Suggested Itineraries
PLANNING YOUR VISIT
Make the Most of Your Time in Eleuthera
Whether you’re planning a weekend escape or a full island immersion, Eleuthera offers an unforgettable experience for every traveler.

Overview
Our suggested itineraries help you make the most of your time at Wonderful Winding Bay and beyond. With a blend of relaxation, exploration, and cultural experiences, these curated plans highlight the best that Eleuthera has to offer—from sunrise beach walks to stargazing under the Out Island sky.
3-Day Itinerary: The Perfect Island Getaway
🌅 Day 1: Arrival & Relaxation
- Arrive at Rock Sound Airport and transfer to Wonderful Winding Bay
- Settle in, explore the beach, and enjoy a welcome drink
- Dinner at Frigate’s Bar & Grill or prepared by a private chef
🌊 Day 2: South Eleuthera Discovery
- Breakfast at the villa
- Swim at Ocean Hole and visit Tarpum Bay for local art
- Afternoon kayaking in Winding Bay
- Sunset beach walk and bonfire dinner
✈️ Day 3: Lighthouse Beach Adventure & Departure
- Early morning trip to Lighthouse Beach (pack a picnic!)
- Return, refresh, and transfer back to the airport for departure


7-Day Itinerary: Full Eleuthera Experience
🌴 Day 1: Arrival & Orientation
- Pick up rental car and arrive at Wonderful Winding Bay
- Explore the villa, relax, and enjoy your first beach sunset
🌊 Day 2: Ocean Adventures
- Paddleboarding or snorkeling in Winding Bay
- Seafood lunch at Sammy’s Place
- Yoga or stargazing in the evening
🎨 Day 3: Arts & Culture
- Visit Tarpum Bay and Governor’s Harbour
- Stop at local galleries and historic landmarks
- Attend the Friday Fish Fry (if timing allows)
🕳️ Day 4: Natural Wonders
- Swim in Ocean Hole
- Visit the Glass Window Bridge and Queen’s Baths
- Scenic drive through central Eleuthera
🏖️ Day 5: Remote Beaches
- Lighthouse Beach or Ten Bay Beach picnic day
Optional private snorkeling charter
🎁 Day 6: Local Shopping & Leisure
- Souvenir shopping and lunch in Governor’s Harbour
- Sunset cocktails at a beach bar
✈️ Day 7: Departure
- Final sunrise swim or walk
- Pack and return to Rock Sound Airport
Tips for Customizing Your Stay
- Add a private chef night or beach picnic for a special evening
- Plan around local events like the Pineapple Festival or Regatta
- Mix activity days with rest days to fully unwind
- Ask your host about hidden beaches and pop-up local markets
