Name: First 44 (2026) Smile Inside for charter in Italy - Sicily
Brand: First 44
Availability: InStock"
Rating: 3.8 (3 reviews)

1/10

From: Portorosa (Italy - Sicily)

Start 6:00 PM

End 8:00 AM

Number of people

Price for 7 days

$4,954 $4,954

$4,954 for 7 days

Technical specification FIRST 44

Model First 44

Engine 57 hp

Year/Refit 2026

Length 14.15 m

Cabins 3

Beam 4.25 m

Bathroom 2

Draught 2.15 m

Berths 6

Water tank 570 L

Max. Capacity (people) 6

Fuel tank 200 L

Equipment & amenities

AC
Watermaker
Electric heads
Electric winch
Bow thruster
GPS / Chartplotter
Outdoor speakers
VHF radio
Oven

CLIMATE

AC
Electric heads

NAVIGATION & ELECTRONICS

Watermaker
GPS / Chartplotter
VHF radio
Inverter
Autopilot

DECK & MANEUVERING

Electric winch
Bow thruster
Anchor windlass
Sprayhood
Outside shower
Bimini top

ENTERTAINMENT

Outdoor speakers

GALLEY

Oven
Coffee maker

Other

Cockpit Table
Shore power connector
Liferaft
Cutlery
Teak deck
Sailsrepair kit
Bosuns chair
Distress flares
Fire extinguishers
mosquitonet
Holding Tank
Warm water
Spare anchor

Description

The First 44 Smile Inside is a 14.15 m long and 4.25 m wide sailboat, offering space for up to 6 guests on board. Built in 2026. It features 3 cabins and 6 berths. Powered by 57 hp, with a 200 L fuel tank, this model delivers confident handling and relaxed cruising.

This sailboat is equipped with 2 bathrooms and 570 L water tank — convenient for extended trips. Additional amenities include ac, watermaker, electric heads, bow thruster and standard safety equipment.

The boat is available for bareboat charter from Portorosa, a great starting point to explore Sicily sailing grounds. A professional skipper is available upon request from $1,833 per week

Price list - cost per week

Start 6:00 PM

End 8:00 AM

Number of people

BOAT

Price for 7 days

$4,954 $4,954

0% due at reservation

Free cancellation within 3 days

Extras

Mandatory services
$2,211
Optional services
$0
Total price
$4,954
Damage deposit
$4,010

Location

Portorosa, Italy - Sicily

Check-in / Checkout

Check-in: from 6:00 PM

Check-out: until 8:00 AM

Minimum charter duration is 7 days

Charter options

Bareboat

For bareboat charter in Italy - Sicily, a valid sailing license is required: IPC (International Proficiency Certificate) issued by ASA, US Sailing, NauticEd, RYA, IYT, or another certified school. Upon reservation of First 44 Sailboat, please upload your sailing certificate to your personal account for verification.

Skippered

A professional skipper can be provided for $1,833 per week. A food allowance and a dedicated cabin are required and are not included in the price.

Security Deposit

A damage deposit of $4,010 must be paid on site at Portorosa before embarkation. The deposit will be refunded at the end of the charter, provided there is no damage to the boat.
The damage deposit represents your maximum liability in case of any damage to the Sailboat First 44, Smile Inside.
Your maximum liability, can be reduced to $0 by purchasing additional insurance (damage waiver) for $298 per charter.

Payment & Cancellation

No-obligation reservation (3-day hold).
No payment is required until the booking agreement is signed.

Payment terms:

Down payment: 50%
Balance: due 42 days before departure
Extras: payable in advance, at least 42 days before the charter

Cancellation policy:

50% of the charter fee is retained for cancellations made 43 days before departure
100% of the total charter fee is non-refundable for cancellations made 42 days or less prior to the charter

Payment and cancellation terms are provided for reference only. Final terms are defined in the booking agreement.

Boat location

Current base: Marina Portorosa, Italy - Sicily

Customer reviews

How customer reviews and ratings work

We use the Average with Prior (also known as Bayesian Average) to calculate the total rating for each fleet operator/charter company.

Since new companies could have very few reviews, each review can significantly impact the average score, potentially leading to misleading representations of the total score (e.g., one very positive or very negative review skewing the overall rating). To mitigate this, we use a "prior" or "default" score.

This means that each company rating, by default, starts 4, which is calculated from 3 hypothetical reviews, each rated 4. This assumption provides a baseline level of performance that is neutral-to-positive.

