We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chatham Classic Yacht Charters
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (45)
Full view
Traveller Overview
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain matt”(2 reviews)
“cape cod”(2 reviews)
Suggested duration: 2-3 hours
Local Weather
Powered by Weather Underground
Stage Harbor Road, Chatham, MA 02646-0673
+1 508-432-8397
Reviews (16)
Filter reviews
16 results
Traveller rating
Traveller type
Time of year
Show reviews that mention
All reviews captain matt beautiful boat cape cod sail skiing adventure ship
Updating list...
1 - 10 of 16 reviews
Reviewed 18 November 2017

I have had the pleasure to sail on this timeless beauty many times. Tyrone, named after a county in Ireland by its first owner, is of sturdy build with exquisite lines. She dances nimbly, even with her great size and weight. She has won many...More

Thank Topherlicious
Matt S, Owner at Chatham Classic Yacht Charters, responded to this reviewResponded 24 November 2017

Thank you for the kind words and the support!!

Reviewed 21 August 2017

We reluctantly went on an evening sail with Captain Matt at the end of a cold and windy day in July, but the gods smiled on us and rewarded us with a calm and smooth sail that ended with a spectacular sunset. Matt was happy...More

3  Thank Becky R
Reviewed 16 August 2017

We went out for a midday sail with Matt and it was the highlight of our summer! Eight of us ranging in age from teenagers to a seventy year old had an amazing time -- how often can you please that wide-ranging a group?! We...More

3  Thank marlissa b
Reviewed 6 August 2017

The 6 of us had an amazing 2 hour sail with Matt on the Tyrone. She's a beautiful boat and Matt made our trip so enjoyable. Definitely worth adding this to your visit to the Cape.

3  Thank Tarnow12
Reviewed 22 June 2017

My Daughter, her friend and I took a tour while the tall ships were visiting Boston, Ma. I was delighted by the adventure that we had on the Tyrone. Matt, the skipper and his Mate Topher did everything to make our experience amazing. We sailed...More

3  Thank PatriciaDianeM
Reviewed 7 June 2016

We've just returned from three weeks in Boston/Cape Cod environs that included several days aboard the schooner TYRONE out of Harwich/Chatham. Both my wife and I are basking in the richness and beauty of our second sail with the delightful, funny and very capable Matthew...More

2  Thank Rucky
Reviewed 27 February 2016

My family and friends had a wonderful time sailing on the Tyrone. I called Matt to book a post-wedding sail for 17, not knowing if he could accommodate a group that large. Matt was very pleasant and explained this was indeed possible with a commercial...More

1  Thank Michael L
Reviewed 9 February 2016

I've boated around Chatham for 50 years, and last year decided to charter the Tyrone when our extended family were in town, now a rare event. As it turned out, sailing on the Tyrone ranks among my top boating experiences in Chatham. We went twice...More

1  Thank David C
Reviewed 1 February 2016

My family took my dad out on the Tyrone in celebration of my father's 80th birthday. We brought my two nieces (who are nine years old) with us and every one of all ages had a great time. We sailed from Chatham to Nantucket, had...More

1  Thank Stephen K
Reviewed 28 January 2016

We looked for quite a few boats, I did not want a catamaran as I prefer mono-hulls. I was looking for something special. This boat was just what we were looking for, a beautiful classic boat. We opted for a half day charter, which was...More

1  Thank Tom S
View more reviews
Nearby HotelsSee all 9 nearby hotels
The Chatham Wayside Inn
281 reviews
.97 km away
Chatham Inn At 359 Main
452 reviews
1.10 km away
Chatham Highlander
107 reviews
1.48 km away
Hawthorne Motel
515 reviews
1.53 km away
Nearby RestaurantsSee all 71 nearby restaurants
Chatham Wine Bar and Restaurant
258 reviews
1.11 km away
Blue Fins Sushi & Sake Bar
281 reviews
.94 km away
Impudent Oyster
1 414 reviews
.94 km away
Chatham Squire Restaurant & Tavern
1 477 reviews
.90 km away
Nearby AttractionsSee all 87 nearby attractions
Atwood House & Museum
87 reviews
.10 km away
Chatham's Godfrey Windmill
66 reviews
.58 km away
Eldredge Public Library
27 reviews
.93 km away
Oyster Pond
22 reviews
.72 km away
Questions & Answers
Get quick answers from Chatham Classic Yacht Charters staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines