Elegant, romantic, and steeped in naval history.

• Perdika or Agistri: Perfect for swimming stops and quiet nights at anchor.
  

Costs on Land:
Greece offers incredible value. Expect €15–€30 per person for dinner, €3–€6 for wine or beer, and €20–€50 per night for mooring fees, depending on location.

Best For:

• Culture, cuisine, and scenic sailing

• Exploring both iconic and off-the-beaten-path islands

• Warm hospitality, and warm sunshine!
  

The Vagabonde Adventures Difference

At Vagabonde Adventures, our Outremer base is in the Abaco Islands, in TheBahamas, where the freedom of sailing meets true island simplicity. Our founders live in Croatia, and love Greece - so you can see we love everywhere. Every charter is crafted to match your style, from all-inclusive relaxation to hands-on sailing and ASA certification courses.The good news? You can’t go wrong either way, you just have to decide which adventure calls you first.