header cover

Yacht sailing holidays & skippered tours in USA and Canada

Discover more than 0 sailing holidays in USA and Canada. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

0

experiences

search

No holiday found.

Currently there are no listed holidays matching your search.

How about widening your search?

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in USA and Canada

1 reviews

avatar placeholder

Sailing Expedition in the Gulf of Alaska - Alaska's "Inside Passage"

06/28/2023

Jerry N.

Fabulous itinerary, including Glacier Bay, Wrangell Narrows and the hot springs; lots of Alaskan wildlife ba potted on land and water; and great food too, accommodating non meat eaters. Captain and. Few hood fun, easy to get on with and highly experienced. Overall a wonderful, highly recommended 10 days. Ideal for travellers who are up for a challenge, have sone sailing experience and can muck in. Make sure you are suitably equipped, can be very wet and cold. Don’t expect luxury.

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964