Call us: 1 (305) 735-3460
CHESAPEAKE BAY
Chesapeake Bay


Chesepeake Yacht Charters

Base: Annapolis

Rent a boat in Chesapeake Bay. Our bareboat fleet out of Annapolis Marina is composed of excellent maintained and equipped monohull and catamarans, all superbly equipped for your comfort and safety. Please keep in mind that skipper, hostess/cook, provisions and leisure equipment remain options to make your yachting vacation complete. For more information check out Frequently Asked Questions about Chesapeake Bay Please note that Tropical Yachts has a Best Price Policy (Click for more info.) Please choose from our great selection, shown below in order of yacht size.

● CHESAPEAKE BAY MONOHULL RENTALS● CHESAPEAKE BAY CATAMARAN RENTALS


CHESAPEAKE BAY MONOHULL RENTALS

Sun Odyssey 389 Monohull From $4,100/week 3 cabins/1 head sleeps 6
• Specifications: •Year: 2018 • Length: 11.75 m / 38 ft 6 in • Beam: 3.76 m / 12 ft 4 in • Draft: 1.52 m / 4 ft 11 in • Water: 200 L /52 gal • Fuel: 130 L / 34 gal • Engines: 29 CV Electric: Inverter 12v/220v • Cabins: 3 cabins/ 1 head Sleeps 6/8 • Navigation/ Electronics: • Dockside Air... >>
Chesapeake Bay Yacht Charter: Sun Odyssey 389 Monohull From $4,100/week 3 cabins/1 head sleeps 6

Sun Odyssey 440 Monohull From $4,700/week 3 cabins/2 head sleeps 6
• Specifications: • Year: 2018 • Lenght: 14.05 m / 46 ft 1.14 in • Beam: 4.24 m / 13 ft 10.9 in • Draft: 1.6 m / 5 ft 2.9 in • Water: 530 L / 140 gal • Fuel: 200 L / 52 gal • Engine: Yanmar 57 HP • Electric: Inverter 12v/220v • Cabins: 3 cabins / 2 head / Sleeps 6 • Navigation/ Electroni... >>
Chesapeake Bay Yacht Charter: Sun Odyssey 440 Monohull From $4,700/week 3 cabins/2 head sleeps 6

Dufour 412 Monohull From $3,978/week 3 cabin/2 head sleeps 6/8
• Specificatios: • Year: 2020 • Length: 12.7 m / 42 ft • Beam: 4.20 m / 13 ft 9 in • Draft: 2.10 m/ 6 ft 10 in • Water: 380 L / 100 gal • Fuel: 200 L / 53 gal • Engines: 55 HP • Electric: Converter 12v/220v • Cabins: 3 cabin + salon / 2 Head / Sleeps 6/8 • Navigation/ Electronics: • Dock... >>
Chesapeake Bay Yacht Charter: Dufour 412 Monohull From $3,978/week 3 cabin/2 head sleeps 6/8

Dufour 430 Monohull From $5,694/week 4 cabin/2 head sleeps 8
• Specifications: • Year: 2019 • Length: 13.24 m / 43 ft 5 • Beam: 4.30 m / 14 ft 1.2 in • Draft: 1.75 m / 5 ft • Water: 380 L / 100 gal • Fuel: 200 L / 52 gal • Engines: 60 HP • Cabins: 4 cabin + conv saloon, 2 Head / Sleeps 8 • Navigation: • GPS Plotter • Auto Pilot • Wind Instruments ... >>
Chesapeake Bay Yacht Charter: Dufour 430 Monohull From $5,694/week 4 cabin/2 head sleeps 8

