5 Days of Beaches & Happy Hours in Southwest Florida

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Advisor - Ann Pappas
Curated By

Ann Pappas

  • Florida

  • USA

  • Beaches

  • City Travel

  • Foodie

  • Local Culture

  • Coastal

starfish in the shallow water of a beach
Curator’s statement

Southwest Florida is still a great place to vacation, and after hurricane Ian, the area is still rebuilding and cleaning up. Many business and hotels have reopened; some beaches and parking are now open; and outdoor activities include hiking, biking, kayaking and jet skiing. Downtown Fort Myers has opened up most of the restaurants and stores while Naples has a different feel. Naples downtown is upscale with boutiques and 30+ restaurants, and continues to be agreat basecamp for visiting the Everglades and Marco Island if you have extra time. Southwest Florida has amazing weather in the winter but I also love the summer. The Gulf water is warm in the summer, great for swimming. Hotels and restaurants are less crowded and you can get better rates at the hotels during the summer months. Explore both Fort Myers and Naples. Just know that hurricane season is from June through October, so make sure you have travel insurance or able to change reservations.

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Day 1: Fort Myers

white sand beach with bathers in the water and on the shore

Spend two nights downtown Fort Myers at the Luminary. The Luminary rooftop, Beacon Social Drinkery, is on the 12th floor and offers tapas, wine and craft beer. Enjoy their cozy outdoor patio for views of the Caloosahatchee River. If you are looking for some night time entertainment, check out the Social House which is just across the street from the Luminary. They offer dinner, live bands on the patio, happy hour and rooftop dancing. Ladies night is on Thursdays from 8-10pm, which means free house cocktails for the ladies!

Day 2: Sanibel Island

a bike leans against a tree on a tree covered path leading to the beach

Relax or go shelling on Sanibel Island. The hurricane destroyed so much of the area but a few beaches are now open - Blind Pass Beach, Tarpon Beach, Bowmans Beach and Turner beach. Parking is $5.00/ hour to park. Keep in mind some restroom facilities are closed. Debris continues to wash onshore, so best to always wear beach shoes, and always be cautious of red tide. Tip: You can check here for red tide status.

Day 3: Naples

beach with wooden dock supports

Drive over to Naples for your 3rd night! Choose from one of their many beaches, either Clam Pass Park which has 35 acres of costal habitat and is just a 3/4 mile walk on the boardwalk or a Tram ride over to the beach. Or, if you want an easy walk from parking to the beach, then go to Loudermilk Park, just south of Clam Pass park. Their showers and bathrooms are working again! For dinner go to Tin City, a waterfront boardwalk with casual shopping and restaurants.

Day 4: Naples Botanical Gardens

tropical plants and a blue sunny sky

Naples Botanical Gardens has 90 acres of garden habitats and walking trails. It features plants from around the world. Admission for adults is $25.

Back at the hotel, if staying at the Inn on Fifth boutique hotel, you can have access to 30+ restaurants just outside the hotel. There is also upscale boutique shopping along 5th Avenue.

For happy hour try Caffe Milano, Monday through Friday from 3pm to 4:45pm, with 50% off selected food and drink. Vergina's and Del Mar also both have happy hours!

Day 5: Choose your own adventure

a orange sunset on the ocean

If you stay another night, here are some options:

  • Visit Fort Myers Beach. Most of it was destroyed from Hurricane Ian but there are some restaurants that have reopened. The Beach Bar is open with live music, or try Wahoo Willies with live entertainment with all day Happy Hour.

  • Try one of favorite restaurants east of the beaches, Tommy Bahama Marlin Bar. Yes, its connected to the Tommy Bahama retail store. They have two locations, Estero and Naples. It's a laidback outdoor restaurant and bar with live music and happy hour from 4-6pm (Estero) and 3-5pm (Naples). The restaurants have that relaxed beachy tropical feel. Reservations are recommended for the Naples location.

  • If you want to skip the happy hours, try a sunset cruise! They are very fun and if you are lucky you will see dolphins and manatees.

  • If you want to take a drive to Marco Island, it is about 30 minutes to an hour from Naples.

  • Visiting the Everglades National Park and taking an airboat ride is another fun option but it can be hot in the summer.

Need to Know

For more travel tips, check out Fora AdvisorAmber Rose Power's guide, Laid-Back Luxury Guide to Naples, Florida.

Advisor - Ann Pappas

Travel Advisor

Ann Pappas

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This guide is part of our ongoing series on travel to Florida.