Enchanting City Streets

Art & History

Winter Park & the Golden Isles


Day 1



  • Arrive at Orlando International Airport
  • Reside at the Alfond Hotel, a boutique hotel in downtown Winter Park
  • Stroll through the public lakefront, Kraft Azalea Garden
Day 2
  • Discover  beautiful sculptures and gardens during a tour through Polasek Museum, located lakeside
  • Stroll through Central Park
  • Visit dozens of shops on Park Avenue
  • Enjoy the dining atmosphere and delicious food at Luma on Park
Day 3
  • Begin the morning by joining in a popular community gathering at the Winter Park’s Farmers Market
  • Explore Casa Feliz, a restored Spanish Farmhouse
  • Lunch at Bistro on Park Ave
  • Rest
  • Listen to the sounds of the Bach Festival Society’s choir and orchestra
Day 4
  • Spend the morning enjoying the true beauty of Winter Park on a scenic boat tour
  • Explore the wetlands and natural habitats surrounding Winter Park at the Howell Branch Preserve
  • Rest
  • Enjoy the innovative culinary creations at The Ravenous Pig
Day 5
  • Spend the day celebrating spectacular Florida artists at the Annual Winter Park Autumn Art Festival
Day 6
  • Check-out of the Alfond Hotel
  • Drive to St. Simons Island
  • Reside at King & Prince
  • Enjoy classic coastal cuisine at Echo oceanfront restaurant
Day 7
  • Hop on board of a Lighthouse Trolley tour around St. Simons and visit every historical site
  • Rest
  • Shop and dine at the Pier Village
Day 8
  • Make a day trip to Jekyll Island
  • Explore Jekyll Island through a variety of eco tours offered
Day 9
  • Take time for a nice walk on Driftwood Beach
  • Visit Jekyll Island Historic District
  • Dinner at Courtyard Crane
Day 10
  • Set a tee time at the King and Prince Golf Course
  • Enjoy the evening at the Shops at Sea Island for upscale dining, shopping and entertainment
Day 11
  • Spend the day exploring the Golden Isles from the water, aboard a boat tour
  • Rest
  • Experience the fine dining and, the featured piano and martini bar offered at J. Mac’s Island Restaurant
Day 12
  • Check-out of King & Prince
  • Drive to Orlando


More information on Things to do in Winter Park.

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Photography by GFDL and CC-By-SA-2.5. Published under the Creative Commons 3.0 Unported Licence