The best day ever - Charter for the day

“Timeless” is filled with charm and style and is the perfect platform to explore for the day or beyond on a multi-day adventure. Whether for a special occasion or romantic getaway or to unwind with family and friends during a memorable summer trip in Maine or during the winter months in sunny, warm Southwest Florida, we ensure a perfect day on the water.

Timeless has been continually upgraded and maintained to the highest standard providing a relaxed but luxurious platform to build your custom charter or event. Visit the islands, swim, spend time at a hidden beach, the tube behind “Little Time,” or enjoy your captained vessel in luxury. Choose to venture further in total comfort and explore at your pace and desired destination, or let us choose the perfect itinerary.

Whether you visit an island for lunch, spend time watching wildlife such as dolphins, seals, and eagles, or hunt for shells on an island beach, this boat can do it all with an experienced captain providing unforgettable memories the entire way. Chill out to your tunes on our Bluetooth sound system with a cold beverage in hand, or have a full catered meal in total comfort, in the shade or sun. A full head (bathroom) rounds the necessary amenities to create a fantastic day.

Pick up and drop off are available at several Harbor, Bay, or beyond locations.



  • The experienced crew will cover all the details to create an exceptional experience like none other.

  • This stabilized yacht will allow you to cruise comfortably between islands and ports, no matter the conditions.

  • Plenty of public space onboard will enable you to find sun or shade and enjoy outside or inside climate-controlled spaces.

  • Gourmet meals are prepared to your preferences.

  • Separate crew space, allowing for guest privacy.

  • High-speed Wifi, whether at the dock or underway, allows you to stay connected even while we encourage you to unwind.

What guests are saying

Jenna was a wonderful captain! She brought us to some great spots. As parents we aren’t use to someone waiting on us!

Dolphin Lover

Winter 2024 Charter specials in Southwest Florida

These special charters are available for limited dates in January, February and March (bookings must be completed before March 21). Book early as they are filling quickly!

Romantic Getaway: Honeymoon, Anniversary, Special Occasion $7400

This all inclusive charter provides Timeless all to yourselves (of course, in addition to crew)

  • 3 Nights: Night 1, board Timeless at the dock, night 2 spend anchored in a romantic cove, night 3 spend at a memorable marina with a romantic restaurant for that special dinner

  • Includes: breakfast, lunch and one dinner (while anchored), fuel and dockage

  • Prosecco, flowers and a special dessert complete this memorable package

Family Fun Days $8400

This private charter for your family of up to 5 (children 8-18 accommodated) creating the most amazing memories

  • 3 Nights: Night 1, board Timeless at the dock, night 2 spend anchored, night 3 spend at a an island marina

  • Stop at Cabbage Key for lunch, hike the water tower, visit the tortoise, and enjoy a cheeseburger in paradise

  • Spend days at a pristine beach, enjoying watersports including tubing, paddle boarding, searching for sand dollars and those perfect shells on an island beach, only accessible by boat

  • Includes: breakfast, lunch and one dinner (while anchored), fuel and dockage

Relax, Rest and Rejuvenate $7400

This charter provides a private experience for up to 2 people (add another couple for just $1000)

  • 3 Nights: Night 1, board Timeless at the dock then spent two nights, anchored away in peaceful island settings

  • Stop at Cabbage Key for lunch or dinner and enjoy an island stroll

  • Enjoy special spa products to allow you to relax and rejuvenate as you spend your time away from it all

  • Spend the days at a secluded beach, or simply float off the back of your own, private yacht

  • Includes: breakfast, lunch and two dinners, fuel and dockage

Create your unforgettable luxury charter experience

Whether for a few hours to watch the sunset or for a week, we can tailor your charter to create just the right experience.

Click for sample itineraries.

Keep Up With Us

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