Couple’s Itineraries to Inspire

As your vacation planning specialist I still believes in fairy-tale endings so I’m impassioned by creating the kinds of trips that luxury honeymoons and trips for two were made for.

In my eyes there are few travel experiences as important as your first real adventure together or taking that time to reconnect as a couple. From champagne sailing charters to private beach massages, your perfect honeymoon or vacation awaits.

Here is a suggested 7 Day Itinerary to start exploring Anna Maria Island. Tackle them individually or string them together to customize your own epic adventure.


Day 1 Arrival

Your relaxing getaway starts first thing in the morning with a couples’ massage on the beach. Sea-renity provides couples with their private beach cabana right on the Gulf.  But be warned: it’s hard to go back to a regular massage once you’ve done it with the soothing sounds of the tide in the background.

Take time today to relax in the shade under an umbrella with your cooler full of ice, your toes in the sand, and taking in some quality beach time together.  Choose from Custom Beach Service Packages that can include as many things as you want, including paddle boards, kayaks, and snorkel gear.

After you’ve had enough beach time, head out for a romantic catamaran sailing tour so you can lay back and take in the sights and sounds of the Gulf. If you’re lucky, you’ll see a dolphin or two jumping alongside the boat. At the very least, the two of you will end the day in peace – surrounded by the quiet solitude of the water and a breathtaking sunset.

Day 2

In the morning enjoy a special breakfast at the Island Creperie on Bridge Street.  Then explore the Coquina Trail in true Island fashion on beach bikes or practice your couples communication on a bike built for two.

In the afternoon take enjoy the sights and sounds of our aquatic birds and search for dolphins/manatee along the protected waters of Palma Sola Bay with a paddle tour.  You have a choice of Stand Up Paddle Board, Single Kayak or Tandem. A lesson is included for first time paddlers.

In the evening take in the romance of Anna Maria Island Sunsets via a walk on the beach and dinner at the Beach House Restaurant.

Day 3 

Get an early start with a delicious breakfast menu at the Anna Maria Oyster Bar on the Bradenton Beach Pier at the end of Historic Bridge Street. Then, it’s off to soar the heights over the Gulf of Mexico with YOLO Adventures.  At YOLO Adventures, experience the thrill of a lifetime by soaring above the Anna Maria Island and Gulf Coast parasailing. Gentle takeoffs, water dips when requested and smooth landings are always provided by their experienced USCG licensed crew. The two of you can either go solo or fly together, either way you’ll get to see AMI and Cortez, FL from a whole new perspective!

Head back to Bridge Street for lunch at the Bridge Tender Inn and check out the stores along the street.  Its time to act like kids again so enjoy a round or two of mini gulf at the Fish Hole’s little piece of tropical paradise.  Follow up with ice cream at Joe’s Sweets, remember to each get your own flavor so you can share.

Day 4

What do boats, snorkeling, and sandbars have in common? On this 2 Hour Sandbar Tour you get it all! Head out on an exciting boat tour out to the Sandbar near Longboat Pass. When you reach the Sandbar, your snorkeling adventure begins. Explore the crystalline waters around the Longboat Pass Sandbar and the mangroves near beautiful Jew Fish Key. You may even see dolphins, manatees, and stingrays! This is a great snorkeling adventure and Boat Tour in one!

Day 5 

Now it’s time to check off a fun experience on everyone’s bucket list. Take a scenic Segway Tour with Segs by the Sea. Exploring An Island Has Never Been This Much Fun! Segways help you explore beautiful Bradenton Beach & Anna Maria Island areas in a whole new way!

Enjoy lunch at the Star Fish Company. This dockside restaurant was started in the early 1920’s and not much has changed since. You can still go into their fish market, but even better is their just-caught grouper sandwiches.  Relax at the picnic tables on the dock surrounded by fishing boats and pelicans.  Your food will come served in white lunch boxes.

Enjoy an afternoon of shopping on Pine Avenue and Two Scoops for ice-cream.  Be sure to stop for a photo op in front of the Anna Maria City Jail.  This tiny concrete structure that held the local “rowdies” from 1927 to the 1940’s.

In the evening take in one of Anna Maria Island’s breathtaking sunsets via a romantic sunset cruise.

Day 6

No Adventure to Anna Maria Island would be complete without some pictures to take home of your big catch of the day. The Sun Coast is an extraordinary place to go fishing.  A two hour Intercoastal Fishing excursion is an inexpensive way for the two of you to practice your fishing skills and there’s no need to worry about getting sea sick.  If the thrill of catching something larger has you excited then a six hour Off Shore Charter can be arranged.

You may have seen small three wheel scooter cars cruising around the island.  In the afternoon see what the rage is all about and a take a fun half day rental with a scooter car to explore.

Day 7 Departure

If time allows on your departure day close out your time together with a little additional adventure. Jetskis provide everyone will a thrill, there are scenic tours to chose from or the two of you can rent them on your own and do a little last minute exploring.