Winter Park, one of the hidden gems of Florida, is calling.

This charming, compact and walkable city has a European feel. Home to Rollins College, art museums, Spanish Mediterranean-style mansions and a chain of blue lakes, Winter Park is an intimate community often cited as one of the best small towns in the country. It’s also one of those desirable places where life is lived outdoors, in cafes and restaurants as well as in parks and on tree-lined streets. It offers the kind of safe, breezy, open-air environment that everyone is looking for right now, making it an ideal getaway for outdoor living and social distancing.

Winter Park is also home to The Alfond Inn at Rollins, named one of the Best Hotels in Florida by Condé Nast Traveler Readers’ Choice Awards. The hotel is welcoming guests back to Winter Park with its Yay!cation Getaway Package.


Winter Park, Florida
Winter Park offers a variety of outdoor activities.

Shopping & Walking, Biking & Boating

Built in the 19th century, Winter Park’s pedestrian-friendly downtown is a far cry from a mall. It’s anchored by architecturally distinct shops and cafes along Park Avenue, with covered walkways and passageways that lead to boutiques. Many of the shops and more than two dozen restaurants are dog-friendly.

The city boasts a number of public parks that are well-worth exploring, like the Kraft Azalea Garden on the shores of Lake Maitland, which is known for its towering cypress trees. Mead Botanical Garden is a 47.6-acre park that offers a butterfly garden and a bike trail. At the 23-acre green space on Lake Baldwin, dogs can run off leash during specific posted hours.  The residential streets are perfect for strolling under the town’s signature oak trees hung with Spanish moss.  Winter Park is also a very bike-friendly community with its bike rental shops and miles of tranquil streets for easy peddling.

Visitors can also take to the city’s tranquil lakes on the Scenic Boat Tours, a Winter Park fixture since 1938, which have just resumed. These are leisurely pontoon boat excursions that ply Winter Park’s chain of lakes. Departing from Lake Osceola, a few minutes stroll from The Alfond Inn at Rollins, these hour-long, guided cruise travels through three of the seven lakes and two, narrow manmade canals. Guests may spot cranes and even alligators as they cruise past some of the city’s most beautiful estates and gardens.

Art in the Park

Winter Park has long been a haven for art lovers. The Albin Polasek Museum & Sculpture Gardens has a lakeside sculpture garden and gallery that has just reopened to visitors. The Alfond Inn at Rollins itself was designed to exhibit rotating installations of works from The Alfond Collection of Contemporary Art, which is part of the collection of the Cornell Fine Arts Museum at Rollins College, making it the only hotel in the United States that serves as an actual extension of an art museum.


Courtesy Winter Park Chamber of Commerce

Alfresco Dining in Winter Park

Park Avenue is lined with inviting street side cafes, wine bars, brunch spots and restaurants that offer alfresco seating on the sidewalk or in a patio setting, offering a wide range of tastes, from classic Florida seafood, barbecue and stylish New American cooking to Italian, French, Mexican, Indian, Turkish, Thai and Japanese cuisine. Hamilton’s Kitchen at The Alfond Inn at Rollins has a spacious outdoor patio, with a menu created by Chef Stephen Doyle and wines curated by Sommelier Nassine Campos from a list that has garnered an Award of Excellence from Wine Spectator.


The Alfond Inn, The Alfond Collection, Rollins College
One of the pieces from The Alfond Collection of Contemporary Art on view at the Alfond Inn. Photo by Scott Cook.

Check into The Alfond Inn at Rollins 

The Yay!cation Getaway Package provides a luxury getaway with one night’s accommodation, free self-parking and one $50 hotel credit per stay, which is valid toward hotel services such as the Bar and Hamilton’s Kitchen. The Alfond Inn at Rollins is also pup-friendly, which is in keeping with the canine-friendly town of Winter Park.

Yay!cation Getaway Package

  • One night stay in a Classic Room.
  • Complimentary self-parking during the stay.
  • One $50 hotel credit per stay, valid toward hotel services, including Hamilton’s Kitchen and the Bar.
  • Rates start at $219 per night, per room, based on double occupancy.*
  • Taxes are extra and the package is based on availability.
  • Florida residents receive a 10% discount on the package rate.
  • Visit The Alfond Inn at Rollins for details.

*Additional $50 nightly pet fee applies for guests bringing a pup. It includes a keepsake water bowl and signature treats at turndown.