Over the years, I’ve been lucky enough to sail in some of the most stunning places on Earth. Each destination has its own personality—some easy and relaxing, others more adventurous or challenging—but all have left their mark in one way or another. In this post, I’m sharing real talk about the highs and lows of each place I’ve sailed, from the dreamy waters of Tahiti to the cool currents of the San Juan Islands.
Whether you’re planning your first bareboat charter or looking for your next bucket list sailing trip, I hope this helps you decide where to hoist the sails next.
🌴 Grenada, Caribbean
- When I Sailed: Multiple times, most recently in January 2025
- Type of Sailing: Liveaboard course and island hopping, day sails, J/80’s
- The Vibe: Laid-back and authentic Caribbean, with a strong local culture
- Best Parts:
- Quiet anchorages with fewer charter boats than other Caribbean spots, you never have to fight for a gorgeous anchorage
- Delicious, authentic food
- Welcoming locals and strong sailing community
- Challenges:
- Strong winds can make for dramatic weather, learning here is a great opportunity to experience both strong and mild winds.
- It’s hot! Located 13 degrees above the equator, the sun is close. Wear sunscreen!
- Top Tip: Make your way north and explore the Tobago Cays. The turtles are waiting.
- Would I Go Back? I will and I do!
🌺 Tahiti, French Polynesia
- When I Sailed: October 2018
- Type of Sailing: Bareboat charter, Catamaran, organized a four boat flotilla
- The Vibe: Postcard-perfect paradise—lush mountains, crystal-clear lagoons, and a relaxed pace
- Best Parts:
- Unreal scenery and water clarity. Hiking in the mountains felt like a Jurassic Park movie.
- Anchoring in a lagoon surrounded by reef? Yes, please. No need for an over the water bungalow!
- Snorkeling with rays and nurse sharks right off the boat.
- Delicious French-Polynesian fusion food, pearl and vanilla farms, friendly locals
- Challenges:
- Navigation around reefs requires focus—chart plotters + eyeballs
- Charter base logistics can be a little chaotic, getting to the base requires a ferry or small air plane.
- Top Tip: Use your dinghy to explore shallow reef areas you can’t access by boat—it’s like your own private aquarium.
- Would I Go Back? 100%. It was something I never thought I would do, and now that I have, I will do it again!
🐠 Belize
- When I Sailed: June 2022
- Type of Sailing: Bareboat charter, catamaran, organized a two boat flotilla
- The Vibe: Eco-adventure meets remote exploration
- Best Parts:
- Dozens of tiny cays to anchor near—feels like private islands
- Clear, warm water and world-class snorkeling
- Dinner in a tree house was perfection.
- Challenges:
- Shallow reef navigation can be difficult, follow the guides
- Less protected anchorages mean bouncy nights if the wind shifts
- Top Tip: Plan your route based on the wind and always have a backup anchorage in mind.
- Would I Go Back? Yes, especially with a confident crew and good weather window.
🍝 Sicily, Italy
- When I Sailed: September 2022
- Type of Sailing: Bareboat charter, Catamaran, organized a three boat flotilla
- The Vibe: Mediterranean charm with a fiery twist (volcanoes, anyone?)
- Best Parts:
- Sailing past active volcano Stromboli at night!
- Picturesque harbors and dramatic coastline (did you see White Lotus season 2? Been there.)
- Pasta, pizza, and gelato at every port
- Challenges:
- Can be pricey, especially at marinas
- Travel to the marina on the north end requires planning
- Top Tip: Visit Tenuta di Castellaro, a winery that sits on top of a mountain. Sunset and wine tasting was magical!
- Would I Go Back? Yes—just pack a flexible mindset and a love of carbs.