Dufour 430 Monohull From $5,199/week 3 cabin/2 head sleeps 8
• Specifications: • Year: 2022 • Length: 13.24 m / 43 ft 5 • Beam: 4.30 m / 14 ft 1.2 in • Draft: 1.75 m / 5 ft • Water: 380 L / 100 gal • Fuel: 200 L / 52 gal • Engines: 60 HP • Cabins: 3 cabin + conv saloon, 2 Head / Sleeps 8 • Navigation: • Air Conditioning • Generator • GPS Plotter •... >>
Chesapeake Bay Yacht Charter: Dufour 430 Monohull From $5,199/week 3 cabin/2 head sleeps 8

Jeanneau 53 Monohull From $6,134/week 3 cabins/3 heads sleeps 6 Air
• Specifications: • Year: 2011 • Length: 16.06 m / 52 ft 8 in • Beam: 4.77 m / 15 ft 7 in • Draft: 1.80 m / 5 ft 10 in • Water: 251 gal / 950 l • Fuel: 63 gal /238 l • Engines: 110 HP • Electric: Inverter 12v/220v • Cabins: 3 dbl cabins / 3 heads / Sleeps 6 • Navigation/ Electronics: • A... >>
Chesapeake Bay Yacht Charter: Jeanneau 53 Monohull From $6,134/week 3 cabins/3 heads sleeps 6 Air


CHESAPEAKE BAY CATAMARAN RENTALS

Fountaine Pajot Isla 40 Catamaran From $7,200/week 3 cabin/2 head sleeps
• Specifications: • Year: 2022 • Length: 40 ft 5 in / 12.33 m • Beam: 21.7 ft / 7 m • Draft: 3.9 ft / 1.19 m • Water: 1022 l / 270 gal • Fuel: 300 l /79 gal • Engines: Volvo 2 x 30 • Cabins: 3 dbl cabins / 2 heads / Sleeps 6 • Navigation/ Electronics: • Air Conditioning • Generator • GPS... >>
Chesapeake Bay Yacht Charter: Fountaine Pajot Isla 40 Catamaran From $7,200/week 3 cabin/2 head sleeps

Bali 4.1 Catamaran From $6,788/week 3 cabin/3 head sleeps 6 Air
• Specifications: • Year: 2019 • Length: 12.19 m / 40 ft • Beam: 6.7 m / 22 ft • Draft: 1.11 m / 3.67 ft • Water: 800 l / 211 gal • Fuel: 400 l / 105 gal • Engines: Volvo 2 x 40 hp • Cabins: 3 dbl cabins + 1 sgl / 3 heads / Sleeps 6 • Navigation/ Electronics: • Air Conditioning • Generat... >>
Chesapeake Bay Yacht Charter: Bali 4.1 Catamaran From $6,788/week 3 cabin/3 head sleeps 6 Air

Bali Catspace Catamaran From $7,989/week 3 cabin/3 head sleeps 6 Air
• Specifications: • Year: 2022 • Length: 40 ft 5 in / 12.33 m • Beam: 21.62 ft / 6.59 m • Draft: 3.61 ft / 1.1 m • Water: 700 l / 185 gal • Fuel: 400 l /105 gal • Engines: Volvo 2 x 30 hp • Cabins: 3 dbl cabins / 3 heads / Sleeps 6 • Navigation/ Electronics: • Air Conditioning • Generato... >>
Chesapeake Bay Yacht Charter: Bali Catspace Catamaran From $7,989/week 3 cabin/3 head sleeps 6 Air

Astrea 42 Luxe Catamaran From $7,945/week 4 cabins/4 heads sleeps 8/11
• Specifications: • Year: 2020 • Length: 12.58 m / 41 ft 3 in • Beam: 7.2 m / 23 ft 7 in • Draft: 1.25 m / 4 ft 1 in • Water: 700 L / 184 gal • Fuel: 470 L / 124 gal • Engines: 2 x 40 HP Volvo • Electric: Inverter 12v/220v • Cabins: 4 dbl cabins/ 4 heads /Sleeps 8/11 • Navigation/ Electr... >>
Chesapeake Bay Yacht Charter: Astrea 42 Luxe Catamaran From $7,945/week 4 cabins/4 heads sleeps 8/11

