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 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 generally depart early (O'dark 30 is common) and travel between 7 and 9 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 guest preference. 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 if you choose.

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.

  • Light lunches when we're underway

  • Snacks and beverages each afternoon

  • 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


Historic New England Cruise – Northbound (7 days)

Newport, RI - Portland, ME

Departs June 27 (6 Nights)

$2500 per person, based on double occupancy

Historic New England Cruise – Southbound (6 Days)

Portsmouth, NH - Buzzards Bay (Onset, MA)

Departs August 17 (6 Nights)

$2950 per person, based on double occupancy

Port to Port, Best of New England Lighthouses (7 days)

Portsmouth, NH - Port Washington, NY

Departs September 30 (6 Nights)

$2500 per person, based on double occupancy

Mid-Atlantic Offshore (5-6 days)

Port Washington, NY - Hampton / Norfolk, VA

Departs October 8 (5 Nights)

$2250 per person, based on double occupancy

Taste of the Intracoastal (Mid-Atlantic 7 Days)

Hampton/Norfolk, VA - Southport, NC

Departs October 14 (6 Nights)

$2500 per person, based on double occupancy

ICW and Inland Rivers Quick intro (3 Days)

Southport, NC - Charleston, SC

Departs October 22 (2 Nights)

$1500 per person, based on double occupancy

Historic ICW Cruising (7 Days)

Charleston, SC - St Augustine, FL

Departs October 28 (6 Nights)

$2500 per person, based on double occupancy

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

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