Off the beaten track, Anna Maria Island off Florida's Gulf of Mexico coast offers a relaxed and authentic sub-tropical vibe that makes it a perfect family vacation.

There is a place in Florida that does not have the very best in beaches, the most Caribbean-like climate, the most upscale or hottest resorts or nightlife in the state.  So, why is an island peninsula community of 15,000 residents on the Gulf Coast considered by many to be a “best kept secret”?  For those in the know, it is an affordable subtropical nirvana. 

Just south of Tampa Bay and the Sunshine Skyway Bridge, west of Bradenton and north of Sarasota and glitzy Siesta and Longboat Keys, Anna Maria holds this honor.  The most remote and outlying town on the island of the same name, Anna Maria combines with two other municipal communities to the south, Holmes Beach and Bradenton Beach, for the total Anna Maria Island experience.

The secret is that the town of Anna Maria does not have any fast food or convenience franchises, chain stores, highrises or a stoplight and the community intends to keep it that way.  Yet, prominent destinations such as the Tampa, Sarasota, and St. Petersburg areas are only 45 to 90 minutes away.  What Anna Maria does have is a Florida Keys charm of 30 years ago, spectacular ocean sunsets, solitude without remoteness, secluded beaches with sea turtle egg nests, wildlife, easy bike riding, friendly people, exemplary dining opportunities and a free local trolley. 

The late winter and spring throngs do affect the area somewhat and visitors may hear a multitude of German-speaking visitors who seem share my tastes. While not as crowded as other popular Florida destinations during peak travel season, mainland traffic access along the causeways to and from the nearest city, Bradenton, can occasionally gridlock. Other negatives: waiting for restaurant seating can be excruciating. 

For these reasons, Northerners may best appreciate this eclectic community in the summer – when the coastal climate is cooler (high 80s) than many North American regions and the sparse attendance and competitive pricing is just right.  This allows you to experience the otherwise camouflaged and friendly local beach populace of year-round residents -- best described as a blend of small family businesses, artists, commuters, retirees and escapees from big cities with a slow-paced Mayberry quality and a smattering of international flavor.

The Unique Anna Maria Beach Scene

Bring paperbacks, sandals, shorts, swimwear and plenty of sunscreen but leave most clothes at home.  A typical summer day starts out sunny and clear with an afternoon or evening thunderstorm; it's like clockwork so schedule your outdoor time in the mornings and midday. As noteworthy as regional attractions are, the reality is that after numerous visits, I am seldom drawn out of the subtropical cocoon of Anna Maria even during the winter and spring seasons.

The best way to explore Anna Maria and Holmes Beach is by foot and bicycle. Rent some at a shop near a general store and enjoy the flat and scenic terrain.  If feeling adventurous, do it with roller blades.  Some local and low maintenance activities within walking distance can begin with going right to the beach to soak in the warm and gentle blue waters.  Read a book and beach comb.  Try to find prize seashells and discover how this total focus makes the real world fade.  Be careful with the deceptive water currents at the northern tip of the island and the midday sun -- it may feel the same as up north but rays are near equatorial intensity.

The Anna Maria City Pier and Restaurant (and “gift shop”) is a great starting point to get acquainted with the destination. This historic pier serenely thrusts one out deep onto calm waters teaming with critters and serves the best casual seafood on a pier enjoyed by view seekers and local surf fishing enthusiasts alike.  Even if not eating there, the Pier is the best spot for an evening stroll to enjoy ogling the catches of the day, grabbing a beer, listening to music or watching dolphins play.  Despite the human presence, wildlife abounds due to the byproducts of the surf fishing regulars who capture the zen of true relaxation.  Wild birds look for scraps, dolphin pods actually come eerily close to shore, actively herding fish schools for elegant dining -- just like a scene from the Discovery Channel.

Gift shop is in quotes above because it is actually a vendor table near the restaurant entrance teaming with nicely priced jewelry and fossils including pre-historic Megaloden shark teeth. If visiting in summer, the position of the sun in the sky is just right for the most spectacular area sunset from the end of the pier facing north to the mouth of Tampa Bay.

Have a family cookout at the Anna Maria beach front park and play area on the Bay.  Lounge by the pool but don't forget to watch the Gulf sunsets each evening with everyone else.   A word of caution: if you find yourself excessively scheduling and planning, you don't belong here.