Bali 4.2 Catamaran From $7,568/week 4 cabin/2 head sleeps 8 Air
• Specifications: • Year: 2021 • Length: 40 ft / 12.19 m • Beam: 22 ft / 6.7 m • Draft: 3.67 ft / 1.11 m • Water: 800 l / 211 gal • Fuel: 400 l /105 gal • Engines: Volvo 2 x 40 hp • Cabins: 4 dbl cabins / 2 heads / Sleeps 8 • Navigation/ Electronics: • Air Conditioning (in hulls only) • ... >>
Chesapeake Bay Yacht Charter: Bali 4.2 Catamaran From $7,568/week 4 cabin/2 head sleeps 8 Air

Lagoon 450 Catamaran From $10,384/week 4 cabin/4 head sleeps 8/12
• Specifications: • Year: 2017 • Beam: 7.84 m / 25 ft 8.66 in • Draft: 1.30 m / 4 ft 3 in • Displacement: 15,5 t • Water: 4 x 175 l / 184 gal • Fuel: 2 x 500 l / 264 gal • Engines: Yanmar 2 x 54 hp • Cabins: 4 dbl cabins + 2 sgl + conv salon / 4 heads / Sleeps 8/12 • Navigation/ Electron... >>
Chesapeake Bay Yacht Charter: Lagoon 450 Catamaran From $10,384/week 4 cabin/4 head sleeps 8/12

Saona 47 Catamaran From $11,428/week 5 cabin/5 head sleeps 11 Air
• Specifications: • Year: 2020 • Length: 13.94 m / 45 7 in • Beam: 7.70 m / 25 ft 3 in • Draft: 1.30 m / 4 ft 3 in • Water: 700 L / 184 gal • Fuel: 2 x 470 L / 248 gal • Engines: 2 x 60 HP • Cabins: 4 dbl + front peak /5 Heads / Sleeps 10 • Navigation/ Electronics: • Air conditioning • G... >>
Chesapeake Bay Yacht Charter: Saona 47 Catamaran From $11,428/week 5 cabin/5 head sleeps 11 Air

Bali 4.8 Catamaran From $7,908/week 5 cabin/5 head sleeps 10 Air Conditioning,
• Specifications: • Year: 2020 • Length: 46 ft 10 in / 14.28 m • Beam: 26 ft / 7.88 m • Draft: 4 ft /1.35 m • Water: 230 gal / 1000 l • Fuel: 230 gal / 1000 l • Engines: Yanmar 2 x 57 hp • Cabins: 5 dbl cabins / 5 heads / Sleeps 10 • Navigation/ Electronics: • Air Conditioning • GPS plot... >>
Bahamas Yacht Charter: Bali 4.8 Catamaran From $7,908/week 5 cabin/5 head sleeps 10 Air Conditioning,

Lagoon 50 Catamaran From $8,794/week 6 cabin/4 head sleeps 12 Air Conditioning,
• Specifications: • Year: 2020 • Length: 14.75 m / 48 ft 4 in • Beam: 8.10 m / 26 ft 6 in • Draft: 1.40 m / 4 ft 7 in • Water: 830 L / 219 gal • Fuel: 2 x 520 L / 274 gal • Engines: Yanmar 2 x 80 hp • Cabins: 6 dbl cabins + 2 sgl / 4 heads / Sleeps 12 • Navigation/ Electronics: • Air Con... >>
Chesapeake Yacht Charter: Lagoon 50 Catamaran From $8,794/week 6 cabin/4 head sleeps 12 Air Conditioning,

Lagoon 52 F Catamaran From $14,777/week 6 cabin/6 head sleeps 12/14
• Specifications: • Year: 2022 • Length: 15.84 m / 51 ft 11.6 in • Beam: 8.6 m /28 ft 2 in • Draft: 1.5 m/ 4 ft 11 in • Water: 960 l / 253 gal • Fuel: 992 / 262 gal • Engines: Yanmar 2 x 75 hp • Cabins: 6 dbl cabins + 2 sgl / 6 heads / Sleeps 12/14 • Navigation/ Electronics: • Air Condit... >>
Chesapeake Bay Yacht Charter: Lagoon 52 F Catamaran From $14,777/week 6 cabin/6 head sleeps 12/14

Please note: Information on this sheet is believed to be correct but not guaranteed,
and images are for illustrative purpose only.


