For the 50+ Traveler
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Pensacola is known for the miles of white quartz sand beaches and the clear emerald waters of the Pensacola Bay. What you might not know is that the city is much more than just a beach town. There’s an abundance of historic sites, plenty of hiking and outdoor activities, plus a vibrant downtown district with shopping and the arts. The city is small enough to feel quaint yet large enough to offer a variety of activities.

I was heading to Mobile, Alabama, when my flight landed at the Pensacola airport. After my visit to Mobile was complete, I knew I wanted to extend the trip and spend a long weekend in Pensacola before returning home. I was glad I did because it’s an unparalleled beachside retreat that of course has plenty of relaxing and vigorous water activities but also a spirited downtown arts scene, plenty of seafood dining options, and unique places to shop or just stop for a bit and enjoy a cocktail.

Here are a variety of ways to spend a long weekend in scenic Pensacola, Florida.

Boardwalk trails at at Big Lagoon State Park in Florida.

Things To Do In Pensacola

You’ll spend plenty of time outdoors enjoying the sunshine and salty breeze, whether it’s hiking and exploring, taking in historic sites, or spending time at the beach or on the water.

Hit The Trails

If exploring unpaved or paved trails, and immersing in nature brings you joy, there are plenty of choices in Pensacola.

Walk along the raised boardwalk at Discovery Nature Trail to see dunes and salt marsh outlooks, ending with a stunning view of Grand Lagoon. It’s about a half-mile leisurely hike.

For a more strenuous hike (or bike ride, if you prefer), the Pensacola Beach Eco-Trail runs 8.5 miles and showcases Pensacola Beach’s island ecology at 29 stops with stories about the region.

Birders will enjoy the 4.9-mile birding trail and 2-mile estuary trail at Big Lagoon State Park. Located on the Great Florida Birding and Wildlife Trail, more than 23 species of wood-warbler, plus ducks, sandpipers, and black-bellied plovers make stops there. While you’re at the park, you might enjoy trying your hand at crabbing, fishing, or swimming.

See rare plant and animal species on a hike on the elevated boardwalk at the Tarkiln Bayou Preserve State Park. Choose from the 6.5-mile Perdido Bay Trail or the 1.5-mile, wheelchair-accessible Tarkiln Bayou Trail.

Paddleboarding off the coast of Pensacola, Florida.

Go Kayaking Or Paddle Boarding

While I’ve tried -- and enjoy -- both kayaking and paddleboarding, I prefer kayaking so I can sit and cruise at a leisurely pace in comfort. Whichever you prefer, there are so many great places to get out and ’yak in Pensacola, you may want to bring your own instead of renting one.

You’ll have to paddle to get to White Island. If you put into the water at Civilian Park it’s a little less than a half-mile paddle to get there. If you enjoy camping, bring a tent and spend the night. Or spend the day and relish the white sandy island with a picnic.

The coastal sanctuary at Big Sabine Bay is a delightful estuary for boating where you’ll see herons, gulls, and bald eagles overhead, and plenty of sea life beneath you.

If you visit Big Lagoon State Park for the hiking trail, allow a few more hours for paddling Big Sabine Bay. There’s a kayak launch for easy access.

For a truly unique paddling experience, Outdoor Gulf Coast recommends paddling to a restaurant for lunch or dinner. You’ll launch from Sanders Beach and kayak about a half-mile to The Oar House to enjoy American fare with a view of Bahia Mar Marina.

The Fort Pickens military fort in Pensacola, Florida.

Visit Historic Sites

History buffs will enjoy exploring the various sites. A few worth adding to your list include a visit to Historic Pensacola in downtown Pensacola to tour 28 properties including museums and historic homes, plus history interpreters are dressed in period clothing. See Fort Pickens military fort, see the first and only federal tree farm at Naval Live Oaks Reservation, or take in the view from above at the Pensacola Lighthouse.

Pro Tip: The Pensacola Lighthouse has 177 steps to the top, so it isn’t advised for anyone with bad knees or other mobility limitations. No bags or purses are allowed on the property, so leave those in the car.

The Saenger Theatre in Pensacola, Florida.

Appreciate The Arts

The visual arts offerings are thriving in Pensacola. Take in a show at the historic Saenger Theatre, Pensacola Little Theatre, the Pensacola Symphony Orchestra, Ballet Pensacola, or the Pensacola Opera. There’s also the Pensacola Museum of Art, First City Art Center, and many galleries downtown. Or watch live music at Vinyl Music Hall.