For example, if a new company receives a 5-star review, the total rating will be adjusted to 4.25. Here's how it is calculated: (4 × 3) + 5 = 17 and then divided by the total number of reviews 4 (3 default + 1 actual review), resulting in 4.25

As more reviews come in, the weight of the actual reviews increases, and the influence of the prior diminishes.

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Rating based on reviews from customers who rented other boats in this charter company

5 star

67%

4 star

3 star

2 star

1 star

33%

Jonathan W.

United States

Grenada

19 Mar 2023 - 26 Mar 2023

Lagoon 450F / Cor Caroli

Apr 2023

“Everything was great”

Everything was great with NSS and the vessel. Davide and his daughter, Tatiana, were awesome and added to the successful experience.

Keali Pyvis

Australia

Grenada

01 Jul 2025 - 12 Jul 2025

Copernicus - Lagoon 42

Jul 2025

“If I could give a 10 star rating I would”

If you are looking for a boat charter, look no further. We did a 12 day bare-boat charter with a hired skipper sailing from Grenada to St. Vincent and the Grenadines. 12 knots had excellent communication and was prompt and helpful with answering questions leading up to the charter. I had a lot of questions and felt fully supported throughout the entire process. NSS Charters also had impeccable communication (shout-out to Tatiana) both before and while on charter. Boat was clean, well-maintained and very comfortable. The boat came with all the necessary essentials, I was particularly impressed with the stocked galley, even the knives were sharp! We were lucky enough to get Davide as our skipper who gave us the trip of a lifetime with his local knowledge. He included us in tailoring the trip to our wants and needs and even helped us make reservations for unique dinners on local islands. He knew the islands like the back of his hand, observed what we enjoyed and made recommendations that made our trip unforgettable. I honestly can not say enough positive things about both 12 knots and our experience with NSS Charters. I've already recommended them to friends and family and will hands down be chartering through them again. While we were sailing around, numerous island locals told us we were with one of the best charter companies around, so if you don't trust my endorsement, trust the locals!

Italia

Aug 2021

“Marina d'Arechi, Catamarano rental. Bad experience.”

Extremely negative review for NSS. Society to be avoided strictly. 3 boats (our two boats of acquaintances) have drawn up lists of damage for the purpose of collecting the deposit or insurance deductible. Attention, do not trust delivery, ask for a list of damages compiled by hand and countersigned. They denied having found the commander to have no responsibility for the conduct. Bad experience, no assistance when we have reported tender (laundry) and engine problems (repaired 2 times at our expense). Think about it 2 times, there are many very serious non -Italian companies to contact. Very little professionalism by the manager of the NSS base in Marina d'Arechi, unable to seriously manage the problems as well as to give assistance of any kind. Useless.

Frequently asked questions of the First 44 Smile Inside charter

Does First 44 Smile Inside have insurance?

Yes. First 44 Smile Inside is offered by professional charter company and has hull and third-party liability insurance.

What is the Damage Deposit for renting First 44 Smile Inside

The Damage Deposit is the amount you are liable for in case of any damages to the Sailboat First 44 Smile Inside. A deposit of 4010 USD must be paid on site at Portorosa, Italy - Sicily before embarkation. It will be refunded at the end of the charter if no damages are found. The deposit is usually paid by credit card.

What is Damage waiver (insurance)?

A Damage Waiver is optional insurance that reduces the standard 4010 USD Damage Deposit for this Sailboat to a smaller amount. If it is not available, you can purchase separate deposit insurance to cover potential deductions in case of boat damage. Click here to purchase deposit insurance via OuestAssurances

Do I need a sailing license to charter First 44 Smile Inside bareboat in Italy - Sicily?

Yes. A valid sailing license such as ICC, IYT Bareboat Skipper, RYA Day Skipper, or ASA 104 with IPC is required for bareboat rentals in Portorosa, Italy - Sicily. Please ask your booking manager for specific requirements. Detailed information is available here: Sailing license - things to know.

What is the cancellation policy for the First 44 Smile Inside charter?

Free cancellation within 4 days of the online reservation. Once you reserve the First 44 on the 12 Knots website, it will be held for you free of charge for 4 days.

If the booking is cancelled 46 days or more before the charter, 50% of the charter fee will be retained. No refund is available for cancellations made less than 46 days before the charter.

Please check the booking agreement and charter terms for the exact cancellation policy, as conditions may vary from the example above. charter.

Travel insurance is available. Click here for details

How does the booking procedure work?

Make an online reservation by clicking Available. Reserve now (no payment required).
Complete the sailing resume if booking a bareboat charter.
Sign the booking agreement electronically for the First 44 Smile Inside charter in Italy - Sicily.
Make the down payment according to the agreement.