Set Sail with Olympian Lara Dallman-Weiss

Experiences Overview

August 25th to 27th


  • Overnight Package


  • Intermediate Clinic,

    Resort guest - $100
    Non resort guest - $150

  • Interactive Sail,

    Resort guest - $150
    Non resort guest - $200

  • Reception Meet & Greet


For one weekend only, the U.S. Olympic Sailor will teach sailing clinics and lessons to hotel guests and the general public on Pleasant Bay. With the support of the local Pleasant Bay Community Boating, guests will have access to Lara’s expert insight, hands-on training, and skillset, which successfully led her to the 2020 Tokyo Summer Olympics and to compete in next year’s Summer Olympics in Paris and America’s Cup in Barcelona.


Lara and her team are honored to represent the Inland Lakes Yachting Association. Growing up on White Bear Lake, MN, Lara spent her summers sailing in ILYA and continues raising awareness and donations for ILYA Olympic Teams to further the association’s goal of encouraging, developing, promoting, and fostering amateur yachting and yacht racing. Finding her love for competitive sailing at Eckerd College, Lara has continued to race on the professional sailing circuit for five years, working with diverse teams until she started campaigning full-time in the 470 classes. She qualified to represent Team USA at the 2020 Summer Olympics in Tokyo, where she competed in the Women’s Two-Person Dinghy – 470 event.

On Friday, we invite guests to meet Lara and have the opportunity to ask her questions about her Olympic journey and how she fell in love with the sport. On Saturday, Lara will teach clinics exclusively to our resort guests which will consist of a classroom session followed by water time! Private lessons will be available on Sunday to both resort guests and the public.


Friday August 25th:

  • 7:00 to 9:00PM The Road to Paris Reception with Lara under our poolside Cabanas.  Meet and mingle with an Olympian while enjoying delicious food and the evening’s signature cocktail, the French Negroni.  Open to all ages and to the public.  Book Here

Saturday August 26th:

  • 10:30 to 12:00PM – Interactive Group Sail – Take a sail on the Maria with Captain Lara and learn how she navigates the waters of Pleasant Bay.  Up to 8 passengers and open to the public.  Book Here
  • 12:30 to 2:00PM – Interactive Group Sail – A second sail on the Maria with Captain Lara.  Up to 8 passengers and open to the public.  Book Here
  • 2:30 to 4:00PM- Intermediate Clinic – A mix of classroom and on the water time with Lara.  Up to 12 people and open to the public.  Book Here

Sunday August 27th:

  • Private lessons and experiences available.  BYOB – Bring Your Own Boat!  All proceeds donated to Lara’s trip to Paris and her Olympic games in 2024!  To learn more about her journey click here.

Sailing Obsessed?

Book our Overnight Package which includes:

  • 10% off your guest room rate
  • Welcome amenity including Wequassett hats
  • Entry to The Road to Paris Reception with Lara for four people
  • One clinic or Interactive Sail for up to four people