• Tennis
    Be sure to take advantage of Wequassett’s first-rate tennis courts
    Tennis Pro Bio

    Tennis enthusiasts will appreciate the resort’s four Har-Tru tennis courts with custom trellises for privacy. The courts are complemented by a raised viewing terrace and an adjacent barbecue area making it an ideal setting for tennis parties.


    Our resident pro is available for lessons and will gladly fill in as a doubles partner when needed, or arrange tournaments and round robin play for groups and families. In addition, certified instructors provide quality instruction to every level or player. A pro shop offers quality equipment, resort activity wear and gifts. An adult lap pool and Jacuzzi are located next to the tennis center.

    Court Fees

    $30 per hour


    Private Lessons 

    $95 per hour

    $55 per half hour (includes court fees)


    $375 per 2 hour round robin for 16 people. Customize upon request.



    $45 per one person


    Dave Messersmith returns for his 30th season this spring after his 29th winter as Tennis Pro at Rancho de Los Caballeros. Dave has taught and played In Open Tournaments in Florida, Texas and California, as well as Cape Cod, where he is ranked #1.


    He has won virtually every major Cape Cod tournament, both singles and doubles, as well as the coveted Lower Cape Singles title. Off the courts, Dave is possibly the greatest East Coast expert on any topic in sports history. After a day on the courts and a night at the ballpark, he relaxes by playing the guitar, tending bar, visiting one of his five siblings or plugging into a late game on the radio.

  • Pool & Beaches
    Dive right in
    Pool & Beaches

    The beautiful pool and Jacuzzi are complemented with oversized urns with lush flowers and plantings. A boardwalk of rich Brazilian wood wraps around the pool providing a breathtaking elevation to lounge in a luxurious cabana. When the sun sets and stars dot the sky, guests may enjoy a sensuous fire pit with an oversized circular seating area. What’s more, a lap pool for adults is located next to our tennis center. It features two Olympic size lanes and a Jacuzzi surrounded by lounge chairs and beautiful plantings and gardens.

    For the ultimate in luxury Cape Cod recreation, spend the day in one of our private cabanas. Our oversized, poolside retreats offer the most spectacular views of Pleasant Bay and the Atlantic Ocean, and are appointed with all kinds of extras to make your day at the pool even more relaxing!

  • Watersports
    Down Cape Charters & Boat Rentals offers an array of guided tours and watercraft rentals

    Located adjacent to the Wequassett dock, Down Cape Charters & Boat Rentals offers an array of guided tours and watercraft rentals on protected Pleasant Bay and beyond. Bring the family and admire the spectacular scenery that defines the coast of Cape Cod and the famed Cape Cod National Seashore.


    Visit Down Cape Charters & Boat Rentals for more information.

    Let's go sailing!

    Pitch in and help handle the sails or sit back and relax aboard the luxury daysailer, Maria. Available for private charter throughout the week, she offers the area’s finest sailing experience. During the months of July and August, watch the summer sun slowly descend over Pleasant Bay on one of our popular scheduled Sunset Sails!

    Private Kayak Tour Monomoy River

    Recent conservation efforts, led by the Harwich Conservation Trust and backed by generous donors including the Wequassett Resort and Golf Club, have resulted in the preservation of the Monomoy River – aka “Muddy Creek.”  Join us on a Private Kayak Tour as we celebrate newfound access to over 64 acres of untouched water teeming with Blue Heron, Red-tailed Hawks, Egrets and more.  This paddle is sure to be the perfect escape for the nature lover and kayaking enthusiast alike.  The tour will start from the Wequassett Resort beach and will take guests through the newly widened inlet into the estuary and back – a round trip of approximately 3.5 miles.  As currents and winds can sometimes present a challenge, some previous paddling experience is helpful.  Tour may not be suitable for young children.

    Private Fishing Charter

    For those interested in experiencing some of New England’s premier fishing grounds, Down Cape Charters & Boat Rentals offers the following half day and full day excursions.


    Striped Bass and Bluefish
    Striped Bass are one of the most sought after game fish on the east coast and along with hard-fighting Bluefish, they represent the mainstay of the Cape Cod charter fleet.  Stripers and Blues traditionally stay in our waters from May through October.  Offered as a half-day charter (4 hrs).


    Atlantic Bluefin Tuna are the largest and hardest fighting of all fish in the ocean.  To many, they represent the greatest trophy in all of sport fishing.  These giants generally arrive in mid-July, with August, September and early October representing peak season.  Offered as a full-day trip only (8 hrs).

    Let's go boating

    Rental options include small and large powerboats, Hobie catamarans, kayaks and stand up paddle boards. Always dreamed of sailing or motoring your own powerboat but lack experience? Now is the perfect time to learn. Friendly and knowledgeable instructors are available to help you to navigate the boat of your choice.

  • Leisure Sports
    Morning walks, dance classes, swimming lessons and a variety of other fantastic options to keep you active and entertained

    Enjoy Fulfilling Leisure Sports

    Our state-of-the-art fitness center is open 6:00am – 11:00pm seven days a week.


    During July and August, we maintain a full schedule of resort activities, including morning walks, dance classes, swimming lessons and a variety of other fantastic options to keep you active and entertained. For bicyclists, the nearby Cape Cod Rail Trail offers 36 miles of flat paved bike path through the scenic heart of the Cape.