Tropical Yachts
4906 N Travelers Palm Lane. Tamarac, FL 33319
Tel: 1 (305) 735-3460

Copyright© 2003-2025, Tropical Discovery Services Inc. or its affiliates
Bonded State of Florida Seller of Travel - Reg. No. ST35634
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SUGGESTED CHESAPEAKE
SAILING ITINERARIES

Annapolis, North: 7 day Boat Charter Cruising Program
Annapolis, South: 7 day Boat Charter Cruising Program
Annapolis: 14 day Boat Charter Cruising Program

Choosing the Right Boat for Your Chesapeake Bay Charter

The Chesapeake Bay offers a diverse sailing experience, from calm, sheltered waters and scenic coves to busier open channels and bustling port towns. Selecting the right boat depends on your sailing style, group size, the areas you plan to visit, and the season of your trip. Planning ahead ensures you enjoy a safe and comfortable charter in the Chesapeake.

Vacation Style

  • Leisurely cruising: Catamarans are ideal for stability, space, and ease of anchoring in calm waters, perfect for families or groups seeking relaxed sightseeing and beach stops.
  • Active sailing: Monohulls provide a traditional sailing experience with tacking and heeling, ideal for sailors who enjoy the challenge of windward passages.
  • Luxury and comfort: Crewed yachts offer full service, including meals, water sports, and extra amenities. These are suited for those who want to focus on relaxation and socializing without handling the boat.

Waters & Areas

  • Protected coves and inlets: Northern Chesapeake Bay is filled with sheltered anchorages, calm waters, and scenic landscapes, ideal for casual cruising and family-friendly activities.
  • Open channels and southern Bay: The southern Chesapeake can feature stronger currents, winds, and more open water, requiring a well-equipped boat and experienced crew for safe navigation.
  • Plan your route with attention to marinas, fuel stations, and local services, particularly if exploring more remote areas of the Chesapeake.

Group Size & Comfort

  • Small parties: A monohull or smaller catamaran offers intimate space, easy handling, and sufficient amenities for 2–4 people.
  • Larger groups: For groups of 6–10 or families with mixed ages, a spacious catamaran or a luxury yacht ensures ample cabins, heads, and living space.
  • Consider privacy, cabin layout, and onboard facilities when choosing your Chesapeake boat, particularly for longer trips.

Season & Weather

  • Spring (April–June): Mild temperatures, calm waters, and blooming landscapes create excellent sailing conditions.
  • Summer (July–August): Warmer temperatures, more boat traffic, and occasional afternoon thunderstorms; ideal for those seeking lively waterfront communities.
  • Fall (September–October): Cooler, stable weather, fewer crowds, and spectacular autumn colors; often considered the optimal Chesapeake sailing season.
  • Winter (November–March): Shorter days, colder water, and potential for storms; generally not recommended for leisure charters.

Practical Tips Before Booking

  • Check the exact boat specifications: number of cabins, heads, draft, tender, safety equipment, and onboard electronics.
  • Decide between bareboat or crewed charter based on your experience and comfort with handling the vessel in the Bay’s currents and variable weather.
  • Review fuel, provisioning policies, and cancellation or insurance rules, especially if your trip spans summer thunderstorms or fall weather changes.

Final Tip: Choose a boat that fits your group size, preferred sailing style, and the Chesapeake areas you plan to explore. Prioritize safety, comfort, and amenities, and plan your season carefully for the best sailing conditions in the Bay.

To check availability & get personal assistance, fill the form on this page or call 1 (305) 735 34 60.