Anna Maria Island Non-Beach Activities

Other favorite activities among most visitors are the numerous boat charters (both sightseeing and fishing), ultralight air tours, kayak, jet ski and boat rentals and parasailing.  The visitor literature in your room or lobby lists numerous vendor sources.  Select whatever is closest to you.

For a guy’s day, have the men in the family head to Island Lumber & Hardware for a tropical trip back to an Andy Griffith-type, neighborhood hardware store quietly hidden away.  While the boys are busy, the ladies can head to the Acqua Salon Spa.  Already on some “best of” lists and billing itself as where surf meets sophistication, this is the place to pamper yourself while the hubby goes to the hardware store.  Lest I be sexist, I confess they have men’s services and succumbed to a pedicure with foot massage. This Aveda (I am told this is the best) product salon not only throws every service your way such as hair, nails, cosmetics, exotically-named body treatments, and massage, but they have a decadent full body water massage steam tent I am told is the ultimate.

Getting around the town is easy (and free too!) with the Anna Maria Island Trolley.  Whether site-seeing, beach hopping or going to the store, take advantage of this especially efficient service as often as possible using the numerous marked stops from Coquina Beach all the way to the public pier on the north side of Anna Maria town.  Trolleys run about every 30 minutes but make sure to sit at an official Trolley bench and not another type - trolley benches are painted green and say – of all things - "Trolley" on them.  Most accommodations and stores have maps.

For shopping head to St. Armands Circle on Lido Key in Sarasota. Created from a group of islands in the 1920s, by John Ringling of circus fame, into a major and elegant attraction, the international and world class destination of St. Armands Circle provides contemporary architecture, superb shops, galleries, exotic boutiques, gourmet restaurants and nightlife.  Sometimes described as a more affordable and less pretentious Beverly Hills of Southwest Florida, this continental market place of 130 stores can reduce your charge card to crumbling debris if you are not careful.

Beaches & Jetski Adventures near Anna Maria Island

Siesta Beach is the best public beach in the region and is actually considered one of the best and beautiful beaches in the world. The beach's sand is 99% quartz - so even on the hottest days, the sand is so reflective that it feels cool underfoot.  Estimated to be millions of years old from Appalachian sediment deposition, Siesta Beach has a vast near-shore shallow water depth with year round lifeguard protection, playgrounds, bath houses, beach volleyball, fitness trails, athletic fields and parking (but get there early).  Closer for families looking to stay local is the Anna Maria Beach.  Stroll west along Spring Avenue past the Sandbar eatery to experience the serenity of what Florida was like many years ago. While not crowded, parking can be difficult, but the sunsets can be spectacular.

For about $65, you and a companion can zoom around the Bay for an hour on jet skis, observing isolated mangrove wetland islands and bird rookeries – but here is the best part -- do not be surprised if you meet frolicking dolphins or manatees.  If this happens, just shut off the motor and float while they jump.  This is a great opportunity for parent/child quality time, but you may enjoy it more than your child.  There are several great watersports vendors around; I like Florida Discount Water Sports‎ (941/798-3721). They have easy access to the calm bay waters, and an attentive staff.  They may give you a bit more than an hour on a slow day – tips are welcome.

Rainy Day Activities near Anna Maria

Although this is a beach town for the occasional day of rain, there are plenty of fun museums in the area. The Ringling Museum (941/359-5700) is a circus!  The Ringlings acquired the Barnum and Bailey Circus in 1919 to create the Greatest Show on Earth.  The Sarasota museum not only houses the Circus Museum but the products of other Ringling family efforts such the Museum of Art, Cà d'Zan (their winter gothic mansion), Archives and Library, sculptures, musical performances and public education programs.

Also of interest is the Mote Marine Aquarium (941/388 4441).  Actually part of the Mote Marine Laboratory founded by Dr. Eugenie Clark, one the most world famous marine biologists and shark researches in history, this prime experience for naturalists and budding marine biologists is a must for those interested in fish, reefs, sea turtles, marine mammals and science.  Children will also like the hands on touch tank.  The South Florida Museum (941/746-4131) is home to Snooty the Manatee, born in 1947 and a de facto mascot for the region.  This educational complex includes a natural history museum, aquarium and planetarium.  You can discover Florida’s story from the prehistoric to the present including fossil exhibits, Florida’s First Peoples and local maritime history.   Don't miss the planetariums laser shows created around musical themes such as the Beach Boys.