Pensacola beach views in Florida.

Relax On The Beach

A visit to Pensacola wouldn’t be complete without some downtime at the beach. Whether you prefer a shallow beach for the family at Quietwater Beach, a beach with both bayside and gulf side views at Johnson Beach, or Pensacola Beach, selected as one of TripAdvisor’s Top 25 Beaches in the U.S., there are a variety of options.

A dolphin cruise via Jolly Sailing in Pensacola, Florida.

See Dolphins At Play

Seeing dolphins at play has to be one of the most memorable life experiences. You can book a guided cruise with Jolly Sailing and Dolphin Cruise, or purchase an observer’s ticket and walk the 1,470 foot Pensacola Beach Fishing Pier to see dolphins that are drawn nearby because of the fishermen.

Grilled scallops from The Grand Marlin in Pensacola, Florida.

Best Restaurants In Pensacola

I never pass up a chance for fresh seafood, and Pensacola serves a fish and crustacean lover’s feast. Choose from beach dining, downtown dining, and even Southern seafood at these favorite restaurants.

The Grand Marlin

True to its name, The Grand Marlin at Pensacola Beach serves the highest quality seafood at its fine dining restaurant. For those craving oysters, you’ll find a fantastic variety of oysters from Apalachicola, East Bay, and other locales at the oyster bar. Start with oysters or the Ahi Poke, then get ready for a delicious fish entree such as the grilled yellowfin tuna, seared red snapper, or the parmesan-crusted grouper served with sauteed spinach, whipped potatoes, crispy capers, and brown butter.

Peg Leg Pete’s

Also located at Pensacola Beach, Peg Leg Pete’s is an unassuming fish shack selling reasonably priced meals. Oysters are another specialty here, and they’re served 11 different ways. I suggest going with the Sampler so you can taste a variety: Buffalo Blue, Cajun, Parmesan, Rockefeller, Spicy Lafitte, and Imperial. They’re all delicious. If you still have room for more, Blue Crab Claws, either flash-fried or sauteed in garlic butter, are a local’s favorite.

Restaurant Iron

Downtown, Restaurant Iron serves a contemporary version of Southern seafood with flair. Start with the luscious Sliced Florida Heirloom Tomato Salad with truffle goat cheese, pickled blueberry, slivered onion, arugula, Bodacious olive oil, and vinegar, plus focaccia croutons. Or perhaps the Roasted Pheasant and Andouille Gumbo for a Southern-inspired starter. For a main course, choose either the Creole Seared Skuna Bay Salmon or the Crispy Coconut Curry Tofu.

Where To Shop In Pensacola

You’ll find local boutiques and specialty shops in Pensacola. The walkable downtown area is a great place to spend the day strolling the streets looking for a unique local find, some baked goods, and antiques. After, stop for a cocktail or locally brewed beer at one of the many downtown bars.

The Pensacola Victorian Bed and Breakfast in Florida.

Best Hotels In Pensacola

There’s a lodging choice for every interest, whether you prefer a beachside hotel, a quaint bed and breakfast, or a historic hotel downtown.

Pensacola Victorian

Stay in a restored Queen Anne Victorian at Pensacola Victorian. The bed and breakfast provides comfortable elegance in four furnished guest rooms. Each has a private bath, queen-size bed, and cable TV. Breakfast each morning is home-cooked and there are complimentary beverages and homemade treats to enjoy as well. Located downtown, the theater and farmers market are a short walk from the bed and breakfast.

Surf And Sand Hotel

If you prefer a beach location, Surf and Sand Hotel is a pet-friendly hotel with 100 rooms that overlooks Little Sabine Bay. There’s an outdoor pool as well as the nearby beach for relaxing. The hotel provides free amenities to make your stay even more fun, including floats, paddleboards, beach cruisers, kayaks, and more.

New World Inn

Stay in the historic downtown area at New World Inn. This modern boutique hotel is decorated with antique and period pieces that lend to the Southern Old-World charm. Each room is uniquely decorated and named after a historical person. The historical notes allow you to learn about the person your room is named for and their effect on local as well as national history. Stay in the Elias And Rebecca Durnford (1739-1794) suite that’s set in a private corner of the inn with an angled ceiling, king bed, writing desk, private bath, and amenities. Elias Durnford was Acting Governor, and his wife Rebecca helped to form cultural activities in the early Pensacola community. Or choose one of the other delightfully named and decorated rooms at this charming inn.

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