Annapolis / Eastern Shore golf scenery

Chesapeake Bay · MD

Annapolis / Eastern Shore

MD • Chesapeake Bay

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Best season

Spring-Fall

May · Sep · Oct

Trip cost · per golfer

$1,600–$4,200

3-night trip

Nearest airport

BWI

23 mi · BWI

Difficulty

mixed

Handicap 0–20

Overview

Why play Annapolis / Eastern Shore

Experience championship golf amidst stunning Chesapeake Bay scenery, combining historic charm with challenging courses and vibrant coastal culture.

Top courses

Best golf courses in Annapolis / Eastern Shore

Editor-picked layouts ranked by prestige, conditioning and player experience.

#1

Queenstown Harbor Golf Course (River Course)

Design by Arthur Hills · Par 72 · 7,096 yds

A links-style course offering breathtaking views of the Chester River and challenging winds. Play in the morning to beat the afternoon winds, and take time to enjoy the scenic vistas on nearly every hole.

Moderate-HardLinks$90–180
#2

Baywood Greens

Design by Jake Claussen · Par 72 · 6,983 yds

Known as the \"Augusta of the North,\" this course is renowned for its immaculate conditions and floral beauty. Don't rush; take in the stunning landscaping, especially the array of colorful flowers and waterfalls.

ModerateParkland/Strategic$100–200
#3

Renditions Golf Course

Design by Ault, Clark & Associates · Par 72 · 6,736 yds

Play a collection of replica holes from golf's most famous courses, offering a unique and memorable experience. Be sure to read the descriptions at each tee box to appreciate the history behind these iconic holes.

ModerateTribute$80–160
#4

U.S. Naval Academy Golf Course

Design by William S. Flynn / Arthur Hills (renovation) · Par 70 · 6,415 yds

An historic course with a classic design, providing a challenging yet enjoyable round close to Annapolis. Book tee times well in advance, especially during peak season, as it's a popular choice for locals and visitors.

ModerateClassic American Parkland$60–120

Stay & play

Where to stay in Annapolis / Eastern Shore

Resort packages bundle lodging, rounds, range access, and on-site dining. Hotel-only options give you flexibility to course-hop.

The Graduate Annapolis

Boutique Hotel

A stylish hotel blending historic charm with modern amenities, located steps from downtown Annapolis.

Inn at Perry Cabin Resort & Spa

Luxury Resort

A luxurious waterfront retreat offering unparalleled service, gourmet dining, and a serene setting.

Hilton Garden Inn Annapolis

Mid-range Hotel

A comfortable and reliable option with convenient access to golf courses and attractions.

Hampton Inn & Suites Grasonville

Budget Hotel

An affordable and friendly stay close to Queenstown Harbor, perfect for golf groups.

Off the course

Things to do in Annapolis / Eastern Shore

Non-golf experiences worth building into your trip — from local landmarks to nature, food, and culture.

Explore Historic Annapolis

History & Sightseeing

Wander the cobblestone streets, visit the U.S. Naval Academy, and learn about colonial history.

Chesapeake Bay Sailing Tour

Water Activities

Enjoy a relaxing boat cruise on the Chesapeake Bay, offering stunning views and potential wildlife sightings.

Maryland State House Tour

History & Culture

Discover the oldest state capitol in continuous legislative use, rich in American history.

Antiquing on Maryland's Eastern Shore

Shopping & Exploration

Browse charming small towns known for their antique shops and unique local finds.

Kayaking or Paddleboarding

Water Sports

Rent a kayak or paddleboard to explore the calm creeks and rivers off the Chesapeake Bay.

Itineraries

Sample itineraries

Choose your trip length. Each plan is built around the marquee courses, with rest, dining, and travel days dialed in.

  1. 1

    Day 1

    Arrive & warm up

    Land at BWI, transfer to your hotel, hit the range, and grab a casual dinner at O'Leary's Seafood Restaurant.

  2. 2

    Day 2

    Round 1 — Queenstown Harbor Golf Course (River Course)

    Morning tee time at Queenstown Harbor Golf Course (River Course). Lunch at the clubhouse, afternoon recovery, dinner at Preserve.

  3. 3

    Day 3

    Final round & departure

    Early tee time at U.S. Naval Academy Golf Course, light lunch, then transfer back to BWI.

Budget

Budget breakdown · per golfer

Realistic ranges sourced from current resort rates, public green fees, and group dining averages.

Lodging
3 nights · $229/nt
$687
Golf
2 rounds · $133 avg
$266
Food & drink
~$110/day
$330
Ground transport
Rideshare + cart fees
$180
Flights
Search Skyscanner for live fares
Variable
Estimated total · per golfer$1,463

Season

Best time of year to visit Annapolis / Eastern Shore

humid subtropical

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Ideal Good Off-season

When to book: 3-6 months out

Dining

Where to eat in Annapolis / Eastern Shore

From clubhouse classics to chef-driven dinners worth a reservation.

O'Leary's Seafood Restaurant

$$$$

Seafood

An upscale seafood dining experience famous for its inventive dishes and intimate atmosphere.

Boatyard Bar & Grill

$$

American/Seafood

A lively nautical-themed spot in Eastport, renowned for its fresh seafood, crab cakes, and casual vibe.

Preserve

$$$

New American

Offering a farm-to-table experience with a seasonal menu and handcrafted cocktails in a chic setting.

Cantler's Riverside Inn

$$

Seafood

A quintessential Maryland crab shack experience, offering steamed crabs and fresh seafood right on the water.

Cafe Normandie

$$$

French

An authentic French bistro in historic Annapolis, serving classic dishes in a charming setting.

Davis' Pub

$

Pub Fare

A beloved local dive bar with classic pub food and a friendly atmosphere, perfect for a casual meal.

After dark

Nightlife in Annapolis / Eastern Shore

Where the buddy trips end up after the 19th hole.

Pusser's Caribbean Grille

Bar/Restaurant

A vibrant waterfront bar in City Dock offering tropical drinks and live music with scenic views.

Stan and Joe's Saloon

Pub

A popular local spot known for its lively atmosphere, craft beers, and live music.

Middleton Tavern

Historic Tavern

An historic tavern dating back to 1750, offering a cozy atmosphere and occasional live entertainment.

Tee times

Book tee times in Annapolis / Eastern Shore

Live inventory from GolfNow plus flight comparison from Skyscanner. Prices update in real time.

FAQ

Annapolis / Eastern Shore golf trip FAQs

What is the best time of year to golf in Annapolis / Eastern Shore?

+

Spring-Fall (May, Sep, Oct). humid subtropical

How much does a golf trip to Annapolis / Eastern Shore cost?

+

Plan on $1,600–$4,200 per golfer for a 3-night trip including lodging, rounds, food and ground transport. Flights are extra.

What airport should I fly into for Annapolis / Eastern Shore?

+

BWI, about 23 miles from the resort area. Most national hubs offer non-stop service via BWI.

How many days should I plan for a Annapolis / Eastern Shore golf trip?

+

3 nights is the sweet spot — enough for 2 full rounds plus a rest or sightseeing day.

Is Annapolis / Eastern Shore good for buddy trips?

+

Yes — popular with solo, families, couples. Strong nightlife close to the courses.

Ready to book

Book your Annapolis / Eastern Shore golf trip

Lock in tee times on GolfNow, secure your stay on Booking.com, or let our AI planner build the entire itinerary for your group in under a minute.

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Trip snapshot

Destination
Annapolis / Eastern Shore, MD
Best months
May, Sep, Oct
Length
3 nights
Per golfer
$1,600–$4,200
Fly into
BWI

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