While Away Days & Nights Sampling Anna Maria Cuisine

There is certainly no shortage of grocery stores and unique eateries in this town.  One of the coolest general stores is Ginny's and Jane E's.  Previously the only local IGA store, this is a cozy one-stop-shop for café and bakery, collectibles and chotchkes, crafts, quirky gifts, furnishings, gourmet grocery, free wireless internet and two PC work stations.

The Sign of the Mermaid (941/778-9399) is sparsely advertised and modest in appearance.  This secret and restored historic 1913 cottage serves the best food on the island and probably the region.  The menu boasts an extensive and unusual variety of Florida and European selections as well as wines and beers - not inexpensive but well worth it.  In case you are curious, the varied menu selections are based entirely on what customers request the most and the name of the establishment came to the owners in a dream.

For casual dining head to Jamrocks Jamaican Grill (866/575-7184).  This outstanding and modest looking authentic taste of Jamaica is easy to miss and specializes in authentic dishes including jerk and curry chicken and goat with rice and peas.  Enjoy the friendly patronage and relax at the tiki bar while listening to Reggae music every Friday night from local acts.  Another fantastic spot is the Beach Bistro.  Visible only from the beach, this small retreat is carved out of a hotel to provide a cozy yet semi-formal dining experience where one would not expect it.  Incredibly, this boasts the highest Zagat rating for food and service in the state of Florida.  The menu is a snapshot of the best of New York menus in one location with impeccable service.  The owner, Sean Murphy, a Canadian native, might even recommend a wine for the specials.

The Sandbar (941/778 0444) is probably the most popular restaurant on the island due to excellent dining as well as an outdoor beach-accessible bar with music - also a popular spot to buy souvenir tee shirts.  If dining by sunset is your goal, inside or out, this is the place to be.  Long lines and large crowds in peak seasons can sometimes make this experience a formidable challenge.  For economical beach dining head to the Cafe on the Beach.  Known for all-you-can-eat pancake and sausage breakfasts and walking up in a bathing suit, this old standby is a landmark for economical and casual family fare among the beach goers.

For great chowder, Sharkey’s Grill is a smallish yet popular eatery with a casual atmosphere.  The chowder stands out as an excellent meal alternative for the hungry who do not want to weigh themselves down with a big meal or need to deviate from grilled fish or meat.  Add a bit of hot sauce while no one is looking.

I have yet to have anything but superior seafood dining experiences in the region especially the abundance of grilled fish and stone crab claws, which I recommend the most.  Blackened Grouper, Roughy and Snapper are my favorite fish entrees and Conch stew or soup is my favorite appetizer.  But be warned - as much as they try, even the best restaurants unfortunately fail to adequately replicate Blue Crab Cakes indigenous to the Chesapeake Bay region.  You will see these on almost every menu but do not get them.  Order, the regional equivalent, Conch Fritters and you will not be disappointed.

But, there is more to eat in Anna Maria besides seafood.  For some southern barbecue head to Mr. Bones where patrons can give into their inner carnivore with pulled meats, ribs and even some unique Asian style rice dishes done up right by Louisiana chefs who are very proud of their sauces – so much so that a sign strictly prohibits requests for ketchup, salt, and pepper – quoting “don’t even ask” making it a popular tee shirt as well.  For some pizza, Oma’s serves up a little slice of NY and NJ among the palms and has the best of anything Italian.  With barely any room for in-seating dining, carryout and delivery is the staple of this eatery. Directly across from the beach, Oma’s won the 2007 "Reader's Choice" award for best pizza in the Anna Maria Sun.  For over 25 years, Oma's also has served up its own specialties.

For delicious homemade ice cream, fudge and chocolate covered bananas, Joe's Eats and Sweets, voted best dessert by AOL City Guide 2006 and 2007, has the most awesome and decadent desserts. My favorite is a good old fashioned hot fudge sundae but choices abound from frozen yogurts, smoothies, fat and sugar free ice cream, and homemade fudge they ship all over the world.

