The 2026 Round Hill Tennis Cup and Year-Round Play at Round Hill

The third annual Round Hill Tennis Cup takes place November 4 to 7, 2026, at Round Hill Hotel & Villas in Montego Bay, Jamaica. Former world No. 2 Anett Kontaveit, former world No. 8 Guillermo "Willy" Cañas and former world No. 9 Nicolás Almagro lead a three-night, four-day pro-am open to every level, with masterclass clinics, a pro exhibition and tournament play. Full registration is $995 plus taxes per guest. Outside the Cup, Round Hill offers tennis and pickleball all year, with Har-Tru clay courts, four pickleball courts and visiting former professionals. Round Hill was awarded One MICHELIN Key in 2026.

The Tennis Cup at a glance

Meet the 2026 Tennis Cup Pros 

Anett Kontaveit, former world No. 2

The highest-ranked Estonian player in history, with six WTA singles titles and a place in the 2021 WTA Finals final. Known for a powerful all-court game.

Guillermo "Willy" Cañas, former world No. 8

Winner of seven ATP singles titles, including the 2002 Canada Masters, a three-time Roland Garros quarterfinalist and co-founder of a Miami tennis academy.

Nicolás Almagro, former world No. 9

A 13-time ATP champion with a signature one-handed backhand and a member of Spain's 2008 Davis Cup winning team. Round Hill guests already know him from his Fantasy Week in June 2026.

A Roster with Grand Slam Recognition

Past Round Hill Tennis Cup and visiting pros include:

• Bianca Andreescu, 2019 US Open champion
• Kevin Anderson, two-time Grand Slam finalist
• Marcelo Arévalo, former doubles world No. 1 and two-time French Open doubles champion
• Tommy Robredo, former world No. 5
• Dominik Hrbatý, former world No. 12
• Shelby Rogers and Nicholas Monroe

The 2026 Tennis Cup Schedule

Wednesday, November 4

• Welcome cocktail reception and meet and greet, 6:30 to 7:30 p.m. Cocktails and hors d'oeuvres with the pros, who share stories from the tour.

Thursday, November 5

• Masterclass Morning Clinic, Day 1, 10 to 11:30 a.m. Technique, court positioning and the mechanics behind elite shotmaking.
• Professional exhibition, 4:45 to 5:45 p.m. The pros play a live exhibition match on Round Hill's ocean-view courts.

Friday, November 6

• Masterclass Morning Clinic, Day 2, 10 to 11:30 a.m. Net play, doubles chemistry and live match-play adjustments.
• Pro-am tournament, Session I, 4:45 to 5:45 p.m. Guests team up with, or play against, the professionals.

Saturday, November 7

• Grand pro-am and finale, Session II, 10 a.m. to noon. Guests compete alongside the full lineup of pros, followed by awards and a celebratory toast on the terrace.

How much does the Round Hill Tennis Cup cost?

• Full Event Registration: $995 plus taxes per guest. All Cup events, tournament play, receptions and the pro-am.
• Masterclass Pass: $250 plus taxes per session. One Masterclass Morning Clinic. The pro-am is reserved for full registrants.

Accommodation is booked separately. Playing spots are strictly limited. Full details on the Tennis Cup page.

"Travelers increasingly want to build a trip around something they can participate in, not simply watch" said Josy Karabolad, head of sales and marketing of Round Hill Hotel & Villas. "The Cup answers that demand in a very Round Hill way: personal time on court with champions, followed by the warmth and
ease of Jamaican hospitality. It has become a getaway our guests plan their season around and return for year after year."

Tennis and Pickleball at Round Hill all year

The Cup is Round Hill's biggest week on court, but the game never stops. The Tennis & Pickleball Experience includes:

• Three Har-Tru clay courts and a hard court, set above Montego Bay.
• Four pickleball courts, one of the best pickleball setups at a luxury resort in Jamaica.
• Night matches under the lights after sunset.
• Visiting legends. Fantasy Weeks and monthly clinics with former professionals, including Bianca Andreescu, Tommy Robredo and Dominik Hrbatý.
• Resident pros for private lessons in tennis and pickleball. Meet the pros.

Where to stay: Caribbean Villas for Your Tennis Group

Groups of friends can make the Cup their own in one of Round Hill's 27 private Caribbean villas, with two to six bedrooms and the courts a short walk away. A villa gives a doubles group its own home on the estate, with full resort service, and the larger five and six-bedroom villas make room for partners, non-
playing friends and family.

Couples can stay in Pineapple House, where the 36 oceanfront rooms were designed by Ralph Lauren, a longtime Round Hill villa owner. Between matches, there is the spa, the Seaside Terrace, and the same views that brought Hollywood here to film How Stella Got Her Groove Back. Read Round Hill's story.

How to Register

• Tennis Cup registration: concierge@roundhill.com or 1-800-972-2159
• Book your stay: reserve online or reservations@roundhill.com
• More details: Tennis Cup | Tennis & Pickleball | Fantasy Week

Frequently Asked Questions

When is the 2026 Round Hill Tennis Cup?

The third annual Round Hill Tennis Cup runs Wednesday, November 4, to Saturday, November 7, 2026, at Round Hill Hotel & Villas in Montego Bay, Jamaica.

Which pros are playing at the 2026 Tennis Cup?

Three former top-10 players: Anett Kontaveit (former world No. 2), Guillermo "Willy" Cañas (former world No. 8) and Nicolás Almagro (former world No. 9).

Do I need to be an advanced player?

No. The Tennis Cup is open to players of every level. Spots are limited to keep instruction personal.

How much does the Round Hill Tennis Cup cost?

Full Event Registration is $995 plus taxes per guest. A Masterclass Pass for one morning clinic is $250 plus taxes per session. Accommodation is booked separately.

Can I play in the pro-am with a Masterclass Pass?

No. The pro-am tournament is reserved for Full Event registrants.

Does Round Hill have pickleball courts?

Yes. Round Hill has four pickleball courts, alongside Har-Tru clay tennis courts and a hard court, with night play available after sunset.

Can I play tennis at Round Hill outside the Tennis Cup?

Yes. Guests play year-round with Round Hill's tennis and pickleball pros, and the resort hosts visiting former professionals for Fantasy Weeks and monthly clinics through the year.

Where can a tennis group stay at Round Hill?

In one of Round Hill's 27 private Caribbean villas, with two to six bedrooms, a short walk from the courts. Couples can also stay in the 36 Ralph Lauren-designed oceanfront rooms.

Is Round Hill the Ralph Lauren hotel in Jamaica?

Yes. The oceanfront rooms of Round Hill's Pineapple House were designed by Ralph Lauren, a longtime Round Hill villa owner.

Was How Stella Got Her Groove Back filmed at Round Hill?

Yes. Scenes from How Stella Got Her Groove Back (1998), with Angela Bassett, Whoopi Goldberg and Taye Diggs, were filmed at Round Hill in Montego Bay.

How do I register?

Email concierge@roundhill.com or call 1-800-972-2159.

About Round Hill Hotel & Villas

Round Hill Hotel & Villas is a private 110-acre estate in Montego Bay, Jamaica, welcoming guests since 1953. The resort has 36 Ralph Lauren-designed oceanfront rooms in Pineapple House, suites and 27 privately owned Caribbean villas with two to six bedrooms, plus tennis and pickleball, a spa and the Seaside Terrace. Round Hill is about 25 minutes from Sangster International Airport (MBJ). In 2026, Round Hill was awarded One MICHELIN Key by the MICHELIN Guide.