🏛 Athens, Greece (Saronic Gulf)
- When I Sailed: October 2021
- Type of Sailing: Bareboat charter, Catamaran. Organized a three boat flotilla
- The Vibe: A perfect blend of ancient history, island hopping, and great food
- Best Parts:
- Easy sailing conditions, great for all experience levels
- Lots of options for anchorages, marinas, and tavernas
- Everything you love about Greece—olives, ouzo, ruins
- Challenges:
- Can be very busy in summer, visit toward fall for quieter anchorages
- Mooring stern-to in small harbors takes practice
- Top Tip: Have dinner under the temple of Poseidon after a hike up the hillside.
- Would I Go Back? Definitely. It’s a solid choice for groups and newer sailors.
🏝 Corfu, Greece (Ionian Sea)
- When I Sailed: September 2016
- Type of Sailing: Bareboat charter, Catamaran, organized a three boat flotilla
- The Vibe: Greener, quieter, and more chill than the Cyclades or Saronic
- Best Parts:
- Lush, hilly landscapes with beautiful water
- Less crowded than Athens-area sailing
- Easy hops between islands
- Challenges:
- Not as dramatic as other Greek destinations—more mellow than wild
- Top Tip: Anchor off Paxos or Antipaxos for blue water that rivals the Caribbean.
- Would I Go Back? Yes—for a relaxed, slow-paced itinerary.
🐚 Bahamas (The Abaco’s)
- When I Sailed: February 2025
- Type of Sailing: Bareboat charter Catamaran, organized two boat flotilla
- The Vibe: Tropical minimalism—shallow, stunning, and a little wild
- Best Parts:
- Unbelievable water colors—turquoise, teal, neon blue
- Endless sandbars and remote beaches
- Swimming pigs, iguanas, and nurse sharks
- Challenges:
- Tides and shallows can be tricky—charts don’t always match reality (have your apps updated!)
- Strong currents in some cuts
- Top Tip: Plan ahead and spend a little more time at each anchorages, a 7 day trip wasn’t enough!
- Would I Go Back? Yes, especially for an off-the-grid kind of trip.
🌲 San Juan Islands, Washington
- When I Sailed: September 2019
- Type of Sailing: Day sail
- The Vibe: Pacific Northwest charm with rocky shores and misty mornings
- Best Parts:
- Wildlife—whales, seals, and eagles galore
- Cozy, forested coastline and dramatic clouds
- Challenges:
- Cold water, layered clothing, and strong tidal currents (one of the only occasions I sailed with long pants on!)
- Top Tip: Great for shoulder-season sailing—peaceful and quiet if you’re bundled up. Fall slows down so make sure reservations on shore are made in advance.
- Would I Go Back? Yes, for a longer trip to explore more islands at a slow pace.
🌋 St. Lucia
- When I Sailed: April 2024
- Type of Sailing: Day sail, organized 10 day sailing trip
- The Vibe: Lush and mountainous, with a dramatic coastline
- Best Parts:
- Anchoring under the Pitons is iconic
- Local food and music add a rich cultural flavor
- Challenges:
- Boat boys can be aggressive, make sure you use guides like Doyle Guides to get their best opinions
- Top Tip: Stay a few extra days to explore on land—hot springs, hikes, and waterfalls await.
- Would I Go Back? Yes, absolutely.
🏖 British Virgin Islands
- When I Sailed: May 2025
- Type of Sailing: Bareboat Catamaran, organized three boat flotilla
- The Vibe: Be ready for delicious cocktails and Kenny Chesney like vibes.
- Best Parts:
- Amazing sailing conditions and weather
- Spending the day at the Baths
- Challenges:
- Anchorages can be busy and reserving mooring balls can feel stressful
- Top Tip: Check out the Cruise ship schedules and try to avoid their ports.
- Would I Go Back? If the timing was right. It was very touristy but the weather and sailing was great.
Final Thoughts
Every sailing destination has something special—whether it’s jaw-dropping scenery, chill anchorages, or unbeatable food. My top three so far? Tahiti for the beauty, Grenada for the raw culture, and Sicily for the combo of active volcanoes and amazing food. That said, I’m always chasing the next horizon.
Be on the look out for our next desitnations! We are thinking La Paz or Thailand…