During the offseason, Bortell's Lounge & D Coy Duck's Bar and Grille are two great neighborhood bars.  Bortell’s is truly local even among the occasional tourist throngs at the Sandbar next door.  Not for everyone, this bar has been here since 1977 before anyone out of town heard of the island and offers cold beer, pinball and pool tables into late evening and is also a prime after beach happy hour.  D Coy Duck's is a bit more of a contemporary favorite with dominoes tournaments Monday, Texas Hold 'em Poker matches Thursday, and live good music Friday through Saturday. Music includes local reggae, funk, and R&B.

Day Trips from Anna Maria

The most challenging part of your stay might be deciding whether to go anywhere else.  If so, then sprinkle some half-day family excursions on your vegetative experience among the palms. 

For those of you comfortable operating a motor boat, rent one and motor out to Egmont Key State Park, an uninhabited island in the Gulf at the opening of Tampa Bay.  Or as an alternative, sign up for a guided charter and let others do the work.  This Gilligan's Island is the area’s best snorkeling spot and still has uncompleted relic walk ways and building foundations left over from turn of the century Spanish American War fortifications and is presently overrun with large tortoises and lizards.  Home of the only manned lighthouse in the U.S., this island is also a wildlife refuge managed by the Florida Department of Environmental Protection, the U.S. Fish and Wildlife Service and the U.S. Coast Guard.  Budding young marine biologist snorkelers will appreciate the easy three to five foot deep calm water over vast expanses of turtle grass beds.  Just float and look down to catch glimpses of fish and bottom dwellers such as mollusks and rays.  Make sure to bring plenty of drinking water, a picnic lunch and sunscreen.

Boasting one of Florida's largest and most diverse natural areas, Myakka River State Park is 45 square miles of wetlands, prairies, hammocks and pinelands. The river and its two shallow lakes attract a myriad of wetland creatures such as alligators up close, turtles, and an amazing number of different types of birds and a boardwalk out on the Upper Lake enhances wildlife viewing opportunities making birding, canoeing, fishing and wildlife observation popular activities.   A seven-mile scenic drive winds through shady oak-palm hammocks and along the shore of the Upper Myakka Lake. Over 39 miles of hiking trails and many miles of dirt roads provide access to the remote interior.

Accommodations in Anna Maria

Anna Maria is not completely immune to peak travel, so book your accommodations ahead of time as well as your flight and car rental if you are coming via the extremely visitor friendly and efficient Tampa airport.  The smaller and closer community airport of Sarasota is also available but may require an additional plane change.  A multitude of customary accommodation options await especially in the contiguous communities of Holmes Beach and Bradenton Beach to the south but I recommend that for the first visit, make the total commitment of residing in the town of Anna Maria itself.

My favorite place to stay is the jointly owned and managed Seaside Inn Beach Resort, Tradewinds Resort and Tortuga Inn Beach Resort.  Admittedly this is a tough one given the multitude of other outstanding accommodations – some more upscale and larger and some more rustic and simple.  So while I have enjoyed other locations, this stands out for several reasons. 

Mostly it is a bargain in that you get very clean, very neat and comfortable lodgings with effectively used spaces and none of the bells and whistles a family might not need or want to pay for at an excellent value.  These beachfront lodges, while not far from anything, are surprisingly isolated and devoid of crowds even in peak season.  But rest assured you will not rough it with back porch Gulf access, rooftop patios, cable, and wifi.  Unlike other arrangements, customers reserve rooms directly with owner and management leaving out cumbersome and customer service-lacking real estate rental agencies which tend to add overhead costs – without falling back on standard hotel fare.  Even better is the absence of any requirement for minimum stays as well as the owner’s personal sincere interest in your satisfaction.  Nothing will go wrong with your stay here.  Make sure you reserve in advance for peak seasons though and don’t forget to ask for their seasonal packages.

If beachfront accommodations are not a requirement, cut costs without cutting comfort and amenities by staying just a bit inland. This is the more economical way to experience Anna Maria - as it is strategically located within walking distance of both sides of the island shoreline, the community's best restaurants, a small museum, a video rental, dry cleaner, general stores, and gift shops.  The most common lodgings, include house and condo rentals, are usually available by the week.  In most of this area, the Gulf of Mexico will be to the west and Tampa Bay to the east.  For more information about hotels in the area, see Anna Maria Accommodations.