WHEN AND IF
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WHEN AND IF

Alden · Sailing Monohull

Starting at $26,000 base charter rate
  • USA - New England, USA - Florida East Coast
  • 64 ft (19.4 m) Sailing Monohull
  • Accommodates up to 6 guests
  • 3 cabins · 2 Double, 1 Twin
  • 2 crew
  • Rendezvous diving with a local dive operator

About WHEN AND IF

WHEN AND IF is a 64 ft Alden sailing monohull accommodating up to 6 guests in 3 cabins. Built in 1939 and refitted in 2014. Cruising areas: USA - New England, USA - Florida East Coast.

Master Cabin: Double berth to port, single berth to starboard, access to ensuite. Large overhead hatch creates a light, airy cabin.

Starboard Cabin: Cosy double berth with plenty of storage space

Focsle: One wide-single and one single bunk, both with privacy curtains. Large overhead hatch makes a light, airy space

Destinations & cruising areas

  • USA - New England
  • USA - Florida East Coast

Charter rates & seasons

Low Season

Jan 1, 2026 – Dec 31, 2026

$26,000Base charter rate

Area
USA - New England, USA - Florida East Coast
Base port
Salem, MA
Charter terms
Plus Expenses · + ALL
Rate details

Summer New England / Winter Florida weekly rate - $26,000 per week plus all expenses
Christmas and New Year in Florida - $30,000 + expenses
DAYSAILS:
Maximum 32 guests. BYO food and drink. Coolers provided with ice and bottled water. Prices included yacht deliver and re-delivery fees.
8 hours: $6,600 + all expenses
4 hours: $5,800 + all expenses

Rates are subject to change, please verify.

REGATTAS:
Maximum 12 guests. Prices include 6 party/event/dinner tickets, guests must have overnight accommodation ashore. Prices included yacht delivery and re-delivery fees.

Photo shoot pricing:
Inquire within for more details

Rates are as published by the yacht and may exclude expenses, taxes and gratuities depending on the charter terms. Final pricing is confirmed in your charter quote.

Availability

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Specifications

Type
Sailing Yacht (Monohull)
Builder
Alden
Year built
1939
Refit
2014
Length
64 ft (19.4 m)
Beam
15 ft (4.6 m)
Draft
9 ft (2.6 m)
Flag
USA
Cruising range
1200 NM
Fuel consumption
1.2 US Gall/Hr
Air conditioning
Partial
A/C at night
No
Stabilizers
No
Communications
SATNAVGPSRadarCellular Phone

Accommodation & cabin layout

Cabins
3
Guests
6
Double cabins
2
Twin cabins
1
Heads
1
Showers
1
Children welcome
Yes

Charter preferences

Kosher meals
Yes
Special diets
Yes
LGBTQ+ charters
Yes
Clothing-optional charters
Yes
Crew smokes
No

Amenities & onboard facilities

  • Sun Awning
  • Hammock
  • BBQ
  • Hair Dryer

Tender & water toys

  • Dinghysize: RIB, engine: 40 HP
  • Snorkel Gear × 8

Scuba diving

Scuba diving
Yacht offers Rendezvous Diving only
Air compressor
Not Onboard

Meet the crew

Captain Dylan Salzmann:

Spending my childhood and teenage years living between the Florida Keys and the coast of Maine there was no getting around the draw of the ocean. From a young age I could be found roaming the docks of Key West, FL picking up work scrubbing decks, sanding, painting and eventually crewing and captaining aboard the may traditional boats that winter there. During my high school years I was able to combine my love of being on the water with high school credits by creating a number of independent studies that revolved around maritime heritage and tradition. When I was 18 I purchased my first boat, a 32' cutter in Key West. I lived aboard and fixed her up before making the offshore passage to Blue Hill, ME. Shortly after my 20th birthday I received my USCG 100-ton Masters Credential and went on to run numerous vessels ranging from traditionally rigged schooners between the Bahamas and the coast of Maine, to fishing boats, dive vessels and small sailing charter boats in the Florida Keys, to piloting hovercrafts and jet drive catamarans in Alaska. Today, 11 years later I find myself sailing aboard the historic schooner When And If, sharing her history while showing off her elegance and speed to each guest who steps aboard. I look forward to racing her as a serious contender in the many Classic regattas New England has to offer in the Summer season. Sailing has become a tradition in my family - starting with my older brother who now owns When And If - and quickly spreading through all of us; it is hard to imagine a life that does not revolve around the wind and tide.

Stew/Deck/Cook: Zoe Moncheur

My love for sailing started when I was 7 years old and I crewed for my father at our local yacht club in Wellington, New Zealand where I was raised. I spent every weekend on the water and competed in national regattas throughout the country. Sailing is an integral part of my life and I feel extremely fortunate to be able to work and live on the extraordinary When and If.

While my formal education is in Law, having graduated with a Law degree from Victory University of Wellington Law School in 2016, my true love is in the culinary arts. My father is a wonderful chef, he grew up working at a resort in New York where he learned to cook and has since then taught me everything he knows. I worked my way through university waitressing at a fine-dining restaurant The Cobar, it was here I learned the importance of dish presentation.

In 2018 I was able to combine my passion for sailing and my love for cooking, as well as the skills I learnt from my father and my time at The Cobar when I was hired as the live aboard cook on the When and If. Living and working aboard this vessel has been a great experience, allowing me to introduce a creative element into my dishes with a focus on local flavours from wherever we sail. I look forward to more adventures and exciting dishes with our charter guests.

Ready to sail aboard WHEN AND IF?

Tell us your dates and group size and a charter specialist will confirm availability and send a tailored quote.

Request yacht details

Yacht information is supplied by the yacht’s central agent and may change. We verify every detail with the yacht before you book. Listing last updated October 19, 2026.

Yacht data provided by Central Yacht Agent.