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

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 14 (8 Nights)

$3350 Sold Out!

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

Clearwater, FL - Punta Gorda, FL

Departs November 23 (7 Nights)

$2950 Sold Out!

Fort Pierce to Marathon – Florida Keys

Fort Pierce, FL - Marathon, FL

Departs February 8 (7 Nights)

$3950 per person, based on double occupancy

Marathon to Punta Gorda / Florida Keys

Marathon, Florida - Punta Gorda, Florida

Departs February 15 (7 Nights)

$3950 per person, based on double occupancy

Keys and Clearwater
(Triangle Loop Leg 1)

Punta Gorda, Florida - Miami, Florida

Departs March 21 (7 Nights)

$3250 Sold Out!
Miami to St Augustine

Best of South Florida
(Triangle Loop Leg 2)

Miami, Florida - St Augustine, Florida

Departs March 29 (6 Nights)

$3000 Sold Out!

Golden Isles Low Country Historic Cruise
(Triangle Loop Leg 3)

St. Augustine, FL - Savanah, GA

Departs April 5 (6 Nights)

$3000 per person, based on double occupancy

Low Country ICW Cruising
(Triangle Loop Leg 4)

Savannah, GA - Southport, NC

Departs April 12 (6 Nights)

$3000 per person, based on double occupancy

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

Southport, NC - Hampton, VA

Departs April 19 (10 Nights)

$5050 per person, based on double occupancy

Cruising North Carolina Bald Head
(Triangle Loop Leg 5)

Southport, NC - Beaufort, NC

Departs April 19 (3 Nights)

$2050 per person, based on double occupancy

Cruising North Carolina and Virginia ICW
(Triangle Loop Leg 6)

Beaufort, NC - Hampton, VA

Departs April 23 (7 Nights)

$3250 per person, based on double occupancy

Cruising the Southern Chesapeake
(Triangle Loop Leg 7)

Hampton, VA - Annapolis, MD

Departs May 11 (7 Nights)

$3250 per person, based on double occupancy

Hudson River Highlights
(Triangle Loop Leg 8)

Staten Island, NY - Waterford, NY

Departs June 4 (6 Nights)

$3000 per person, based on double occupancy

Erie Canal: Waterford, NY to Brewerton, NY
(Triangle Loop Leg 9)

Waterford, NY - Clay / Brewerton, NY

Departs June 11 (6 Nights)

$3000 per person, based on double occupancy

Oswego Canal: Clay, NY to Alexandria, NY
(Triangle Loop Leg 10)

Clay, NY - Alexandria, NY

Departs June 28 (6 Nights)

$3000 per person, based on double occupancy

Cruising the St Lawrence Seaway – Thousand Island to Montreal
(Triangle Loop Leg 11)

Alexandria, NY - Montreal, QC

Departs July 13 (6 Nights)

Contact us

Montreal to Burlington, Cruising the Chambly
(Triangle Loop Leg 12)

Montreal, QC - Burlington, VT

Departs July 22 (6 Nights)

Contact us

Burlington, NY to Troy, NY Cruising the Champlain Canal
(Triangle Loop Leg 13)

Burlington, VT - Troy, NY

Departs July 31 (6 Nights)

$3000 per person, based on double occupancy

Hudson River Highlights
(Triangle Loop Leg 14)

Troy, NY - Sandy Hook, NJ

Departs August 9 (5 Nights)

$2750 per person, based on double occupancy

Cruising the Northern Chesapeake
(Triangle Loop Leg 15)

Annapolis, MD - Baltimore, MD

Departs August 20 (5 Nights)

$2750 per person, based on double occupancy

Cruising the Southern Chesapeake
(Triangle Loop Leg 16)

Annapolis, MD - Hampton, VA

Departs August 26 (5 Nights)

$2750 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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