Exquisite Recreation

Wequassett Resort offers a wide variety of recreational activities to keep you invigorated during your stay. Two pools, vast beaches and manicured lawns offer the perfect backdrop for some recreational fun. Take advantage of the first-rate tennis courts, endless bike trails and the calm waters of Pleasant Bay.

Whether you're a pro or play just for fun, be sure to take advantage of
Wequassett's first-rate tennis courts and fall in love with the game.

Tennis enthusiasts will appreciate the resort's four new 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 new pro shop offers quality equipment, resort wear and gifts. An adult lap pool and Jacuzzi are located next to the tennis center.

Court Fees

Private Lessons



$30 per hour

$80 per hour

$45 per half hour
Includes court fees.

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

$45 per one person

$20 per person
for groups of four or more.

Clinics are a daily sign up based on availability, and run an hour in length.

Meet the Tennis Pro

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.

Escape reality and enter a paradise filled with every indulgence you will ever need. A magnificent elevated entrance with a peaceful fountain and exquisite gardens overlooks Pleasant Bay, Round Cove and the ocean beyond with a sweeping 270 degree view at our main pool. Pamper yourself at the tucked away adult only lap pool and let relaxation settle in if serenity is what you are looking for. Take a boat shuttle to Cape Cod’s National Seashore and explore the exquisite Outer Beaches or pick a chaise on the sandy shores of Pleasant Bay.
It will be shore to please!


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, 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!

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.

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 descent over Pleasant Bay on one of our popular scheduled Sunset Sails!

Leave the crowds behind on a private tour of Chatham Harbor and the windswept sand dunes which help form Pleasant Bay. Home to one of the largest concentrations of gray and harbor seals in North America and the famous Chatham Lighthouse, bay tours can be catered to your wishes. Those traveling with children will enjoy the hands-on Pleasant Bay Explorer excursion, which includes clamming on the beach and hauling lobster traps!

For those interested in experiencing New England's premier fishing and whale watching grounds, Down Cape Charters & Boat Rentals offers several half-day and full-day excursions. Let our skilled captains guide you into the Atlantic Ocean in search of Striped Bass, Bluefin Tuna, Humpback and Minke whales, dolphins or possibly even a Great White Shark!

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.

Down Cape Charters and Rentals ›

Water Sports Pricing

One Hour

Two Hours

Half Day

Single Kayak




Double Kayak




Paddle Boards








Hobie Cat Wave




Hobie Cat Getaway




Cat Boat








15' Boston Whaler




17' Edgewater




23' Bowrider




24' Fundeck




About Water Sports ›

Shore to please

The most peaceful way to spend your day is on the ocean side of Pleasant Bay.

It’s Cape Cod’s treasured National Seashore, one of the country’s most secluded stretches of quiet and relaxation. The pristine seashore is only accessible by boat. With views of seals and sea life all around, getting there is only half the fun. We provide regularly scheduled drop-off and pick-up shuttle service throughout the day along with beach chairs, umbrellas and towels. We’ll even pack a picnic lunch if you desire. We know you’ll find this a shore winner.

This summer the resort will feature a wide variety of cool entertainment featuring live musical performances, special events and surprise visits from from our Good Humor truck.

The Summer Jazz Festival Line-up will be announced soon.

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.


Is anyone ready for some beach volleyball? Let the recreation team know you are interested and they will be more than willing to get the volleyball court ready for you. Let the games begin!

Personal Training

Looking for a private training session? Let our recreation team know and they will be able to coordinate a trainer during your stay. These trainers have a vast knowledge of strength training, conditioning and nutrition. Don't compromise your fitness goals while on vacation.


Take advantage of the nearby bike path and have an adventure touring Cape Cod. Beginning in Dennis, the trail roams through forests, fields, marshes and cranberry bogs all the way through Wellfleet. It is splendid and safe place to ride, especially for children.


We bring a touch of Latin to the Cape! Enjoy a fun and aerobic exercise class with our very own Zumba instructor. The class is an hour long with fast paced and upbeat music. It will make you smile especially while the calories are burning away!


Grab some friends or gather up the family for some croquet fun. The recreation department will be more than happy to set up a friendly game of croquet for you on our Croquet Lawn. The view and the competition is hard to beat!


There is no better way to begin a sunny day than with a relaxing yet challenging yoga-fit class. The hour long class combines light aerobic exercise with flexibility-building yoga. You will feel energized and ready for your day.