Pick your boat, we crew it.

36' Aquila

Built for Florida's Gulf Coast lifestyle, this spacious power catamaran combines the stability of a twin-hull design with multiple outdoor gathering spaces, comfortable shade and two private cabins below. Cruise Clearwater's coastline, anchor near Caladesi, explore the barrier islands or settle in for sunset. At 36 feet with an impressive 14'7" beam, she delivers the space and social atmosphere of a much larger yacht.

Up to 12 passengers, plus the charterer: 13 aboard in total.

From$2,229Captain, crew and fuel included

38' Sea Ray

A classic express cruiser with the space to celebrate and the comfort to settle in. Based at Maximo Marina in St. Petersburg, this 38' Sea Ray is made for Tampa Bay days that move easily from cruising beneath the Skyway to swimming near Shell Key and lingering on the water for sunset.

Up to 10 passengers, plus the charterer: 11 aboard in total. · Maximo Marina

From$1,723Captain, crew and fuel included

41' Sea Ray Express

A Well Played-owned Sea Ray 410 built for the kind of St. Petersburg day that ends with sandy feet. Her approximately 3'4" draft gives her an advantage over many of the larger yachts in the fleet: when depth, conditions and local anchoring rules allow, she can anchor closer to suitable shallow-water areas, making swim stops and Shell Key-style days especially easy and inviting.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$1,581Captain, crew and fuel included

42' Aquila

A true yacht-style power catamaran with an extraordinary 21-foot beam, elevated flybridge and multiple outdoor gathering spaces. Home-ported at MarineMax St. Petersburg on Boca Ciega Bay, the Aquila 42 gives guests room to spread out for a polished Gulf Coast day - from Gulfport and Shell Key to the beaches, islands and open-water views beyond.

Up to 12 passengers, plus the charterer: 13 aboard in total. · MarineMax St. Petersburg (Gulfport)

From$2,460Captain, crew and fuel included

44' Aquila

A 44' Aquila Yacht power catamaran built for space, stability and easy Florida days. From Maximo Marina in St. Petersburg, she turns Tampa Bay into a wide, level living room — flybridge above, salon amidships, and water on both sides. She is made for celebrations, executive entertaining, sunset gatherings and unhurried destination days toward Shell Key, Egmont Key and the open water beyond the Skyway.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$2,086Captain, crew and fuel included

44' Fountaine Pajot

Elegance, style, and an elevated day on Tampa Bay. A stunning 44' Fountaine Pajot power catamaran, one of our top-tier yachts, offered exclusively through Well Played Editions for families, corporate hosts and discerning guests. Three levels of luxury, three private cabins with en-suite baths, a spacious flybridge and a fully equipped galley. Smooth, stable and quiet underway.

Up to 10 passengers, plus the charterer: 11 aboard in total. · Westshore Yacht Club Marina, Tampa

From$3,990Captain, crew and fuel included

44' Regal

A Well Played-owned 2001 Regal Commodore 4160 built around two distinct outdoor social levels: a lower aft cockpit close to the swim platform and water, plus a stepped-up helm deck with a table and generous seating beside the helm. Add a wide 14-foot beam and a published draft just under three feet, and she becomes an especially versatile choice for Shell Key, swimming, floating and relaxed St. Petersburg beach days.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$1,713Captain, crew and fuel included

45' Sea Ray Sundancer

Sleek, sporty and made for a day on the bay. Stretch out on the bow sunpad, gather in the open cockpit, or slip into the air-conditioned salon. She's built for Tampa Bay's favorite sandbars and island hangouts.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Westshore Yacht Club Marina, Tampa

From$2,254Captain, crew and fuel included

48' Formula

Up to 12 passengers, plus the charterer: 13 aboard in total. · Safe Harbor Pier 77 (Anna Maria)

From$1,925Captain, crew and fuel included

50' Prestige

A sophisticated 50' flybridge motor yacht designed for the days that deserve a little more. Meeting guests at the Gandy Boat Ramp in Tampa, the Prestige 500 pairs expansive outdoor entertaining space with a beautifully connected salon, galley and private accommodations - ideal for sunset cruising, milestone celebrations, corporate entertaining and elevated days on Tampa Bay.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Westshore Yacht Club Marina, Tampa

From$2,786Captain, crew and fuel included

60' Flybridge

A substantial 58' Sea Ray motor yacht with the space, comfort and presence for a truly elevated St. Petersburg charter. From Maximo Marina, her expansive flybridge, generous salon and multi-stateroom layout create an exceptional setting for milestone celebrations, corporate entertaining, family outings and longer Tampa Bay days toward Shell Key, the Sunshine Skyway and Egmont Key.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$2,992Captain, crew and fuel included

68' Uniesse

A sleek 68' Italian sport yacht with unmistakable presence, serious performance and the space to turn a Tampa Bay charter into an event. Based at Maximo Marina in St. Petersburg, the Uniesse is made for milestone celebrations, executive entertaining, sophisticated social outings and destination-style days toward Shell Key, Egmont Key and the open waters beyond the Skyway.

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$4,905Captain, crew and fuel included

It’s All Good

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$3,322Captain, crew and fuel included

Saxdor

The Saxdor: sporty, sleek, and built for a good time. Based in St. Pete, this sexy Saxdor brings sporty luxury to every trip on the water, with sharp modern lines and a fast, smooth ride. The best boat in the fleet for bachelor parties and sandbar days, especially when your crew wants to pull right into the middle of the action at John's Pass.

Up to 9 passengers, plus the charterer: 10 aboard in total. · Maximo Marina

From$1,530Captain, crew and fuel included

Triple Stack

Up to 12 passengers, plus the charterer: 13 aboard in total. · Maximo Marina

From$2,316Captain, crew and fuel included