Cruise with us

What is the difference between a Cruise and a Charter?

A cruise you join us on an existing itinerary that we have pre-planned. You're joining the yacht for 5 to 7 days (or occasionally shorter or longer) as the yacht travels from port to port. We provide suggested itineraries, but you can join anywhere along an existing trip.

A charter provides your private use of Timeless with captain and crew to cater to your needs and provide a custom itinerary that is special for you and your guests whether for part of a day, a week, or more.

 

What To Expect When you Cruise

When you join Timeless on a cruise, you travel comfortably with all the amenities, as we explore the coast and small ports only accessible by a boat the size of Timeless. No two cruises are the same; itineraries and ports change regularly and can't be guaranteed. However, we provide embarkation and departure ports and unforgettable experiences.

We occasionally depart early (O'dark 30 is common) and travel between 6 and 8 hours (and occasionally more), arriving in port mid to late afternoon, with time to explore the port. We'll stay an extra day in some ports of interest, dictated by the crew, weather, and itinerary. This will provide an excellent opportunity for those who want to learn about voyage planning, navigating, weather forecasting, line handling, etc. While you're not "crew," you can work with the crew and learn about the cruising lifestyle.  We welcome the help.

All Cruise pricing is based on double occupancy.

 

What's included each week:

  • Breakfast each morning. Many mornings we'll be underway, but when we're in port, expect one of Darlene's famous breakfasts.

  • Coffee, Tea, soft drinks, and water is always available.

  • Lunches when we're underway

  • Snacks and beverages

  • One to Two dinners each week with wine and beer

  • Dockage, marina fees, fuel, etc., are all included in the cruise fare.

 

 

What's not included:

  • Transportation to and from the yacht

  • Meals a shore

  • Excursions, shopping, museums, and nights on the town

  • Crew gratuity

Itineraries

Scroll down through the itineraries in chronological order
Not all "Great Loop" legs are open for booking

Cruising the Inland Rivers
(Great Loop Leg 13)

Chicago, IL - Grafton, IL

Departs September 22 (7 Nights)

$2950 Sold Out!

Cruising the Inland Rivers
(Great Loop Leg 14)

Grafton, IL - Grand Rivers, KY

Departs September 30 (6 Nights)

$2950 per person, based on double occupancy

Cruising the Inland Rivers
(Great Loop Leg 15)

Grand Rivers, KY - Columbus, MS

Departs October 13 (6 Nights)

$2950 per person, based on double occupancy

Rivers to Tidal Water
(Great Loop Leg 16)

Columbus, MS - Orange Beach, AL

Departs October 20 (7 Nights)

$3150 per person, based on double occupancy

Best of the Pan Handle
(Great Loop Leg 18)

Orange Beach, AL - Panama City, FL

Departs November 8 (6 Nights)

$2950 per person, based on double occupancy

Transiting the Gulf
(Great Loop Leg 19)

Panama City, FL - Clearwater, FL

Departs November 13 (8 Nights)

$3350 per person, based on double occupancy

The Grand Finale – Best of Southwest Florida
(Great Loop Leg 20)

Clearwater, FL - Punta Gorda, FL

Departs November 23 (7 Nights)

$2950 per person, based on double occupancy

Keys and Clearwater (Great Loop 2027 Leg 1)

Punta Gorda, Florida - Miami, Florida

Departs March 21 (7 Nights)

$3250 per person, based on double occupancy
Miami to St Augustine

Best of South Florida (Great Loop 2027 Leg 2)

Miami, Florida - St Augustine, Florida

Departs March 29 (6 Nights)

$3000 per person, based on double occupancy

Golden Isles Low Country Historic Cruise
(Great Loop 2027 Leg 3)

St. Augustine, FL - Savanah, GA

Departs April 5 (6 Nights)

$3000 per person, based on double occupancy

Low Country ICW Cruising
(Great Loop 2027 Leg 4)

Savannah, GA - Southport, NC

Departs April 12 (6 Nights)

$3000 per person, based on double occupancy

Cruising North Carolina Bald Head
(Great Loop 2027 Leg 5)

Southport, NC - Beaufort, NC

Departs April 19 (3 Nights)

$2050 per person, based on double occupancy

Cruising North Carolina and Virginia ICW
(Great Loop 2027 Leg 5/6)

Southport, NC - Hampton, VA

Departs April 19 (10 Nights)

$5050 per person, based on double occupancy

Cruising North Carolina and Virginia ICW
(Great Loop 2027 Leg 6)

Beaufort, NC - Hampton, VA

Departs April 23 (7 Nights)

$3250 per person, based on double occupancy

Cruising the Southern Chesapeake
(Great Loop 2027 Leg 7)

Hampton, VA - Annapolis, MD

Departs May 11 (7 Nights)

$3250 per person, based on double occupancy

Cruising the Northern Chesapeake
(Great Loop 2027 Leg 8)

Annapolis, MD - Baltimore, MD

Departs May 25 (7 Nights)

$3250 per person, based on double occupancy

Looking for where we've already cruised? Check out our Previous Cruises.

Keep Up With Us

Timeless Yacht logo stacked
PORTLAND, ME | PORT CHARLOTTE, FL
[email protected]

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